Ectonucleotidase Inhibitory and Redox Activity of Imidazole-Based Organic Salts and Ionic Liquids

Veaceslav Boldescu; Natalia Sucman; Sidra Hassan; Jamshed Iqbal; Mariana Neamtu; Joanna Lecka; Jean Sévigny; Denis Prodius; Fliur Macaev

doi:10.1002/cmdc.201800520

Ectonucleotidase Inhibitory and Redox Activity of Imidazole-Based Organic Salts and Ionic Liquids

ChemMedChem. 2018 Nov 6;13(21):2297-2304. doi: 10.1002/cmdc.201800520. Epub 2018 Oct 23.

Authors

Veaceslav Boldescu¹, Natalia Sucman¹, Sidra Hassan², Jamshed Iqbal², Mariana Neamtu³, Joanna Lecka^{4

5}, Jean Sévigny^{4

5}, Denis Prodius^{6

7}, Fliur Macaev¹

Affiliations

¹ Laboratory of Organic Synthesis and Biopharmaceuticals, Institute of Chemistry, 3 Academiei str., 2028, Chisinau, Moldova.
² Department of Pharmaceutical Sciences, COMSATS Institute of Information Technology, 22060, Abbottabad, Pakistan.
³ Interdisciplinary Research Department, "Alexandru Ioan Cuza" University, 54 Lascar Catargi str., 700107, Iasi, Romania.
⁴ Département de microbiologie-infectiologie et d'immunologie, Faculté de Médecine, Université Laval, Québec, QC, G1V 0A6, Canada.
⁵ Centre de Recherche du CHU de Québec, Université Laval, Québec, QC, G1V 4G2, Canada.
⁶ Laboratory of Bioinorganic Chemistry and Nanocomposites, Institute of Chemistry, 3 Academiei str., 2028, Chisinau, Moldova.
⁷ Current address: US Department of Energy and Critical Materials Institute, Ames, IA, 50011-3020, USA.

PMID: 30192439
DOI: 10.1002/cmdc.201800520

Abstract

Cytotoxicity against cancer and normal cells, inhibition of ectonucleotidase, and redox properties of a new group of imidazole-based organic salts and ionic liquids were studied. The tetrachloroferrate salt of a 1-methylimidazole derivative of salicylic aldehyde had most prominent inhibitory activity against ectonucleotidase as well as a higher cytotoxicity against HeLa cells and lower cytotoxicity against BHK-21 cells than the reference compound carboplatin. The studied compounds exhibited a moderate level of antioxidant activity with better results for the salicylic aldehyde derivatives than for spiropyrans. Moreover, these compounds did not generate singlet oxygen.

Keywords: antioxidants; cancer; ectonucleotidase; ionic liquids; organic salts.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

5'-Nucleotidase / antagonists & inhibitors*
Animals
Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Antioxidants / chemical synthesis
Antioxidants / chemistry
Antioxidants / pharmacology
Apoptosis / drug effects
Benzaldehydes / chemical synthesis
Benzaldehydes / chemistry
Benzaldehydes / pharmacology
Carboplatin / pharmacology
Cell Line, Tumor
Cell Proliferation / drug effects
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology*
Humans
Imidazoles / chemical synthesis
Imidazoles / chemistry
Imidazoles / pharmacology*
Ionic Liquids / chemical synthesis
Ionic Liquids / chemistry
Ionic Liquids / pharmacology*
Mesocricetus
Molecular Structure
Structure-Activity Relationship

Substances

Antineoplastic Agents
Antioxidants
Benzaldehydes
Enzyme Inhibitors
Imidazoles
Ionic Liquids
Carboplatin
5'-Nucleotidase