Enantiomeric pairs of copper(II) polypyridyl-alanine complex salts: anticancer studies

The anticancer properties of two previously characterized pairs of optically pure chiral complex salts [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; x = number of lattice water molecules)...

Full description

Bibliographic Details
Main Authors: Ng, Pei Ying, Chye, Soi Moi, Tiong, Yee Liang, Chan, Cheang Wei, Tan, Kong Wai, Ooi, Ing Hong, Ng, Chew Hee
Format: Article
Published: Springer Verlag 2018
Subjects:
_version_ 1796961373415014400
author Ng, Pei Ying
Chye, Soi Moi
Tiong, Yee Liang
Chan, Cheang Wei
Tan, Kong Wai
Ooi, Ing Hong
Ng, Chew Hee
author_facet Ng, Pei Ying
Chye, Soi Moi
Tiong, Yee Liang
Chan, Cheang Wei
Tan, Kong Wai
Ooi, Ing Hong
Ng, Chew Hee
author_sort Ng, Pei Ying
collection UM
description The anticancer properties of two previously characterized pairs of optically pure chiral complex salts [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; x = number of lattice water molecules) are reported herein, together with the crystal structure of the d-enantiomer 4. Unlike cisplatin which is ineffective against MCF-7 cancer cells with the absence of caspase-3 protein expression, these two pairs of complex salts were effective against this cell line and they were able to induce an increase in intracellular ROS, loss in mitochondrial membrane potential, cell cycle arrest mainly at SubG1 phase , caspase-9 activation, and caspase-3/caspase-7-independent apoptosis. Screening of 1 on the NCI-60 panel of human cancer cell lines showed that it was effective against most of the cell lines. MTT-NCI modified assay screening was also done on other cancer cell lines, viz. A549, CNE1, and HepG2, and two normal cell lines, viz. MCF-10A and CHANG. The effects of chirality of these Cu(II) compounds, especially the greater selectivity of d-enantiomers over the l-counterparts, on their anticancer properties are also reported herein.
first_indexed 2024-03-06T05:53:17Z
format Article
id um.eprints-21141
institution Universiti Malaya
last_indexed 2024-03-06T05:53:17Z
publishDate 2018
publisher Springer Verlag
record_format dspace
spelling um.eprints-211412019-05-07T06:40:42Z http://eprints.um.edu.my/21141/ Enantiomeric pairs of copper(II) polypyridyl-alanine complex salts: anticancer studies Ng, Pei Ying Chye, Soi Moi Tiong, Yee Liang Chan, Cheang Wei Tan, Kong Wai Ooi, Ing Hong Ng, Chew Hee Q Science (General) QD Chemistry The anticancer properties of two previously characterized pairs of optically pure chiral complex salts [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; x = number of lattice water molecules) are reported herein, together with the crystal structure of the d-enantiomer 4. Unlike cisplatin which is ineffective against MCF-7 cancer cells with the absence of caspase-3 protein expression, these two pairs of complex salts were effective against this cell line and they were able to induce an increase in intracellular ROS, loss in mitochondrial membrane potential, cell cycle arrest mainly at SubG1 phase , caspase-9 activation, and caspase-3/caspase-7-independent apoptosis. Screening of 1 on the NCI-60 panel of human cancer cell lines showed that it was effective against most of the cell lines. MTT-NCI modified assay screening was also done on other cancer cell lines, viz. A549, CNE1, and HepG2, and two normal cell lines, viz. MCF-10A and CHANG. The effects of chirality of these Cu(II) compounds, especially the greater selectivity of d-enantiomers over the l-counterparts, on their anticancer properties are also reported herein. Springer Verlag 2018 Article PeerReviewed Ng, Pei Ying and Chye, Soi Moi and Tiong, Yee Liang and Chan, Cheang Wei and Tan, Kong Wai and Ooi, Ing Hong and Ng, Chew Hee (2018) Enantiomeric pairs of copper(II) polypyridyl-alanine complex salts: anticancer studies. Transition Metal Chemistry, 43 (6). pp. 479-496. ISSN 0340-4285, DOI https://doi.org/10.1007/s11243-018-0234-4 <https://doi.org/10.1007/s11243-018-0234-4>. https://doi.org/10.1007/s11243-018-0234-4 doi:10.1007/s11243-018-0234-4
spellingShingle Q Science (General)
QD Chemistry
Ng, Pei Ying
Chye, Soi Moi
Tiong, Yee Liang
Chan, Cheang Wei
Tan, Kong Wai
Ooi, Ing Hong
Ng, Chew Hee
Enantiomeric pairs of copper(II) polypyridyl-alanine complex salts: anticancer studies
title Enantiomeric pairs of copper(II) polypyridyl-alanine complex salts: anticancer studies
title_full Enantiomeric pairs of copper(II) polypyridyl-alanine complex salts: anticancer studies
title_fullStr Enantiomeric pairs of copper(II) polypyridyl-alanine complex salts: anticancer studies
title_full_unstemmed Enantiomeric pairs of copper(II) polypyridyl-alanine complex salts: anticancer studies
title_short Enantiomeric pairs of copper(II) polypyridyl-alanine complex salts: anticancer studies
title_sort enantiomeric pairs of copper ii polypyridyl alanine complex salts anticancer studies
topic Q Science (General)
QD Chemistry
work_keys_str_mv AT ngpeiying enantiomericpairsofcopperiipolypyridylalaninecomplexsaltsanticancerstudies
AT chyesoimoi enantiomericpairsofcopperiipolypyridylalaninecomplexsaltsanticancerstudies
AT tiongyeeliang enantiomericpairsofcopperiipolypyridylalaninecomplexsaltsanticancerstudies
AT chancheangwei enantiomericpairsofcopperiipolypyridylalaninecomplexsaltsanticancerstudies
AT tankongwai enantiomericpairsofcopperiipolypyridylalaninecomplexsaltsanticancerstudies
AT ooiinghong enantiomericpairsofcopperiipolypyridylalaninecomplexsaltsanticancerstudies
AT ngchewhee enantiomericpairsofcopperiipolypyridylalaninecomplexsaltsanticancerstudies