Ternary copper(ii)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property

Chiral enantiomers [Cu(phen)(L-threo)(H2O)]NO31 and [Cu(phen)(D-threo)(H2O)]NO32 (threo = threoninate) underwent aldol-type condensation with formaldehyde, with retention of chirality, to yield their respective enantiomeric ternary copper(II) complexes, viz.L- and D-[Cu(phen)(5MeOCA)(H2O)]NO3·xH2O (...

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Main Authors: Ng, Chew-Hee, Wang, Wai-San, Chong, Kok-Vei, Win, Yip-Foo, Neo, Kian-Eang, Lee, Hong-Boon, San, Swee-Lan, Raja Abd. Rahman, Raja Noor Zaliha, Leong, Weng Kee
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2013
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Online Access:https://hdl.handle.net/10356/99767
http://hdl.handle.net/10220/17572
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Institution: Nanyang Technological University
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spelling sg-ntu-dr.10356-997672020-03-07T12:34:48Z Ternary copper(ii)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property Ng, Chew-Hee Wang, Wai-San Chong, Kok-Vei Win, Yip-Foo Neo, Kian-Eang Lee, Hong-Boon San, Swee-Lan Raja Abd. Rahman, Raja Noor Zaliha Leong, Weng Kee School of Physical and Mathematical Sciences Chemistry and Biological Chemistry Chiral enantiomers [Cu(phen)(L-threo)(H2O)]NO31 and [Cu(phen)(D-threo)(H2O)]NO32 (threo = threoninate) underwent aldol-type condensation with formaldehyde, with retention of chirality, to yield their respective enantiomeric ternary copper(II) complexes, viz.L- and D-[Cu(phen)(5MeOCA)(H2O)]NO3·xH2O (3 and 4; phen = 1,10-phenanthroline; 5MeOCA = 5-methyloxazolidine-4-carboxylate; x = 0–3) respectively. These chiral complexes were characterized by FTIR, elemental analysis, circular dichroism, UV-Visible spectroscopy, fluorescence spectroscopy (FL), molar conductivity measurement, ESI-MS and X-ray crystallography. Analysis of restriction enzyme inhibition by these four complexes revealed modulation of DNA binding selectivity by the type of ligand, ligand modification and chirality. Their interaction with bovine serum albumin was investigated by FL and electronic spectroscopy. With the aid of the crystal structure of BSA, spectroscopic evidence suggested their binding at the cavity containing Trp134 with numerous Tyr residues in subdomain IA. The products were more antiproliferative than cisplatin against cancer cell lines HK-1, MCF-7, HCT116, HSC-2 and C666-1 except HL-60, and were selective towards nasopharyngeal cancer HK-1 cells over normal NP69 cells of the same organ type. 2013-11-11T05:27:52Z 2019-12-06T20:11:11Z 2013-11-11T05:27:52Z 2019-12-06T20:11:11Z 2013 2013 Journal Article Ng, C.-H., Wang, W.-S., Chong, K.-V., Win, Y.-F., Neo, K.-E., Lee, H.-B., et al. (2013). Ternary copper(ii)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property. Dalton Transactions, 42(28), 10233-10243. https://hdl.handle.net/10356/99767 http://hdl.handle.net/10220/17572 10.1039/c3dt50884f en Dalton transactions
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic Chemistry and Biological Chemistry
spellingShingle Chemistry and Biological Chemistry
Ng, Chew-Hee
Wang, Wai-San
Chong, Kok-Vei
Win, Yip-Foo
Neo, Kian-Eang
Lee, Hong-Boon
San, Swee-Lan
Raja Abd. Rahman, Raja Noor Zaliha
Leong, Weng Kee
Ternary copper(ii)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property
description Chiral enantiomers [Cu(phen)(L-threo)(H2O)]NO31 and [Cu(phen)(D-threo)(H2O)]NO32 (threo = threoninate) underwent aldol-type condensation with formaldehyde, with retention of chirality, to yield their respective enantiomeric ternary copper(II) complexes, viz.L- and D-[Cu(phen)(5MeOCA)(H2O)]NO3·xH2O (3 and 4; phen = 1,10-phenanthroline; 5MeOCA = 5-methyloxazolidine-4-carboxylate; x = 0–3) respectively. These chiral complexes were characterized by FTIR, elemental analysis, circular dichroism, UV-Visible spectroscopy, fluorescence spectroscopy (FL), molar conductivity measurement, ESI-MS and X-ray crystallography. Analysis of restriction enzyme inhibition by these four complexes revealed modulation of DNA binding selectivity by the type of ligand, ligand modification and chirality. Their interaction with bovine serum albumin was investigated by FL and electronic spectroscopy. With the aid of the crystal structure of BSA, spectroscopic evidence suggested their binding at the cavity containing Trp134 with numerous Tyr residues in subdomain IA. The products were more antiproliferative than cisplatin against cancer cell lines HK-1, MCF-7, HCT116, HSC-2 and C666-1 except HL-60, and were selective towards nasopharyngeal cancer HK-1 cells over normal NP69 cells of the same organ type.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Ng, Chew-Hee
Wang, Wai-San
Chong, Kok-Vei
Win, Yip-Foo
Neo, Kian-Eang
Lee, Hong-Boon
San, Swee-Lan
Raja Abd. Rahman, Raja Noor Zaliha
Leong, Weng Kee
format Article
author Ng, Chew-Hee
Wang, Wai-San
Chong, Kok-Vei
Win, Yip-Foo
Neo, Kian-Eang
Lee, Hong-Boon
San, Swee-Lan
Raja Abd. Rahman, Raja Noor Zaliha
Leong, Weng Kee
author_sort Ng, Chew-Hee
title Ternary copper(ii)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property
title_short Ternary copper(ii)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property
title_full Ternary copper(ii)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property
title_fullStr Ternary copper(ii)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property
title_full_unstemmed Ternary copper(ii)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property
title_sort ternary copper(ii)-polypyridyl enantiomers: aldol-type condensation, characterization, dna-binding recognition, bsa-binding and anticancer property
publishDate 2013
url https://hdl.handle.net/10356/99767
http://hdl.handle.net/10220/17572
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