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·xH 2O...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Royal Society of Chemistry
2013
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| Online Access: | http://psasir.upm.edu.my/id/eprint/28122/ http://psasir.upm.edu.my/id/eprint/28122/1/Ternary%20copper.pdf |
| _version_ | 1848846028957024256 |
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| author | Ng, Chew Hee Wang, Wai San Chong, Kok Vei Win, Yip Foo Neo, Kian Eang Lee, Hong Boon San, Swee Lan Raja Abdul Rahman, Raja Noor Zaliha Leong, Weng Kee |
| author_facet | Ng, Chew Hee Wang, Wai San Chong, Kok Vei Win, Yip Foo Neo, Kian Eang Lee, Hong Boon San, Swee Lan Raja Abdul Rahman, Raja Noor Zaliha Leong, Weng Kee |
| author_sort | Ng, Chew Hee |
| building | UPM Institutional Repository |
| collection | Online Access |
| 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·xH 2O (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. |
| first_indexed | 2025-11-15T08:56:12Z |
| format | Article |
| id | upm-28122 |
| institution | Universiti Putra Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T08:56:12Z |
| publishDate | 2013 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | upm-281222016-09-28T03:52:22Z http://psasir.upm.edu.my/id/eprint/28122/ 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 Abdul Rahman, Raja Noor Zaliha Leong, Weng Kee 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·xH 2O (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. Royal Society of Chemistry 2013-07-28 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/28122/1/Ternary%20copper.pdf Ng, Chew Hee and Wang, Wai San and Chong, Kok Vei and Win, Yip Foo and Neo, Kian Eang and Lee, Hong Boon and San, Swee Lan and Raja Abdul Rahman, Raja Noor Zaliha and Leong, Weng Kee (2013) Ternary copper(II)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property. Dalton Transactions, 42 (28). pp. 10233-10243. ISSN 1477-9226; ESSN: 1477-9234 10.1039/c3dt50884f |
| spellingShingle | Ng, Chew Hee Wang, Wai San Chong, Kok Vei Win, Yip Foo Neo, Kian Eang Lee, Hong Boon San, Swee Lan Raja Abdul Rahman, Raja Noor Zaliha Leong, Weng Kee Ternary copper(II)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property |
| title | 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_short | 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 |
| url | http://psasir.upm.edu.my/id/eprint/28122/ http://psasir.upm.edu.my/id/eprint/28122/ http://psasir.upm.edu.my/id/eprint/28122/1/Ternary%20copper.pdf |