Synthesis of rhodamine B-benzenesulfonamide conjugates and their inhibitory activity against human alpha- and bacterial/fungal beta-carbonic anhydrases.
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Rami M, Innocenti A, Montero JL, Scozzafava A, Winum JY, Supuran CT
Synthesis of rhodamine B-benzenesulfonamide conjugates and their inhibitory activity against human alpha- and bacterial/fungal beta-carbonic anhydrases.
Bioorg Med Chem Lett. 2011 Sep 15;21(18):5210-3. doi: 10.1016/j.bmcl.2011.07.045. Epub 2011 Jul 21.
- PubMed ID
- 21821413 [ View in PubMed]
- Abstract
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 alpha-CA isoforms (hCA I-hCA XIV), three bacterial and one fungal beta-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 beta-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.
DrugBank Data that Cites this Article
- Binding Properties
Drug Target Property Measurement pH Temperature (°C) Acetazolamide Carbonic anhydrase 1 Ki (nM) 250 N/A N/A Details Acetazolamide Carbonic anhydrase 12 Ki (nM) 5.7 N/A N/A Details Acetazolamide Carbonic anhydrase 14 Ki (nM) 41 N/A N/A Details Acetazolamide Carbonic anhydrase 2 Ki (nM) 12 N/A N/A Details Acetazolamide Carbonic anhydrase 3 Ki (nM) 20000 N/A N/A Details Acetazolamide Carbonic anhydrase 4 Ki (nM) 74 N/A N/A Details Acetazolamide Carbonic anhydrase 7 Ki (nM) 2.5 N/A N/A Details