Synthesis and Photophysical Properties of Hetero‐Bischelated Complexes of Rhodium(III) Containing Phenyl‐Pyridin‐2‐Ylmethylene‐Amine

Lee, Jen Rong; Lung, Jin Wang; Huang, Wen Liang

doi:10.1002/jccs.200300033

Cited by 5 publications

(2 citation statements)

References 36 publications

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“…[Rh(phen)(chrysi)(PPO)]Cl 2 and [Rh(bpy) 2 (chrysi)]Cl 3 were synthesized following the published protocols. , New metal complexes were synthesized in a similar manner to published procedures. ,, A description of the general synthetic procedures is below. Complete synthetic details for each complex, including specific amounts (masses, volumes, and ratios) as well as slight deviations from the synthetic scheme below, can be found in the Supporting Information (SI).…”

Section: Experimental Methodsmentioning

confidence: 99%

A Family of Rhodium Complexes with Selective Toxicity toward Mismatch Repair-Deficient Cancers

Boyle

Barton

2018

J. Am. Chem. Soc.

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Rhodium metalloinsertors are a unique set of metal complexes that bind specifically to DNA base pair mismatches in vitro and kill mismatch repair (MMR)-deficient cells at lower concentrations than their MMR-proficient counterparts. A family of metalloinsertors containing rhodium-oxygen ligand coordination, termed “Rh–O” metalloinsertors, has been prepared and shown to have a significant increase in both overall potency and selectivity towards MMR-deficient cells regardless of structural changes in the ancillary ligands. Here we describe DNA-binding and cellular studies with the second generation of Rh–O metalloinsertors in which an ancillary ligand is varied in both steric bulk and lipophilicity. These complexes, of the form [Rh(L)(chrysi)(PPO)]2+, all include the O-containing PPO ligand (PPO = 2-(pyridine-2-yl)propan-2-ol) and the aromatic inserting ligand chrysi (5,6-chrysene quinone diimine) but differ in the identity of their ancillary ligand L, where L is a phenanthroline or bipyridyl derivative. The Rh–O metalloinsertors in this family all show micromolar binding affinities for a 29-mer DNA hairpin containing a single CC mismatch. The complexes display comparable lipophilic tendencies and pKa values of 8.1–9.1 for dissociation of an imine proton on the chrysi ligand. In cellular proliferation and cytotoxicity assays with MMR-deficient cells (HCT116O) and MMR-proficient cells (HCT116N), the complexes containing the phenanthroline-derived ligands show highly selective cytotoxic preference for the MMR-deficient cells at nanomolar concentrations. Using mass spectral analyses, it is shown that the complexes are taken into cells through a passive mechanism and exhibit low accumulation in mitochondria, an off-target organelle that, when targeted by parent metalloinsertors, can lead to non-selective cytotoxicity. Overall, these Rh–O metalloinsertors have distinct and improved behavior compared to previous generations of parent metalloinsertors, making them ideal candidates for further therapeutic assessment.

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Section: Experimental Methodsmentioning

confidence: 99%

A Family of Rhodium Complexes with Selective Toxicity toward Mismatch Repair-Deficient Cancers

Boyle

Barton

2018

J. Am. Chem. Soc.

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“…A reported procedure was generally followed to synthesize Rh-P and Rh-DMP (Lee et al, 2003). Cu-DMP was synthesized by the reaction of DMP with CuCl 2 •2H 2 O in tetrahydrofuran at room temperature (Wang et al, 2009).…”

Section: Synthesis Of Zn-p Zn-dmp Rh-p Cu-dmp and Rh-dmpmentioning

confidence: 99%

Cytotoxicity of zinc, copper and rhodium complexes with 1,10-phenanthroline or 2,9-dimethyl-1,10-phenanthroline in cultured vascular endothelial cells

Hara

Matsuzaki

Nakamura

et al. 2016

Fundam. Toxicol. Sci.

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Organic-inorganic hybrid molecules, which have organic structure and metal atoms, can exhibit various biological activities that are distinctly different from their components. Consequently, organic-inorganic hybrid molecules are considered an effective tool to analyze biological systems. Herein, we investigated the cytotoxicity of zinc, copper, and rhodium complexes, with either 1,10-phenanthroline or 2,9-dimethyl-1,10-phenanthroline as a common ligand, in cultured vascular endothelial cells. The copper complexes, that is, dichloro(1,10-phenanthroline) copper and dichloro(2,9-dimethyl-1,10-phenanthroline) copper, exhibited high cytotoxicity accompanied by considerable accumulation inside the cells. Potassium tetrachloro(1,10-phenanthroline) rhodate also exhibited cytotoxicity and considerable accumulation. Thus, it was found that the cytotoxicity of organic-inorganic hybrid molecules to vascular endothelial cells depends on the interaction between the intramolecular metal and ligand, which facilitates their uptake by the cells.

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Photophysical studies of hetero-bischelated complexes of rhodium(III) containing 2,2′-dipyridylamine

Tseng

Huang

et al. 2006

Inorganica Chimica Acta

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Synthesis and Photophysical Properties of Hetero‐Bischelated Complexes of Rhodium(III) Containing Phenyl‐Pyridin‐2‐Ylmethylene‐Amine

Cited by 5 publications

References 36 publications

A Family of Rhodium Complexes with Selective Toxicity toward Mismatch Repair-Deficient Cancers

A Family of Rhodium Complexes with Selective Toxicity toward Mismatch Repair-Deficient Cancers

Cytotoxicity of zinc, copper and rhodium complexes with 1,10-phenanthroline or 2,9-dimethyl-1,10-phenanthroline in cultured vascular endothelial cells

Photophysical studies of hetero-bischelated complexes of rhodium(III) containing 2,2′-dipyridylamine

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