Catalytic transfer hydrogenation and anticancer activity of arene-ruthenium compounds incorporating bi-dentate precursors

Yu Hsiang Chang, Wohn Jenn Leu, Amitabha Datta, Hung Chang Hsiao, Chia Her Lin, Jih Hwa Guh, Jui Hsien Huang

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Ruthenium based organometallic compounds are presently a subject of great attention as anticancer drugs and appear to work reasonably well on tumor cells. We develop a series of mononuclear arene-ruthenium compounds incorporating N,O and N,N bidentate ligands, and their activity as anticancer drugs against human hormone-refractory metastatic prostate cancer (HRMPCs) cell lines are investigated. The ruthenium compounds also act as effective catalysts in the transfer hydrogenation of the -C=O- → -CH(OH)- system. Three types of ligands, namely, sodium glutamate, C4H3NH(2-CH2NHtBu), and C4H3NH(2-CH=NR) are separately coupled with [(η6-cymene)RuCl2]2 (1) (cymene = 4-isopropyltoluene) to synthesize five Ru-derivatives: [(η6-cymene)RuCl(κ2-N,O-OOCCHNH2CH2CH2COOH)] (2), {(η6-cymene)RuCl[C4H3N(2-CH2NHtBu)]} (3), {(η6-cymene)RuCl[C4H3N(2-CH=NCH2Ph)]} (4), {(η6-cymene)RuCl{C4H3N[2-CH=NCH2(C4H7O)]}} (5) and {(η6-cymene)RuCl[C4H3N(2-CHnBuNHCH2(C4H7O))]} (7). To the best of our knowledge, the aforementioned Ru compounds are not only characterized by 1H and 13C NMR spectroscopy, but for the first time their structures have been established by single crystal X-ray diffractometry. Compound 4 influences a concentration-dependent apoptosis in PC-3 cells and initiates the conversion rate in transfer hydrogenation.

Original languageEnglish
Pages (from-to)16107-16118
Number of pages12
JournalDalton Transactions
Volume44
Issue number36
DOIs
Publication statusPublished - 2015 Aug 4

Fingerprint

Ruthenium Compounds
Hydrogenation
Organometallic Compounds
Cells
Ligands
Sodium Glutamate
Ruthenium
Pharmaceutical Preparations
Refractory materials
X ray diffraction analysis
Nuclear magnetic resonance spectroscopy
Tumors
Single crystals
Hormones
Apoptosis
Derivatives
Catalysts

All Science Journal Classification (ASJC) codes

  • Inorganic Chemistry

Cite this

Chang, Yu Hsiang ; Leu, Wohn Jenn ; Datta, Amitabha ; Hsiao, Hung Chang ; Lin, Chia Her ; Guh, Jih Hwa ; Huang, Jui Hsien. / Catalytic transfer hydrogenation and anticancer activity of arene-ruthenium compounds incorporating bi-dentate precursors. In: Dalton Transactions. 2015 ; Vol. 44, No. 36. pp. 16107-16118.
@article{21c404ccc19447e289eaa3f7b5ba8552,
title = "Catalytic transfer hydrogenation and anticancer activity of arene-ruthenium compounds incorporating bi-dentate precursors",
abstract = "Ruthenium based organometallic compounds are presently a subject of great attention as anticancer drugs and appear to work reasonably well on tumor cells. We develop a series of mononuclear arene-ruthenium compounds incorporating N,O and N,N bidentate ligands, and their activity as anticancer drugs against human hormone-refractory metastatic prostate cancer (HRMPCs) cell lines are investigated. The ruthenium compounds also act as effective catalysts in the transfer hydrogenation of the -C=O- → -CH(OH)- system. Three types of ligands, namely, sodium glutamate, C4H3NH(2-CH2NHtBu), and C4H3NH(2-CH=NR) are separately coupled with [(η6-cymene)RuCl2]2 (1) (cymene = 4-isopropyltoluene) to synthesize five Ru-derivatives: [(η6-cymene)RuCl(κ2-N,O-OOCCHNH2CH2CH2COOH)] (2), {(η6-cymene)RuCl[C4H3N(2-CH2NHtBu)]} (3), {(η6-cymene)RuCl[C4H3N(2-CH=NCH2Ph)]} (4), {(η6-cymene)RuCl{C4H3N[2-CH=NCH2(C4H7O)]}} (5) and {(η6-cymene)RuCl[C4H3N(2-CHnBuNHCH2(C4H7O))]} (7). To the best of our knowledge, the aforementioned Ru compounds are not only characterized by 1H and 13C NMR spectroscopy, but for the first time their structures have been established by single crystal X-ray diffractometry. Compound 4 influences a concentration-dependent apoptosis in PC-3 cells and initiates the conversion rate in transfer hydrogenation.",
author = "Chang, {Yu Hsiang} and Leu, {Wohn Jenn} and Amitabha Datta and Hsiao, {Hung Chang} and Lin, {Chia Her} and Guh, {Jih Hwa} and Huang, {Jui Hsien}",
year = "2015",
month = "8",
day = "4",
doi = "10.1039/c5dt01310k",
language = "English",
volume = "44",
pages = "16107--16118",
journal = "Dalton Transactions",
issn = "1477-9226",
publisher = "Royal Society of Chemistry",
number = "36",

}

Catalytic transfer hydrogenation and anticancer activity of arene-ruthenium compounds incorporating bi-dentate precursors. / Chang, Yu Hsiang; Leu, Wohn Jenn; Datta, Amitabha; Hsiao, Hung Chang; Lin, Chia Her; Guh, Jih Hwa; Huang, Jui Hsien.

In: Dalton Transactions, Vol. 44, No. 36, 04.08.2015, p. 16107-16118.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Catalytic transfer hydrogenation and anticancer activity of arene-ruthenium compounds incorporating bi-dentate precursors

AU - Chang, Yu Hsiang

AU - Leu, Wohn Jenn

AU - Datta, Amitabha

AU - Hsiao, Hung Chang

AU - Lin, Chia Her

AU - Guh, Jih Hwa

AU - Huang, Jui Hsien

PY - 2015/8/4

Y1 - 2015/8/4

N2 - Ruthenium based organometallic compounds are presently a subject of great attention as anticancer drugs and appear to work reasonably well on tumor cells. We develop a series of mononuclear arene-ruthenium compounds incorporating N,O and N,N bidentate ligands, and their activity as anticancer drugs against human hormone-refractory metastatic prostate cancer (HRMPCs) cell lines are investigated. The ruthenium compounds also act as effective catalysts in the transfer hydrogenation of the -C=O- → -CH(OH)- system. Three types of ligands, namely, sodium glutamate, C4H3NH(2-CH2NHtBu), and C4H3NH(2-CH=NR) are separately coupled with [(η6-cymene)RuCl2]2 (1) (cymene = 4-isopropyltoluene) to synthesize five Ru-derivatives: [(η6-cymene)RuCl(κ2-N,O-OOCCHNH2CH2CH2COOH)] (2), {(η6-cymene)RuCl[C4H3N(2-CH2NHtBu)]} (3), {(η6-cymene)RuCl[C4H3N(2-CH=NCH2Ph)]} (4), {(η6-cymene)RuCl{C4H3N[2-CH=NCH2(C4H7O)]}} (5) and {(η6-cymene)RuCl[C4H3N(2-CHnBuNHCH2(C4H7O))]} (7). To the best of our knowledge, the aforementioned Ru compounds are not only characterized by 1H and 13C NMR spectroscopy, but for the first time their structures have been established by single crystal X-ray diffractometry. Compound 4 influences a concentration-dependent apoptosis in PC-3 cells and initiates the conversion rate in transfer hydrogenation.

AB - Ruthenium based organometallic compounds are presently a subject of great attention as anticancer drugs and appear to work reasonably well on tumor cells. We develop a series of mononuclear arene-ruthenium compounds incorporating N,O and N,N bidentate ligands, and their activity as anticancer drugs against human hormone-refractory metastatic prostate cancer (HRMPCs) cell lines are investigated. The ruthenium compounds also act as effective catalysts in the transfer hydrogenation of the -C=O- → -CH(OH)- system. Three types of ligands, namely, sodium glutamate, C4H3NH(2-CH2NHtBu), and C4H3NH(2-CH=NR) are separately coupled with [(η6-cymene)RuCl2]2 (1) (cymene = 4-isopropyltoluene) to synthesize five Ru-derivatives: [(η6-cymene)RuCl(κ2-N,O-OOCCHNH2CH2CH2COOH)] (2), {(η6-cymene)RuCl[C4H3N(2-CH2NHtBu)]} (3), {(η6-cymene)RuCl[C4H3N(2-CH=NCH2Ph)]} (4), {(η6-cymene)RuCl{C4H3N[2-CH=NCH2(C4H7O)]}} (5) and {(η6-cymene)RuCl[C4H3N(2-CHnBuNHCH2(C4H7O))]} (7). To the best of our knowledge, the aforementioned Ru compounds are not only characterized by 1H and 13C NMR spectroscopy, but for the first time their structures have been established by single crystal X-ray diffractometry. Compound 4 influences a concentration-dependent apoptosis in PC-3 cells and initiates the conversion rate in transfer hydrogenation.

UR - http://www.scopus.com/inward/record.url?scp=84940762594&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84940762594&partnerID=8YFLogxK

U2 - 10.1039/c5dt01310k

DO - 10.1039/c5dt01310k

M3 - Article

AN - SCOPUS:84940762594

VL - 44

SP - 16107

EP - 16118

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 36

ER -