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Journal of Enzyme Inhibition and Medicinal Chemistry Volume 29, 2014 - Issue 1
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Research Article

Benzenesulfonamides with benzimidazole moieties as inhibitors of carbonic anhydrases I, II, VII, XII and XIII

Asta ZubrienėDepartment of Biothermodynamics and Drug Design, Institute of BiotechnologyCorrespondence[email protected] [email protected]
,
Edita ČapkauskaitėDepartment of Biothermodynamics and Drug Design, Institute of Biotechnology;Department of Organic Chemistry, Faculty of Chemistry, Vilnius University VilniusLithuania
,
Joana GylytėDepartment of Biothermodynamics and Drug Design, Institute of Biotechnology
,
Miglė KišonaitėDepartment of Biothermodynamics and Drug Design, Institute of Biotechnology
,
Sigitas TumkevičiusDepartment of Organic Chemistry, Faculty of Chemistry, Vilnius University VilniusLithuania
&
Daumantas MatulisDepartment of Biothermodynamics and Drug Design, Institute of Biotechnology
Pages 124-131 | Received 18 Oct 2012, Accepted 06 Dec 2012, Published online: 28 Jan 2013

Figures & data

Figure 1. Chemical structures of some clinically used sulfonamides.

Figure 1. Chemical structures of some clinically used sulfonamides.

Figure 2. The structure of N-alkylated benzimidazole derivatives.

Figure 2. The structure of N-alkylated benzimidazole derivatives.

Scheme 1. Synthesis of compounds 1–3(a–j).

Scheme 1. Synthesis of compounds 1–3(a–j).

Figure 3. TSA data of 1–4d binding to CA XIII. The top panels compare denaturation curves observed by fluorescence at 0–200 µM added compound concentrations. The bottom panel shows the dependence of the protein melting temperatures Tm on compound concentrations.

Figure 3. TSA data of 1–4d binding to CA XIII. The top panels compare denaturation curves observed by fluorescence at 0–200 µM added compound concentrations. The bottom panel shows the dependence of the protein melting temperatures Tm on compound concentrations.

Figure 4. TSA data of 2a, 2d, 2h and 2j binding to CA XII.

Figure 4. TSA data of 2a, 2d, 2h and 2j binding to CA XII.

Figure 5. The binding constants of 1i, 2i, 3i and 4i to CAI, II, VII, XII and XIII.

Figure 5. The binding constants of 1i, 2i, 3i and 4i to CAI, II, VII, XII and XIII.

Table 1. Dissociation constants for compounds binding to five human recombinant CA isoforms, determined by TSA (37 °C, pH 7.0).

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