Synthesis, anticancer activity, and mechanistic investigations of aryl-alkyl diorganotin arylformylhydrazone complexes.

J Inorg Biochem

Key Laboratory of Green Chemistry, Jiangxi Province, College of Chemistry and Materials, Jiangxi Normal University, Nanchang, Jiangxi 330022, China. Electronic address:

Published: January 2025

AI Article Synopsis

  • Diorganotin acylhydrazone complexes show promise as alternatives to platinum-based drugs due to their strong anticancer effects.
  • Twelve such complexes were synthesized using a quick "one-pot" microwave method and thoroughly analyzed using various techniques like FT-IR and NMR.
  • Among the tested complexes, complex 8 was most effective against HepG2 cancer cells, demonstrating its ability to induce cell death through mitochondrial pathways and halt the cell cycle at the G2/M phase.

Article Abstract

Diorganotin acylhydrazone complexes with mitochondrial targeting demonstrate significant potential as replacements for platinum-based complexes due to their potent anticancer properties. Twelve methylphenyltin arylformylhydrazone complexes have been synthesized by microwave "one-pot" reaction. The complexes have been characterized by FT-IR, multinuclear NMR (H, C, and Sn), TGA, and HRMS. Crystal structures were determined for 10 out of the 12 complexes under study. Structures 1 through 8, 10 and 12 possessed a central symmetric structure of a di-nuclear SnO tetrahedral ring. All complexes were tested for their inhibitory activity against human cell lines NCI-H460, MCF-7, and HepG2. Complex 8 exhibited the most effective inhibitory effect on HepG2 cells, with an IC value of 1.34 ± 0.04 μM. Preliminary studies on the anticancer mechanism suggest that complex 8 induces apoptosis in HepG2 cells via the mitochondrial pathway, accompanied by G2/M phase cell cycle arrest.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.jinorgbio.2024.112756DOI Listing

Publication Analysis

Top Keywords

arylformylhydrazone complexes
8
hepg2 cells
8
complexes
7
synthesis anticancer
4
anticancer activity
4
activity mechanistic
4
mechanistic investigations
4
investigations aryl-alkyl
4
aryl-alkyl diorganotin
4
diorganotin arylformylhydrazone
4

Similar Publications

Synthesis, anticancer activity, and mechanistic investigations of aryl-alkyl diorganotin arylformylhydrazone complexes.

J Inorg Biochem

January 2025

Key Laboratory of Green Chemistry, Jiangxi Province, College of Chemistry and Materials, Jiangxi Normal University, Nanchang, Jiangxi 330022, China. Electronic address:

Article Synopsis
  • Diorganotin acylhydrazone complexes show promise as alternatives to platinum-based drugs due to their strong anticancer effects.
  • Twelve such complexes were synthesized using a quick "one-pot" microwave method and thoroughly analyzed using various techniques like FT-IR and NMR.
  • Among the tested complexes, complex 8 was most effective against HepG2 cancer cells, demonstrating its ability to induce cell death through mitochondrial pathways and halt the cell cycle at the G2/M phase.
View Article and Find Full Text PDF

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

Bioorg Chem

August 2024

Key Laboratory of Green Chemistry, Jiangxi Province, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, China. Electronic address:

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.

View Article and Find Full Text PDF

Synthesis, crystal structures, and biological activity of aroylhydrazone di-m-chlorobenzyltin complexes.

J Biol Inorg Chem

February 2024

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, 421008, Hunan, China.

Six aroylhydrazone di-m-chlorobenzyltin complexes {[X-CH(O)C=N-N=C(Me)COO](MeOH)(m-Cl-CHCH)Sn} (X = p-Me- (1), p-MeO- (2), p-t-Bu- (3), p-NO- (4), p-OH- (5) or o-OH- (6)) were synthesized and characterized by HRMS (high-resolution mass spectrometry), NMR (nuclear magnetic resonance spectroscopy), IR (Fourier transform infrared spectroscopy), and TGA (thermogravimetric analysis) techniques. The molecular structure of complexes 1-6 was confirmed by single-crystal X-ray crystallography. The structure of complexes showed a distorted pentagonal bipyramidal configuration around the tin atom center, and the ligands adopted a tridentate chelating mode.

View Article and Find Full Text PDF

Self-assembly synthesis of diorganotin complexes based on arylformylhydrazone possessing ONO donor set: anticancer activity and mechanism.

Metallomics

May 2022

Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Organometallic New Materials, College of Hunan Province, Hunan Provincial Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the Upper Reaches of XiangJiang River, College of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421008, China.

Fourteen new organotin(IV) complexes were successfully synthesized and characterized by elemental analyses, Fourier transform infrared spectroscopy (FT-IR), multinuclear (1H, 13C, and 119Sn) NMR spectroscopy, high-resolution mass spectrometry (HRMS), and X-ray single-crystal techniques. Crystallographic data showed that the complexes 1b, 2b, 3b, and 5b were macrocyclic compounds, 4b exhibited a one-dimensional spiral chain structure with distorted trigonal bipyramidal geometry, other complexes were centrosymmetric dimers, and there was an Sn2O2 four-membered ring in the middle of the molecule. In-vitro anticancer activity against the three human tumor cell lines NCI-H460, MCF-7, and HepG2 was studied, and the dibutyltin complex 5a is a more potent antitumor agent than other complexes and cisplatin.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!