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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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 |
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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 |
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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. |
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School of Physical and Mathematical Sciences |
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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 |
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Article |
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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 |
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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 |
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2013 |
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https://hdl.handle.net/10356/99767 http://hdl.handle.net/10220/17572 |
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1681043747988570112 |