Synthesis, characterization and cancer cell growth inhibition activity of ruthenium(II) complexes bearing bidentate pyrrole-imine ligands

Guan Hao Chen; Wohn Jenn Leu; Jih Hwa Guh; Chia Her Lin; Jui Hsien Huang

doi:10.1016/j.jorganchem.2018.05.012

Synthesis, characterization and cancer cell growth inhibition activity of ruthenium(II) complexes bearing bidentate pyrrole-imine ligands

Guan Hao Chen, Wohn Jenn Leu, Jih Hwa Guh, Chia Her Lin, Jui Hsien Huang^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

A series of bidentate pyrrole-imine ligands, [C₄H₃NH-(2-CH=N-R)] (1, R = cyclohexenyl; 2, R = CH₂CH₂-1-cyclohexenyl; 3, R = ^tBu; 4, R = CH₂-2-furyl; 5, R = 2-methoxylphenyl; 6, R = phenyl; 7, R = 3-nitrophenyl; 8, R = 2,6-di-isopropylphenyl; 9, R = 2,4,6-trimethylphenyl), were synthesized and their corresponding ruthenium metal compounds {Ru (ɳ⁶-p-cymene)[C₄H₃N-(2-CH=N-R)]Cl} (Ru-1∼Ru-9) were also synthesized. These ligands and ruthenium compounds were all characterized by ¹H and ¹³C NMR spectroscopy and some of their structures are also determined by single crystal X-ray crystallography. The Ru-1∼Ru-9 showed excellent GI₅₀ for PC-3 and DU-145 with the range of 3.83–12.13 and 4.25–11.22 μM, respectively. Among of these ruthenium compounds, Ru-6 has the best activity indicating phenyl ring is the key group on the imine substituents of these ruthenium compounds.

Original language	English
Pages (from-to)	122-130
Number of pages	9
Journal	Journal of Organometallic Chemistry
Volume	868
DOIs	https://doi.org/10.1016/j.jorganchem.2018.05.012
Publication status	Published - 2018 Aug 1
Externally published	Yes

Keywords

Cancer cell growth inhibition
Pyrrole-imine
Ruthenium

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.jorganchem.2018.05.012

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title = "Synthesis, characterization and cancer cell growth inhibition activity of ruthenium(II) complexes bearing bidentate pyrrole-imine ligands",

abstract = "A series of bidentate pyrrole-imine ligands, [C4H3NH-(2-CH=N-R)] (1, R = cyclohexenyl; 2, R = CH2CH2-1-cyclohexenyl; 3, R = tBu; 4, R = CH2-2-furyl; 5, R = 2-methoxylphenyl; 6, R = phenyl; 7, R = 3-nitrophenyl; 8, R = 2,6-di-isopropylphenyl; 9, R = 2,4,6-trimethylphenyl), were synthesized and their corresponding ruthenium metal compounds {Ru (ɳ6-p-cymene)[C4H3N-(2-CH=N-R)]Cl} (Ru-1∼Ru-9) were also synthesized. These ligands and ruthenium compounds were all characterized by 1H and 13C NMR spectroscopy and some of their structures are also determined by single crystal X-ray crystallography. The Ru-1∼Ru-9 showed excellent GI50 for PC-3 and DU-145 with the range of 3.83–12.13 and 4.25–11.22 μM, respectively. Among of these ruthenium compounds, Ru-6 has the best activity indicating phenyl ring is the key group on the imine substituents of these ruthenium compounds.",

keywords = "Cancer cell growth inhibition, Pyrrole-imine, Ruthenium",

author = "Chen, {Guan Hao} and Leu, {Wohn Jenn} and Guh, {Jih Hwa} and Lin, {Chia Her} and Huang, {Jui Hsien}",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier B.V.",

year = "2018",

month = aug,

day = "1",

doi = "10.1016/j.jorganchem.2018.05.012",

language = "English",

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journal = "Journal of Organometallic Chemistry",

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publisher = "Elsevier",

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TY - JOUR

T1 - Synthesis, characterization and cancer cell growth inhibition activity of ruthenium(II) complexes bearing bidentate pyrrole-imine ligands

AU - Chen, Guan Hao

AU - Leu, Wohn Jenn

AU - Guh, Jih Hwa

AU - Lin, Chia Her

AU - Huang, Jui Hsien

PY - 2018/8/1

Y1 - 2018/8/1

N2 - A series of bidentate pyrrole-imine ligands, [C4H3NH-(2-CH=N-R)] (1, R = cyclohexenyl; 2, R = CH2CH2-1-cyclohexenyl; 3, R = tBu; 4, R = CH2-2-furyl; 5, R = 2-methoxylphenyl; 6, R = phenyl; 7, R = 3-nitrophenyl; 8, R = 2,6-di-isopropylphenyl; 9, R = 2,4,6-trimethylphenyl), were synthesized and their corresponding ruthenium metal compounds {Ru (ɳ6-p-cymene)[C4H3N-(2-CH=N-R)]Cl} (Ru-1∼Ru-9) were also synthesized. These ligands and ruthenium compounds were all characterized by 1H and 13C NMR spectroscopy and some of their structures are also determined by single crystal X-ray crystallography. The Ru-1∼Ru-9 showed excellent GI50 for PC-3 and DU-145 with the range of 3.83–12.13 and 4.25–11.22 μM, respectively. Among of these ruthenium compounds, Ru-6 has the best activity indicating phenyl ring is the key group on the imine substituents of these ruthenium compounds.

AB - A series of bidentate pyrrole-imine ligands, [C4H3NH-(2-CH=N-R)] (1, R = cyclohexenyl; 2, R = CH2CH2-1-cyclohexenyl; 3, R = tBu; 4, R = CH2-2-furyl; 5, R = 2-methoxylphenyl; 6, R = phenyl; 7, R = 3-nitrophenyl; 8, R = 2,6-di-isopropylphenyl; 9, R = 2,4,6-trimethylphenyl), were synthesized and their corresponding ruthenium metal compounds {Ru (ɳ6-p-cymene)[C4H3N-(2-CH=N-R)]Cl} (Ru-1∼Ru-9) were also synthesized. These ligands and ruthenium compounds were all characterized by 1H and 13C NMR spectroscopy and some of their structures are also determined by single crystal X-ray crystallography. The Ru-1∼Ru-9 showed excellent GI50 for PC-3 and DU-145 with the range of 3.83–12.13 and 4.25–11.22 μM, respectively. Among of these ruthenium compounds, Ru-6 has the best activity indicating phenyl ring is the key group on the imine substituents of these ruthenium compounds.

KW - Cancer cell growth inhibition

KW - Pyrrole-imine

KW - Ruthenium

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Synthesis, characterization and cancer cell growth inhibition activity of ruthenium(II) complexes bearing bidentate pyrrole-imine ligands

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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