Bioinorganic chemistry of corrole metal complexes: interactions with proteins and cells

Gross, Zeev; Mahammed, Atif; Abdales, Meirav; Weaver, Jeremy J.; Gray, Harry B.

doi:10.1016/s0162-0134(03)80629-3

Cited by 7 publications

(4 citation statements)

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“…In 2003, Gross et al reported that anionic sulfonated corrole 1 could bind to human serum albumin and cause selective damage to HeLa, HEK293, and MDA‐MB‐435 cell lines . They found the cell uptake of anionic gallium corrole 2 was poor due to the negatively charged cell membrane.…”

Section: Uptake and Subcellular Localization Of Corrole In Tumor Cellsmentioning

confidence: 99%

Corrole‐based photodynamic antitumor therapy

Jiang

Liu

et al. 2019

J Chinese Chemical Soc

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Study of photodynamic therapy (PDT) based on corroles has become one of the most important topics in corrole chemistry. Advances in synthetic methodology have made it possible for the preparation of structurally diverse corrole photosensitizers. This review covers the recent progress in the study of corrole as a photosensitizer in the photodynamic antitumor therapy. The content is organized in three sections: cellular uptaking and localization of corrole in tumor cells; morphological changes and cytotoxicity after corrole PDT treatment; and the animal level corrole PDT test. The possible mechanism of corrole‐based PDT antitumor activity is also summarized.

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Section: Uptake and Subcellular Localization Of Corrole In Tumor Cellsmentioning

confidence: 99%

Corrole‐based photodynamic antitumor therapy

Jiang

Liu

et al. 2019

J Chinese Chemical Soc

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“…Corrole is a ring‐contracted analogue of porphyrin . The application of free base corrole or its metal complexes as cancer therapeutic agents has attracted considerable attention in recent years . Preliminary research shows corrole derivatives are promising candidates for cancer drugs.…”

Section: Introductionmentioning

confidence: 99%

Photocytotoxicity and G‐quadruplex DNA interaction of water‐soluble gallium(III) tris(N‐methyl‐4‐pyridyl)corrole complex

Zhang

Wen

et al. 2015

Applied Organom Chemis

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A water-soluble cationic gallium corrole, 5,10,15-tris(N-methyl-4-pyridyl)corrolatogallium(III) (3), was prepared and characterized. The photocytotoxicity of 3 was investigated using Hep G2 cancer cell line. Upon treatment with corrole 3 and irradiation, fragmentation of tumor cell nuclei was observed, which led to apoptosis. Flow cytometric analysis clearly showed the efficient induction of apoptotic cell death, and corrole 3 exhibited high photocytotoxicity towards Hep G2 cancer cells (IC 50 = 60 nM). Furthermore, the binding behavior of corrole 3 with c-MYC G-quadruplex DNA, a potent target for antitumor drugs, was investigated using spectroscopic methods and molecular docking simulation.

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“…Many efforts have been made to use the powerful oxidation potential of photogenerated ruthenium(III) polypyridyl complexes to catalyze oxidation of water, − DNA, and RNA. − Ruthenium complexes were also incorporated into specific sites of proteins and nucleic acids and were used to study photoinduced electron-transfer processes in these biopolymeric systems. ,− …”

Section: Introductionmentioning

confidence: 99%

“…[8][9][10][11][12][13][14][15] Ruthenium complexes were also incorporated into specific sites of proteins and nucleic acids and were used to study photoinduced electron-transfer processes in these biopolymeric systems. 8,[16][17][18][19][20][21][22][23][24][25][26][27][28] Quenching the excited states of ruthenium tris bipyridine complexes by molecular oxygen leads to either an energytransfer process that yields singlet oxygen and the Ru(II) ion in its ground state (Scheme 1B) or an electron-transfer process that yields superoxide radicals and Ru(III) ions (Scheme 1A). Using transient absorption spectroscopy of Ru(II), Zhang and Rodgers 29 have suggested that a 'cage' complex consisting of Ru(III) and superoxide radical is formed when the electron transfer is the process of choice.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Electron Transfer in Ruthenium Bipyridyl Complexes: Evidence for the Existence of a Cage with Molecular Oxygen

et al. 2004

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Ruthenium complexes with three bipyridyl ligands, one of which is modified by attaching one or two hydroxamic acids groups (Ru-1 and Ru-2, respectively), were synthesized. Using EPR spectroscopy, we have found that photoexcitation leads to formation of nitroxyl radicals. The nitroxyl radical concentration in Ru-2 increased dramatically in the presence of spin traps DMPO (5,5‘-dimethyl-1-pyrroline-N-oxide) and PBN (N-tert-butyl-α-phenylnitrone) characterized by strong affinity to superoxide radicals. We have attributed this behavior to the formation of a cage complex between Ru-2 and the superoxide radical. This paper concerns the study of cages formed between ruthenium complexes and molecular oxygen and the effect of functional groups attached to modified bipyridyl ligands on cage formation. The complex between Ru-2 and O2 was formed in the ground state, probably with participation of the hydroxamic acid groups. The equilibrium constant of this complex was determined by EPR as K eq ∼ 3 M-1. The formation of the Ru-2 −O2 complex is supported by the temperature-dependent rate of appearance of the EPR signal in the presence of PBN. Additional evidence comes from observation of paramagnetic shifts of the peaks in the 1H NMR spectrum of specific aromatic protons in the substituted bipyridyl ring upon exposure to O2. Similar shifts were observed in the spectrum of Os-2, with osmium replacing ruthenium. Model compounds with functional groups that replace the hydroxamic acid or compounds without the metal center, but with the two hydroxamic acids, were synthesized. No shifts in the 1H NMR spectra of these derivatives were observed in the presence of O2. These results lead to the conclusion that both metal ions, Ru(II) or Os(II), and hydroxamic acid groups are essential components for the formation of the oxygen cage.

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Bioinorganic chemistry of corrole metal complexes: interactions with proteins and cells

Cited by 7 publications

References 0 publications

Corrole‐based photodynamic antitumor therapy

Corrole‐based photodynamic antitumor therapy

Photocytotoxicity and G‐quadruplex DNA interaction of water‐soluble gallium(III) tris(N‐methyl‐4‐pyridyl)corrole complex

Photoinduced Electron Transfer in Ruthenium Bipyridyl Complexes: Evidence for the Existence of a Cage with Molecular Oxygen

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