Synthesis, characterization and anticancer activity of novel hydrazide-hydrazones derived from ethyl paraben

• Published in: Journal of Research in Pharmacy 2020-01, Vol.24 (3), p.341-349
• Main Authors: ATALAY, Pınar, İMAMOĞLU, Nalan, KÜÇÜKGÜZEL, Ş. Güniz, HAN, M. İhsan
• Format: Article
• Language: English
• Subjects: Liver cancer
• ISSN: 2630-6344; 2630-6344
• DOI: 10.35333/jrp.2020.156

Parabens, which are hydroxybenzoic acid esters, are particularly used as protective against mold and fungus. Ethyl paraben is a compound open to modification for the synthesis of new molecules due to the ester group in its structure. In this study, ethyl paraben was used as a starting material. A new series of novel hydrazide-hydrazones from derived ethyl paraben were synthesized and characterized by spectroscopic techniques such as NMR, FT-IR besides elemental analysis. In order to determine the anticancer activity of the aimed ethyl paraben hydrazide-hydrazones we evaluated their cytotoxic activity on liver cancer cell line liver hepatocellular carcinoma (HepG2). Herein we described several 4-hydroxy-N'-[substituted methylidene] benzohydrazides (3a-j) as anticancer agents. We designed, synthesized and characterized the series of novel hydrazide-hydrazones from ethyl paraben. All of the compounds evaluated for anticancer activity by using MTT assay for 24 and 48 h. mRNA transcription levels of Bax, Bcl-2 and caspase-3 genes were determined by realtime polymerase chain reaction (qRT-PCR) analysis. Compounds 3i and 3j showed anticancer activity with 42.4 and 37.4 μM IC50 values, respectively. Doxorubicin was used as a positive sensitivity reference standard. qRTPCR analysis approved that there was a timedependent rise in the expression levels of Bax, Bcl-2 and Caspase 3 on apoptosis. The activities of the synthesized compounds changed depending on the dose and time of treatment and some of the molecules started to show activity within 48 hours.