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Synthesis of Triphenylethylene‐Naphthalimide Conjugates as topoisomerase‐IIα inhibitor and HSA binder
Author(s) -
Rani Sudesh,
Luxami Vijay,
Paul Kamaldeep
Publication year - 2021
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.202100034
Subject(s) - conjugate , chemistry , topoisomerase , pharmacology , combinatorial chemistry , stereochemistry , biochemistry , medicine , enzyme , mathematical analysis , mathematics
A series of triphenylethylene‐naphthalimide (TPE‐naph) conjugates was synthesized by a molecular hybridization technique, and their anticancer activity was evaluated in vitro on 60 human cancer cell lines through their cytotoxicity. The ratios of E and Z isomers were determined on the basis of HPLC methodology and NMR spectroscopy. The structure‐activity relationship for anticancer activity was deduced on the basis of the nature and bulkiness of the amine attached to the C‐4 position of the naphthalene ring. Experimental and molecular modeling studies of the most active TPE‐naph conjugate bearing a morpholinyl group showed that it was able to inhibit topoisomerase‐II (TOPO‐II) as a possible intracellular target. Moreover, the transportation behavior of TPE‐naph conjugate towards human serum albumin (HSA) indicated efficient binding affinity. The steady‐state and time‐dependent fluorescent results suggested that this conjugate quenched HSA significantly through static as well as dynamic quenching. Thus, this report discloses the scope of triphenylethylene‐naphthalimide (TPE‐naph) conjugates as efficient anticancer agents.