Neutral and cationic half-sandwich arene d6 metal complexes containing pyridyl and pyrimidyl thiourea ligands with interesting bonding modes

Synthesis, structural and anti-cancer studies

Sanjay Adhikari, Omar Hussain, Roger M. Phillips, Werner Kaminsky, Mohan Rao Kollipara

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The reaction of [(p-cymene)RuCl2]2 and [Cp*MCl2]2 (M = Rh/Ir) with benzoyl (2-pyrimidyl) thiourea (L1) and benzoyl (4-picolyl) thiourea (L2) led to the formation of cationic complexes bearing formula [(arene) M (L1)к2 (N,S)Cl]+ and [(arene) M (L2)к2 (N,S)Cl]+ [(arene) = p-cymene, M = Ru, (1, 4); Cp*, M = Rh (2, 5) and Ir (3, 6)]. Precursor compounds reacted with benzoyl (6-picolyl) thiourea (L3) affording neutral complexes having formula [(arene) M (L3)к1 (S)Cl2] [arene = p-cymene, M = Ru, (7); Cp*, M = Rh (8), Ir (9)]. X-ray studies revealed that the methyl substituent attached to the pyridine ring in ligands L2 and L3 affects its coordination mode. When methyl group is at the para position of the pyridine ring (L2), the ligand coordinated metal in a bidentate chelating N, S- mode whereas methyl group at ortho position (L3), it coordinated in a monodentate mode. Further the anti-cancer studies of the thiourea derivatives and its complexes carried out against HCT-116, HT-29 (human colorectal cancer), Mia-PaCa-2 (human pancreatic cancer) and ARPE-19 (non-cancer retinal epithelium) cell lines showed that the thiourea ligands are inactive but upon complexation, the metal compounds displayed potent and selective activity against cancer cells in vitro. Iridium complexes were found to be more potent as compared to ruthenium and rhodium complexes.

Original languageEnglish
Article numbere4476
Number of pages13
JournalApplied Organometallic Chemistry
Volume32
Issue number9
DOIs
Publication statusPublished - 1 Sep 2018

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Thiourea
Coordination Complexes
Ligands
Bearings (structural)
Metals
Cells
Iridium
Rhodium
Ruthenium
Chelation
Complexation
Derivatives
X rays
4-cymene

Cite this

@article{a90b411fbb1f49d9830e655661fdb27a,
title = "Neutral and cationic half-sandwich arene d6 metal complexes containing pyridyl and pyrimidyl thiourea ligands with interesting bonding modes: Synthesis, structural and anti-cancer studies",
abstract = "The reaction of [(p-cymene)RuCl2]2 and [Cp*MCl2]2 (M = Rh/Ir) with benzoyl (2-pyrimidyl) thiourea (L1) and benzoyl (4-picolyl) thiourea (L2) led to the formation of cationic complexes bearing formula [(arene) M (L1)к2 (N,S)Cl]+ and [(arene) M (L2)к2 (N,S)Cl]+ [(arene) = p-cymene, M = Ru, (1, 4); Cp*, M = Rh (2, 5) and Ir (3, 6)]. Precursor compounds reacted with benzoyl (6-picolyl) thiourea (L3) affording neutral complexes having formula [(arene) M (L3)к1 (S)Cl2] [arene = p-cymene, M = Ru, (7); Cp*, M = Rh (8), Ir (9)]. X-ray studies revealed that the methyl substituent attached to the pyridine ring in ligands L2 and L3 affects its coordination mode. When methyl group is at the para position of the pyridine ring (L2), the ligand coordinated metal in a bidentate chelating N, S- mode whereas methyl group at ortho position (L3), it coordinated in a monodentate mode. Further the anti-cancer studies of the thiourea derivatives and its complexes carried out against HCT-116, HT-29 (human colorectal cancer), Mia-PaCa-2 (human pancreatic cancer) and ARPE-19 (non-cancer retinal epithelium) cell lines showed that the thiourea ligands are inactive but upon complexation, the metal compounds displayed potent and selective activity against cancer cells in vitro. Iridium complexes were found to be more potent as compared to ruthenium and rhodium complexes.",
keywords = "cytotoxicity, iridium, rhodium, ruthenium, thiourea",
author = "Sanjay Adhikari and Omar Hussain and Phillips, {Roger M.} and Werner Kaminsky and Kollipara, {Mohan Rao}",
year = "2018",
month = "9",
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doi = "10.1002/aoc.4476",
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volume = "32",
journal = "Applied Organometallic Chemistry",
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Neutral and cationic half-sandwich arene d6 metal complexes containing pyridyl and pyrimidyl thiourea ligands with interesting bonding modes : Synthesis, structural and anti-cancer studies. / Adhikari, Sanjay; Hussain, Omar; Phillips, Roger M.; Kaminsky, Werner; Kollipara, Mohan Rao.

In: Applied Organometallic Chemistry, Vol. 32, No. 9, e4476, 01.09.2018.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Neutral and cationic half-sandwich arene d6 metal complexes containing pyridyl and pyrimidyl thiourea ligands with interesting bonding modes

T2 - Synthesis, structural and anti-cancer studies

AU - Adhikari, Sanjay

AU - Hussain, Omar

AU - Phillips, Roger M.

AU - Kaminsky, Werner

AU - Kollipara, Mohan Rao

PY - 2018/9/1

Y1 - 2018/9/1

N2 - The reaction of [(p-cymene)RuCl2]2 and [Cp*MCl2]2 (M = Rh/Ir) with benzoyl (2-pyrimidyl) thiourea (L1) and benzoyl (4-picolyl) thiourea (L2) led to the formation of cationic complexes bearing formula [(arene) M (L1)к2 (N,S)Cl]+ and [(arene) M (L2)к2 (N,S)Cl]+ [(arene) = p-cymene, M = Ru, (1, 4); Cp*, M = Rh (2, 5) and Ir (3, 6)]. Precursor compounds reacted with benzoyl (6-picolyl) thiourea (L3) affording neutral complexes having formula [(arene) M (L3)к1 (S)Cl2] [arene = p-cymene, M = Ru, (7); Cp*, M = Rh (8), Ir (9)]. X-ray studies revealed that the methyl substituent attached to the pyridine ring in ligands L2 and L3 affects its coordination mode. When methyl group is at the para position of the pyridine ring (L2), the ligand coordinated metal in a bidentate chelating N, S- mode whereas methyl group at ortho position (L3), it coordinated in a monodentate mode. Further the anti-cancer studies of the thiourea derivatives and its complexes carried out against HCT-116, HT-29 (human colorectal cancer), Mia-PaCa-2 (human pancreatic cancer) and ARPE-19 (non-cancer retinal epithelium) cell lines showed that the thiourea ligands are inactive but upon complexation, the metal compounds displayed potent and selective activity against cancer cells in vitro. Iridium complexes were found to be more potent as compared to ruthenium and rhodium complexes.

AB - The reaction of [(p-cymene)RuCl2]2 and [Cp*MCl2]2 (M = Rh/Ir) with benzoyl (2-pyrimidyl) thiourea (L1) and benzoyl (4-picolyl) thiourea (L2) led to the formation of cationic complexes bearing formula [(arene) M (L1)к2 (N,S)Cl]+ and [(arene) M (L2)к2 (N,S)Cl]+ [(arene) = p-cymene, M = Ru, (1, 4); Cp*, M = Rh (2, 5) and Ir (3, 6)]. Precursor compounds reacted with benzoyl (6-picolyl) thiourea (L3) affording neutral complexes having formula [(arene) M (L3)к1 (S)Cl2] [arene = p-cymene, M = Ru, (7); Cp*, M = Rh (8), Ir (9)]. X-ray studies revealed that the methyl substituent attached to the pyridine ring in ligands L2 and L3 affects its coordination mode. When methyl group is at the para position of the pyridine ring (L2), the ligand coordinated metal in a bidentate chelating N, S- mode whereas methyl group at ortho position (L3), it coordinated in a monodentate mode. Further the anti-cancer studies of the thiourea derivatives and its complexes carried out against HCT-116, HT-29 (human colorectal cancer), Mia-PaCa-2 (human pancreatic cancer) and ARPE-19 (non-cancer retinal epithelium) cell lines showed that the thiourea ligands are inactive but upon complexation, the metal compounds displayed potent and selective activity against cancer cells in vitro. Iridium complexes were found to be more potent as compared to ruthenium and rhodium complexes.

KW - cytotoxicity

KW - iridium

KW - rhodium

KW - ruthenium

KW - thiourea

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U2 - 10.1002/aoc.4476

DO - 10.1002/aoc.4476

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JO - Applied Organometallic Chemistry

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