Tetranuclear Cu(ii)-chiral Complexes: Synthesis, Characterization and Biological Activity

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 9

PMID 35527904

Authors

Krisana Peewasan

Marcel P Merkel

Kristof Zarschler

Holger Stephan

Christopher E Anson

Annie K Powell

Affiliations

Soon will be listed here.

Abstract

Tetranuclear chiral Cu(ii)-Schiff-base complexes S-1 and R-1, were synthesised using enantiomerically pure ()-(HvanPheol) and ()-(HvanPheol) ligands respectively in the ratio of 1 : 1 of Cu(NO) to (/)-(HvanPheol) in MeOH at room temperature. A pair of polynuclear chiral Cu(ii)-cluster complexes were characterized using single-crystal X-ray diffraction, elemental analysis, infrared and CD spectroscopy. The results revealed the importance of these chiral ligands encouraging the arrangement of copper metal in non-centrosymmetric polar packing. The potential of the novel [Cu(/-vanPheol)(/-HvanPheol)(CHOH)](NO) complexes as biologically active compounds was assessed in particular regarding their anti-proliferative and anti-microbial properties.

References

Yoshii J, Yoshiji H, Kuriyama S, Ikenaka Y, Noguchi R, Okuda H . The copper-chelating agent, trientine, suppresses tumor development and angiogenesis in the murine hepatocellular carcinoma cells. Int J Cancer. 2001; 94(6):768-73. DOI: 10.1002/ijc.1537. View

Pan Q, Kleer C, van Golen K, Irani J, Bottema K, Bias C . Copper deficiency induced by tetrathiomolybdate suppresses tumor growth and angiogenesis. Cancer Res. 2002; 62(17):4854-9. View

Shibata M, Nakajima K, Nishibayashi Y . Enantioselective intramolecular propargylic amination using chiral copper-pybox complexes as catalysts. Chem Commun (Camb). 2014; 50(58):7874-7. DOI: 10.1039/c4cc01676a. View

Hu G . Copper stimulates proliferation of human endothelial cells under culture. J Cell Biochem. 1998; 69(3):326-35. DOI: 10.1002/(sici)1097-4644(19980601)69:3<326::aid-jcb10>3.0.co;2-a. View

Griffith D, Parker J, Marmion C . Enzyme inhibition as a key target for the development of novel metal-based anti-cancer therapeutics. Anticancer Agents Med Chem. 2010; 10(5):354-70. DOI: 10.2174/1871520611009050354. View

Stacy A, Palanimuthu D, Bernhardt P, Kalinowski D, Jansson P, Richardson D . Zinc(II)-Thiosemicarbazone Complexes Are Localized to the Lysosomal Compartment Where They Transmetallate with Copper Ions to Induce Cytotoxicity. J Med Chem. 2016; 59(10):4965-84. DOI: 10.1021/acs.jmedchem.6b00238. View

Qin X, Yang L, Le F, Yu Q, Sun D, Liu Y . Structures and anti-cancer properties of two binuclear copper complexes. Dalton Trans. 2013; 42(41):14681-4. DOI: 10.1039/c3dt51548f. View

Graf N, Lippard S . Redox activation of metal-based prodrugs as a strategy for drug delivery. Adv Drug Deliv Rev. 2012; 64(11):993-1004. PMC: 3342443. DOI: 10.1016/j.addr.2012.01.007. View

Cox C, Teknos T, Barrios M, Brewer G, DICK R, Merajver S . The role of copper suppression as an antiangiogenic strategy in head and neck squamous cell carcinoma. Laryngoscope. 2001; 111(4 Pt 1):696-701. DOI: 10.1097/00005537-200104000-00024. View

10.

Zhou X, Sun Q, Jiang L, Li S, Gu W, Tian J . Synthesis, characterization, DNA/BSA interactions and anticancer activity of achiral and chiral copper complexes. Dalton Trans. 2015; 44(20):9516-27. DOI: 10.1039/c5dt00931f. View

11.

MacLachlan M, Park M, Thompson L . Coordination Compounds of Schiff-Base Ligands Derived from Diaminomaleonitrile (DMN): Mononuclear, Dinuclear, and Macrocyclic Derivatives. Inorg Chem. 1996; 35(19):5492-5499. DOI: 10.1021/ic960237p. View

12.

Ho Y, Au-Yeung S, To K . Platinum-based anticancer agents: innovative design strategies and biological perspectives. Med Res Rev. 2003; 23(5):633-55. DOI: 10.1002/med.10038. View

13.

Qin X, Wang Y, Yang X, Liang J, Liu J, Luo Z . Synthesis, characterization, and anticancer activity of two mixed ligand copper(ii) complexes by regulating the VEGF/VEGFR2 signaling pathway. Dalton Trans. 2017; 46(47):16446-16454. DOI: 10.1039/c7dt03242k. View

14.

Yoh K, Kubota K, Ohmatsu H, Goto K, Niho S, Ohe Y . Feasibility study of zoledronic acid plus cisplatin-docetaxel as first-line treatment for advanced non-small cell lung cancer with bone metastases. Anticancer Res. 2012; 32(9):4131-5. View

15.

Adao P, Kuznetsov M, Barroso S, Martins A, Avecilla F, Pessoa J . Amino alcohol-derived reduced Schiff base V(IV)O and V(V) compounds as catalysts for asymmetric sulfoxidation of thioanisole with hydrogen peroxide. Inorg Chem. 2012; 51(21):11430-49. DOI: 10.1021/ic301153p. View

16.

Rajesh C, Ray M . Characterization of a meso-chiral isomer of a hexanuclear Cu(II) cage from racemization of the L-alanine Schiff base. Dalton Trans. 2014; 43(34):12952-60. DOI: 10.1039/c4dt01443j. View

17.

Finney L, Vogt S, Fukai T, Glesne D . Copper and angiogenesis: unravelling a relationship key to cancer progression. Clin Exp Pharmacol Physiol. 2008; 36(1):88-94. PMC: 4230479. DOI: 10.1111/j.1440-1681.2008.04969.x. View

18.

Sen C, Khanna S, Venojarvi M, Trikha P, Ellison E, Hunt T . Copper-induced vascular endothelial growth factor expression and wound healing. Am J Physiol Heart Circ Physiol. 2002; 282(5):H1821-7. DOI: 10.1152/ajpheart.01015.2001. View

19.

Barry N, Sadler P . Exploration of the medical periodic table: towards new targets. Chem Commun (Camb). 2013; 49(45):5106-31. DOI: 10.1039/c3cc41143e. View

20.

Dasari S, Tchounwou P . Cisplatin in cancer therapy: molecular mechanisms of action. Eur J Pharmacol. 2014; 740:364-78. PMC: 4146684. DOI: 10.1016/j.ejphar.2014.07.025. View