TY - JOUR
T1 - Synthesis and antitumor activity of selenium-containing quinone-based triazoles possessing two redox centres, and their mechanistic insights
AU - Da Cruz, Eduardo H G
AU - Silvers, Molly A.
AU - Jardim, Guilherme A M
AU - Resende, Jarbas M.
AU - Cavalcanti, Bruno C.
AU - Bomfim, Igor S.
AU - Pessoa, Claudia
AU - De Simone, Carlos A.
AU - Botteselle, Giancarlo V.
AU - Braga, Antonio L.
AU - Nair, Divya K.
AU - Namboothiri, Irishi N N
AU - Boothman, David A.
AU - Da Silva Júnior, Eufrânio N.
N1 - Funding Information:
This research was funded by grants from the Conselho Nacional de Desenvolvimento Científico e Tecnológico , numbers: 480719/2012-8 , PVE 401193/2014-4 , 449348/2014-8 , 474797/2013-9 and 454171/2014-5 . We would also like to thank FAPEMIG (APQ-02478-14), FUNCAP, FAPESP, FAPESC, CAPES, INCT-catálise and also the Physics Institute of USP (São Carlos) for kindly allowing the use of the KappaCCD diffractometer. Finally, these studies were also supported by NIH/NCI grant# CA102792 to DAB.
Funding Information:
This research was funded by grants from the Conselho Nacional de Desenvolvimento Científico e Tecnologico, numbers: 480719/ 2012-8, PVE 401193/2014-4, 449348/2014-8, 474797/2013-9 and 454171/2014-5.We would also like to thank FAPEMIG (APQ-02478- 14), FUNCAP, FAPESP, FAPESC, CAPES, INCT-catalise and also the Physics Institute of USP (Sao Carlos) for kindly allowing the use of the Kappa CCD diffractometer. Finally, these studies were also supported by NIH/NCI grant# CA102792 to DAB.
Publisher Copyright:
© 2016 Elsevier Masson SAS. All rights reserved.
PY - 2016
Y1 - 2016
N2 - Selenium-containing quinone-based 1,2,3-triazoles were synthesized using click chemistry, the copper catalyzed azide-alkyne 1,3-dipolar cycloaddition, and evaluated against six types of cancer cell lines: HL-60 (human promyelocytic leukemia cells), HCT-116 (human colon carcinoma cells), PC3 (human prostate cells), SF295 (human glioblastoma cells), MDA-MB-435 (melanoma cells) and OVCAR-8 (human ovarian carcinoma cells). Some compounds showed IC50values < 0.3 μM. The cytotoxic potential of the quinones evaluated was also assayed using non-tumor cells, exemplified by peripheral blood mononuclear (PBMC), V79 and L929 cells. Mechanistic role for NAD(P)H:Quinone Oxidoreductase 1 (NQO1) was also elucidated. These compounds could provide promising new lead derivatives for more potent anticancer drug development and delivery, and represent one of the most active classes of lapachones reported.
AB - Selenium-containing quinone-based 1,2,3-triazoles were synthesized using click chemistry, the copper catalyzed azide-alkyne 1,3-dipolar cycloaddition, and evaluated against six types of cancer cell lines: HL-60 (human promyelocytic leukemia cells), HCT-116 (human colon carcinoma cells), PC3 (human prostate cells), SF295 (human glioblastoma cells), MDA-MB-435 (melanoma cells) and OVCAR-8 (human ovarian carcinoma cells). Some compounds showed IC50values < 0.3 μM. The cytotoxic potential of the quinones evaluated was also assayed using non-tumor cells, exemplified by peripheral blood mononuclear (PBMC), V79 and L929 cells. Mechanistic role for NAD(P)H:Quinone Oxidoreductase 1 (NQO1) was also elucidated. These compounds could provide promising new lead derivatives for more potent anticancer drug development and delivery, and represent one of the most active classes of lapachones reported.
KW - Chalcogens
KW - Click chemistry
KW - Quinone
KW - Selenium
KW - β-Lapachone
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U2 - 10.1016/j.ejmech.2016.06.019
DO - 10.1016/j.ejmech.2016.06.019
M3 - Article
C2 - 27341379
AN - SCOPUS:84975261053
SN - 0223-5234
VL - 122
SP - 1
EP - 16
JO - European Journal of Medicinal Chemistry
JF - European Journal of Medicinal Chemistry
ER -