Synthesis of novel dipeptide sulfonamide conjugates with effective carbonic anhydrase I, II, IX, and XII inhibitory properties

被引：22

作者：

Bugday, Nesrin ^{[1
]}

Kucukbay, F. Zehra ^{[2
]}

Kucukbay, Hasan ^{[1
]}

Bua, Silvia ^{[3
,4
]}

Bartolucci, Gianluca ^{[3
,4
]}

Leitans, Janis ^{[5
]}

Kazaks, Andris ^{[5
]}

Tars, Kaspars ^{[5
]}

Supuran, Claudiu T. ^{[3
,4
]}

机构：

[1] Inonu Univ, Fac Arts & Sci, Dept Chem, TR-44280 Malatya, Turkey

[2] Inonu Univ, Fac Pharm, Dept Basic Pharmaceut Sci, TR-44280 Malatya, Turkey

[3] Univ Firenze, Dipartimento Neurofarba, Sez Sci Farmaceut & Nutraceut, Florence, Italy

[4] Univ Firenze, Lab Chim Bioinorgan, Florence, Italy

[5] Latvian Biomed Res & Study Ctr, Ratsupites 1, Riga, Latvia

来源：

BIOORGANIC CHEMISTRY | 2018年 / 81卷

关键词：

Carbonic anhydrase; Inhibitor; Homosulfanilamide; Dipeptide; Conjugate; BIOCHEMICAL-CHARACTERIZATION; PORPHYROMONAS-GINGIVALIS; BIOLOGICAL EVALUATION; AMINO-ACIDS; DERIVATIVES; ANTIBACTERIAL; DESIGN; ANTICANCER; PEPTIDES; BIOASSAY;

D O I：

10.1016/j.bioorg.2018.08.032

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Twenty-four novel sulfonamide derivatives incorporating dipeptide tails were synthesized by facile acylation reactions of homosulfanilamide through benzotriazole or dicyclohexyl carbodiimide (DCC) mediated coupling reactions. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was assessed against four human (h) isoforms, hCA I, hCA II, hCA IX and hCA XII. Most of the synthesized compounds showed good in vitro carbonic anhydrase inhibitory properties, with inhibition constants in the low nanomolar range. Particularly, the new dipeptide-sulfonamide conjugates incorporating Ala, Phe and met in the dipeptide sequence, showed the most effective inhibitory activity against to CA IX and XII.

引用

页码：311 / 318

页数：8

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