An overview of carbohydrate-based carbonic anhydrase inhibitors

Published on Oct 20, 2020in Journal of Enzyme Inhibition and Medicinal Chemistry4.673
· DOI :10.1080/14756366.2020.1825409
Doretta Cuffaro5
Estimated H-index: 5
(UniPi: University of Pisa),
Elisa Nuti25
Estimated H-index: 25
(UniPi: University of Pisa),
Armando Rossello28
Estimated H-index: 28
(UniPi: University of Pisa)
Carbonic anhydrases (CAs) are metalloenzymes responsible for the reversible hydration of carbon dioxide to bicarbonate, a fundamental reaction involved in various physiological and pathological pro...
📖 Papers frequently viewed together
43 Citations
2 Authors (Richard L. Day)
33 Citations
17 Citations
#1Alessandro Bonardi (UniFI: University of Florence)H-Index: 10
#2Alessio Nocentini (UniFI: University of Florence)H-Index: 26
Last. Claudiu T. Supuran (UniFI: University of Florence)H-Index: 152
view all 12 authors...
The “tail-approach” has become a milestone in human carbonic anhydrase inhibitor (hCAI) design for various therapeutics, including antiglaucoma agents. Beside the classical hydrophobic/hydrophilic ...
18 CitationsSource
#1Sonia Del PreteH-Index: 29
#2Alessio Nocentini (UniFI: University of Florence)H-Index: 26
Last. Clemente CapassoH-Index: 58
view all 4 authors...
The carbonic anhydrases (CAs, EC catalyse a simple but physiologically crucial reversible reaction, the carbon dioxide hydration with the production of bicarbonate and protons. In the last years, and especially, to the rapid emergence of the bacterial antibiotic resistance that is occurring worldwide, the understanding of the function of bacterial CAs has increased significantly. Recently, a new CA-class (iota-CA) was discovered in the marine diatom T. pseudonana. It has been reported t...
34 CitationsSource
#1Claudiu T. Supuran (UniFI: University of Florence)H-Index: 152
ABSTRACTIntroduction: The spacious active site cavity of the metalloenzyme carbonic anhydrase (CA, EC shows a great versatility for a variety of binding modes for modulators of activity, i...
41 CitationsSource
#1Zhuang Hou (SPU: Shenyang Pharmaceutical University)H-Index: 8
#2Chuanchao Li (SPU: Shenyang Pharmaceutical University)H-Index: 1
Last. Yang Liu (SPU: Shenyang Pharmaceutical University)H-Index: 15
view all 9 authors...
AbstractA series of new carbohydrate-based sulphonamide derivatives were designed, synthesised by employing the so-call ‘sugar-tail’ approach. The compounds were evaluated in vitro against a panel ...
7 CitationsSource
#1Dorcas A. Annan (Hokkaido University)H-Index: 5
#2Nako Maishi (Hokkaido University)H-Index: 22
Last. Kyoko Hida (Hokkaido University)H-Index: 38
view all 15 authors...
Tumor endothelial cells (TECs) perform tumor angiogenesis, which is essential for tumor growth and metastasis. Tumor cells produce large amounts of lactic acid from glycolysis; however, the mechanism underlying the survival of TECs to enable tumor angiogenesis under high lactic acid conditions in tumors remains poorly understood. The metabolomes of TECs and normal endothelial cells (NECs) were analyzed by capillary electrophoresis time-of-flight mass spectrometry. The expressions of pH regulator...
9 CitationsSource
#1Alessio Nocentini (UniFI: University of Florence)H-Index: 26
#2Claudiu T. Supuran (UniFI: University of Florence)H-Index: 152
ABSTRACTIntroduction: Of the 15 human carbonic anhydrase (CA, EC isoforms known to date, for 11 the crystal structure is known. Many different classes of CA inhibitors (CAIs) were reported...
68 CitationsSource
#1Xiangyi Jiang (SDU: Shandong University)H-Index: 5
#2Xia Hao (SDU: Shandong University)H-Index: 4
Last. Peng Zhan (SDU: Shandong University)H-Index: 37
view all 7 authors...
ABSTRACTIntroduction: Click chemistry has been exploited widely in the past to expedite lead discovery and optimization. Indeed, Copper-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry ...
54 CitationsSource
#1A.B. Murray (UF: University of Florida)H-Index: 7
#2Marta Quadri (UF: University of Florida)H-Index: 8
Last. Nicole A. Horenstein (UF: University of Florida)H-Index: 20
view all 5 authors...
Abstract Carbonic anhydrase IX (CA IX) has been identified as a biomarker and drug target for several malignant tumors due to its role in cancer cell growth and proliferation. Simple cyclic sulfonamides, like saccharin (SAC), have shown up to a 60-fold selectivity towards CA IX over other ubiquitous CA isoforms, with greater selectivity obtained applying the “tail-approach” to derivatize SAC with a methylene triazole linker that connected to a “tail” beta glucoside. These modifications of SAC le...
5 CitationsSource
#1Erik Jensen (AMU: Aix-Marseille University)H-Index: 13
#2Romain Clement (AMU: Aix-Marseille University)H-Index: 9
Last. Brigitte Gontero (AMU: Aix-Marseille University)H-Index: 31
view all 5 authors...
Most aquatic photoautotrophs depend on CO2-concentrating mechanisms (CCMs) to maintain productivity at ambient concentrations of CO2, and carbonic anhydrase (CA) plays a key role in these processes. Here we present different lines of evidence showing that the protein LCIP63, identified in the marine diatom Thalassiosira pseudonana, is a CA. However, sequence analysis showed that it has a low identity with any known CA and therefore belongs to a new subclass that we designate as iota-CA. Moreover...
83 CitationsSource
#1Felicia D'Andrea (UniPi: University of Pisa)H-Index: 19
#2Elisa Nuti (UniPi: University of Pisa)H-Index: 25
Last. Armando Rossello (UniPi: University of Pisa)H-Index: 28
view all 15 authors...
: Selective and potent matrix metalloproteinase 12 (MMP-12) inhibitors endowed with improved hydrophilicity are highly sought for potential use in the treatment of lung and cardiovascular diseases. In the present paper, we modified the structure of a nanomolar MMP-12 inhibitor by incorporating an ionic liquid (IL) moiety to improve aqueous solubility. Four biologically active salts were obtained by linking the sulfonamide moiety of the MMP-12 inhibitor to imidazolium-, pyrrolidinium-, piperidini...
2 CitationsSource
Cited By3
#1Claudiu T. Supuran (UniFI: University of Florence)H-Index: 152
#2Alessio Nocentini (UniFI: University of Florence)H-Index: 26
Last. Mikhail Krasavin (SPbU: Saint Petersburg State University)H-Index: 24
view all 6 authors...
The non-nucleoside reverse transcriptase inhibitor VM1500A is approved for the treatment of HIV/AIDS in its N-acyl sulphonamide prodrug form elsulfavirine (Elpida®). Biochemical profiling against twelve human carbonic anhydrase (CA, EC isoforms showed that while elsulfavirine was a weak inhibitor of all isoforms, VM1500A potently and selectively inhibited human (h) hCA VII isoform, a proven target for the therapy of neuropathic pain. The latter is a common neurologic complication of HIV...
1 CitationsSource
#1Aişe Ünlü (GIT: Gebze Institute of Technology)H-Index: 4
#2Zeynep Efsun Duman-Özdamar (GIT: Gebze Institute of Technology)H-Index: 1
Last. Barış Binay (GIT: Gebze Institute of Technology)H-Index: 9
view all 4 authors...
The accumulation of carbon dioxide in the atmosphere as a result of human activities has caused a number of adverse circumstances in the world. For this reason, the proposed solutions lie within the aim of reducing carbon dioxide emissions have been quite valuable. However, as the human activity continues to increase on this planet, the possibility of reducing carbon dioxide emissions decreases with the use of conventional methods. The emergence of compounds than can be used in different fields ...
#1Doretta Cuffaro (UniPi: University of Pisa)H-Index: 5
#2Elisa Nuti (UniPi: University of Pisa)H-Index: 25
Last. Armando Rossello (UniPi: University of Pisa)H-Index: 28
view all 4 authors...
Matrix metalloproteinases (MMPs) and A disintegrin and Metalloproteinase (ADAMs) are zinc-dependent endopeptidases belonging to the metzincin superfamily. Upregulation of metzincin activity is a major feature in many serious pathologies such as cancer, inflammations, and infections. In the last decades, many classes of small molecules have been developed directed to inhibit these enzymes. The principal shortcomings that have hindered clinical development of metzincin inhibitors are low selectivi...