Synthesis, structural and chemosensitivity studies of arena d6 metal complexes having N-phenyl-N'-(pyridyl/pyrimidyl) thiourea derivatives

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

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Abstract

The d6 metal complexes of thiourea derivatives were synthesized to investigate its cytotoxicity. Treatment of various N‐phenyl‐N ́ pyridyl/pyrimidyl thiourea ligands with half‐sandwich d6 metal precursors yielded a series of cationic com- plexes. Reactions of ligand (L1‐L3) with [(p‐cymene)RuCl2]2 and [Cp*MCl2]2 (M = Rh/Ir) led to the formation of a series of cationic complexes bearing gen- eral formula [(arene)M(L1)к2(N,S)Cl]+, [(arene)M(L2)к2(N,S)Cl]+ and [(arene) M(L3)к2(N,S)Cl]+ [arene = p‐cymene, M = Ru (1, 4, 7); Cp*, M = Rh (2, 5, 8); Cp*, Ir (3, 6, 9)]. These compounds were isolated as their chloride salts. X‐ray crystallographic studies of the complexes revealed the coordination of the ligands to the metal in a bidentate chelating N,S‐ manner. Further the cytotox- icity studies of the thiourea derivatives and its complexes evaluated against HCT‐116 (human colorectal cancer), MIA‐PaCa‐2 (human pancreatic cancer) and ARPE‐19 (non‐cancer retinal epithelium) cancer cell lines showed that the thiourea ligands displayed no activity. Upon complexation however, the metal compounds possesses cytotoxicity and whilst potency is less than cisplatin, several complexes exhibited greater selectivity for HCT‐116 or MIA‐ PaCa‐2 cells compared to ARPE‐19 cells than cisplatin in vitro. Rhodium complexes of thiourea derivatives were found to be more potent as compared to ruthenium and iridium complexes.
Original languageEnglish
Article numbere4362
Number of pages13
JournalApplied Organometallic Chemistry
Volume32
Issue number6
Early online date6 Apr 2018
DOIs
Publication statusPublished - 1 Jun 2018

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Thiourea
Coordination Complexes
Derivatives
Cytotoxicity
Ligands
Metals
Cisplatin
Bearings (structural)
Iridium
Rhodium
Ruthenium
Chelation
Complexation
Chlorides
Salts
Cells

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title = "Synthesis, structural and chemosensitivity studies of arena d6 metal complexes having N-phenyl-N'-(pyridyl/pyrimidyl) thiourea derivatives",
abstract = "The d6 metal complexes of thiourea derivatives were synthesized to investigate its cytotoxicity. Treatment of various N‐phenyl‐N ́ pyridyl/pyrimidyl thiourea ligands with half‐sandwich d6 metal precursors yielded a series of cationic com- plexes. Reactions of ligand (L1‐L3) with [(p‐cymene)RuCl2]2 and [Cp*MCl2]2 (M = Rh/Ir) led to the formation of a series of cationic complexes bearing gen- eral formula [(arene)M(L1)к2(N,S)Cl]+, [(arene)M(L2)к2(N,S)Cl]+ and [(arene) M(L3)к2(N,S)Cl]+ [arene = p‐cymene, M = Ru (1, 4, 7); Cp*, M = Rh (2, 5, 8); Cp*, Ir (3, 6, 9)]. These compounds were isolated as their chloride salts. X‐ray crystallographic studies of the complexes revealed the coordination of the ligands to the metal in a bidentate chelating N,S‐ manner. Further the cytotox- icity studies of the thiourea derivatives and its complexes evaluated against HCT‐116 (human colorectal cancer), MIA‐PaCa‐2 (human pancreatic cancer) and ARPE‐19 (non‐cancer retinal epithelium) cancer cell lines showed that the thiourea ligands displayed no activity. Upon complexation however, the metal compounds possesses cytotoxicity and whilst potency is less than cisplatin, several complexes exhibited greater selectivity for HCT‐116 or MIA‐ PaCa‐2 cells compared to ARPE‐19 cells than cisplatin in vitro. Rhodium complexes of thiourea derivatives were found to be more potent as compared to ruthenium and iridium complexes.",
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Synthesis, structural and chemosensitivity studies of arena d6 metal complexes having N-phenyl-N'-(pyridyl/pyrimidyl) thiourea derivatives. / Adhikari, Sanjay; Hussain, Omar; Phillips, Roger; Kaminsky, Werner; Kollipara, Mohan Rao.

In: Applied Organometallic Chemistry, Vol. 32, No. 6, e4362, 01.06.2018.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis, structural and chemosensitivity studies of arena d6 metal complexes having N-phenyl-N'-(pyridyl/pyrimidyl) thiourea derivatives

AU - Adhikari, Sanjay

AU - Hussain, Omar

AU - Phillips, Roger

AU - Kaminsky, Werner

AU - Kollipara, Mohan Rao

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Y1 - 2018/6/1

N2 - The d6 metal complexes of thiourea derivatives were synthesized to investigate its cytotoxicity. Treatment of various N‐phenyl‐N ́ pyridyl/pyrimidyl thiourea ligands with half‐sandwich d6 metal precursors yielded a series of cationic com- plexes. Reactions of ligand (L1‐L3) with [(p‐cymene)RuCl2]2 and [Cp*MCl2]2 (M = Rh/Ir) led to the formation of a series of cationic complexes bearing gen- eral formula [(arene)M(L1)к2(N,S)Cl]+, [(arene)M(L2)к2(N,S)Cl]+ and [(arene) M(L3)к2(N,S)Cl]+ [arene = p‐cymene, M = Ru (1, 4, 7); Cp*, M = Rh (2, 5, 8); Cp*, Ir (3, 6, 9)]. These compounds were isolated as their chloride salts. X‐ray crystallographic studies of the complexes revealed the coordination of the ligands to the metal in a bidentate chelating N,S‐ manner. Further the cytotox- icity studies of the thiourea derivatives and its complexes evaluated against HCT‐116 (human colorectal cancer), MIA‐PaCa‐2 (human pancreatic cancer) and ARPE‐19 (non‐cancer retinal epithelium) cancer cell lines showed that the thiourea ligands displayed no activity. Upon complexation however, the metal compounds possesses cytotoxicity and whilst potency is less than cisplatin, several complexes exhibited greater selectivity for HCT‐116 or MIA‐ PaCa‐2 cells compared to ARPE‐19 cells than cisplatin in vitro. Rhodium complexes of thiourea derivatives were found to be more potent as compared to ruthenium and iridium complexes.

AB - The d6 metal complexes of thiourea derivatives were synthesized to investigate its cytotoxicity. Treatment of various N‐phenyl‐N ́ pyridyl/pyrimidyl thiourea ligands with half‐sandwich d6 metal precursors yielded a series of cationic com- plexes. Reactions of ligand (L1‐L3) with [(p‐cymene)RuCl2]2 and [Cp*MCl2]2 (M = Rh/Ir) led to the formation of a series of cationic complexes bearing gen- eral formula [(arene)M(L1)к2(N,S)Cl]+, [(arene)M(L2)к2(N,S)Cl]+ and [(arene) M(L3)к2(N,S)Cl]+ [arene = p‐cymene, M = Ru (1, 4, 7); Cp*, M = Rh (2, 5, 8); Cp*, Ir (3, 6, 9)]. These compounds were isolated as their chloride salts. X‐ray crystallographic studies of the complexes revealed the coordination of the ligands to the metal in a bidentate chelating N,S‐ manner. Further the cytotox- icity studies of the thiourea derivatives and its complexes evaluated against HCT‐116 (human colorectal cancer), MIA‐PaCa‐2 (human pancreatic cancer) and ARPE‐19 (non‐cancer retinal epithelium) cancer cell lines showed that the thiourea ligands displayed no activity. Upon complexation however, the metal compounds possesses cytotoxicity and whilst potency is less than cisplatin, several complexes exhibited greater selectivity for HCT‐116 or MIA‐ PaCa‐2 cells compared to ARPE‐19 cells than cisplatin in vitro. Rhodium complexes of thiourea derivatives were found to be more potent as compared to ruthenium and iridium complexes.

KW - chemosensitivity

KW - iridium

KW - rhodium

KW - ruthenium

KW - thiourea

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JO - Applied Organometallic Chemistry

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