Group 6 photo-activable carbon monoxide-releasing molecules (PhotoCORMs) with 1'10-phenanthroline based ligand as potential anti-proliferative and anti-microbial agents

A new series of group 6 UV activable photoCORMs were synthesized by reacting the ligand (((1,10-phenanthroline-5-yl)imino)methyl)naphthalen-2-ol (1) with group 6 (Cr, Mo, and W) hexacarbonyl to form 2, 3, and 4, respectively. The structural elucidations of all compounds were conducted via IR, NMR, a...

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Main Authors: Lee, Shiaw Xian, Tan, Chun Hoe, Mah, Wee Li, Wong, Richard Chee Seng, Abdul Manan, Ninie Suhana, Cheow, Yuen Lin, Sim, Kae Shin, Tan, Kong Wai
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Published: Elsevier 2022
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Online Access:http://eprints.um.edu.my/42295/
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spelling my.um.eprints.422952023-10-09T01:55:33Z http://eprints.um.edu.my/42295/ Group 6 photo-activable carbon monoxide-releasing molecules (PhotoCORMs) with 1'10-phenanthroline based ligand as potential anti-proliferative and anti-microbial agents Lee, Shiaw Xian Tan, Chun Hoe Mah, Wee Li Wong, Richard Chee Seng Abdul Manan, Ninie Suhana Cheow, Yuen Lin Sim, Kae Shin Tan, Kong Wai QD Chemistry A new series of group 6 UV activable photoCORMs were synthesized by reacting the ligand (((1,10-phenanthroline-5-yl)imino)methyl)naphthalen-2-ol (1) with group 6 (Cr, Mo, and W) hexacarbonyl to form 2, 3, and 4, respectively. The structural elucidations of all compounds were conducted via IR, NMR, and CHN elemental analyses. The crystal structures of all the synthesized compounds were obtained and the half-life of the photoCORMs were determined by using the three-layered myoglobin solution assay. Results showed that the half-life of the compounds decreased down the group 6 in a concentration-dependent manner, with compound 2 displaying the shortest half-life (7.1 s) at 60 mu M. In the absence of UV light, compounds 1 and 3 showed cytotoxicity and selectivity against human-derived colorectal adenocarcinoma HT-29 and carcinoma HCT 116, with ligand 1 being the most cytotoxic compound. Nonetheless, most compounds were inactive against bacteria and fungi when UV light is absent, while only 1 showed appreciable activity against B. cereus, B. subtilis, E. faecalis, and S. aureus. In the presence of UV light, the cytotoxicity and selectivity of photoCORMs 2, 3, and 4 were significantly elevated, with 2 and 4 demonstrating the most drastic improvement against HT-29 (from IC50 >= 100 to 26.03 and 38.03 mu M, respectively). The growth inhibitory activity of 2, 3, and 4 were also considerably enhanced in the presence of UV illumination when tested against B. cereus, B. subtilis, S. aureus, E. coli, K. pneumoniae, and S. flexneri, with compound 2 demonstrating the biggest leap among the three photoCORMs. Elsevier 2022-07-01 Article PeerReviewed Lee, Shiaw Xian and Tan, Chun Hoe and Mah, Wee Li and Wong, Richard Chee Seng and Abdul Manan, Ninie Suhana and Cheow, Yuen Lin and Sim, Kae Shin and Tan, Kong Wai (2022) Group 6 photo-activable carbon monoxide-releasing molecules (PhotoCORMs) with 1'10-phenanthroline based ligand as potential anti-proliferative and anti-microbial agents. Inorganica Chimica Acta, 537. ISSN 0020-1693, DOI https://doi.org/10.1016/j.ica.2022.120931 <https://doi.org/10.1016/j.ica.2022.120931>. 10.1016/j.ica.2022.120931
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic QD Chemistry
spellingShingle QD Chemistry
Lee, Shiaw Xian
Tan, Chun Hoe
Mah, Wee Li
Wong, Richard Chee Seng
Abdul Manan, Ninie Suhana
Cheow, Yuen Lin
Sim, Kae Shin
Tan, Kong Wai
Group 6 photo-activable carbon monoxide-releasing molecules (PhotoCORMs) with 1'10-phenanthroline based ligand as potential anti-proliferative and anti-microbial agents
description A new series of group 6 UV activable photoCORMs were synthesized by reacting the ligand (((1,10-phenanthroline-5-yl)imino)methyl)naphthalen-2-ol (1) with group 6 (Cr, Mo, and W) hexacarbonyl to form 2, 3, and 4, respectively. The structural elucidations of all compounds were conducted via IR, NMR, and CHN elemental analyses. The crystal structures of all the synthesized compounds were obtained and the half-life of the photoCORMs were determined by using the three-layered myoglobin solution assay. Results showed that the half-life of the compounds decreased down the group 6 in a concentration-dependent manner, with compound 2 displaying the shortest half-life (7.1 s) at 60 mu M. In the absence of UV light, compounds 1 and 3 showed cytotoxicity and selectivity against human-derived colorectal adenocarcinoma HT-29 and carcinoma HCT 116, with ligand 1 being the most cytotoxic compound. Nonetheless, most compounds were inactive against bacteria and fungi when UV light is absent, while only 1 showed appreciable activity against B. cereus, B. subtilis, E. faecalis, and S. aureus. In the presence of UV light, the cytotoxicity and selectivity of photoCORMs 2, 3, and 4 were significantly elevated, with 2 and 4 demonstrating the most drastic improvement against HT-29 (from IC50 >= 100 to 26.03 and 38.03 mu M, respectively). The growth inhibitory activity of 2, 3, and 4 were also considerably enhanced in the presence of UV illumination when tested against B. cereus, B. subtilis, S. aureus, E. coli, K. pneumoniae, and S. flexneri, with compound 2 demonstrating the biggest leap among the three photoCORMs.
format Article
author Lee, Shiaw Xian
Tan, Chun Hoe
Mah, Wee Li
Wong, Richard Chee Seng
Abdul Manan, Ninie Suhana
Cheow, Yuen Lin
Sim, Kae Shin
Tan, Kong Wai
author_facet Lee, Shiaw Xian
Tan, Chun Hoe
Mah, Wee Li
Wong, Richard Chee Seng
Abdul Manan, Ninie Suhana
Cheow, Yuen Lin
Sim, Kae Shin
Tan, Kong Wai
author_sort Lee, Shiaw Xian
title Group 6 photo-activable carbon monoxide-releasing molecules (PhotoCORMs) with 1'10-phenanthroline based ligand as potential anti-proliferative and anti-microbial agents
title_short Group 6 photo-activable carbon monoxide-releasing molecules (PhotoCORMs) with 1'10-phenanthroline based ligand as potential anti-proliferative and anti-microbial agents
title_full Group 6 photo-activable carbon monoxide-releasing molecules (PhotoCORMs) with 1'10-phenanthroline based ligand as potential anti-proliferative and anti-microbial agents
title_fullStr Group 6 photo-activable carbon monoxide-releasing molecules (PhotoCORMs) with 1'10-phenanthroline based ligand as potential anti-proliferative and anti-microbial agents
title_full_unstemmed Group 6 photo-activable carbon monoxide-releasing molecules (PhotoCORMs) with 1'10-phenanthroline based ligand as potential anti-proliferative and anti-microbial agents
title_sort group 6 photo-activable carbon monoxide-releasing molecules (photocorms) with 1'10-phenanthroline based ligand as potential anti-proliferative and anti-microbial agents
publisher Elsevier
publishDate 2022
url http://eprints.um.edu.my/42295/
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