Structure of 13040-21-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Advances in the Development of Photonic Crystal Hydrogels as Versatile Biomolecular Sensors
Sarah Ann Goda ;
Abstract: We expanded the understandings of photonic crystal hydrogel fabrication and swelling behavior pertaining to their use as sensing materials. Our hydrogels are comprised of a polymer network containing a recognition group and a photonic crystal array embedded within the hydrogel network. The molecular recognition groups within the hydrogel allow us to make these sensors highly selective to target analytes. Hydrogel changes from analyte binding result in a volume phase transition (VPT). Hydrogel VPTs alter the distance between particles that make up the photonic crystal array, leading to changes in diffracted light according to the Bragg condition. Studies reported herein demonstrate the use of photonic crystal hydrogel sensors as sensing platforms that are easily adaptable. We investigated the use of oxyamine functionalized hydrogels to monitor lactate dehydrogenase’s enzymatic conversion of lactate to pyruvate. Pyruvate’s covalent attachment to the hydrogel enables a swelling response which corresponds to lactate concentrations in solution. We detected < 0.5 mM lactate in buffer solutions within an hour with detection limits < 4 mM lactate in serum solutions. This work is the first to demonstrate indirect detection of analytes by coupling enzymatic reactions with photonic crystal hydrogel sensors. DNA aptamers are small biomolecules that are highly selective in their binding and are stable under a variety of conditions. We incorporated hybridized DNA aptamers into 2DPC hydrogels forming crosslinks. These DNA crosslinks break due to analyte-DNA binding which enables hydrogel swelling. We demonstrated this aptamer sensing motif is easily modified from detecting the small molecule adenosine to the large protein thrombin. Poly (N-isopropylacrylamide) (pNIPAM) hydrogels are thermoresponsive, undergoing large VPTs at temperatures above their lower critical solution temperature (LCST). pNIPAM’s LCST is shifted due to changes in the hydrophobicity of pNIPAM’s environment from disruptions to pNIPAM’s solvation shell. This enables detection of hydrophobic analytes that can typically require complex detection methods. We are the first to investigate using shifts in pNIPAM’s LCST for detection of hydrophobic analytes such as Xe. We spectroscopically investigated Xe-protein binding to monitor favorable Xe binding environments and increase pNIPAM’s sensitivity to the presence of Xe.
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CAS No. : | 13040-21-6 |
Formula : | C9H9NO2 |
M.W : | 163.17 |
SMILES Code : | C=CC(NC1=CC=CC(O)=C1)=O |
MDL No. : | MFCD00599810 |
Boiling Point : | No data available |
InChI Key : | PMHOLXNNEPPFNZ-UHFFFAOYSA-N |
Pubchem ID : | 275403 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 47.11 |
TPSA ? Topological Polar Surface Area: Calculated from |
49.33 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.43 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.32 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.33 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.15 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.22 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.29 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.86 |
Solubility | 2.28 mg/ml ; 0.014 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.96 |
Solubility | 1.8 mg/ml ; 0.011 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.26 |
Solubility | 0.899 mg/ml ; 0.00551 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.36 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.43 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 3.5 h; | Tetrahydrofuran (100 mL) and water (30 mL) was added to 3-aminophenyl (5.0 g, 0.045 mol), sodium hydrogen carbonate (5.6 g, 0.067 mol) was added thereto, and acroyl chloride (3.6 mL, 0.045 mol) was added dropwise. The reaction solution was stirred for 3.5 hours at room temperature, added with dichloromethane, and washed with an aqueous solution of ammonium chloride. The organic layer was separated, dried over sodium sulfate, filtered and distilled under reduced pressure. The resulting residue was distilled with dichloromethane and ether to obtain the title compound (2.9 g, yield: 40percent). 'H-NMR(300 MHZ, DMSO-d6) δ 5.73 (dd, 1 H), 6.24 (dd, 1 H), 6.42 (m, 2H), 7.04 (m, 2H), 7.24(s, 1 H), 9.39 (s, 1H), 9.97 (s, 1 H) |
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