Synthesis and carbonic anhydrase inhibitory effects of new N-glycosylsulfonamides incorporating the phenol moiety.

Published on Aug 15, 2016in Bioorganic & Medicinal Chemistry Letters2.823
· DOI :10.1016/J.BMCL.2016.07.015
Leonardo Ezequiel Riafrecha7
Estimated H-index: 7
 (UNLP: National University of La Plata), Silvia Bua21
Estimated H-index: 21
 (UniFI: University of Florence)+ 1 AuthorsPedro A. Colinas15
Estimated H-index: 15
 (UNLP: National University of La Plata)
Sources
Abstract
A small series of N-glycosylsulfonamides incorporating the phenol moiety has been prepared by Ferrier sulfonamidoglycosylation of d-glycals. N-Glycosides were tested for the inhibition of four isoforms of carbonic anhydrase. In this study, all compounds showed good inhibitory activity against hCA I and II, with selectivity against the cytosolic hCA II versus the tumor associated isozymes. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves and enhances its inhibitory activity.
📖 Papers frequently viewed together
20154.34ACS Medicinal Chemistry Letters
5 Authors (Joanna Ombouma, ..., Jean-Yves Winum)
20165.05Journal of Enzyme Inhibition and Medicinal Chemistry
4 Authors (Erhan Başar, ..., Muharrem Kaya)
20165.05Journal of Enzyme Inhibition and Medicinal Chemistry
4 Authors (Taner Gokcen, ..., Ahmet C. Gören)
References24
Newest
Nov 15, 2015·Bioorganic & Medicinal Chemistry3.64
#1Anastasia Karioti (A.U.Th.: Aristotle University of Thessaloniki)H-Index: 29
#2Mariangela Ceruso (UniFI: University of Florence)H-Index: 28
Last. Claudiu T. Supuran (UniFI: University of Florence)H-Index: 155
view all 5 authors...
Carbonic anhydrases (CAs, EC 4.2.1.1) catalyze the fundamental reaction of CO2 hydration in all living organisms, being actively involved in the regulation of a plethora of patho/physiological conditions. They represent a typical example of enzyme convergent evolution, as six genetically unrelated families of such enzymes were described so far. The need to find selective CA inhibitors (CAIs) triggered the investigation of natural product libraries, which proved to be a valid source of agents wit...
Source
Jun 5, 2015·ACS Medicinal Chemistry Letters4.34
#1Joanna Ombouma (ENSCM: École nationale supérieure de chimie de Montpellier)H-Index: 5
#2Daniella Vullo (UniFI: University of Florence)H-Index: 8
Last. Jean-Yves Winum (ENSCM: École nationale supérieure de chimie de Montpellier)H-Index: 54
view all 5 authors...
A general approach for the synthesis of carbonic anhydrases glycoinhibitors belonging to an aminoxysulfonamide series is presented using a Ferrier sulfonamidoglycosylation reaction on glycals. All the compounds showed good in vitro inhibitory activity against four human carbonic anhydrase isoforms, with selectivity against the cytosolic (hCA II) vs the tumor associated (hCA IX and XII) enzymes.
Source
Introduction: The η-class of carbonic anhydrases (CAs, EC 4.2.1.1) was recently discovered as the sixth genetic family of this metalloenzyme superfamily, and seems to be present only in various Plasmodium species, the malaria-provoking pathogens. The present review through detailed biochemical, kinetic and phylogenetic studies afford a clear view regarding the differences between η- and the other CA families.Areas covered: In this review, the authors underlined as the η-CAs, like α-, γ- and δ-cl...
Source
Feb 13, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry5.05
#1Leonardo Ezequiel Riafrecha (UNLP: National University of La Plata)H-Index: 7
#2Daniela Vullo (UniFI: University of Florence)H-Index: 69
Last. Pedro A. Colinas (UNLP: National University of La Plata)H-Index: 15
view all 8 authors...
Fil: Riafrecha, Leonardo Ezequiel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Quimica. Laboratorio de Estudio de Compuestos Organicos; Argentina
Source
Nov 15, 2014·Bioorganic & Medicinal Chemistry3.64
#1Joanna Ombouma (ENSCM: École nationale supérieure de chimie de Montpellier)H-Index: 5
#2Daniela Vullo (UniFI: University of Florence)H-Index: 69
Last. Jean-Yves Winum (ENSCM: École nationale supérieure de chimie de Montpellier)H-Index: 54
view all 4 authors...
Abstract Ferrier sulfamidoglycosylation of glycals catalyzed by nitrosonium tetrafluoroborate allowed the preparation of hydroxysulfamide glycosides in good yields with a good α stereoselectivity. A variety of mono-saccharide derivatives was synthesized using this new methodology leading to selective and powerful glycoinhibitors of the tumor associated carbonic anhydrases (CA, EC 4.2.1.1) isoforms CA IX and CA XII.
Source
#1Pedro Alfonso Colinas (CONICET: National Scientific and Technical Research Council)H-Index: 1
Source
#1John L. MagnaniH-Index: 1
Complex carbohydrates contain dense structural information that is decoded in recognition processes among cells, their pathogens and products, as well as many other functional proteins and represent a new source of novel therapeutics. Native carbohydrate ligands, however, lack classic drug-like properties and in general suffer from poor pharmacokinetics, bioavailability, stability, and low affinity. One solution is to rationally design glycomimetic drugs based on the bioactive conformation of th...
May 17, 2013·Expert Opinion on Therapeutic Patents6.68
#1Andrea Scozzafava (UniFI: University of Florence)H-Index: 111
#2Claudiu T. Supuran (UniFI: University of Florence)H-Index: 155
Last. Fabrizio Carta (UniFI: University of Florence)H-Index: 52
view all 3 authors...
Introduction: Obesity is ranked as one of the top 10 global health problems and the major concern deriving from it is the exposure of the population to a vast array of chronic pathologies such as cardiovascular and musculoskeletal disorders, type 2 diabetes, cancer, such as colon, breast and endometrial cancer, together with psychological disorders derived from this condition. The discovery that the clinically used anticonvulsants topiramate (TPM) and zonisamide (ZNS) induced weight loss in obes...
Source
May 17, 2013·Expert Opinion on Therapeutic Patents6.68
#1Fabrizio Carta (UniFI: University of Florence)H-Index: 52
#2Claudiu T. Supuran (UniFI: University of Florence)H-Index: 155
Introduction: The benzothiadiazines and high ceiling diuretics (hydrochlorothiazide, hydroflumethiazide, quinethazone, metolazone, chlorthalidone, indapamide, furosemide and bumetanide) contain primary sulfamoyl moieties acting as zinc-binding groups in the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). These drugs are widely used clinically and were recently shown to weakly inhibit isoforms CA I and II, but to possess stronger activity against isoforms involved in other important pathologie...
Source
Introduction: All microorganisms that cause diseases or illnesses to their host are defined as pathogens. In this paper we will review the current state of the art for inhibiting parasite carbonic anhydrases (CAs, EC 4.2.1.1) with a goal of developing antibacterial, antifungal or antiprotozoan agents possessing a different mechanism of action compared with the clinically used drugs to which a considerable degree of drug resistance has been reported. Areas covered: Cloning of the genomes of many ...
Source
123
Cited By5
Newest
Oct 7, 2021·Carbohydrate Research2.10
#1Agustín H. Rojas (UNLP: National University of La Plata)H-Index: 2
#2Leticia Lafuente (UNLP: National University of La Plata)H-Index: 3
Last. Agustín Ponzinibbio (UNLP: National University of La Plata)H-Index: 10
view all 6 authors...
Single crystal X-ray and NMR investigations on multidomain structured N-(4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-en-2-iodo-pyranosyl)-methylsulfonamide are reported. This is the first crystallographic diffraction data report related to a 2-halo-2,3-unsaturated galactoside derivative. A complete structural study, including conformations and crystal packing, was performed by analyzing the spectroscopic data in solid state (XRD) and in solution (NMR).
Source
Jan 1, 2021·New Journal of Chemistry3.59
#1Ariza Khanam (Central Drug Research Institute)H-Index: 3
#2Pintu Kumar Mandal (Central Drug Research Institute)H-Index: 10
Source
Sep 3, 2020·Tetrahedron Letters2.42
#1Agustín H. Rojas (UNLP: National University of La Plata)H-Index: 2
#2Leticia Lafuente (UNLP: National University of La Plata)H-Index: 3
Last. Agustín Ponzinibbio (UNLP: National University of La Plata)H-Index: 10
view all 6 authors...
Abstract We obtained a series of novel N-(2-iodo-2,3-dideoxy-2-en-glycopyranosides)-sulfonamides via the Aza-Ferrier rearrangement of protected-2-iodoglycals in good yields and high stereoselectivity. Their structure and conformation features were determined by NMR. Moreover, we report here the first in detail structure analysis by X-ray diffraction techniques of a 2-iodo-pseudoglycal.
Source
Aug 21, 2020·Antioxidants6.31
#1Giosuè CostaH-Index: 23
#2Annalisa MarucaH-Index: 9
Last. Claudiu T. Supuran (UniFI: University of Florence)H-Index: 155
view all 13 authors...
The tumor-associated isoenzymes hCA IX and hCA XII catalyze the hydration of carbon dioxide to bicarbonate and protons. These isoforms are highly overexpressed in many types of cancer, where they contribute to the acidification of the tumor environment, promoting tumor cell invasion and metastasis. In this work, in order to identify novel dual hCA IX and XII inhibitors, virtual screening techniques and biological assays were combined. A structure-based virtual screening towards hCA IX and XII wa...
Source
Jul 21, 2020·Medicinal Research Reviews12.94
#1Chandra Bhushan Mishra (Sookmyung Women's University)H-Index: 15
#2Manisha Tiwari (DU: University of Delhi)H-Index: 23
Last. Claudiu T. Supuran (UniFI: University of Florence)H-Index: 155
view all 3 authors...
Carbonic anhydrases (CAs, EC 4.2.1.1) are widely distributed metalloenzymes in both prokaryotes and eukaryotes. They efficiently catalyze the reversible hydration of carbon dioxide to bicarbonate and H+ ions and play a crucial role in regulating many physiological processes. CAs are well-studied drug target for various disorders such as glaucoma, epilepsy, sleep apnea, and high altitude sickness. In the past decades, a large category of diverse families of CA inhibitors (CAIs) have been develope...
Source
Jan 1, 2017·Expert Opinion on Drug Discovery6.10
#1Claudiu T. Supuran (UniFI: University of Florence)H-Index: 155
ABSTRACTIntroduction: The enzyme carbonic anhydrase (CA, EC 4.2.1.1) is found in numerous organisms across the tree of life, with seven distinct classes known to date. CA inhibition can be exploited for the treatment of edema, glaucoma, seizures, obesity, cancer and infectious diseases. A myriad of CA inhibitor (CAI) classes and inhibition mechanisms have been identified over the past decade, mainly through structure-based drug design approaches. Five different CA inhibition mechanisms are prese...
Source
1
This website uses cookies.
We use cookies to improve your online experience. By continuing to use our website we assume you agree to the placement of these cookies.
To learn more, you can find in our Privacy Policy.