Bioorg Med Chem Lett. 2003 Mar 10;13(5):841-5.

Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV.

Casini A, Antel J, Abbate F, Scozzafava A, David S, Waldeck H, Schäfer S, Supuran CT.

Source

Dipartimento di Chimica, Laboratorio di Chimica Bioinorganica, Università degli Studi di Firenze, Rm. 188, Via della Lastruccia 3, I-50019 Sesto Fiorentino, Florence, Italy.

Abstract

A series of sugar sulfamate/sulfamide derivatives were prepared and assayed as inhibitors of three carbonic anhydrase (CA) isozymes, hCA I, hCA II and bCA IV. Best inhibitory properties were observed for the clinically used antiepileptic drug topiramate, which is a low nanomolar CA II inhibitor, and possesses good inhibitory properties against the other two isozymes investigated here, similarly with acetazolamide, methazolamide or dichlorophenamide. The X-ray structure of the complex of topiramate with hCA II has been solved and it revealed a very tight association of the inhibitor, with a network of seven strong hydrogen bonds fixing topiramate within the active site, in addition to the Zn(II) coordination through the ionized sulfamate moiety. Structural changes in this series of sugar derivatives led to compounds with diminished CA inhibitory properties as compared to topiramate.

PMID:: 12617904; [PubMed - indexed for MEDLINE]

LinkOut - more resources

Full Text Sources

Other Literature Sources

COS Scholar Universe

Chemical Information

BindingDB

Molecular Biology Databases

Supplemental Content

Save items

Related citations in PubMed

Carbonic anhydrase inhibitors: anticonvulsant sulfonamides incorporating valproyl and other lipophilic moieties. [J Med Chem. 2002]
Carbonic anhydrase inhibitors: anticonvulsant sulfonamides incorporating valproyl and other lipophilic moieties.
Masereel B, Rolin S, Abbate F, Scozzafava A, Supuran CT. J Med Chem. 2002 Jan 17; 45(2):312-20.
Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides. [Bioorg Med Chem Lett. 2005]
Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides.
Innocenti A, Firnges MA, Antel J, Wurl M, Scozzafava A, Supuran CT. Bioorg Med Chem Lett. 2005 Feb 15; 15(4):1149-54.
Carbonic anhydrase inhibitors: aliphatic N-phosphorylated sulfamates--a novel zinc-anchoring group leading to nanomolar inhibitors. [J Enzyme Inhib Med Chem. 2004]
Carbonic anhydrase inhibitors: aliphatic N-phosphorylated sulfamates--a novel zinc-anchoring group leading to nanomolar inhibitors.
Bonnac L, Innocenti A, Winum JY, Casini A, Montero JL, Scozzafava A, Barragan V, Supuran CT. J Enzyme Inhib Med Chem. 2004 Jun; 19(3):275-8.
Review Sulfamates and their therapeutic potential. [Med Res Rev. 2005]
Review Sulfamates and their therapeutic potential.
Winum JY, Scozzafava A, Montero JL, Supuran CT. Med Res Rev. 2005 Mar; 25(2):186-228.
Review New zinc binding motifs in the design of selective carbonic anhydrase inhibitors. [Mini Rev Med Chem. 2006]
Review New zinc binding motifs in the design of selective carbonic anhydrase inhibitors.
Winum JY, Scozzafava A, Montero JL, Supuran CT. Mini Rev Med Chem. 2006 Aug; 6(8):921-36.

See reviews... See all...

Cited by 5 PubMed Central articles

Coumarinyl-substituted sulfonamides strongly inhibit several human carbonic anhydrase isoforms: solution and crystallographic investigations. [Bioorg Med Chem. 2010]
Coumarinyl-substituted sulfonamides strongly inhibit several human carbonic anhydrase isoforms: solution and crystallographic investigations.
Wagner J, Avvaru BS, Robbins AH, Scozzafava A, Supuran CT, McKenna R. Bioorg Med Chem. 2010 Jul 15; 18(14):4873-8. Epub 2010 Jun 15.
Measurement of nanomolar dissociation constants by titration calorimetry and thermal shift assay - radicicol binding to Hsp90 and ethoxzolamide binding to CAII. [Int J Mol Sci. 2009]
Measurement of nanomolar dissociation constants by titration calorimetry and thermal shift assay - radicicol binding to Hsp90 and ethoxzolamide binding to CAII.
Zubriene A, Matuliene J, Baranauskiene L, Jachno J, Torresan J, Michailoviene V, Cimmperman P, Matulis D. Int J Mol Sci. 2009 Jun 10; 10(6):2662-80. Epub 2009 Jun 10.
Review Carbonic anhydrase as a model for biophysical and physical-organic studies of proteins and protein-ligand binding. [Chem Rev. 2008]
Review Carbonic anhydrase as a model for biophysical and physical-organic studies of proteins and protein-ligand binding.
Krishnamurthy VM, Kaufman GK, Urbach AR, Gitlin I, Gudiksen KL, Weibel DB, Whitesides GM. Chem Rev. 2008 Mar; 108(3):946-1051.

See all...

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
BioAssay
PubChem BioAssay experiments on the biological activities of small molecules that cite the current articles. The depositors of BioAssay data provide these references.
Compound (MeSH Keyword)
PubChem chemical compound records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Cited in PMC
Full-text articles in the PubMed Central Database that cite the current articles.

Recent activity

Clear Turn Off Turn On

Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the inte...
Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV.
Bioorg Med Chem Lett. 2003 Mar 10 ;13(5):841-5.

PubMed
Developmental expression of EphA4-tyrosine kinase receptor in the mouse brain an...
Developmental expression of EphA4-tyrosine kinase receptor in the mouse brain and spinal cord.
Gene Expr Patterns. 2002 Dec ;2(3-4):267-74.

PubMed
Diplopia after refractive surgery: occurrence and prevention.
Diplopia after refractive surgery: occurrence and prevention.
Arch Ophthalmol. 2003 Mar ;121(3):315-21.

PubMed
Delayed onset muscle soreness : treatment strategies and performance factors.
Delayed onset muscle soreness : treatment strategies and performance factors.
Sports Med. 2003 ;33(2):145-64.

PubMed
Biochemical aspects of overtraining in endurance sports : the metabolism alterat...
Biochemical aspects of overtraining in endurance sports : the metabolism alteration process syndrome.
Sports Med. 2003 ;33(2):83-94.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Result Filters

Display Settings:

Send to:

Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV.

Source

Abstract

MeSH Terms, Substances

MeSH Terms

Substances

LinkOut - more resources

Full Text Sources

Other Literature Sources

Chemical Information

Molecular Biology Databases

Supplemental Content

Save items

Related citations in PubMed

Cited by 5 PubMed Central articles

Related information

Recent activity

Simple NCBI Directory

Getting Started

Resources

Popular

Featured

NCBI Information