Evaluation of antioxidant activity and cytotoxicity of polyfluorinated diarylacetylenes and indoles toward human cancer cells

Evaluation of antioxidant activity and cytotoxicity of polyfluorinated diarylacetylenes and indoles toward human cancer cells Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2019, Volume: 226, Article number : UNSP 109353, Pages count : DOI: 10.1016/j.jfluchem.2019.109353

Tags

Polyfluorinated 2-arylindoles; Polyfluorinated diarylacetylenes; Cytotoxicity; Structure-activity relationship; Mutagenic and antioxidant properties

Authors

Zakharova Olga ¹ , Nevinsky Georgy ^1,2 , Politanskaya Larisa ^2,3 , Baev Dmitry ^2,3 , Ovchinnikova Ludmila ⁴ , Tretyakov Evgeny ^2,3

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, Inst Chem Biol & Fundamental Med, Ac Lavrentiev Ave 8, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova Str 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Inst Organ Chem, Ac Lavrentiev Ave 9, Novosibirsk 630090, Russia
4	(Данные Web of science) Russian Acad Sci, Siberian Div, Inst Cytol & Genet, Ac Lavrentiev Ave 10, Novosibirsk 630090, Russia

A large series of polyfluorinated diarylacetylenes and indoles was evaluated for antitumor activity in MCF-7, RPMI 8226, T98 G, HCT 116 human cancer cells and for cytotoxicity effect on HEK-293, WI-38, LMTK, AG 17 normal mammalian cell lines. It was found that with the increased number of fluorine atoms on the benzene ring of the compounds, their cytotoxicity increases, reaching a maximum in case of the perfluorinated structures. Polyfluorinated diarylacetylenes containing three fluorine atoms and trifluoromethyl and amino groups in one aryl ring, inhibit the proliferation of human myeloma RPMI 8226 and human breast cancer MCF-7 cells. Indoles showed more pronounced cytotoxicity as compared with their arylacetylene precursors. Compounds I-9, I-11, and I-13 were found to have a high growth-inhibitory activity toward the human cancer cell lines tested, with halfinhibitory concentrations (IC50) of 1-10 mu M. The structures of these compounds are characterized by complete fluorination of the benzene part of the indole core and the presence of an aromatic moiety at the 2nd position of the five-membered ring. Further, DNA fragmentation and Annexin V-FITC/PI staining assays confirm that I-9-I-11 induce apoptosis. Mutagenic and antioxidant properties of the polyfluorinated indoles and of selected diarylacetylenes were also studied. On a Salmonella tester strain, it was demonstrated that the compounds are good antioxidants.

Zakharova O. , Nevinsky G. , Politanskaya L. , Baev D. , Ovchinnikova L. , Tretyakov E.
Evaluation of antioxidant activity and cytotoxicity of polyfluorinated diarylacetylenes and indoles toward human cancer cells
Journal of Fluorine Chemistry. 2019. V.226. UNSP 109353 . DOI: 10.1016/j.jfluchem.2019.109353 WOS Scopus РИНЦ OpenAlex

Published print:

Oct 1, 2019

Web of science:	WOS:000497250900006
Scopus:	2-s2.0-85069837937
Elibrary:	41635656
OpenAlex:	W2962706140

DB	Citing
Web of science	10
Scopus	10
Elibrary	9
OpenAlex	10