Synthesis and Comparative Evaluation of Polymethoxy Substituted 1,4-Naphthoquinones and their Acetyl-O-glucosides as Cytotoxic Agents

Synthesis and Comparative Evaluation of Polymethoxy Substituted 1,4-Naphthoquinones and their Acetyl-O-glucosides as Cytotoxic Agents Full article

Journal

Natural Product Communications
ISSN: 1555-9475 , E-ISSN: 1934-578X

Output data

Year: 2017, Volume: 12, Number: 7, Pages: 1081-1089 Pages count : 9 DOI: 10.1177/1934578x1701200721

Authors

Sabutski Yuri E. ¹ , Semenova Marina N. ² , Yurchenko Ekaterina A. ¹ , Polonik Nikita S. ³ , Denisenko Vladimir A. ¹ , Dmitrenok Pavel S. ¹ , Semenov Victor V. ⁴ , Polonik Sergey G. ¹

Affiliations

1	G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Vladivostok, 690022, Russian Federation
2	N. K. Kol'tsov Institute of Developmental Biology, RAS, Vavilov Str., 26, 119334 Moscow, Russian Federation
3	Far Eastern Federal University, School of Biomedicine, Sukhanova Str., 8, 690000 Vladivostok, Russian Federation
4	N. D. Zelinsky Institute of Organic Chemistry, RAS, 47 Leninsky Prospect, 119991 Moscow, Russian Federation

Twenty five hydroxy-, chloro- and methoxy derivatives of natural and synthetic naphthazarins and their acetylated O-glycosides were synthesized. Targeted compounds were screened as cytotoxic agents on mouse Ehrlich ascites carcinoma cells using MTT test. Chloro- and methoxy-substituted naphthoquinones as well as naphthoquinone O-acetylglucosides were the most potent with IC50 in low micromolar concentration range. Glucosidation of hydroxynaphthoquinones was shown to enhance cytotoxicity, whereas methoxylation yielded both more active and less active derivatives depending on the number and position of methoxy groups. Evaluation using a phenotypic sea urchin embryo assay suggested that naphthazarins exerted their cytotoxic effects through tubulin-unrelated mechanism.

Sabutski Y.E. , Semenova M.N. , Yurchenko E.A. , Polonik N.S. , Denisenko V.A. , Dmitrenok P.S. , Semenov V.V. , Polonik S.G.
Synthesis and Comparative Evaluation of Polymethoxy Substituted 1,4-Naphthoquinones and their Acetyl-O-glucosides as Cytotoxic Agents
Natural Product Communications. 2017. V.12. N7. P.1081-1089. DOI: 10.1177/1934578x1701200721 Scopus OpenAlex

Scopus:	2-s2.0-85026452283
OpenAlex:	W2927042776

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