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Design, Synthesis and Bioevaluation of Novel N ‐Substituted‐3,5‐Bis(Arylidene)‐4‐piperidone Derivatives as Cytotoxic and Antitumor Agents with Fluorescent Properties
Author(s) -
Sun Jufeng,
Zhang Shuping,
Yu Chen,
Hou Guige,
Zhang Xiaofan,
Li Keke,
Zhao Feng
Publication year - 2014
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12254
Subject(s) - cytotoxic t cell , fluorescence , chemistry , stereochemistry , cytotoxicity , combinatorial chemistry , biochemistry , in vitro , physics , quantum mechanics
Ten new N ‐substituted‐3,5‐bis(arylidene)‐4‐piperidone derivatives (series 1 and 2 ) were synthesized and subsequently evaluated against human carcinoma cell lines SW 1990, MIA PaCa‐2, PG ‐ BE 1, NCI ‐H460, and SK ‐ BR ‐3 for cytotoxic activity by the CCK ‐8 method, and their fluorescent properties were investigated as well. The compounds were confirmed to display greater cytotoxic activity to the neoplastic cells, and approximately 50% of the IC 50 values were lower than 5 μ m . In particular, compounds 1a , 1c , 1d, and 1e bearing 3‐bromophenyl groups were revealed as the most active antitumor drug candidates and had the average IC 50 values of 1.94, 1.11, 1.16, and 0.817 μ m , respectively. Furthermore, their fluorescent properties were interesting and might contribute to the visualization of their distribution in tumor cells. Some possible reasons for the disparity between cytotoxic activity and fluorescent properties in the two series of compounds were explored. This study revealed high potential of these molecules for further development as fluorescent cytotoxic and antitumor agents.