Esterase Activities of Human Carbonic Anhydrases B and C

Verpoorte, Jacob A.; Mehta, S. N.; Edsall, John T.

doi:10.1016/s0021-9258(18)95800-x

Cited by 864 publications

(248 citation statements)

References 32 publications

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“…Carbonic anhydrase can catalyze the hydrolysis of 4-nitrophenyl acetate (4-NPA). According to the method reported in the literature, the reaction rate was monitored by measuring the change of absorbance at 405 nM [ 8 , 29 , 30 ]. The experimental buffer consisted of 15 mmol/L 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES) (pH = 7.40), 0.01% tetraethylene glycol monododecyl ether (Brij), and 100 mmol/L NaCl.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives

Zhang

Zhong

Han

et al. 2021

IJMS

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A series of saccharide-modified thiadiazole sulfonamide derivatives has been designed and synthesized by the “tail approach” and evaluated for inhibitory activity against carbonic anhydrases II, IX, and XII. Most of the compounds showed high topological polar surface area (TPSA) values and excellent enzyme inhibitory activity. The impacts of some compounds on the viability of HT-29, MDA-MB-231, and MG-63 human cancer cell lines were examined under both normoxic and hypoxic conditions, and they showed certain inhibitory effects on cell viability. Moreover, it was found that the series of compounds had the ability to raise the pH of the tumor cell microenvironment. All the results proved that saccharide-modified thiadiazole sulfonamides have important research prospects for the development of CA IX inhibitors.

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Section: Methodsmentioning

confidence: 99%

Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives

Zhang

Zhong

Han

et al. 2021

IJMS

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“…During catalysis, the zinc ion functions as a nucleophilic Lewis acid, lowering the pK a of a bound water molecule, thus forming a reactive hydroxide ion. 6 Some of the catalytically active α CAs can also catalyze the hydrolysis of esters, for example, 4-nitrophenyl acetate (4-NPA) 7,8 via a zinc-hydroxide mechanism. Known α-CA inhibitors (CAIs) include various anions, imidazole, phenol, hydroxyurea, carboxylates, organic phosphates and phosphonates, and various sulfonamide compounds (R-C-SO 2 NH 2 ).…”

Section: Introductionmentioning

confidence: 99%

Inhibition Profiling of Human Carbonic Anhydrase II by High-Throughput Screening of Structurally Diverse, Biologically Active Compounds

et al. 2006

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Human carbonic anhydrase II (CA II), a zinc metalloenzyme, was screened against 960 structurally diverse, biologically active small molecules. The assay monitored CA II esterase activity against the substrate 4-nitrophenyl acetate in a format allowing high-throughput screening. The assay proved to be robust and reproducible with a hit rate of approximately 2%. Potential hits were further characterized by determining their IC(50) and K(d) values and tested for nonspecific, promiscuous inhibition. Three known sulfonamide CA inhibitors were identified: acetazolamide, methazolamide, and celecoxib. Other hits were also found, including diuretics and antibiotics not previously identified as CA inhibitors, for example, furosemide and halazone. These results confirm that many sulfonamide drugs have CA inhibitory properties but also that not all sulfonamides are CA inhibitors. Thus many, but not all, sulfonamide drugs appear to interact with CA II and may target other CA isozymes. The screen also yielded several novel classes of nonsulfonamide inhibitors, including merbromin, thioxolone, and tannic acid. Although these compounds may function by some nonspecific mechanism (merbromin and tannic acid), at least 1 (thioxolone) appears to represent a genuine CA inhibitor. Thus, this study yielded a number of potentially new classes of CA inhibitors and preliminary experiments to characterize their mechanism of action.

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“…Sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) was carried out for registration of both isoforms purity. Human CA isoforms activity designation was observed spectrophotometrically (Shimadzu, UV-VIS Spectrophotometer, UVmini-1240, Kyoto, Japan) (Verpoorte et al, 1967). In this test, variations in absorbance were obtained during 3 min at 30°C.…”

Section: Hca Inhibition Studiesmentioning

confidence: 99%

Design, Synthesis and Biological Activities of Chalcones with Piperonal Moiety

Tuğrak

Gül

Anil

et al. 2020

Erzincan Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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Heterocyclic compounds are of specific significance between pharmacologically active compounds. In this study, some piperonal-based chalcones (PC1-PC10) were synthesized with Claisen-Schmidt Condensation with the reaction between 3,4-methylenedioxybenzaldehyde and several acetophenones. Inhibition potency of the chalcones were evaluated toward human carbonic anhydrase I and II enzymes (hCA I and hCA II), and acetylcholinesterase (AChE). The chalcone derivatives were found to have IC50 values in the range of 5.11-109.70 μM for hCA I, 17.05-162.59 μM for hCA II, and 18.52-98.69 μM for AChE. All compounds showed lower inhibition potential than reference compounds. While the PC3 (methoxy derivative) compound was the most effective compound against both hCA I and hCA II, PC5 (fluorine derivative) showed the strongest inhibition effect against AChE in the series. Results confirmed that the chalcone derivatives PC3 and PC5 can be considered as favorable candidates against hCA I, hCA II and AChE isoenzymes to design more potent enzyme inhibitors.

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Esterase Activities of Human Carbonic Anhydrases B and C

Cited by 864 publications

References 32 publications

Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives

Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives

Inhibition Profiling of Human Carbonic Anhydrase II by High-Throughput Screening of Structurally Diverse, Biologically Active Compounds

Design, Synthesis and Biological Activities of Chalcones with Piperonal Moiety

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