Functionalized aliphatic selenols, straightforwardly obtained through ring-opening reaction of strained heterocycles, represent a new chemotype acting as carbonic anhydrase inhibitors (CAIs). These compounds showed pronounced selectivity towards the cytosolic human (h) isoforms such as the hCA I, II and VII rather than the membrane tumor associate hCA IX. In addition, we reported for the first time the X-ray crystal structure of an aliphatic selenol bound to the hCA I zinc ion, and that afforded the opportunity to decipher in detail the inhibition mechanism underpinning such a new class of CAIs. In this context selenols are interesting leads worth developing for the obtainment of novel and efficient selective CAIs potentially useful for the management of a variety of diseases including glaucoma, retinitis pigmentosa, epilepsy and arthritis.

Direct and Straightforward access to substituted alkyl selenols as novel carbonic anhydrase inhibitors / Tanini, Damiano; Capperucci, Antonella; Ferraroni, Marta; Carta, Fabrizio; Angeli, Andrea; Supuran, Claudiu T.. - In: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0223-5234. - ELETTRONICO. - (2019), pp. 111811-111817. [10.1016/j.ejmech.2019.111811]

Direct and Straightforward access to substituted alkyl selenols as novel carbonic anhydrase inhibitors

Tanini, Damiano;Capperucci, Antonella;Ferraroni, Marta;Carta, Fabrizio;Angeli, Andrea;Supuran, Claudiu T.
2019

Abstract

Functionalized aliphatic selenols, straightforwardly obtained through ring-opening reaction of strained heterocycles, represent a new chemotype acting as carbonic anhydrase inhibitors (CAIs). These compounds showed pronounced selectivity towards the cytosolic human (h) isoforms such as the hCA I, II and VII rather than the membrane tumor associate hCA IX. In addition, we reported for the first time the X-ray crystal structure of an aliphatic selenol bound to the hCA I zinc ion, and that afforded the opportunity to decipher in detail the inhibition mechanism underpinning such a new class of CAIs. In this context selenols are interesting leads worth developing for the obtainment of novel and efficient selective CAIs potentially useful for the management of a variety of diseases including glaucoma, retinitis pigmentosa, epilepsy and arthritis.
2019
111811
111817
Tanini, Damiano; Capperucci, Antonella; Ferraroni, Marta; Carta, Fabrizio; Angeli, Andrea; Supuran, Claudiu T.
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1176901
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