Synthesis of phenothiazine-corrole dyads: the enhanced DNA photocleavage properties

Shi, Lei; Liu, Haiyang; Peng, Kaimei; Wang, Xiang-Li; You, Lili; Jun, Lu; Zhang, Lei; Wang, Hui; Ji, Liang‐Nian; Jiang, Huanfeng

doi:10.1016/j.tetlet.2010.04.112

Cited by 18 publications

(6 citation statements)

References 37 publications

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“…DNA is the primary intracellular target of anticancer drugs, whose interactions with small molecules can cause damage to cancerous cells by blocking their further division and ultimately resulting in tumor cell apoptosis . In recent years, the investigation of the interactions between corroles and DNA, including G‐quadruplex and double‐helix DNA, has become of considerable interest owing to their importance for developing biomedicines. To investigate the DNA binding abilities of corrole 3 , four different types of DNA, namely c‐MYC G‐quadruplex DNA (parallel), ct‐DNA (duplex), Hras G‐quadruplex DNA (antiparallel) and htg22 G‐quadruplex DNA (hybrid‐type), were selected as model DNAs.…”

Section: Resultsmentioning

confidence: 99%

“…Inspired by these findings and continuing our efforts in the research of the bioinorganic chemistry of corroles, we here report the tumor cell photocytotoxicity of a water‐soluble cationic gallium(III) pyridylcorrole, namely 5,10,15‐tris( N ‐methyl‐4‐pyridyl)corrolatogallium(III) ( 3 ; Scheme ). The cytostatic action of gallium(III) corrole 3 was investigated using flow cytometry and fluorescence microscopy.…”

Section: Introductionmentioning

confidence: 83%

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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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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 83%

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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“…Previously, we have reported freebase corroles show photonuclease activity . Here, freebase corrole 1 and 2 also can photocleavage DNA.…”

Section: Dna Binding Propertiesmentioning

confidence: 99%

Methyl Benzoate Gallium(III) corrole complexes: DNA‐binding, Photocleavage Activity, Cytotoxicity on Tumor Cells

Wang

Yuan

et al. 2016

Applied Organom Chemis

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Two new gallium corrole complexes, 10‐(4‐Methoxycarbonylphenyl) ‐5, 15‐bis(pentafluorophenyl)corrolatogallium(III)(1‐Ga) and 5,15‐bis(4‐Methoxycarbonylphenyl)‐10‐(pentafluorophenyl)corrolatogallium(III)(2‐Ga), were synthesized and characterized. The interaction of these gallium corrole complexes with CT‐DNA was studied by fluorescence methods, UV–visible, viscosity measurements, molecular docking as well as agarose gel electrophoresis. The results revealed that both 1‐Ga and 2‐Ga interact with DNA via major groove binding and could cleavage the supercoiled plasmid DNA efficiently under irradiation. The inhibitor and singlet oxygen test indicated that singlet oxygen was the reactive oxygen species involved in the photocleavage DNA initiated by 1‐Ga or 2‐Ga. Cell viability experiments indicated that 1‐Ga and 2‐Ga show high photocytotoxicity and low dark toxicity towards tested QGY‐7701 and MHCC‐H/L tumor cell lines. Fluorescence probe tests showed the absorbed 1‐Ga and 2‐Ga in tumor cells are mainly localized in mitochondria, and the mitochondria membrane potential disruption was observed after irradiation.

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“…The absence of a meso ‐carbon resulting from a direct linkage between the α‐carbons of two adjacent pyrrole rings is a key structural difference between corrole and porphyrin . This feature induces a symmetry change from the D 2 h point group ( D 4 h for metalloporphyrins) to C s , and a bond alteration pattern resulting in the presence of three N−H (pyrrolic) centers and one pyrrolenic center . The presence of the three pyrrolic N−H centers leads two distinct tautomeric species ( T1 and T2 ; Figure ) that exist in a dynamic equilibrium .…”

Section: Introductionmentioning

confidence: 99%

Excited State N−H Tautomer Selectivity in the Singlet Energy Transfer of a Zinc(II)‐Porphyrin–Truxene–Corrole Assembly

Langlois

Karsenti

et al. 2017

Chemistry A European J

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An original corrole-containing polyad for S energy transfer, in which one zinc(II)-porphyrin donor is linked to two free-base corrole acceptors by a truxene linker, is reported. This polyad exhibits a rapid zinc(II)-porphyrin*→free-base corrole transfer (4.83×10 s ; 298 K), even faster than the tautomerization in the excited state processes taking advantage of the good electronic communication provided by the truxene bridge. Importantly, the energy transfer process shows approximately 3-fold selectivity for one corrole N-H tautomer over the other even at low temperature (77 K). This selectivity is due to the difference in the J-integral being effective in both the Förster and Dexter mechanisms. The data are rationalized by DFT computations.

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Synthesis of phenothiazine-corrole dyads: the enhanced DNA photocleavage properties

Cited by 18 publications

References 37 publications

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

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

Methyl Benzoate Gallium(III) corrole complexes: DNA‐binding, Photocleavage Activity, Cytotoxicity on Tumor Cells

Excited State N−H Tautomer Selectivity in the Singlet Energy Transfer of a Zinc(II)‐Porphyrin–Truxene–Corrole Assembly

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