Chrysin-piperazine conjugates as antioxidant and anticancer agents

0461628 - ÚEB 2017 RIV NL eng J - Journal Article
Patel, Rahul V. - Mistry, B.M. - Syed, R. - Rathi, A.K. - Lee, Y. J. - Sung, J.S. - Shinf, H.S. - Keum, Y.S.
Chrysin-piperazine conjugates as antioxidant and anticancer agents.
European Journal of Pharmaceutical Sciences. Roč. 88, JUN 10 (2016), s. 166-177. ISSN 0928-0987. E-ISSN 1879-0720
R&D Projects: GA MŠMT(CZ) LO1204
Institutional support: RVO:61389030
Keywords : Chrysin * Antioxidant * Piperazines
Subject RIV: EB - Genetics ; Molecular Biology
Impact factor: 3.756, year: 2016

Synthesis of 7-(4-bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one intermediate treating chrysin with 1,4-dibromobutane facilitated combination of chrysin with a wide range of piperazine moieties which were equipped via reacting the corresponding amines with bis(2-chloroethyl) amine hydrochloride in diethylene glycol monomethyl ether solvent. Free radical scavenging potential of prepared products was analyzed in vitro adopting DPPH and ABTS bioassay in addition to the evaluation of in vitro anticancer efficacies against cervical cancer cell lines (HeLa and CaSki) and an ovarian cancer cell line SK-OV-3 using SRB assay. Bearable toxicity of 7a-w was examined employing Madin-Darby canine kidney (MDCK) cell line. In addition, cytotoxic nature of the presented compounds was inspected utilizing Human bone marrow derived mesenchymal stem cells (hBM-MSCs). Overall, 7a-w indicated remarkable antioxidant power in scavenging DPPH. and ABTS(+), particularly analogs 7f, 7j, 7k, 7l, 7n, 7q, 7v, 7w have shown promising free radical scavenging activity. Analogs 7j and 7o are identified to be highly active candidates against HeLa and CaSki cell lines, whereas 7h and 7l along with 7j proved to be very sensitive towards ovarian cancer cell line SKOV-3. None of the newly prepared scaffolds showed cytotoxic nature toward hBM-MSCs cells. From the structure-activity point of view, nature and position of the electron withdrawing and electron donating functional groups on the piperazine core may contribute to the anticipated antioxidant and anticancer action. Different spectroscopic techniques (FT-IR, H-1 NMR, C-13 NMR, Mass) and elemental analysis (CHN) were utilized to confirm the desired structure of final compounds.
Permanent Link: http://hdl.handle.net/11104/0261227