Synthesis of rhodamine B–benzenesulfonamide conjugates and their inhibitory activity against human α- and bacterial/fungal β-carbonic anhydrases

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• 作者：Marouan Rami^a ; Alessio Innocenti^b ; Jean-Louis Montero^a ; Andrea Scozzafava^b ; Jean-Yves Winum^a ; ^{jean-yves.winum@univ-montp2.fr"" rel=""nofollow} ; Claudiu T. Supuran^b ; ^{claudiu.supuran@unifi.it"" rel=""nofollow}
• 关键词：Carbonic anhydrase ; Sulfonamide ; Rhodamine B ; Fluorescence ; Tumor imaging ; Bacterial/fungal carbonic anhydrase
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2011
• 出版时间：15 September 2011
• 年：2011
• 卷：21
• 期：18
• 页码：5210-5213
• 全文大小：257 K

文摘

A series of fluorescent sulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitors were obtained by attaching rhodamine B moieties to the scaffold of benzenesulfonamides. The new compounds have been investigated for the inhibition of 12 human α-CA isoforms (hCA I–hCA XIV), three bacterial and one fungal β-class enzymes from the pathogens Mycobacterium tuberculosis and Candida albicans. All types of inhibitory activities have been detected, with several compounds showing low nanomolar inhibition against the transmembrane isoforms hCA IX, XII (cancer-associated) and XIV. The β-CAs were inhibited in the micromolar range by these compounds which may have applications for the imaging of hypoxic tumors or bacteria due to their fluorescent moieties.