Transformable cis–trans isomerism of ruthenium(ii) complexes with photoactivated anticancer activity

Chen Pan; Pui Yu Ho; Wan Qiong Huang; Gui Feng Huang; Li Hua Zhang; Daniel Nnaemaka Tritton; Shek Man Yiu; Wai Lun Man; Chi Chiu Ko; Chi Fai Leung; Wen Xiu Ni

doi:10.1039/d4qi02665a

Transformable cis–trans isomerism of ruthenium(ii) complexes with photoactivated anticancer activity

Chen Pan, Pui Yu Ho, Wan Qiong Huang, Gui Feng Huang, Li Hua Zhang, Daniel Nnaemaka Tritton, Shek Man Yiu, Wai Lun Man, Chi Chiu Ko, Chi Fai Leung^*, Wen Xiu Ni^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

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Abstract

Photoactivated chemotherapy (PACT) provides a new alternative cancer treatment strategy compared to conventional therapy. In this study, a series of diisocyano ruthenium(ii) complexes Ru(PBO)₂(RNC)₂ containing the 2-benzoxazol-2-ylphenolate (PBO) auxiliary ligand and their potential application as PACT agents are reported. The complexes exhibit two geometric isomers, i.e., trans, trans, trans (T1-T3) and cis, trans, cis (C1-C3) forms. Although C1-C3 show minimal cytotoxicity (IC₅₀ = 60.1 to >100 μM) toward various cancer cells in the dark, the corresponding T1-T3 complexes exhibit much stronger cytotoxic effects (IC₅₀ = 3.7-39.4 μM). C1 can be readily photoconverted into T1 upon visible-light irradiation (white light), as shown by UV/vis and ¹H NMR spectroscopy. The increased toxicity of the T-form is partially attributed to its reaction with glutathione, in contrast to the C-form analogue. The anticancer activities of T1 were studied in vitro and in vivo. This is the first study that demonstrates the photoisomerization of the isocyano ruthenium(ii) complex Ru(PBO)₂(CNR)₂ as an attractive approach for PACT.

Original language	English
Pages (from-to)	1969-1978
Number of pages	10
Journal	Inorganic Chemistry Frontiers
Volume	12
Issue number	5
Early online date	13 Jan 2025
DOIs	https://doi.org/10.1039/d4qi02665a
Publication status	Published - 7 Mar 2025

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@article{f9d08fc99bc74e36b9c9fb6db0cd5f54,

title = "Transformable cis–trans isomerism of ruthenium(ii) complexes with photoactivated anticancer activity",

abstract = "Photoactivated chemotherapy (PACT) provides a new alternative cancer treatment strategy compared to conventional therapy. In this study, a series of diisocyano ruthenium(ii) complexes Ru(PBO)2(RNC)2 containing the 2-benzoxazol-2-ylphenolate (PBO) auxiliary ligand and their potential application as PACT agents are reported. The complexes exhibit two geometric isomers, i.e., trans, trans, trans (T1-T3) and cis, trans, cis (C1-C3) forms. Although C1-C3 show minimal cytotoxicity (IC50 = 60.1 to >100 μM) toward various cancer cells in the dark, the corresponding T1-T3 complexes exhibit much stronger cytotoxic effects (IC50 = 3.7-39.4 μM). C1 can be readily photoconverted into T1 upon visible-light irradiation (white light), as shown by UV/vis and 1H NMR spectroscopy. The increased toxicity of the T-form is partially attributed to its reaction with glutathione, in contrast to the C-form analogue. The anticancer activities of T1 were studied in vitro and in vivo. This is the first study that demonstrates the photoisomerization of the isocyano ruthenium(ii) complex Ru(PBO)2(CNR)2 as an attractive approach for PACT.",

author = "Chen Pan and Ho, {Pui Yu} and Huang, {Wan Qiong} and Huang, {Gui Feng} and Zhang, {Li Hua} and Tritton, {Daniel Nnaemaka} and Yiu, {Shek Man} and Man, {Wai Lun} and Ko, {Chi Chiu} and Leung, {Chi Fai} and Ni, {Wen Xiu}",

note = "We thank the Guangdong Basic and Applied Basic Research Foundation (No. 2019B030302009 and No. 2023A1515011759) and Shantou University Medical College. Financial support from the Hong Kong Research Grants Council (projects 18300723 and 18300824) and EdUHK (Dean{\textquoteright}s Research Fund: IRS-6 2021/22, ICRS-4 2023/24 and ICRS-4 2024/25) is also acknowledged. Publisher Copyright: {\textcopyright} the Partner Organisations 2025.",

year = "2025",

month = mar,

day = "7",

doi = "10.1039/d4qi02665a",

language = "English",

volume = "12",

pages = "1969--1978",

journal = "Inorganic Chemistry Frontiers",

issn = "2052-1545",

publisher = "Royal Society of Chemistry",

number = "5",

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TY - JOUR

T1 - Transformable cis–trans isomerism of ruthenium(ii) complexes with photoactivated anticancer activity

AU - Pan, Chen

AU - Ho, Pui Yu

AU - Huang, Wan Qiong

AU - Huang, Gui Feng

AU - Zhang, Li Hua

AU - Tritton, Daniel Nnaemaka

AU - Yiu, Shek Man

AU - Man, Wai Lun

AU - Ko, Chi Chiu

AU - Leung, Chi Fai

AU - Ni, Wen Xiu

N1 - We thank the Guangdong Basic and Applied Basic Research Foundation (No. 2019B030302009 and No. 2023A1515011759) and Shantou University Medical College. Financial support from the Hong Kong Research Grants Council (projects 18300723 and 18300824) and EdUHK (Dean’s Research Fund: IRS-6 2021/22, ICRS-4 2023/24 and ICRS-4 2024/25) is also acknowledged. Publisher Copyright: © the Partner Organisations 2025.

PY - 2025/3/7

Y1 - 2025/3/7

N2 - Photoactivated chemotherapy (PACT) provides a new alternative cancer treatment strategy compared to conventional therapy. In this study, a series of diisocyano ruthenium(ii) complexes Ru(PBO)2(RNC)2 containing the 2-benzoxazol-2-ylphenolate (PBO) auxiliary ligand and their potential application as PACT agents are reported. The complexes exhibit two geometric isomers, i.e., trans, trans, trans (T1-T3) and cis, trans, cis (C1-C3) forms. Although C1-C3 show minimal cytotoxicity (IC50 = 60.1 to >100 μM) toward various cancer cells in the dark, the corresponding T1-T3 complexes exhibit much stronger cytotoxic effects (IC50 = 3.7-39.4 μM). C1 can be readily photoconverted into T1 upon visible-light irradiation (white light), as shown by UV/vis and 1H NMR spectroscopy. The increased toxicity of the T-form is partially attributed to its reaction with glutathione, in contrast to the C-form analogue. The anticancer activities of T1 were studied in vitro and in vivo. This is the first study that demonstrates the photoisomerization of the isocyano ruthenium(ii) complex Ru(PBO)2(CNR)2 as an attractive approach for PACT.

AB - Photoactivated chemotherapy (PACT) provides a new alternative cancer treatment strategy compared to conventional therapy. In this study, a series of diisocyano ruthenium(ii) complexes Ru(PBO)2(RNC)2 containing the 2-benzoxazol-2-ylphenolate (PBO) auxiliary ligand and their potential application as PACT agents are reported. The complexes exhibit two geometric isomers, i.e., trans, trans, trans (T1-T3) and cis, trans, cis (C1-C3) forms. Although C1-C3 show minimal cytotoxicity (IC50 = 60.1 to >100 μM) toward various cancer cells in the dark, the corresponding T1-T3 complexes exhibit much stronger cytotoxic effects (IC50 = 3.7-39.4 μM). C1 can be readily photoconverted into T1 upon visible-light irradiation (white light), as shown by UV/vis and 1H NMR spectroscopy. The increased toxicity of the T-form is partially attributed to its reaction with glutathione, in contrast to the C-form analogue. The anticancer activities of T1 were studied in vitro and in vivo. This is the first study that demonstrates the photoisomerization of the isocyano ruthenium(ii) complex Ru(PBO)2(CNR)2 as an attractive approach for PACT.

UR - http://www.scopus.com/inward/record.url?scp=85216365069&partnerID=8YFLogxK

U2 - 10.1039/d4qi02665a

DO - 10.1039/d4qi02665a

M3 - Journal article

AN - SCOPUS:85216365069

SN - 2052-1545

VL - 12

SP - 1969

EP - 1978

JO - Inorganic Chemistry Frontiers

JF - Inorganic Chemistry Frontiers

IS - 5

ER -

Transformable cis–trans isomerism of ruthenium(ii) complexes with photoactivated anticancer activity

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