Design, synthesis and mechanistic studies of novel arylformylhydrazone butylphenyltin complexes as potential anticancer agents.

Autor: Jiang W; Key Laboratory of Green Chemistry, Jiangxi Province, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, China; Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Organometallic New Materials, College of Hunan Province, College of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421008, China. Electronic address: jwj_china@163.com., Fan S; Department of Breast and Thyroid Surgery, The First Affiliated Hospital, Hengyang Medical School, University of South China, Hengyang, Hunan 421000, China., Zhu Z; Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Organometallic New Materials, College of Hunan Province, College of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421008, China., Huang H; Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Organometallic New Materials, College of Hunan Province, College of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421008, China., Tan Y; Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Organometallic New Materials, College of Hunan Province, College of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421008, China., Peng Y; Key Laboratory of Green Chemistry, Jiangxi Province, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, China. Electronic address: yypeng@jxnu.edu.cn.
Jazyk: angličtina
Zdroj: Bioorganic chemistry [Bioorg Chem] 2024 Aug; Vol. 149, pp. 107502. Date of Electronic Publication: 2024 May 26.
DOI: 10.1016/j.bioorg.2024.107502
Abstrakt: Many diorganotin complexes with various alkyl groups exhibit excellent in vitro anticancer activity. However, most diorganotin is the same alkyl group, and the asymmetric alkyl R group has been rarely reported. Hence, in this paper, twenty butylphenyl mixed dialkyltin arylformylhydrazone complexes have been synthesized by microwave "one-pot" reaction with arylformylhydrazine, substituted α-keto acid or its sodium salt and butylphenyltin dichloride. The crystal structures of nine complexes were determined, indicating that the complexes C1, C2, C11, C12, and C16 ∼ C19 possessed a central symmetric structure of a dinuclear Sn 2 O 2 tetrahedral ring; while the complex C9 is a trinuclear tin-oxygen cluster with a 6-membered ring encased in a 12-membered macrocyclic structure. The inhibiting activity of complexes was tested against the human cell lines NCI-H460, MCF-7, HepG2, Huh-7 and HL-7702. Complex C2 demonstrated the optimal inhibitory effect on HepG2 cells, with an IC 50 value of 0.82 ± 0.03 μM. Cellular biology experiments revealed that complex C2 could induce apoptosis and G2/M phase cell cycle arrest in HepG2 and Huh-7 cells. The complex also caused the collapse of the mitochondrial membrane potential and increased intracellular reactive oxygen species in HepG2 and Huh-7 cells. Western blot analysis further clarified that complex C2 could induce cell apoptosis through the mitochondrial pathway along with the release of reactive oxygen species.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2024 Elsevier Inc. All rights reserved.)
Databáze: MEDLINE
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