Synthesis, Structure, and Properties of a Copper(II) Binuclear Complex Based on Trifluoromethyl Containing Bis(pyrazolyl)hydrazone

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2024 Sep 14

PMID 39273361

Authors

Olga G Shakirova

Tatiana D Morozova

Yulia S Kudyakova

Denis N Bazhin

Natalia V Kuratieva

Lyubov S Klyushova

Alexander N Lavrov

Lyudmila G Lavrenova

Affiliations

Soon will be listed here.

Abstract

A new complex of copper(II) with methyl-5-(trifluoromethyl)pyrazol-3-yl-ketazine (HL) was synthesized with the composition [CuL]∙CHOH (). Recrystallization of the sample from DMSO yielded a single crystal of the composition [CuL((CH)SO)] (). The coordination compounds were studied by single-crystal X-ray diffraction analysis, IR spectroscopy, and static magnetic susceptibility method. The data obtained indicate that the polydentate ligand is coordinated by both acyclic nitrogen and heterocyclic nitrogen atoms. The cytotoxic activity of the ligand and complex was investigated on human cell lines MCF7 (breast adenocarcinoma), Hep2 (laryngeal carcinoma), A549 (lung carcinoma), HepG2 (hepatocellular carcinoma), and MRC5 (non-tumor lung fibroblasts). The complex was shown to have a pronounced dose-dependent cytotoxicity towards these cell lines with LC values in the range of 0.18-4.03 μM.

References

Dias H, Singh S, Campana C . Toluene-sandwiched trinuclear copper(I) and silver(I) triazolates and phosphine adducts of dinuclear copper(I) and silver(I) triazolates. Inorg Chem. 2008; 47(10):3943-5. DOI: 10.1021/ic800396t. View

Indrayanto G, Putra G, Suhud F . Validation of in-vitro bioassay methods: Application in herbal drug research. Profiles Drug Subst Excip Relat Methodol. 2021; 46:273-307. DOI: 10.1016/bs.podrm.2020.07.005. View

Zhao X, Verma R, Sridhara M, Sharath Kumar K . Fluorinated azoles as effective weapons in fight against methicillin-resistance staphylococcus aureus (MRSA) and its SAR studies. Bioorg Chem. 2023; 143:106975. DOI: 10.1016/j.bioorg.2023.106975. View

Johnson B, Shu Y, Zhuo X, Meanwell N . Metabolic and Pharmaceutical Aspects of Fluorinated Compounds. J Med Chem. 2020; 63(12):6315-6386. DOI: 10.1021/acs.jmedchem.9b01877. View

Mathivathanan L, Rogez G, Ben Amor N, Robert V, Raptis R, Boudalis A . Origin of Ferromagnetism and Magnetic Anisotropy in a Family of Copper(II) Triangles. Chemistry. 2020; 26(56):12769-12784. DOI: 10.1002/chem.202001028. View

Link J, Rhee M, Tse W, Zheng J, Somoza J, Rowe W . Clinical targeting of HIV capsid protein with a long-acting small molecule. Nature. 2020; 584(7822):614-618. PMC: 8188729. DOI: 10.1038/s41586-020-2443-1. View

Verma R, Verma S, Rakesh K, Girish Y, Ashrafizadeh M, Sharath Kumar K . Pyrazole-based analogs as potential antibacterial agents against methicillin-resistance staphylococcus aureus (MRSA) and its SAR elucidation. Eur J Med Chem. 2021; 212:113134. DOI: 10.1016/j.ejmech.2020.113134. View

Dias H, Lovely C . Carbonyl and olefin adducts of coinage metals supported by poly(pyrazolyl)borate and poly(pyrazolyl)alkane ligands and silver mediated atom transfer reactions. Chem Rev. 2008; 108(8):3223-38. DOI: 10.1021/cr078362d. View

Khan M, Alam M, Verma G, Akhtar W, Akhter M, Shaquiquzzaman M . The therapeutic voyage of pyrazole and its analogs: A review. Eur J Med Chem. 2016; 120:170-201. DOI: 10.1016/j.ejmech.2016.04.077. View

10.

Mykhailiuk P . Fluorinated Pyrazoles: From Synthesis to Applications. Chem Rev. 2020; 121(3):1670-1715. DOI: 10.1021/acs.chemrev.0c01015. View

11.

Liu H, Zhu Y, Chi Y, Sun F, Shan L, Wang Y . Synthetic approaches and application of representative clinically approved fluorine-enriched anti-cancer medications. Eur J Med Chem. 2024; 276:116722. DOI: 10.1016/j.ejmech.2024.116722. View

12.

Wang J, Liu Y, Liu C, Chen J, Yang G . An efficient mixed-valence copper pyrazolate catalyst for the conversion of carbon dioxide and epoxides into cyclic carbonates. Dalton Trans. 2023; 52(27):9275-9281. DOI: 10.1039/d3dt00844d. View

13.

Abdelhaleem E, Kassab A, El-Nassan H, Khalil O . Recent advances in the development of celecoxib analogs as anticancer agents: A review. Arch Pharm (Weinheim). 2022; 355(12):e2200326. DOI: 10.1002/ardp.202200326. View

14.

Zhang Y, Wu C, Zhang N, Fan R, Ye Y, Xu J . Recent Advances in the Development of Pyrazole Derivatives as Anticancer Agents. Int J Mol Sci. 2023; 24(16). PMC: 10454718. DOI: 10.3390/ijms241612724. View

15.

Lusardi M, Spallarossa A, Brullo C . Amino-Pyrazoles in Medicinal Chemistry: A Review. Int J Mol Sci. 2023; 24(9). PMC: 10177828. DOI: 10.3390/ijms24097834. View

16.

Xhafa S, Olivieri L, Di Nicola C, Pettinari R, Pettinari C, Tombesi A . Copper and Zinc Metal-Organic Frameworks with Bipyrazole Linkers Display Strong Antibacterial Activity against Both Gram+ and Gram- Bacterial Strains. Molecules. 2023; 28(16). PMC: 10459509. DOI: 10.3390/molecules28166160. View

17.

Clemett D, Goa K . Celecoxib: a review of its use in osteoarthritis, rheumatoid arthritis and acute pain. Drugs. 2000; 59(4):957-80. DOI: 10.2165/00003495-200059040-00017. View

18.

Bennani F, Doudach L, Cherrah Y, Ramli Y, Karrouchi K, Ansar M . Overview of recent developments of pyrazole derivatives as an anticancer agent in different cell line. Bioorg Chem. 2020; 97:103470. DOI: 10.1016/j.bioorg.2019.103470. View

19.

Karrouchi K, Radi S, Ramli Y, Taoufik J, Mabkhot Y, Al-Aizari F . Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review. Molecules. 2018; 23(1). PMC: 6017056. DOI: 10.3390/molecules23010134. View

20.

Sheldrick G . Crystal structure refinement with SHELXL. Acta Crystallogr C Struct Chem. 2015; 71(Pt 1):3-8. PMC: 4294323. DOI: 10.1107/S2053229614024218. View