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Chemical Structure| 615-43-0 Chemical Structure| 615-43-0
Chemical Structure| 615-43-0

*Storage: Keep in dark place, inert atmosphere, room temperature.

2-Iodoaniline

CAS No.: 615-43-0

Synonyms: 2-Iodophenylamine

4.5 *For Research Use Only !

Cat. No.: A104506 Purity: 98% GC

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Jacob Silzel ; Chengwei Chen ; Colomba Sanchez-Marsetti ; Phillip Farias ; Veronica Carta ; W. Hill Harman , et al.

Abstract: Cysteine is the most reactive naturally occurring amino acid due to the presence of a free thiol, presenting a tantalizing handle for covalent modification of peptides/proteins. Although many mass spectrometry experiments could benefit from site-specific modification of Cys, the utility of direct arylation has not been thoroughly explored. Recently, Spokoyny and coworkers reported a Au(III) organometallic reagent that robustly arylates Cys and tolerates a wide variety of solvents and conditions. Given the chromophoric nature of aryl groups and the known susceptibility of carbon-sulfur bonds to photodissociation, we set out to identify an aryl group that could efficiently cleave Cys carbon-sulfur bonds at 266 nm. A streamlined workflow was developed to facilitate rapid examination of a large number of aryls with minimal sample using a simple test peptide, RAAACGVLK. We were able to identify several aryl groups that yield abundant homolytic photodissociation of the adjacent Cys carbon-sulfur bonds with short activation times (<10 ms). In addition, we characterized the radical products created by photodissociation by subjecting the product ions to further collisional activation. Finally, we tested Cys arylation with human hemoglobin, identified reaction conditions that facilitate efficient modification of intact proteins, and evaluated the photochemistry and activation of these large radical ions.

Keywords: Fragmentation ; photodissociation ; radical-directed dissociation ; cysteine modification

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Mokhtarpour, Nazanin ; Sterling, Alyssa ; Garcia, Joshua J. ; Gutierrez-Rivera, Laura ; Senevirathne, Prasadini ; Luisa Kadekaro, Ana , et al.

Abstract: Reactive oxygen species (ROS) are a heterogeneous group of highly reactive ions and mols. derived from mol. oxygen (O2) which can cause DNA damage and lead to skin cancer. NADPH oxidase 1 (Nox1) is a major producer of ROS in the skin upon exposure to UV light. Functionally, Nox1 forms a holoenzyme complex that generates two superoxide mols. and reduces NADPH. The signaling activation occurs when the organizer subunit Noxo1 translocates to the plasma membrane bringing a cytochrome P 450, through interaction with Cyba. We propose to design inhibitors that prevent Cyba-Noxo1 binding as a topical application to reduce UV-generated ROS in human skin cells. Design started from an apocynin backbone structure to generate a small mol. to serve as an anchor point. The initial compound was then modified by addition of a polyethylene glycol linked biotin. Both inhibitors were found to be non-toxic in human keratinocyte cells. Further in vitro experiments using isothermal calorimetric binding quantification showed the modified biotinylated compound bound Noxo1 peptide with a KD of 2 nM. Both using isothermal calorimetric binding and MALDI (TOF) MS showed that binding of a Cyba peptide to Noxo1 was blocked. In vivo experiments were performed using donated skin explants with topical application of the two inhibitors. Experiments show that UV light exposure of with the lead compound was able to reduce the amount of cyclobutene pyrimidine dimers in DNA, a mol. known to lead to carcinogenesis. Further synthesis showed that the polyethylene glycol but not the biotin was essential for inhibition.

Keywords: Reactive oxygen species ; Apocynin ; UV ; Noxo1 ; Cyba ; Cyclobutane pyrimidine dimer ; CPD ; UV protection

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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.

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Alternative Products

Product Details of 2-Iodoaniline

CAS No. :615-43-0
Formula : C6H6IN
M.W : 219.02
SMILES Code : C1=CC=CC(=C1N)I
Synonyms :
2-Iodophenylamine
MDL No. :MFCD00007680
InChI Key :UBPDKIDWEADHPP-UHFFFAOYSA-N
Pubchem ID :11995

Safety of 2-Iodoaniline

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
Precautionary Statements:P261-P264-P280-P337+P313-P302+P352+P312-P304+P340+P312

Application In Synthesis of 2-Iodoaniline

* 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 [ 615-43-0 ]
  • Downstream synthetic route of [ 615-43-0 ]

[ 615-43-0 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 615-43-0 ]
  • [ 253-66-7 ]
References: [1] Journal of the American Chemical Society, 2002, vol. 124, # 45, p. 13463 - 13473.
  • 2
  • [ 420-04-2 ]
  • [ 615-43-0 ]
  • [ 13939-06-5 ]
  • [ 20198-19-0 ]
References: [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2966 - 2973.
  • 3
  • [ 420-04-2 ]
  • [ 615-43-0 ]
  • [ 121-44-8 ]
  • [ 13939-06-5 ]
  • [ 20198-19-0 ]
References: [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2966 - 2973.
  • 4
  • [ 615-43-0 ]
  • [ 20198-19-0 ]
References: [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2966 - 2973.
  • 5
  • [ 615-43-0 ]
  • [ 75-36-5 ]
  • [ 7212-28-4 ]
YieldReaction ConditionsOperation in experiment
68% With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; Acetyl chloride (6 mmol) was added dropwise to the mixture of 2-iodoaniline (5 mmol) and sodium hydroxide (13 mmol) in THF/H2O (1/1, 4 mL). Stirred the mixture at 0° C. for 2 h, and then at room temperature for overnight. The mixture was diluted with 10 mL water and extracted with diethyl ether 3 times. The combined organic layer was washed with water 3 times and brine. Dried over sodium sulfate, filtered, and removed solvent. The residue was then purified by column chromatography afforded white solid of 2-iodoacetanilide 68percent yield. NMR
References: [1] Patent: US7473786, 2009, B1, . Location in patent: Page/Page column 24.
 

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