Enantiomeric pair of copper(II) polypyridyl-alanine complexes: Effect of chirality on their interaction with biomolecules.

Autor: Ng CH; Department of Pharmaceutical Chemistry, School of Pharmacy, International Medical University, Bukit Jalil, 57000 Kuala Lumpur, Malaysia. Electronic address: NgChewHee@imu.edu.my., Chan CW; Department of Pharmaceutical Chemistry, School of Pharmacy, International Medical University, Bukit Jalil, 57000 Kuala Lumpur, Malaysia; Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia. Electronic address: estichan91@gmail.com., Lai JW; Department of Pharmaceutical Chemistry, School of Pharmacy, International Medical University, Bukit Jalil, 57000 Kuala Lumpur, Malaysia. Electronic address: janice_ljw_92@yahoo.com., Ooi IH; Department of Pharmaceutical Chemistry, School of Pharmacy, International Medical University, Bukit Jalil, 57000 Kuala Lumpur, Malaysia. Electronic address: inghong_ooi@imu.edu.my., Chong KV; Faculty of Science, Universiti Tunku Abdul Rahman, 31900 Kampar, Perak, Malaysia. Electronic address: Destiny.chong.james@gmail.com., Maah MJ; Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia. Electronic address: mjamil@um.edu.my., Seng HL; Department of Biological Sciences, Sunway University, 47500 Bandar Sunway, Malaysia. Electronic address: hoilings@sunway.edu.my.
Jazyk: angličtina
Zdroj: Journal of inorganic biochemistry [J Inorg Biochem] 2016 Jul; Vol. 160, pp. 1-11. Date of Electronic Publication: 2016 Apr 08.
DOI: 10.1016/j.jinorgbio.2016.04.003
Abstrakt: Like chiral organic drugs, the chemical and biological properties of metal complexes can be dependent on chirality. Two pairs of [Cu(phen)(ala)(H2O)]X·xH2O (phen=1.10-phenanthroline: X=NO3(-); ala: l-alanine (l-ala), 1 and d-alanine (d-ala) 2; and (X=Cl(-); ala: l-ala, 3 and d-ala, 4) complex salts (x=number of lattice water molecules) have been synthesized and characterized. The crystal structure of 3 has been determined. The same pair of enantiomeric species, viz. [Cu(phen)(l-ala)(H2O)](+) and [Cu(phen)(d-ala)(H2O)](+), have been identified to be present in the aqueous solutions of both 1 and 3, and in those of both 2 and 4 respectively. Both 3 and 4 bind more strongly to ds(AT)6 than ds(CG)6. There is no or insignificant effect of the chirality of 3 and 4 on the production of hydroxyl radicals, binding to deoxyribonucleic acid from calf thymus (CT-DNA), ds(CG)6, G-quadruplex and 17-base pair duplex, and inhibition of both topoisomerase I and proteasome. Among the three proteasome proteolytic sites, the trypsin-like site is inhibited most strongly by these complexes. However, the chirality of 3 and 4 does affect the number of restriction enzymes inhibited, and their binding constants towards ds(AT)6 and serum albumin.
(Copyright © 2016 Elsevier Inc. All rights reserved.)
Databáze: MEDLINE
Externí odkaz: