Carbonic anhydrase inhibitors: synthesis of sulfonamides incorporating dtpa tails and of their zinc complexes with powerful topical antiglaucoma properties.
Article Details
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Scozzafava A, Menabuoni L, Mincione F, Mincione G, Supuran CT
Carbonic anhydrase inhibitors: synthesis of sulfonamides incorporating dtpa tails and of their zinc complexes with powerful topical antiglaucoma properties.
Bioorg Med Chem Lett. 2001 Feb 26;11(4):575-82.
- PubMed ID
- 11229775 [ View in PubMed]
- Abstract
Reaction of diethylenetriamino pentaacetic acid (dtpa) dianhydride with aromatic/heterocyclic sulfonamides possessing a free amino/imino/hydrazino/hydroxy group afforded bis-sulfonamides containing metal-complexing, polyamino-polycarboxylic acid moieties in their molecule. The corresponding mono-sulfonamide derivatives of dtpa were also obtained by an alternative method, from the free acid. Zn(II) complexes of these new sulfonamides were then prepared. Many of these derivatives showed nanomolar affinity towards isozymes I, II and IV of carbonic anhydrase (CA). Some of the best inhibitors were applied as 2% water solutions/suspensions into the eye of normotensive or glaucomatous albino rabbits, when strong and long-lasting intraocular pressure (IOP) lowering was observed.
DrugBank Data that Cites this Article
- Binding Properties
Drug Target Property Measurement pH Temperature (°C) 4-(2-AMINOETHYL)BENZENESULFONAMIDE Carbonic anhydrase 2 Ki (nM) 160 N/A N/A Details 6-HYDROXY-1,3-BENZOTHIAZOLE-2-SULFONAMIDE Carbonic anhydrase 2 Ki (nM) 8 N/A N/A Details Acetazolamide Carbonic anhydrase 1 Ki (nM) 900 N/A N/A Details Acetazolamide Carbonic anhydrase 2 Ki (nM) 12 N/A N/A Details Acetazolamide Carbonic anhydrase 4 Ki (nM) 220 N/A N/A Details Dorzolamide Carbonic anhydrase 1 Ki (nM) >50000 N/A N/A Details Dorzolamide Carbonic anhydrase 2 Ki (nM) 9 N/A N/A Details Dorzolamide Carbonic anhydrase 4 Ki (nM) 43 N/A N/A Details