Tetrakis(triphenylphosphine)palladium | Tetrakis(triphenylphosphine)palladium(0) | Palladium

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Recombinant–Chemosynthetic Biosensors for Probing Cell Surface Signaling of Red Blood Cells and Other Cells

Ubeysinghe, Sithurandi ; Sebilleau, Chloe O ; Thotamune, Waruna ; Rajarathna, Chathuri ; Azibere, Samuel ; Tennakoon, Mithila , et al.

DOI: 10.1021/cbmi.4c00067 Chem. Biomed. Imaging,2025,3(2):95-110.

Abstract: The complex signaling mechanisms in red blood cells (RBCs) enable them to adapt to physiological stresses such as exposure to low O₂ levels, metabolic demands, oxidative stress, and shear stress. Since Ca²⁺ is a crucial determinant of RBC fate, various ion channels, pumps, and exchangers regulate the delicate balance of Ca²⁺ influx and efflux in RBCs. Elevated intracellular Ca²⁺ can activate processes such as membrane phospholipid scrambling and alter RBC deformability, which is essential for effective capillary transit. However, the dynamic information about Ca²⁺ regulation in RBCs is limited. Although static mapping and bioanalytical methods have been utilized, the absence of a nucleus and the presence of hemoglobin create challenges for real-time probing of RBC signaling, necessitating innovative approaches. This work introduces a synthetic chemistry−recombinant protein-based strategy to assemble sensors at genetically intact healthy human RBC surfaces for measuring dynamic signaling. Using this approach, we measured autocrine regulation of RBC Ca²⁺ influx in response to low O₂ tension-induced ATP release. The study also explores the utilization of synthetic glycosylphosphatidylinositol (GPI) anchor mimics and sortagging for targeting sensors to the surfaces of primary as well as immortalized cells. This demonstrated the wide applicability of this approach to probe dynamic signaling in intact cells.

Keywords: Ca²⁺ ; GCaMP6s ; P2X ; GPI anchor mimics ; TIRF imaging ; RBCs ; sortase A ; cellular signaling

Purchased from AmBeed: 14221-01-3

The modification of DNA with indole-linked nucleotides alters its sensitivity to enzymatic cleavage

Lingala, Suresh ; Fisiuk, Anastasiia ; Stephen, Michelle ; Mohanrao, Raja ; Klingsberg, Judah ; Vecchioni, Simon , et al.

DOI: 10.1101/2025.01.26.634936 bioRxiv,2025.

Abstract: We describe the synthesis of C-5 indole-tagged pyrimidine and C-8 indole-tagged purine nucleoside phosphoramidites and their incorporation into double-stranded DNA 15 base pairs in length. Of the 23 sequence modifications tested, two induced the DNA duplex to adopt a Z-like left-handed conformation under physiological salt conditions, bypassing the specific sequences typically required for a left-handed Z-DNA structure. The impact of these modifications varied with the linker type: flexible propyl linkers exhibited distinct effects compared to rigid propargyl linkers. Notably, modifications positioned directly on or near a restriction site emphasized the pivotal role of linker rigidity in controlling DNA conformation. Specifically, the conformational change induced by the flexible linker impacted nuclease and restriction endonuclease cleavage, reducing sequence specificity. In contrast, the rigid linker suppressed this effect. Furthermore, our findings indicate that nucleic acid duplexes modified with indole-linked nucleotides using a flexible propyl linker have a pronounced tendency to form BZ or Z-like regions in longer DNA sequences. A higher density of modifications may even induce a full Z-like conformation throughout the duplex. These modified nucleotides hold potential for the development of novel antisense therapeutics and introducing valuable tools for in vitro screening of small molecules targeting distorted B-DNA, BZ-DNA, and Z-DNA structures.

Purchased from AmBeed: 14221-01-3 ; 1122-58-3

Fundamental Understanding of Palladium-Based Catalysts: From Pyrene-Based COFs to Size-Controlled Bimetallic Nanostructures

Saha, Hridita Purba ;

Abstract: The catalytic properties of single atoms (SAs) have attracted growing attention due to their unique electronic characteristics and their ability to maximize atomic efficiency compared to nanoparticles. As particle size decreases, the coordination environment around the metal atoms becomes increasingly unsaturated, which raises the surface free energy and enhances the reactivity of the metal species toward supports and adsorbates—this underpins the well-known size effects in metal nanocatalysts. In the extreme case of single-atom catalysts (SACs), the combination of highly active valence electrons, quantum confinement effects, and discrete energy levels leads to maximized surface free energy and distinct chemical behavior. Covalent organic frameworks (COFs), a class of porous and crystalline materials composed of light elements (H, B, C, N, and O), are attractive supports for SACs due to their designable periodic structures and stable covalent bonding. These frameworks offer uniform and tunable binding sites ideal for anchoring metal atoms. Therefore, Single metal atoms anchored on COFs offer a powerful platform for tailoring active sites, enabling the optimization of catalytic activity, selectivity, and stability, with promising potential for use in a wide range of industrial chemical processes. Ethylene hydrogenation has long been used as a model reaction in heterogeneous catalysis to better understand the mechanism of selective acetylene hydrogenation over metal catalysts. Improving selectivity often depends on how strongly the reactants adsorb onto the metal surface. When ethylene binds more weakly to the active sites, selectivity improves—an insight that has led to growing interest in designing catalysts with isolated single metal atoms. Pd single-atom catalysts are highly valued for their activity in ethylene and acetylene hydrogenation under ambient conditions. In this work, we employed PdCl₂-functionalized, pyrene-based COFs that provide uniform binding sites ideal for stabilizing isolated palladium atoms. In this study, we used X-ray photoelectron spectroscopy (XPS) and diffuse reflectance infrared Fourier transform spectroscopy (DRIFTS) with CO as a probe molecule along with catalytic performance evaluation through ethylene hydrogenation kinetics. However, the pyrene-based COF inherently incorporates palladium impurities during synthesis, and the observed catalytic activity of pristine COF can vary significantly depending on the level of these residual Pd species. This makes it difficult to distinguish between the intrinsic activity of the pristine COF and that of atomically dispersed Pd. To reduce these impurities, we implemented two monomer purification methods prior to COF synthesis: triphenylphosphine (PPh₃) treatment and acid column purification. These approaches lowered the Pd content from 0.35% to 0.23% and 0.04%, respectively. PPh₃ purification was not optimal, as it introduced structural defects in the COF, leading to higher catalytic activity compared to the non-purified COF. Conversely, acid column purification preserved the Pd and N coordination environment, revealing distinct activity differences between the 4% Pd-loaded sample and the pristine COF. Notably, even at a reduced 1% Pd loading—critical for stability under reaction conditions—a significantly higher activity than that of the pristine COF was observed. This work highlights the critical role of purification and its underlying mechanisms in shaping the coordination environment and structural integrity of COFs, which in turn significantly impacts their catalytic activity and selectivity in ethylene and acetylene hydrogenation. Bimetallic catalysts often outperform their monometallic counterparts and are widely used in essential chemical transformations such as selective hydrogenation, reforming, coupling, and oxidation. Among them, PdAu alloy catalysts have garnered particular interest due to their ability to undergo dynamic surface restructuring, which plays a critical role in tuning catalytic activity and selectivity. The extent of this restructuring is influenced by factors such as the Pd-to-Au ratio, nanoparticle size, and the nature of adsorbates under reaction conditions. This study investigates how surface structures in Au, Pd, and PdAu nanoparticles evolve with variations in composition, particle size, and temperature. Results show that larger and samller nanoparticles tend to form Au rich surface. Notably, increasing the temperature from cryogenic levels induces Pd migration from the core to the surface, facilitating the formation of Pd trimers. These structural changes are reversible, with Pd atoms re-segregating back into the bulk upon cooling, highlighting the temperature-sensitive and reversible nature of surface restructuring in PdAu catalysts.

Purchased from AmBeed: 214360-73-3 ; 14221-01-3 ; 128-63-2

Extended shortwave infrared absorbing antiaromatic fluorenium-indolizine chromophores

Meador, William E ; Saucier, Matthew A ; Tucker, Max R ; Kruse, Nicholas A ; Mobley, Alexander J ; Brower, Connor R , et al.

DOI: 10.1039/D4SC00733F Chem. Sci.,2024,15,12349-12360.

Abstract: Shortwave infrared (SWIR, 1000-1700 nm) and extended SWIR (ESWIR, 1700-2700 nm) absorbing materials are valuable for applications including fluorescence based biological imaging, photodetectors, and light emitting diodes. Currently, ESWIR absorbing materials are largely dominated by inorganic semiconductors which are often costly both in raw materials and manufacturing processes used to produce them. The development of ESWIR absorbing organic molecules is thus of interest due to the tunability, solution processability, and low cost of organic materials compared to their inorganic counterparts. Herein, through the combination of heterocyclic indolizine donors and an antiaromatic fluorene core, a series of organic chromophores with absorption maxima ranging from 1470-2088 nm (0.84-0.59 eV) and absorption onsets ranging from 1693-2596 nm (0.73-0.48 eV) are designed and synthesized. The photophysical and electrochemical properties of these chromophores, referred to as FluIndz herein, are described via absorption spectroscopy in 17 solvents, cyclic voltammetry, solution photostability, and transient absorption spectroscopy. Molecular orbital energies, predicted electronic transitions, and antiaromaticity are compared to higher energy absorbing chromophores using density functional theory. The presence of thermally accessible diradical states is demonstrated using density functional theory and EPR spectroscopy, while XRD crystallography confirms structural connectivity and existence as a single molecule. Overall, the FluIndz chromophore scaffold exhibits a rational means to access organic chromophores with extremely narrow optical gaps.

Purchased from AmBeed: 131747-63-2 ; 3375-31-3 ; 14221-01-3 ; 53358-54-6

Ligand-Based Virtual Screening as a Path to New Chemotypes for Candidate PET Radioligands for Imaging Tauopathies

Hurtle, Bryan T ; Jana, Susovan ; Cai, Lisheng ; Pike, Victor W ;

DOI: 10.1021/acs.jmedchem.4c00934 PubMed ID: 39108178 JMC,2024,67(16):14095-14109.

Abstract: Ligand-based virtual screening (LBVS) has rarely been tested as a method for discovering new structural scaffolds for PET radioligand development. This study used LBVS to discover potential chemotype leads for developing radioligands for PET imaging of tauopathies. ZINC12, a free database of over 12 million commercially available compounds, was searched to discover novel scaffolds based on similarities to four query compounds. Thirteen high-ranking hits were purchased and assayed for their ability to compete against three tritiated radioligands at their distinct binding sites in Alzheimer’s disease brain tissue. Three hits were 2-substituted 6-methoxy naphthalenes. Synthetic elaboration of this new chemotype yielded three new ligands (25, 26, and 28) with high affinity for the [³H]6 (flortaucipur) neurofibrillary tangle binding site. Compound 28 showed remarkably high affinity (K_i, 7 nM) and other desirable properties for a candidate PET radioligand, including low topological polar surface area, moderate computed log D, and amenability for labeling with carbon-11. LBVS appears to be uniquely valuable for discovering new chemotypes for candidate PET radioligands.

Purchased from AmBeed: 14221-01-3 ; 1122-58-3 ; 72087-21-9 ; 129113-00-4

Synthesis of Bis-Thioacid Derivatives of Diarylethene and Their Photochromic Properties

Aryal, Pramod ; Bietsch, Jonathan ; Grandhi, Gowri Sankar ; Chen, Richard ; Adhikari, Surya B ; Sarabamoun, Ephraiem S , et al.

DOI: 10.1021/acsomega.4c05945 ACS Omega,2024,9(48):47489-47499.

Abstract: Diarylethenes (DAEs) are an important class ofphotoswitchable compounds that typically undergo reversiblephotochemical conversions between the open and closed cyclizedforms upon treatment with UV light or visible light. In this study,we introduced thioacid functional groups to several photochromicdithienylethene (DTE) derivatives and established a method thatcan be used to prepare these photoswitchable thioacids. Fourthioacid-functionalized diarylethene derivatives were synthesizedthrough the activation of carboxylic acids with N-hydroxysuccini-mide, followed by reactions with sodium hydrosulfide with yields over 90%. These derivatives exhibited reversible photoswitchingand photochromic properties upon treatment with ultraviolet (UV) and visible lights. The thioacid groups on these compounds canact as reaction sites for attaching other desirable functionalities. The photochromic properties of these new derivatives werecharacterized by using ultraviolet−visible (UV−vis) spectroscopy. The photocyclizations of one of the derivatives and its potassiumsalt were also characterized by using nuclear magnetic resonance (NMR) spectroscopy. The anions of the thioacid formed water-soluble photochromic systems, and their applications as colorimetric sensors in agarose hydrogels were demonstrated.

Purchased from AmBeed: 4282-31-9 ; 5798-75-4 ; 14221-01-3 ; 1892-57-5

Complexing Carbon Nanomaterials and Reactive Metal Species for Selective Chemical Sensing and Tunable Catalysis

Shao-Xiong Lennon Luo ;

Abstract: This thesis highlights strategies for fiinctionalizing carbon nanomaterials with reactive metaspecies for applications in chemical sensing and electrocatalysis. In Chapter 1, we begin with anintroduction of chemiresistive sensing using functionalized carbon nanotubes (CNTs). Thisintroduction summarizes the design, fabrication, characterization, and evaluation of carbonnanotube-based chemiresistive sensors. Potential strategies for optimizing sensitivity andselectivity are also discussed. Typical applications of'CNT-based chemiresistive sensing are alsosurveyed. In Chapter 2, we report the synthesis of Pentiptycene Polymer/Single-Walled CarbonNanotube Complexes and their applications in the selective detection of benzene, toluene, and o.xylene using chemiresistive and quartz crystal microbalance-based methods. In Chapter 3. wereport a method to efiectively immobilize transition metal selectors in close proximity to theS WCN'T surface using pentiptycene polymers containing metal-chelating backbone structures. Wehave identified sensitive, selective, and robust copper-based chemiresistive ammonia sensorsdisplaying low parts per billion detection limits. We have added these hybrid materials into theresonant radio firequency circuits of commercial near-field communication (NFC) tags to achievewireless detection ofammonia at physiologically relevant levels, offering a non-invasive and cost.efiective approach for early detection and monitoring of chronic kidney diseases. In Chapter 4we report that iptycene-containing poly(arylene ether)s (PAEs) show to limit the palladiumnanoparticles (Pd NPs) growth and stabilize the Pd NPs dispersion. SWCNT-based chemiresistorsand graphene field-efect transistors (GFETs)using these PAE-supported small Pd NPs aresensitive, selective, and robust sensory materials for hydrogen gas under ambient conditions. InChapter 5, we describe chemiresistors based on SWCNTs containing small and highly reactivecopper-based nanoparticles in sulfonated pentiptycene poly(arylene ether)s (PAEs). The sensorsshow exceptional sensitivity to trace hydrogen sulfide in wet air with a low-ppb detection limithigh selectivity over a wide range of interferants, and month-long stability under ambientconditions. In Chapter 6, we report a SWCNT-based chemiresistor catalyst combination that candetect ppb levels of' ethylene in air, driven by the chemoselectivity ofthe catalytic transformationThe utility of this ethylene sensor is demonstrated in the monitoring of senescence in red carnationsand purple lisianthus flowers.In Chapter 7, we report SWCNT-based chemiresistive sensorsbased on a catalytic system comprising a copper complex and TEMPO cocatalyst, enabling thesensitive, selective, and robust detection of trace ethanol in air. In Chapter 8, we report thesynthesis of carbon-nanomaterial-based metal chelates that enable effective electronic coupling toelectrocatalytic transition metals. The defined ligands on the graphene surfaces enable theformation of structurally precise heterogeneous molecular catalysts. We demonstrate that thedensely functionalized metal-chelated carbon nanomaterials are eliective heterogeneous catalystsin the oxygen evolution reaction with low overpotentials and tunable catalytic activity.

Purchased from AmBeed: 100125-12-0 ; 14221-01-3 ; 15862-18-7 ; 7681-65-4

Reorganization Energies for Interfacial Proton-Coupled Electron Transfer to a Water Oxidation Catalyst

Kessinger, Matthew ; Soudackov, Alexander V. ; Schneider, Jenny ; Bangle, Rachel E. ; Hammes-Schiffer, Sharon ; Meyer, Gerald J.

DOI: 10.1021/jacs.2c09672 PubMed ID: 36314899 JACS,2022,144(44):20514-20524.

Abstract: The reorganization energy (λ) for interfacial electron transfer (ET) and proton-coupled ET (PCET) from a conductive metal oxide (In2O3:Sn, ITO) to a surface-bound H2O oxidation catalyst was extracted from kinetic data measured as a function of the thermodn. driving force. Visible light excitation resulted in rapid excited-state injection (kinj > 108 s-1) to the ITO, which photo-initiated the two interfacial reactions of interest. The rate constants for both reactions increased with the driving force, -ΔG°, to a saturating limit, kmax, with rate constants consistently larger for ET than for PCET. Marcus-Gerischer anal. of the kinetic data provided the reorganization energy for interfacial PCET (0.90 ± 0.02 eV) and ET (0.40 ± 0.02 eV), resp. The magnitude of kmax for PCET decreases with pH, behavior that was absent for ET. Both the decrease in kmax and the larger reorganization energy for an unwanted competing PCET reaction from the ITO to the oxidized catalyst showcases a significant kinetic advantage for driving solar H2O oxidation at high pH. Computational anal. revealed a larger inner-sphere reorganization energy contribution for PCET than for ET arising from a more significant change in the Ru-O bond length for the PCET reaction. Extending the Marcus-Gerischer theory to PCET by including the excited electron-proton vibronic states and the proton donor-acceptor motion provided an apparent reorganization energy of 1.01 eV. The Marcus-Gerischer theory initially developed for ET can be reliably extended to PCET for quantifying and interpreting reorganization energies observed exptl.

Purchased from AmBeed: 7447-41-8 ; 14221-01-3 ; 10049-08-8 ; 174397-53-6 ; 18511-71-2 ; 1148-79-4 ; 72905-30-7

Development of reactive oxygen species (ROS) inhibitors and prodrugs for multiple applications

Senevirathne, Priyangika Prasadini ;

Abstract: Reactive oxygen species are a group of highly reactive oxygen-containing entities that are important at a cellular level for multiple biological processes. Low concentrations of ROS can be beneficial as powerful signaling molecules in those biological processes, although excessive concentrations can promote high levels of DNA damage and a variety of diseases such as skin cancer. A newly identified intracellular ROS production source in skin cells is NADPH oxidases. Out of the NOX enzyme family, the NOX1 holoenzyme is most abundantly expressed in the human keratinocyte cells. UV radiation can trigger the activation of NOX1 isoforms which stimulate the assembling of member CYBA and the cytoplasmic protein NOXO1. Inhibition of these enzymes represents a catalytic approach toward reducing ROS for the prevention of ROS inducible diseases. Key disease states include melanoma induced by UV exposure. The first half of the dissertation focuses on investigating new small molecule inhibitors of a key NOX1 holoenzyme to address these challenges. We designed a series of molecules by optimizing the structure of diapocynin and evaluated by in-silico docking methods to determine the binding affinity with NOXO1 cytoplasmic protein (1WLP crystal structure). And have synthesized the series of target molecules for the structure-activity relationship studies. In the first section of the project, we discovered that inhibitor NOX_inh_5 was not cytotoxic, but instead improved the viability of human primary cells from UV exposure, decreased the cellular stress in human skin through the p53 pathway, and reduced the UV-induced DNA damage as monitored by quantification of cyclobutane dimer formation after UV exposure. Then, we characterized the inhibition potential of NOX_inh_5 by using an Isothermal calorimetric (ITC) binding assay and heteronuclear single quantum coherence (HSQC) technique and revealed that the candidate iii molecule can prevent the complex formation of NOXO1 and CYBA membrane protein. In the second section of the project, we did a structure-activity relationship study for the NOX_inh_5 small molecule to optimize the biological characteristics. The last section of the dissertation discussed the development of ROS sensible prodrug to combat the opioid overdose crisis. Here we used oxidative stress conditions caused by opioid overdose to activate the prodrug. Even though opioid antagonist naloxone has a high affinity to bind with opioid receptors to block opioid-induced activation, it is metabolically unstable and has a short half-life of around 33 min. We developed a peroxide-induced prodrug to overcome this issue that can release a steady stream of naloxone. This allows the concentration of naloxone to remain high for longer periods.

Purchased from AmBeed: 1007-16-5 ; 111-24-0 ; 14221-01-3 ; 99769-19-4 ; 351422-73-6 ; 158407-04-6 ; 1462-37-9 ; 583-61-9 ; 13965-03-2 ; 455-85-6 ; 148893-10-1

Design and Synthesis of Novel Donor-Acceptor-Donor Xanthene-Based Dyes from Heteronuclear Ring Systems for Chemical, Electrochemical, and Biological Sensory Materials

Rajapaksha, Ishanka Nirmani ;

Abstract: Small organic dyes are used in many applications, such as heat absorbers, solar cells, biological imaging, and photodynamic therapies for cancers. Xanthene-based dyes exhibit unique structural features and photophysical properties, and good water solubility, allowing them to be used as biological sensory materials. Conventional xanthene dyes (eg: fluorescein and rhodamine) have their absorptions and emissions in the visible region, which limits their use in cellular imaging. Absorptions and emissions at longer wavelengths allow for low background cellular autofluorescence, deep tissue penetration, and minimum cell damage. Chapter I discusses the background of fluorescent dyes and the importance of near-infrared (NIR) emissive dyes for biological applications. Chapter II is based on the design and synthesis of new xanthene-based NIR I dyes using simple and short synthetic routes. This study used pyrrole and indole as donor molecules and combined them to the xanthene core by the Suzuki cross-coupling reaction to prepare the new dyes. After the treatment with trifluoroacetic acid, these new dyes transformed from their non-fluorescent to fluorescent forms and exhibited excellent red shifts in their maximum absorption and emission wavelengths. The novel pyrrole-based xanthene dye was used to investigate the efficacy of the dye as a probe for fluoride ions. We were able to modify this dye with a silyl ester receptor and develop a probe as a colorimetric turn-off fluoride ion sensor. In chapter III, we describe the synthesis of different NIR emissive xanthene dyes using the donor-acceptor-donor concept. New xanthene-based dyes were designed with five-membered heterocycles and fused heteronuclear molecules. Additionally, xanthene-based dyes containing an alkyne spacer were synthesized using the D-pi-A model to extend the pi-conjugation through the alkyne spacer. All of the dyes exhibited absorption and emission maxima in the visible to NIR I region, between 500-850 nm. In chapter IV, we discussed the synthesis of xanthene-based electrochromic materials. These compounds used xanthene as the chromophore and ferrocene as the electrophore units. Novel rhodamine-based symmetric and unsymmetric dyes were synthesized by attaching the ferrocene unit through the lactam ring. The compounds were then investigated as an electrochromic probe using UV-vis , cyclic voltammetry, and spectroelectrochemical analysis.

Purchased from AmBeed: 127-08-2 ; 14221-01-3 ; 850567-47-4

Design, Synthesis, and Biological Evaluation of NADPH Oxidase 1 Inhibitors

Nazanin Mokhtarpour ;

Abstract: Reactive oxygen species (ROS) are a heterogeneous group of highly reactive ions and molecules derived from molecular oxygen (O 2), which can cause DNA damage and lead to skin cancer. High levels of ROS can promote cancer development, cancer cell survival, and resistance to chemotherapeutics. NADPH oxidase (NOX) is a significant producer of ROS in the cell. NOX1 generates two superoxide molecules by reducing NADPH. This only occurs when the membrane-bound NOX cytochrome p450 alpha chain (CYBA) binds to the organizer subunit NOXO1 from the cytosolic portions of the holoenzyme on the cell surface. We propose that stopping NOX1 complex subunits from coming together at this CYBA-NOXO1 junction is a potential way to prevent ROS production in human skin cells when exposed to ultraviolet rays. This dissertation investigates potential small-molecule inhibitors of the crucial NOX1 holoenzyme to solve these issues. We designed and synthesized NOX1 specific Inhibitor 1 using a diapocyin backbone structure. Computational docking studies were used to optimize inhibitor design and evaluate the NOXO1 protein subunit specificity. Due to increased binding interaction with NOXO1 protein and to improve solubility of solution preparation for further physical binding studies, we modified Inhibitor 1 and synthesized Inhibitor 2 by adding the NHS-ester Biotin polyethylene glycol chain to the piperidine ring. Both inhibitors were found to be non-toxic in human keratinocyte cells. The Inhibitor 2 reduced the cyclobutene pyrimidine dimer (CPD) DNA mutation in a human skin explant model. Finally, the isothermal calorimetric (ITC) binding assay and MALDI-TOF mass spectrometry were used for physical binding studies to evaluate the critical molecular interaction, leading to the decreased binding affinity of Inhibitor 1, Inhibitor 2, resulting in additional modifications seen in Inhibitor 3 and Inhibitor 4. The results demonstrate that Inhibitor 2 and Inhibitor 3 reduced the binding affinity between NOXO1 protein and CYBA membrane peptide because of a higher binding interaction of the inhibitors with NOXO1 protein, due to the interaction of the polyethylene glycol chain. In the second section of the project, we computationally design and synthesize NOX1-specific inhibitors using the sequence of CYBA peptides as a modeling tool. Through docking studies, we demonstrated inhibitor interference with NOX1 complexes. Several molecules were designed computationally, and three candidate compounds were tested in vitro and demonstrated a reduction of UVR damage in keratinocyte cells. Biophysical studies, like ITC, were performed to identify interactions. Through these studies, an understanding of protein-protein interactions was gained that are essential for discovering and validating inhibitor candidates, along with information for future inhibitor design. To determine the optimum strategy to utilize the biological features of the small molecule NM-166, a structure-activity relationship analysis was performed.

Purchased from AmBeed: 615-43-0 ; 14221-01-3 ; 158407-04-6 ; 103-67-3

Product Details of Tetrakis(triphenylphosphine)palladium

CAS No. :	14221-01-3
Formula :	C₇₂H₆₀P₄Pd
M.W :	1155.56
SMILES Code :	P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.P(C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6.P(C7=CC=CC=C7)(C8=CC=CC=C8)C9=CC=CC=C9.P(C%10=CC=CC=C%10)(C%11=CC=CC=C%11)C%12=CC=CC=C%12.[Pd]
Synonyms :	Tetrakis(triphenylphosphine)palladium(0)
MDL No. :	MFCD00010012
InChI Key :	NFHFRUOZVGFOOS-UHFFFAOYSA-N
Pubchem ID :	11979704

Safety of Tetrakis(triphenylphosphine)palladium

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P264-P270-P301+P312+P330-P501

Application In Synthesis of Tetrakis(triphenylphosphine)palladium

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 14221-01-3 ]
Downstream synthetic route of [ 14221-01-3 ]

[ 14221-01-3 ] Synthesis Path-Upstream 1~1

1
[ 14221-01-3 ]
[ 1993-03-9 ]
[ 886444-12-8 ]

References: [1] Patent: US2007/37974, 2007, A1, . Location in patent: Page/Page column 23.

[ 14221-01-3 ] Synthesis Path-Downstream 1~19

1
[ 14221-01-3 ]
[ 1007882-04-3 ]
[ 1007882-12-3 ]
[ 1007882-23-6 ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; at 80℃; for 5.75h;	Example 1, Step d di-tert-butyl (2S,2'S)-2,2'-(4,4'-biphenyldiylbis(]H-imidazole-5,2-diyl))di(1-pyrrolidinecarboxylate) Pd(Ph3P)4 (59.9 mg, 0.0518 mmol) was added to a mixture of bromide 1b (576.1 mg, 1.469 mmol), boronate 1c (621.8 mg, 1.415 mmol), NaHCO3 (400.4 mg, 4.766 mmol) in 1,2-dimethoxyethane (12 mL) and water (4 mL). The reaction mixture was flushed with nitrogen, heated with an oil bath at 80 C. for 5.75 hours, and then the volatile component was removed in vacuo. The residue was partitioned between 20% methanol/CHCl3 (60 mL) and water (30 mL), and the aqueous phase was extracted with 20% methanol/CHCl3 (30 mL). The combined organic phase was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. A silica gel mesh was prepared from the resulting crude material and submitted to flash chromatography (ethyl acetate) to provide dimer id, contaminated with Ph3PO, as an off-white solid (563 mg). 1H NMR (DMSO-d6, delta=2.5 ppm, 400 MHz): 6 12.21-12-16/11.95-11.78 (m, 2H), 7.85-7.48/7.32-7.25 (m, 10H), 4.90-4.71 (m, 2H), 3.60-3.32 (m, 4H), 2.30-1.79 (m, 8H), 1.46-1.10 (m, 18H). LC (Cond. 1b): RT=1.77 min; LC/MS: Anal. Calcd. for [M+H]+C36H45BN6O4: 625.35; found 625.48.

References: [1]Patent: US2008/44380,2008,A1 .Location in patent: Page/Page column 73.

2
[ 14221-01-3 ]
[ 93777-26-5 ]
[ 146137-79-3 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide;	PREPARATION 88(1) To a solution of 5-bromo-2-fluorobenzaldehyde (10 g) in dimethylformamide (60 mL) were added zinc cyanide (6.92 g) and tetrakis(triphenylphosphine)palladium(O) (2.28 g), and the mixture was stirred at 80° C. for 6 hours. The resulting mixture was diluted with ethyl acetate and washed successively with water and brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was subjected to a silica gel column chromatography eluding with a mixture of hexane and ethyl acetate (3:1) to give 5-cyano-2-fluorobenzaldehyde (5.3 g) as a solid substance. NMR (DMSO-d6, delta): 7.35 (1H, t, J=9 Hz), 7.91 (1H, m), 8.22 (1H, dd, J=2, 7 Hz), 10.36 (1H, s); Mass m/z: 150 (M++1).

References: [1]Patent: US6384080,2002,B1 .

3
[ 4926-28-7 ]
[ 14221-01-3 ]
[ 80500-27-2 ]
[ 67-63-0 ]
[ 289470-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In 1,2-dimethoxyethane;	Preparation 75 To a suspension of 2-bromo-4-methylpyridine (5.16 g), 4-methyl-3-nitrophenylboronic acid (7.06 g) and tetrakis(triphenylphosphine)-palladium (1.73 g) in 1,2-dimethoxyethane (100 ml) was added 2M aqueous solution of sodium carbonate (39 ml). The mixture was stirred at 80 C. for 12 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. 2-Propanol was added to the residue. The precipitate was collected by filtration and dried under reduced pressure to give 4-(4-methylpyridin-2-yl)-2-nitrotoluene (4.54 g). 1H-NMR (CDCl3): δ2.44(3H,s), 2.65(3H,s), 7.11(1H,d,J=4.3 Hz), 7.43(1H,d,J=8.0 Hz), 7.58(1H,s), 8.17(1H,dd,J=8.0 Hz,1.9 Hz), 8.55(1H,d,J=5.0 Hz), 8.58(1H,d,J=1.9 Hz)

References: [1]Patent: US6521643,2003,B1 .

4
[ 14221-01-3 ]
[ 89488-29-9 ]
[ 80500-27-2 ]
[ 289470-02-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In methanol; 1,2-dimethoxyethane;	Preparation 72 To a suspension of 2-bromo-4-methoxypyridine (2.5 g), 4-methyl-3-nitrophenylboronic acid (3.37 g) and tetrakis(triphenylphosphine)-palladium (768 mg) in 1,2-dimethoxyethane (100 ml) was added 2M aqueous solution of sodium carbonate (18.6 ml). The mixture was stirred at 80 C. for 7 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. Methanol was added to the residue. The precipitate was collected by filtration and dried under reduced pressure to give 4-(4-methoxypyridin-2-yl)-2-nitrotoluene (3.09 g). 1H-NMR (CDCl3): δ2.65(3H,s), 3.93(3H,s), 6.82(1H,dd,J=5.7 Hz,2.4 Hz), 7.25(1H,d,J=2.7 Hz), 7.43(1H,d,J=8.0 Hz), 8.14(1H,dd,J=8.0 Hz,2.0 Hz), 8.53(1H,d,J=5.8 Hz), 8.58(1H,d,J=2.0 Hz)

References: [1]Patent: US6521643,2003,B1 .

5
[ 14221-01-3 ]
[ 105365-51-3 ]
2-(4-butoxyphenyl)5-nitrothiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium carbonate;	Step 9.3 2-(4-butoxyphenyl)5-nitrothiophene. Quantities: <strong>[105365-51-3]4-butoxy-1-phenylboronic acid</strong> (3.38 g, 0.017 mol), compound of compound of step 9.2 (3.31 g, 0.016 mol), tetrakis (triphenylphosphine) palladium(O) (0.910 g, 0.001 mol), sodium carbonate (15.8 ml, 2.0M, 0.03 mol). The experimental procedure is carried out as described in step 8.3 above. The product was purified by column chromatography ?silica gel/petroleum fraction (bp 40-60 C.), dichloromethane, 3:1! and was recrystallized from ethanol to give 4.57 g (94% yield) of pale yellow solid which was dried in vacuo (P2 O5).

References: [1]Patent: US5888421,1999,A .

6
[ 14221-01-3 ]
[ 139911-28-7 ]
[ 144-55-8 ]
[ 497-19-8 ]
[ 139911-29-8 ]
ethyl 2-(2-methyl-4-fluorophenyl)-5-fluorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.4 g (92%)	In ethanol; toluene;	Ethyl 2-(2-Methyl-4-fluorophenyl)-5-fluorobenzoate Tetrakis(triphenylphosphine)palladium(O) (0.02 eq, 0.31 g) was added to a vigorously stirred solution of <strong>[139911-28-7]ethyl 2-bromo-5-fluorobenzoate</strong> (1.0 eq, 3.3 g, 0.013 mol) and 2-methyl-4-fluorophenylboronic acid (1.2 eq, 0.016 mol, 2.4 g) in 45 mL of toluene, 22 mL of 2M aqueous sodium carbonate, and 11 mL of ethanol and the mixture was refluxed for 9 h. The cooled reaction mixture was poured into 50 mLeach of water, ammonium hydroxide, and 2M aqueous sodium bicarbonate and then filtered through Celite. The filtrate was extracted with ethyl acetate an the organics were dried (MgSO4) and concentrated to yield 3.9 g of a yellow oil. Chromatography (silica gel, 20% ethyl acetate/hexane) gave 3.4 g (92%) of product as a light colored oil. 1 H NMR (CDCl3, 60 mHz) delta7.7 (dd, 1H), 7.5 (m, 1H), 7.25-6.75 (m, 4H), 4.0 (q, 2H), 2.0 (s, 3H), 1.0 (t, 3H); IR (CDCl3 solution) 3130, 2220, 1700, 1450, 1080 cm-1; MS m/z 276 (M+), 201 (base peak).

References: [1]Patent: US4864028,1989,A .

7
[ 14221-01-3 ]
[ 695-96-5 ]
[ 144-55-8 ]
[ 13589-72-5 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide;	(1) In 60 ml of N,N-dimethylformamide were dissolved 6.2 g of 2-bromo-4-chlorophenol, 7.2 g of zinc cyanide and 3.5 g of tetrakis(triphenylphosphine) palladium, and the solution was stirred at 120ØC for 2 hours. The reaction mixture was cooled to room temperature, and the formed black precipitate was removed by filtration. After concentrating the filtrate, a saturated aqueous sodium hydrogen carbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (chloroform/ethyl acetate =10/1), and crystallized from n-hexane to give 2.7 g of 2-cyano-4-chlorophenol. m.p.=166-168ØC

References: [1]Patent: EP1323713,2003,A1 .

8
[ 14221-01-3 ]
[ 2042-37-7 ]
[ 80500-27-2 ]
[ 497-19-8 ]
4-methyl-3-nitrobiphenyl-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	Example 6 4-Methyl-3-nitro-phenyl boronic acid (obtained as described in J.A.C.S., 1932, 54 , 4415) (3.0g) was added to a solution of 2-bromobenzonitrile (2.73 g) and tetrakis(triphenylphosphine)palladium(O) (0.525 g) in a mixture of 2M aqueous sodium carbonate (15 ml) and toluene (38 ml). The mixture was heated at 100C for 16 hours, then allowed to cool. The mixture was extracted with ethyl acetate and the extracts washed with saturated sodium chloride solution and dried. The solvent was removed by evaporation and the resultant light brown solid recrystallized from ethyl acetate to give 4--methyl-3--nitrobiphenyl-2-carbonitrile as a solid (3.13 g), m.p. 155-156C; NMR(CDCl3): 2.68(s, 3H), 7.44-7.86(complex m, 6H), 8.14(d, 1H); microanalysis, found: C, 70.3; H, 4.0; N, 11.8%; C14H10N2O2 requires: C, 70.6; H, 4.2; N, 11.8%.

References: [1]Patent: EP470795,1992,A1 .

9
[ 52522-40-4 ]
[ 603-35-0 ]
[ 14221-01-3 ]

Yield	Reaction Conditions	Operation in experiment
	Product distribution / selectivity;	tetrakis(triphenylphosphine)palladium(0) [generated in situ from tris(diphenylmethylideneacetone)dipalladium chloroform adduct (16 mg, 0.016 mmol) and triphenylphosphine 312 mg, 0.12 mmol)] ; tetrakis(triphenylphosphine)palladium (0) [generated in situ from tris(dibenzylideneacetone)dipalladium chloroform adduct (27 mg, 0.025 mmol) and triphenylphosphine (52 mg, 0.20 mmol)]

References: [1]Patent: US2007/203159,2007,A1 .Location in patent: Page/Page column 8; 22.

10
[ 14221-01-3 ]
[ 18163-47-8 ]
[ 136892-76-7 ]

References: [1]Chemische Berichte,1992,vol. 125,p. 9 - 14.

11
[ 14221-01-3 ]
[ 51419-59-1 ]
Pd(P(C₆H₅)3)2Cl(SO₂CH₂C₆H₄CH₃) [ No CAS ]

References: [1]Journal of Organometallic Chemistry,1980,vol. 194,p. 211 - 220.

12
[ 14221-01-3 ]
[ 37091-73-9 ]
PdCl(P(C₆H₅)3)2C₃H₄N₂(CH₃)2⁽¹⁺⁾*Cl^(1-)=PdCl(P(C₆H₅)3)2C₃H₄N₂(CH₃)2Cl [ No CAS ]

References: [1]Organometallics,2003,vol. 22,p. 907 - 909.

13
[ 3141-24-0 ]
[ 14221-01-3 ]
[ 191535-49-6 ]

References: [1]Organometallics,1998,vol. 17,p. 3988 - 3995.
[2]Journal of Organometallic Chemistry,1997,vol. 531,p. 175 - 181.

14
[ 14221-01-3 ]
[ 13826-83-0 ]
[ 58533-15-6 ]
trans-[PdCl((C₇H₅N₂)Et)(PPh₃)2]BF₄ [ No CAS ]

References: [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2013,vol. 639,p. 2450 - 2454.

15
[ 1120-95-2 ]
[ 14221-01-3 ]
C₄₀H₃₃ClN₂P₂Pd [ No CAS ]

References: [1]Chemistry - A European Journal,2015,vol. 21,p. 7858 - 7865.

16
[ 851786-15-7 ]
[ 14221-01-3 ]
C₁₁₂H₁₀₀Br₂N₂O₄P₄Pd₂ [ No CAS ]

References: [1]Journal of the American Chemical Society,2016,vol. 138,p. 10112 - 10115.

17
[ 14221-01-3 ]
[ 3058-39-7 ]
[ 5467-74-3 ]
[ 57774-35-3 ]

References: [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 8290 - 8294.
Angew. Chem.,2017,vol. 129,p. 8405 - 8410.

18
[ 14221-01-3 ]
[ 1003-91-4 ]
C₄₀H₃₃Br₃N₂P₂Pd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In toluene; at 20℃;Inert atmosphere; Schlenk technique;	General procedure: [M(PPh3)4] (1.0 equiv.) was added as a solid to a toluene solution (15mL) of 1 or 2 (1.0 equiv.) in a Schlenk flask and was stirred overnight at room temperature. The solvent was removed under the vacuum. The resulted yellow residue was dissolved in DCM (2mL) and was precipitated by addition of n-pentane (15mL), filtered and dried in vacuum to afford the product as yellow powder.

References: [1]Journal of Organometallic Chemistry,2017,vol. 851,p. 104 - 114.

19
[ 14221-01-3 ]
[ 1139-52-2 ]
C₃₂H₃₅OP [ No CAS ]

References: [1]Journal of Organometallic Chemistry,2017,vol. 853,p. 1 - 4.

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[ 14221-01-3 ] Synthesis Path-Upstream 1~1

[ 14221-01-3 ] Synthesis Path-Downstream 1~19

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