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Structure of 3-Mercaptopropionic acid
CAS No.: 107-96-0
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Chen, Jing ; Ji, Peng ; Gnawali, Giri ; Chang, Mengyang ; Gao, Feng ; Xu, Hang , et al.
Abstract: The current targeting drug delivery mainly relies on cancer cell surface receptors. However, in many cases, binding affinities between protein receptors and homing ligands is relatively low and the expression level between cancer and normal cells is not significant. Distinct from conventional targeting strategies, we have developed a general cancer targeting platform by building artificial receptor on cancer cell surface via a chemical remodeling of cell surface glycans. A new tetrazine (Tz) functionalized chemical receptor has been designed and efficiently installed on cancer cell surface as "overexpressed" biomarker through a metabolic glycan engineering. Different from the reported bioconjugation for drug targeting, the tetrazine labeled cancer cells not only locally activate TCO-caged prodrugs but also release active drugs via the unique bioorthogonal Tz-TCO click-release reaction. The studies have demonstrated that the new drug targeting strategy enables local activation of prodrug, which ultimately leads to effective and safe cancer therapy.
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Keywords: Artificial receptor ; Click and release ; Local activation ; Protein degradation
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Purchased from AmBeed: 3212-75-7 ; 5505-63-5 ; 25316-40-9 ; 1345866-66-1 ; 2645443-13-4 ; 67131-33-3 ; 501-52-0 ; 1949837-12-0 ; 107-96-0 ; 78-39-7 ; 2915291-31-3
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CAS No. : | 107-96-0 |
Formula : | C3H6O2S |
M.W : | 106.14 |
SMILES Code : | O=C(O)CCS |
MDL No. : | MFCD00004897 |
InChI Key : | DKIDEFUBRARXTE-UHFFFAOYSA-N |
Pubchem ID : | 6514 |
GHS Pictogram: | ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H290-H301-H314-H332-H401 |
Precautionary Statements: | P234-P261-P264-P270-P271-P273-P280-P301+P310+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P390-P405-P406-P501 |
Class: | 8(6.1) |
UN#: | 2922 |
Packing Group: | Ⅱ |
Num. heavy atoms | 6 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.67 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 26.24 |
TPSA ? Topological Polar Surface Area: Calculated from | 76.1 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 0.82 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 0.43 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 0.39 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 0.03 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 0.13 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 0.36 |
Log S (ESOL):? ESOL: Topological method implemented from | -0.64 |
Solubility | 24.5 mg/ml ; 0.231 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (Ali)? Ali: Topological method implemented from | -1.6 |
Solubility | 2.69 mg/ml ; 0.0254 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -0.1 |
Solubility | 83.3 mg/ml ; 0.785 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 | No |
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 | -6.64 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 | 2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.56 |
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) | 1.28 |
* 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 |
---|---|---|
With trifluoroacetic acid; | 3-((acetamidomethyl)sulphanyl)propanoic acid (Acm) (IV.2) 3-mercaptopropanoic acid (1.64 ml; 19 mmol) is dissolved into trifluoroacetic acid (30 ml). <strong>[625-51-4]N-(hydroxymethyl)acetamide</strong> (1.6 g; 19 mmol) is next added. After stirring for 30 minutes at room temperature, TFA is evaporated off to obtain IV.2: HPLC tR 7.1 min. (linear gradient, 5-65% B, 20 min); 1H NMR (300 MHz, CDCl3, 298 K) delta 12.4 (s, COOH, 1H); 7.74 (d, NH, J=5.8 Hz, 1H); 4.34 (d, SCH2NH, J=6 Hz, 2H); 2.81 (t, CH2SCH2NH, J=6.4 Hz, 2H); 2.67 (t, CH2COOH, J=6.4 Hz, 2H); 2.1 (s, NHCOCH3, 3H); 13C NMR (300 MHz, CDCl3, 298 K) 177.45 (CO); 174.63 (CO); 41.60 (CH2); 34.37 (CH2); 25.67 (CH2); 21.46 (CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 4 S-(2-phenylcarbamoyl-phenylselenyl)-3-mercaptopropionic acid Prepared similar to example 1 from 5 g (18,2 mmol) of 2-phenyl-1,2-benzisoselenazole-3(2H)-one and 2 g (18,9 mmol) of 3-mercaptopropionic acid. Yield: 5,85 g (85% of the theory), m.p. 203-204 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; | REFERENCE EXAMPLE 4 2.0 ml of methylene chloride, 0.05 ml (0.58 mmol) of 3-mercaptopropionic acid and 120 mg (0.59 mmol) of <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> were charged in a flask, and 261 mg (0.55 mmol) of pentafluoroethylphenyliodonium trifluoromethanesulfonate was added thereto in small portions while stirring at room temperature, followed by stirring the mixture at room temperature for 20 minutes. The resulting white precipitate was filtered, subjected to column chromatography of a small amount of silica gel and, after eluding iodobenzene with hexane, the desired product was eluted with diethyl ether. Diethyl ether was distilled off from the elude to obtain 3-pentafluoroethylthiopropionic acid as a colorless liquid. A sample of the product was purified by gas chromatography. Yield, 83percent. 19 F-NMR (CCl3 F internal standard in CDCl3): -84.00 ppm (t, JCF3,CF2 =3.5 Hz, CF3, 3F), -92.82 ppm (q, JCF3,CF2 =3.5 Hz, CF2, 2F) 1 H-NMR (in CDCl3): 2.79 ppm (t, J=7.0 Hz, CH2 SC2 F5, 2H), 3.15 ppm (t, J=7.0 Hz, --CH2 CO--, 2H), 10.6 ppm (br.s, CO2 H, 1H). IR (neat): 3050 (broad absorption), 2670, 2480, 1720, 1430, 1330, 1215, 1100, 970, 920, 810, 750, 650, 625, 585, 555 cm-1. MS: 224 (M+), 179, 105, 87, 69, 63, 59, 45. Elementary Analysis: Found: C, 26.83; H, 2.31percent. Calc'd: C, 26.79; H, 2.25percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With 1-methylimidazolium tetrafluoroborate; at 140℃; for 0.05h;Microwave irradiation; Ionic liquid; | Pyrex glass vial containing an equimolar mixture (5 mmol) of appropriate indole-2,3-dione (1) and substituted aniline (2) and thioacids (3a/b) adsorbed on 1-methylimidazolium tetrafluoroborate ([MIM]+BF4-) (1 gm) was placed in a screw capped Teflon vessel. Microwave was applied for 5 min at 140 °C. After the completion of reaction (TLC analysis), recyclable ionic liquid was separated by filtration after eluting the product with ethanol under reduced pressure and the residue washed with methanol gave a pure product in high yield (Table 1). All synthesized compounds were characterized by spectral analysis and data summarized in Table 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With N-ethyl-N,N-diisopropylamine; | The drug-linker SMCC-MDC was prepared in the following reactions: (1) 3-mercaptopropanoic acid (MPr) was reacted with N-succinimidyl 4-(maleimidomethyl)cyclohexane-1-carboxylate (SMCC) in the presence of N,N-diisopropylethylamine (DIEA), giving the MPr-SMCC at a yield of over 95percent; |
95% | With N-ethyl-N,N-diisopropylamine; | The drug-linker SMCC-MDC was prepared in the following reactions: (1) 3-mercaptopropanoic acid (MPr) was reacted with N-succinimidyl 4-(maleimidomethyl)cyclohexane-1-carboxylate (SMCC) in the presence of N,N-diisopropylethylamine (DIEA), giving the MPr-SMCC at a yield of over 95percent; |
95% | With N-ethyl-N,N-diisopropylamine; | The drug-linker SMCC-MDC was prepared in the following reactions: (1) 3-mercaptopropanoic acid (MPr) was reacted with N-succinimidyl 4-(maleimidomethyl)cyclohexane-1-carboxylate (SMCC) in the presence of N,N-diisopropylethylamine (DIEA), giving the MPr-SMCC at a yield of over 95percent; |
> 95% | With N-ethyl-N,N-diisopropylamine; | The drug-linker SMCC-MDC was prepared in the following reactions: (1) 3-mercaptopropanoic acid (MPr) was reacted with N-succinimidyl 4-(maleimidomethyl)cyclohexane-1-carboxylate (SMCC) in the presence of DIEA, giving the MPr-SMCC at a yield of over 95percent; Secondly, condensation of N-Me-L-Ala-MDC, which was prepared by deprotection of Fmoc-N-Me-Ala-MDC under a base piperidine in CH3CN, with MPr-SMCC under a coupling reagent EDC, giving the desired coupled product SMCC-MDC in 60-70percent yield over two steps. Antibody Bat0206 (Abu) was diluted to 2.5 mg/mL in solution A (50 mM potassium phosphate, 50 mM NaCl, and 2 mM EDTA, pH 6.5). SMCC-MDC was added to give a ratio of SMCC-MDC to antibody of 7:1 mole equivalent. Then DMA was added to 15percent (v/v) to the reaction and reaction was mixed by stirring for 4 h at ambient temperature. D-Lmcc-Bat0206 conjugate was purified from excess unreacted or hydrolyzed reagent and excess SMCC-MDC using a G25 gel filtration column equilibrated in pH 7.4 phosphate buffer (aqueous). The conjugate was then dialyzed overnight into pH 7.4 phosphate buffer (aqueous) and then filtered through a 0.22 mum filter for final storage. The number of SMCC-MDC molecule per Abu molecule in the final conjugate was measured by determining absorbance of the conjugate at 252 and 280 nm and using known extinction coefficients for SMCC-MDC and antibody at these two wavelengths. A ratio of maytansinoid compound to antibody of 3.5:1.0 was normally obtained. |
95% | With triethylamine; In dichloromethane; at 20℃; for 2h; | In the solution of SMCC (3 g) in anhydrous CH2Cl2 (80 ml), mercaptoacetic acid (0.937 ml) and triethylamine (1.428 ml) wereadded. The mixture was stirred for 2 h at room temperature. After evaporation of the solvent under vacuum, the solid was purified by column chromatography (CH2Cl2:Methanol = 20:1) to yield compound 2(3.76 g, 95percent). The structure was identified by ESI-QTOF-MS, 1H and 13C NMR. (M + H)+ = 441.1591; (M + Na)+ = 463.1132. 1H NMR(400 MHz, DMSO-d6): delta 12.33 (s, 1H), 4.02 (1H,dd, J = 8.9, 3.8 Hz), 3.25(d,2H, J = 7.0 Hz), 3.22?3.13 (m, 1H), 2.94 (dd,1H,J = 13.5, 6.7 Hz),2.86 (dd,1H,J = 13.7, 6.7 Hz), 2.8 (s,3H), 2.69 (t,1H,J = 12.0 Hz), 2.62?2.44 (m, 4H), 2.00 (d,2H,J = 11.1 Hz), 1.69 (d,3H,J = 13.3 Hz), 1.48?1.27 (m, 2H), 1.05 (dd,2H,J = 23.6, 11.0 Hz). 13C NMR (100 MHz,DMSO-d6): delta 177.0, 175.3, 172.8, 170.8, 170.2, 43.7, 35.6, 34.9, 34.0, 28.5,27.8, 26.8, 25.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In N,N-dimethyl-formamide; at 50℃; for 5.0h; | To the solution of compound 13a (0.5g, 1.23mmol) in DMF, 3- mercaptopropanoic acid, 9 (0.157g, 1.48mmol) was added. To this mixture, IN NaOH (2 mL) was added and reaction was allowed to stir at 50 C for 5 h. The crude product 14a was obtained by evaporating the solvent and was used for the next step without any further purification. LCMS m/z calculated for 14a: C17H25NO4S [M+Na]+: 362.15, found 362.17. LCMS m/z calculated for 14b: C19H26N2O4S [M-H+] : 378.20, found 377.14. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dimethyl sulfoxide; at 45℃; for 4h;Inert atmosphere; | Add 0.4mmol compound 3 to a 50mL reaction flask, add 10mL dimethylsulfoxide (DMSO) and stir to dissolve, then add 0.8mmol mercaptopropionic acid, heat to 45, dissolve, and react for 4h under argon protection; After the reaction, 0.12 mmol each of Compound 2, NHS and DCC was added to the mixed solution, and the reaction was stirred at 45 C. for 4 hours, and the reaction was completed. The reaction solution was poured into 50 mL of methyl tert-butyl ether, a green solid was precipitated, and the upper solid was collected by filtering with filter paper. 200-300 mesh silica gel column chromatography for separation and purification. The eluent is a mixture of dichloromethane and methanol with a volume ratio of 25:1 to obtain 11.5 mg of green metallic crystals as near-infrared fluorescent probes |
Tags: 107-96-0 synthesis path| 107-96-0 SDS| 107-96-0 COA| 107-96-0 purity| 107-96-0 application| 107-96-0 NMR| 107-96-0 COA| 107-96-0 structure
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H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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