Design and Syntheses of Novel Fluoroporphyrin–Anthraquinone Complexes as Antitumor Agents

Yang, Guliang; Zhao, Shengzhi; Nian-you, Chen; Li, Shiming

doi:10.1248/cpb.c16-00308

Cited by 4 publications

(2 citation statements)

References 23 publications

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“…Moreover, 9,10-anthraquinones can also be used to tag other molecules, e.g. a novel compound composed of porphyrin and a 9,10-anthraquinone derivative was synthesized to evaluate the anti-proliferation activity in HeLa cells ( Yang et al, 2016 ). Interestingly, the three 9,10-anthraquinones found in this study were observed to be osteophilic.…”

Section: Discussionmentioning

confidence: 99%

Screening in larval zebrafish reveals tissue-specific distributions of fifteen fluorescent compounds

Yao

Sun

Fei

et al. 2017

Disease Models &Amp; Mechanisms

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The zebrafish is a prominent vertebrate model for low-cost in vivo whole organism screening. In our recent screening of the distribution patterns of fluorescent compounds in live zebrafish larvae, fifteen compounds with tissue-specific distributions were identified. Several compounds were observed to accumulate in tissues where they were reported to induce side-effects, and compounds with similar structures tended to be enriched in the same tissues, with minor differences. In particular, we found three novel red fluorescent bone-staining dyes: purpurin, lucidin and 3-hydroxy-morindone; purpurin can effectively label bones in both larval and adult zebrafish, as well as in postnatal mice, without significantly affecting bone mass and density. Moreover, two structurally similar chemotherapeutic compounds, doxorubicin and epirubicin, were observed to have distinct distribution preferences in zebrafish. Epirubicin maintained a relatively higher concentration in the liver, and performed better in inhibiting hepatic hyperplasia caused by the over-expression of krasG12V. In total, our study suggests that the transparent zebrafish larvae serve as valuable tools for identifying tissue-specific distributions of fluorescent compounds.

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Section: Discussionmentioning

confidence: 99%

Screening in larval zebrafish reveals tissue-specific distributions of fifteen fluorescent compounds

Yao

Sun

Fei

et al. 2017

Disease Models &Amp; Mechanisms

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show abstract

“…[1][2][3] Amino-substituted anthraquinones are used to composite porphyrin-anthraquinone hybrids, which are efficient photocleavage agents of DNA. [4][5][6][7] The key to efficient photocleavage is the charge transfer efficiency. [8][9][10][11][12][13] The -NH 2 and -NO 2 groups play a role in a strong electronic donor and acceptor in intramolecular charge transfer, respectively.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study on twisted intramolecular charge transfer of 1-aminoanthraquinone in different solvents

Sun¹,

Zhang²,

Jiang³

et al. 2018

Chinese Phys. B

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The twisted intramolecular charge transfer and the excited state relaxation of 1-aminoanthraquinone (1-NH 2 -AQ) in different solvents are investigated using quantum chemical calculations in this paper. The geometries of the ground state are optimized both in gas and solvents based on the high-level ab initio calculations, the lowest excited singlet state geometry is optimized only in gas for simplicity. An intramolecular charge transfer property is substantiated by the large change of dipole moments between the S 0 and S 1 states. The mechanism of twisted intramolecular charge transfer is proposed by the conformational relaxation on the potential surface of the S 1 state. Quantum chemical calculations present that internal conversion and intersystem crossing are important approaches to the ultrafast deactivation of the S 1 state via the twisting of the amino group. The smaller energy difference between the S 0 and S 1 state shows that the internal conversion process is much faster in a polar solvent than in a nonpolar solvent. Energy intersections between the T 2 and S 1 state in cyclohexane and dioxane indicate a faster intersystem crossing process in them than in ethanol. These theoretical results agree well with the previous experimental results. Energy barriers are predicted on the potential surface of the S 1 state, and they have a positive correlation to solvent viscosity, and the timescale of twisted intra-molecular charge transfer in dioxane is predicted to be longer than in cyclohexane and ethanol.

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Excitation wavelength dependent ICT character and ISC efficiency in a photocleavage agent of 1-aminoanthraquinone

Sun

Qin

Liu

et al. 2020

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Design and Syntheses of Novel Fluoroporphyrin–Anthraquinone Complexes as Antitumor Agents

Cited by 4 publications

References 23 publications

Screening in larval zebrafish reveals tissue-specific distributions of fifteen fluorescent compounds

Screening in larval zebrafish reveals tissue-specific distributions of fifteen fluorescent compounds

Theoretical study on twisted intramolecular charge transfer of 1-aminoanthraquinone in different solvents

Excitation wavelength dependent ICT character and ISC efficiency in a photocleavage agent of 1-aminoanthraquinone

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