A novel photosensitizer, 2-butylamino-2-demethoxy-hypocrellin A (2-BA-2-DMHA) 1. Synthesis of 2-BA-2-DMHA and its phototoxicity to MGC803 cells

Zhang, Wengeng; Weng, Min Hang; Pang, Suzhen; Zhang, Manhua; Yang, Huiling; Zhao, Hongxia; Zhang, Zhiyi

doi:10.1016/s1011-1344(98)00101-8

Cited by 32 publications

(19 citation statements)

References 21 publications

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“…2. The phototoxicities of the hypocrellin dyes are expressed by the numerical indicator, IC 50 , which indicates the concentration to exert 50% growth inhibition against tumor cells, including EMT6/Ed murine tumor cell [1], human oral cavity epithelial carcinoma KB cell [13,14], human gastric adenocarcinoma MGC803 cell [15], and human cervix uteri tumor HeLa cell [16]. The respective IC 50 of all the 20 hypocrellins studied is shown in Table 1.…”

Section: Compoundsmentioning

confidence: 99%

“…We can see from the figures that the hypocrellins studied are separated into two groups, A and B. Group A contains the hypocrellins (compounds 7,9,13,14,15,16,17,19, 20 e see Table 1) with higher degree of phototoxicities against tumor cells, i.e. the molecules with IC 50 < 1.0 mg mL ÿ1 except compounds 14 and 15.…”

Section: Principal Component Analysis (Pca)mentioning

confidence: 99%

“…5 [13,14]. c Phototoxicity against human gastric adenocarcinoma MGC803 cell [15]. d Phototoxicity against human cervix uteri tumor HeLa cell [16].…”

Section: Hierarchical Cluster Analysis (Hca)mentioning

confidence: 99%

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Quantum chemical and statistical study of hypocrellin dyes with phototoxicity against tumor cells

Yang

Huang

2007

Dyes and Pigments

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Section: Compoundsmentioning

confidence: 99%

Section: Principal Component Analysis (Pca)mentioning

confidence: 99%

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Quantum chemical and statistical study of hypocrellin dyes with phototoxicity against tumor cells

Yang

Huang

2007

Dyes and Pigments

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“…[9][10][11] Some of them have shown promising anticancer properties. 12,13 Previously, we have screened another derivative of HB and proved that 2-ethanolamino-2-demethoxy-17-ethanolimino-HB (EAHB) exhibits a strong absorption shoulder peak at 632 nm with a high photopotentiation factor for MGC 803 cells. 14 However, mechanisms of cell death following photosensitization are poorly defined.…”

mentioning

confidence: 99%

Involvement of the Mitochondria-Caspase Pathway in HeLa Cell Death Induced by 2-Ethanolamino-2-Demethoxy-17-Ethanolimino-Hypocrellin B (EAHB)-Mediated Photodynamic Therapy

et al. 2012

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In order to elucidate the mechanism of cytotoxicity photoinduced by 2-ethanolamino-2-demethoxy-17-ethanolimino-hypocrellin B (EAHB), a derivative of hypocrellin B (HB), cellular uptake, subcellular localization as well as photodynamic therapy (PDT) efficiency of EAHB, and cell apoptosis photoinduced by EAHB were investigated in HeLa cells by laser confocal fluorescence microscopy, 3-(4,5-Dimethylthiazol-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide assay, flow cytometry, DNA fragmentation on agarose gel, and Western blot. The results showed EAHB was distributed throughout the cytoplasm of the cell, with no detectable penetration into the nucleus. The proportion of dead cells increased with increases in both the dosage of light and the concentration of EAHB. Its phototoxicity to HeLa cells proceeded via apoptosis. The EAHB-PDT treatment induced a cytochrome c release from the mitochondria into the cytosol followed by the activation of both caspase 3 and caspase 9 in HeLa cells. The results suggested that EAHB-PDT treatment induced apoptosis in HeLa cells, and the cellular apoptosis involved a mitochondria-/caspase-dependent mechanism.

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“…6 Prof. Petrich [5][6][7][8][9][10][11][12] from Iowa University in USA investigated the antiviral activity and cytotoxicity of hypocrellins and the toxicity mechanisms and compared hypocrellin with hypericin. Other scientists and groups also made great contributions to the clarification of the properties of the excited state, the structural modifications, the mechanisms of photosensitization, quantum-chemical calculation, and the photodynamic damage to macrobiomolecules such as lipids and DNA [13][14][15][16][17][18][19][20][21][22][23][24][25].With the development and application of laser technology and optic fiber technology, the light source and delivery of irradiation in photodynamic therapy (PDT) have been settled increasingly, and the photosensitizers are the key issue in PDT application. Currently, the only approved Photofrin II ® has several disadvantages, such as complex composition, weak red absorption, slow clearance from normal tissues and high side effects.…”

mentioning

confidence: 99%

Photophysics, photochemistry and photobiology of hypocrellin photosensitizers

Jiang

2001

Chin.Sci.Bull.

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Hypocrellins are novel photosensitizers from China, which are demonstrated to have significant antitumor and anti-virus activity and to be potential photodynamic therapy (PDT) agents. As compared with hematoporphyrin, the only approved photosensitizer, hypocrellins have several advantages, such as easy preparation and easy purification, high triplet quantum yield, high singlet-oxygen quantum yield, high phototoxicity but low dark toxicity, and rapid clearance from normal issues. This article reviews briefly the photophysics, photochemistry and photobiology of hypocrellins on the basis of the domestic and international research results.Hypocrellins are natural photosensitizers isolated from Hypocrella bambusae (B. et Br.) sacc., a parasitic fungus of Sinarundinaria sp. that grows abundantly in China. Natural hypocrellins mainly include two components, hypocrellin A (HA) and hypocrellin B (HB) ( fig. 1), and 95% of hypocrellins are HA. However, HA can be converted into HB by dehydration in alkaline conditions [l]. Our group started the research on hypocrellins, the novel type of photosensitizers, in the early 1980s and investigated systematically on the characterization of the chemical structures of HA and HB, photophysics, photochemistry and the molecular mechanisms of photodynamic action[2,3]. "C) , OH""'O H}'pocrellill B Fig. IHypocrellins attract more and more international interest, which results in the increasing research on the photophysics, photochemistry and photobiology of hypocrellins. Prof. Lown [4] from Alberta University in Canada focuses his research on the manual synthesis of hypocrellins and isotope-marked hypocrellins, synthesis of aminated hypocrellin, and photobiology of hypocrellins. 6 Prof. Petrich [5][6][7][8][9][10][11][12] from Iowa University in USA investigated the antiviral activity and cytotoxicity of hypocrellins and the toxicity mechanisms and compared hypocrellin with hypericin. Other scientists and groups also made great contributions to the clarification of the properties of the excited state, the structural modifications, the mechanisms of photosensitization, quantum-chemical calculation, and the photodynamic damage to macrobiomolecules such as lipids and DNA [13][14][15][16][17][18][19][20][21][22][23][24][25].With the development and application of laser technology and optic fiber technology, the light source and delivery of irradiation in photodynamic therapy (PDT) have been settled increasingly, and the photosensitizers are the key issue in PDT application. Currently, the only approved Photofrin II ® has several disadvantages, such as complex composition, weak red absorption, slow clearance from normal tissues and high side effects. Presently, the ideal photosensitizers with high PDT efficacy, low dark toxicity and better distribution selectivity are the aims for PDT scientists. Hypocrellins are a novel type of photosensitizers, and have the following advantages as compared with haematoporphyrin derivatives (HPD): easy preparation and purification, high quantum yields of trip...

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A novel photosensitizer, 2-butylamino-2-demethoxy-hypocrellin A (2-BA-2-DMHA) 1. Synthesis of 2-BA-2-DMHA and its phototoxicity to MGC803 cells

Cited by 32 publications

References 21 publications

Quantum chemical and statistical study of hypocrellin dyes with phototoxicity against tumor cells

Quantum chemical and statistical study of hypocrellin dyes with phototoxicity against tumor cells

Involvement of the Mitochondria-Caspase Pathway in HeLa Cell Death Induced by 2-Ethanolamino-2-Demethoxy-17-Ethanolimino-Hypocrellin B (EAHB)-Mediated Photodynamic Therapy

Photophysics, photochemistry and photobiology of hypocrellin photosensitizers

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