Evaluation of Thio- and Seleno-Acetamides Bearing Benzenesulfonamide As Inhibitor of Carbonic Anhydrases from Different Pathogenic Bacteria

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2020 Jan 23

PMID 31963423

Citations 7

Authors

Andrea Angeli

Mariana Pinteala

Stelian S Maier

Bogdan C Simionescu

Andrea Milaneschi

Ghulam Abbas

Sonia Del Prete

Clemente Capasso

Antonella Capperucci

Damiano Tanini

Fabrizio Carta

Claudiu T Supuran

Affiliations

Soon will be listed here.

Abstract

A series of 2-thio- and 2-seleno-acetamides bearing the benzenesulfonamide moiety were evaluated as Carbonic Anhydrase (CA, EC 4.2.1.1) inhibitors against different pathogenic bacteria such as the (VchCA-α and VchCA-β), (BpsCA-β and BpsCA-γ), (Rv3723-β) and the (StCA2-β). The molecules represent interesting leads worth developing as innovative antibacterial agents since they possess new mechanism of action and isoform selectivity preferentially against the bacterial expressed CAs. The identification of potent and selective inhibitors of bacterial CAs may lead to tools also useful for deciphering the physiological role(s) of such proteins.

Citing Articles

Synthesis, Biological and In Silico Studies of Griseofulvin and Usnic Acid Sulfonamide Derivatives as Fungal, Bacterial and Human Carbonic Anhydrase Inhibitors.

Angeli A, Petrou A, Kartsev V, Lichitsky B, Komogortsev A, Capasso C Int J Mol Sci. 2023; 24(3).

PMID: 36769114 PMC: 9917406. DOI: 10.3390/ijms24032802.

Enhancing the Activity of Carboxymethyl Cellulase Enzyme Using Highly Stable Selenium Nanoparticles Biosynthesized by Y4.

Wang Y, Yu Y, Duan Y, Wang Q, Cong X, He Y Molecules. 2022; 27(14).

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Pyrazolo[4,3-c]pyridine Sulfonamides as Carbonic Anhydrase Inhibitors: Synthesis, Biological and In Silico Studies.

Angeli A, Kartsev V, Petrou A, Lichitsky B, Komogortsev A, Pinteala M Pharmaceuticals (Basel). 2022; 15(3).

PMID: 35337114 PMC: 8955975. DOI: 10.3390/ph15030316.

The Role of Selenium in Pathologies: An Updated Review.

Barchielli G, Capperucci A, Tanini D Antioxidants (Basel). 2022; 11(2).

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Novel 1,3,5-Triazinyl Aminobenzenesulfonamides Incorporating Aminoalcohol, Aminochalcone and Aminostilbene Structural Motifs as Potent Anti-VRE Agents, and Carbonic Anhydrases I, II, VII, IX, and XII Inhibitors.

Havrankova E, Garaj V, Mascaretti S, Angeli A, Soldanova Z, Kemka M Int J Mol Sci. 2022; 23(1).

PMID: 35008657 PMC: 8745223. DOI: 10.3390/ijms23010231.

References

Capasso C, Supuran C . Anti-infective carbonic anhydrase inhibitors: a patent and literature review. Expert Opin Ther Pat. 2013; 23(6):693-704. DOI: 10.1517/13543776.2013.778245. View

Supuran C . Structure and function of carbonic anhydrases. Biochem J. 2016; 473(14):2023-32. DOI: 10.1042/BCJ20160115. View

Angeli A, Carta F, Bartolucci G, Supuran C . Synthesis of novel acyl selenoureido benzensulfonamides as carbonic anhydrase I, II, VII and IX inhibitors. Bioorg Med Chem. 2017; 25(13):3567-3573. DOI: 10.1016/j.bmc.2017.05.014. View

Alafeefy A, Ceruso M, Al-Tamimi A, Del Prete S, Capasso C, Supuran C . Quinazoline-sulfonamides with potent inhibitory activity against the α-carbonic anhydrase from Vibrio cholerae. Bioorg Med Chem. 2014; 22(19):5133-40. DOI: 10.1016/j.bmc.2014.08.015. View

Angeli A, Tanini D, Nocentini A, Capperucci A, Ferraroni M, Gratteri P . Selenols: a new class of carbonic anhydrase inhibitors. Chem Commun (Camb). 2018; 55(5):648-651. DOI: 10.1039/c8cc08562e. View

Angeli A, Peat T, Bartolucci G, Nocentini A, Supuran C, Carta F . Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors. Org Biomol Chem. 2016; 14(48):11353-11356. DOI: 10.1039/c6ob02299e. View

Angeli A, Tanini D, Capperucci A, Supuran C . First evaluation of organotellurium derivatives as carbonic anhydrase I, II, IV, VII and IX inhibitors. Bioorg Chem. 2017; 76:268-272. DOI: 10.1016/j.bioorg.2017.12.010. View

Dadara A, Angeli A, Ferraroni M, Supuran C, Skelly P . Crystal structure and chemical inhibition of essential schistosome host-interactive virulence factor carbonic anhydrase SmCA. Commun Biol. 2019; 2:333. PMC: 6728359. DOI: 10.1038/s42003-019-0578-0. View

Angeli A, Di Cesare Mannelli L, Trallori E, Peat T, Ghelardini C, Carta F . Design, Synthesis, and X-ray of Selenides as New Class of Agents for Prevention of Diabetic Cerebrovascular Pathology. ACS Med Chem Lett. 2018; 9(5):462-467. PMC: 5949733. DOI: 10.1021/acsmedchemlett.8b00076. View

10.

Khalifah R . The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem. 1971; 246(8):2561-73. View

11.

Tanini D, Lupori B, Malevolti G, Ambrosi M, Lo Nostro P, Capperucci A . Direct biocatalysed synthesis of first sulfur-, selenium- and tellurium- containing l-ascorbyl hybrid derivatives with radical trapping and GPx-like properties. Chem Commun (Camb). 2019; 55(40):5705-5708. DOI: 10.1039/c9cc02427a. View

12.

Capasso C, Supuran C . An overview of the alpha-, beta- and gamma-carbonic anhydrases from Bacteria: can bacterial carbonic anhydrases shed new light on evolution of bacteria?. J Enzyme Inhib Med Chem. 2014; 30(2):325-32. DOI: 10.3109/14756366.2014.910202. View

13.

Angeli A, Abbas G, Del Prete S, Carta F, Capasso C, Supuran C . Acyl selenoureido benzensulfonamides show potent inhibitory activity against carbonic anhydrases from the pathogenic bacterium Vibrio cholerae. Bioorg Chem. 2017; 75:170-172. DOI: 10.1016/j.bioorg.2017.09.016. View

14.

Supuran C, Capasso C . An Overview of the Bacterial Carbonic Anhydrases. Metabolites. 2017; 7(4). PMC: 5746736. DOI: 10.3390/metabo7040056. View

15.

Aspatwar A, Kairys V, Rala S, Parikka M, Bozdag M, Carta F . -Carbonic Anhydrases: Novel Targets for Developing Antituberculosis Drugs. Int J Mol Sci. 2019; 20(20). PMC: 6834203. DOI: 10.3390/ijms20205153. View

16.

Angeli A, Pinteala M, Maier S, Del Prete S, Capasso C, Simionescu B . Inhibition of bacterial α-, β- and γ-class carbonic anhydrases with selenazoles incorporating benzenesulfonamide moieties. J Enzyme Inhib Med Chem. 2019; 34(1):244-249. PMC: 6327980. DOI: 10.1080/14756366.2018.1547287. View

17.

Angeli A, Abbas G, Del Prete S, Capasso C, Supuran C . Selenides bearing benzenesulfonamide show potent inhibition activity against carbonic anhydrases from pathogenic bacteria Vibrio cholerae and Burkholderia pseudomallei. Bioorg Chem. 2018; 79:319-322. DOI: 10.1016/j.bioorg.2018.05.015. View

18.

Ching C, Orubu E, Wirtz V, Zaman M . Bacterial antibiotic resistance development and mutagenesis following exposure to subminimal inhibitory concentrations of fluoroquinolones in vitro: a systematic literature review protocol. BMJ Open. 2019; 9(10):e030747. PMC: 6830604. DOI: 10.1136/bmjopen-2019-030747. View

19.

Williamson D, Carter G, Howden B . Current and Emerging Topical Antibacterials and Antiseptics: Agents, Action, and Resistance Patterns. Clin Microbiol Rev. 2017; 30(3):827-860. PMC: 5475228. DOI: 10.1128/CMR.00112-16. View

20.

Capasso C, Supuran C . An Overview of the Selectivity and Efficiency of the Bacterial Carbonic Anhydrase Inhibitors. Curr Med Chem. 2014; 22(18):2130-9. DOI: 10.2174/0929867321666141012174921. View