Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI50) study

Kuan Hung Chen; Tzung Han Lin; Tzu En Hsu; Yong Jie Li; Guan Hao Chen; Wohn Jenn Leu; Jih Hwa Guh; Chia Her Lin; Jui Hsien Huang

doi:10.1016/j.jorganchem.2018.07.014

Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI₅₀) study

Kuan Hung Chen, Tzung Han Lin, Tzu En Hsu, Yong Jie Li, 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

9 Citations (Scopus)

Abstract

Two dehydroacetic acid (DHA, L₁H) related imine ligands, L₂H and L₃H were obtained in moderate yields by reacting DHA with 2,4,6-trimethylaniline and phenylhydrazine, respectively. Refluxing [Ru (η⁶-p-cymene)Cl₂]₂ with two equivalents of L₁Na, L₂H and L₃H in methanol generated ruthenium compounds [Ru (η⁶-p-cymene)Cl (L₁)] (1), [Ru (η⁶-p-cymene)Cl (L₂)] (2), [Ru (η⁶-p-cymene)Cl (L₃)] (3), respectively. The chloride atom of 2 and 3 was substituted by ambidentate ligands N₃, NCO and NCS to generate a series of ruthenium compounds 4a-4c and 5a-5b. All of these ligands and ruthenium compounds were characterized by ¹H and ¹³C NMR spectroscopy. Compounds 1–3, 4a-4c, and 5a were also structural determined by single crystal X-ray crystallography showing a three-legged piano stool geometry with the p-cymene acting as the seat plane. Anti-proliferative activity study using these ruthenium complexes against PC-3 and DU-145 cell-lines shows that compounds 2 and 4a-4c have the best activity than other ruthenium compounds. The results indicate that the ruthenium p-cymene compounds with large steric hindrance of dehydroacetic acid imine derivative ligands exhibit higher anti-proliferative activity against PC-3 and DU-145 cell-lines.

Original language	English
Pages (from-to)	150-158
Number of pages	9
Journal	Journal of Organometallic Chemistry
Volume	871
DOIs	https://doi.org/10.1016/j.jorganchem.2018.07.014
Publication status	Published - 2018 Sept 15
Externally published	Yes

Keywords

Anti-proliferation activity
Cancer cell
Dehydroacetic acid
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)

Access to Document

10.1016/j.jorganchem.2018.07.014

Cite this

Chen, K. H., Lin, T. H., Hsu, T. E., Li, Y. J., Chen, G. H., Leu, W. J., Guh, J. H., Lin, C. H., & Huang, J. H. (2018). Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI₅₀) study. Journal of Organometallic Chemistry, 871, 150-158. https://doi.org/10.1016/j.jorganchem.2018.07.014

Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI₅₀) study. / Chen, Kuan Hung; Lin, Tzung Han; Hsu, Tzu En et al.
In: Journal of Organometallic Chemistry, Vol. 871, 15.09.2018, p. 150-158.

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

Chen, KH, Lin, TH, Hsu, TE, Li, YJ, Chen, GH, Leu, WJ, Guh, JH, Lin, CH & Huang, JH 2018, 'Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI₅₀) study', Journal of Organometallic Chemistry, vol. 871, pp. 150-158. https://doi.org/10.1016/j.jorganchem.2018.07.014

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title = "Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI50) study",

abstract = "Two dehydroacetic acid (DHA, L1H) related imine ligands, L2H and L3H were obtained in moderate yields by reacting DHA with 2,4,6-trimethylaniline and phenylhydrazine, respectively. Refluxing [Ru (η6-p-cymene)Cl2]2 with two equivalents of L1Na, L2H and L3H in methanol generated ruthenium compounds [Ru (η6-p-cymene)Cl (L1)] (1), [Ru (η6-p-cymene)Cl (L2)] (2), [Ru (η6-p-cymene)Cl (L3)] (3), respectively. The chloride atom of 2 and 3 was substituted by ambidentate ligands N3, NCO and NCS to generate a series of ruthenium compounds 4a-4c and 5a-5b. All of these ligands and ruthenium compounds were characterized by 1H and 13C NMR spectroscopy. Compounds 1–3, 4a-4c, and 5a were also structural determined by single crystal X-ray crystallography showing a three-legged piano stool geometry with the p-cymene acting as the seat plane. Anti-proliferative activity study using these ruthenium complexes against PC-3 and DU-145 cell-lines shows that compounds 2 and 4a-4c have the best activity than other ruthenium compounds. The results indicate that the ruthenium p-cymene compounds with large steric hindrance of dehydroacetic acid imine derivative ligands exhibit higher anti-proliferative activity against PC-3 and DU-145 cell-lines.",

keywords = "Anti-proliferation activity, Cancer cell, Dehydroacetic acid, Imine, Ruthenium",

author = "Chen, {Kuan Hung} and Lin, {Tzung Han} and Hsu, {Tzu En} and Li, {Yong Jie} and 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",

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day = "15",

doi = "10.1016/j.jorganchem.2018.07.014",

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T1 - Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI50) study

AU - Chen, Kuan Hung

AU - Lin, Tzung Han

AU - Hsu, Tzu En

AU - Li, Yong Jie

AU - Chen, Guan Hao

AU - Leu, Wohn Jenn

AU - Guh, Jih Hwa

AU - Lin, Chia Her

AU - Huang, Jui Hsien

PY - 2018/9/15

Y1 - 2018/9/15

N2 - Two dehydroacetic acid (DHA, L1H) related imine ligands, L2H and L3H were obtained in moderate yields by reacting DHA with 2,4,6-trimethylaniline and phenylhydrazine, respectively. Refluxing [Ru (η6-p-cymene)Cl2]2 with two equivalents of L1Na, L2H and L3H in methanol generated ruthenium compounds [Ru (η6-p-cymene)Cl (L1)] (1), [Ru (η6-p-cymene)Cl (L2)] (2), [Ru (η6-p-cymene)Cl (L3)] (3), respectively. The chloride atom of 2 and 3 was substituted by ambidentate ligands N3, NCO and NCS to generate a series of ruthenium compounds 4a-4c and 5a-5b. All of these ligands and ruthenium compounds were characterized by 1H and 13C NMR spectroscopy. Compounds 1–3, 4a-4c, and 5a were also structural determined by single crystal X-ray crystallography showing a three-legged piano stool geometry with the p-cymene acting as the seat plane. Anti-proliferative activity study using these ruthenium complexes against PC-3 and DU-145 cell-lines shows that compounds 2 and 4a-4c have the best activity than other ruthenium compounds. The results indicate that the ruthenium p-cymene compounds with large steric hindrance of dehydroacetic acid imine derivative ligands exhibit higher anti-proliferative activity against PC-3 and DU-145 cell-lines.

AB - Two dehydroacetic acid (DHA, L1H) related imine ligands, L2H and L3H were obtained in moderate yields by reacting DHA with 2,4,6-trimethylaniline and phenylhydrazine, respectively. Refluxing [Ru (η6-p-cymene)Cl2]2 with two equivalents of L1Na, L2H and L3H in methanol generated ruthenium compounds [Ru (η6-p-cymene)Cl (L1)] (1), [Ru (η6-p-cymene)Cl (L2)] (2), [Ru (η6-p-cymene)Cl (L3)] (3), respectively. The chloride atom of 2 and 3 was substituted by ambidentate ligands N3, NCO and NCS to generate a series of ruthenium compounds 4a-4c and 5a-5b. All of these ligands and ruthenium compounds were characterized by 1H and 13C NMR spectroscopy. Compounds 1–3, 4a-4c, and 5a were also structural determined by single crystal X-ray crystallography showing a three-legged piano stool geometry with the p-cymene acting as the seat plane. Anti-proliferative activity study using these ruthenium complexes against PC-3 and DU-145 cell-lines shows that compounds 2 and 4a-4c have the best activity than other ruthenium compounds. The results indicate that the ruthenium p-cymene compounds with large steric hindrance of dehydroacetic acid imine derivative ligands exhibit higher anti-proliferative activity against PC-3 and DU-145 cell-lines.

KW - Anti-proliferation activity

KW - Cancer cell

KW - Dehydroacetic acid

KW - Imine

KW - Ruthenium

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