Studies on the photoinduced sulfonation of hypocrellins

Hu, Yi-Zhen; J, An; Chiang, Li-chin

doi:10.1016/1010-6030(93)85055-d

Cited by 26 publications

(7 citation statements)

References 10 publications

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“…However, the naturally occurring compounds are only lipid soluble and exhibit little absorption in the photodynamic window (600–900 nm), which limits their application in PDT. To improve water solubility and red absorptivity of hypocrellins, a series of hypocrellin derivatives have been synthesized in the last 20 years (10–17), among which are the amino‐substituted hypocrellins (5,18,19). Their photoresponse was enhanced remarkably, and they possessed higher photodynamic activity than the other derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Three Novel Amphiphilic Aminated Hypocrellins as Photodynamic Therapeutic Agents¶

Chen

Zhang

et al. 2007

Photochemistry and Photobiology

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To improve the amphiphilicities and red absorption of the hypocrellins, three novel 2‐amino‐2‐demethoxy‐hypocrellins were synthesized by the mild reactions of hypocrellin B with 4‐(2‐amino‐ethyl)morpholine, N,N‐dimethylethylenediamine and 1‐(2‐amino‐ethyl)piperazine, respectively. The structures of these derivatives were characterized with proton nuclear magnetic resonance, infrared and mass spectra (MS). The ultraviolet–visible absorption and fluorescence spectra of the derivatives were measured and the new amino‐substituted hypocrellins showed strong absorption in the domain of the phototherapeutic window (600–900 nm). Their amphiphilicities evaluated via the partition coefficients between n‐octanol and phosphate‐buffered saline buffer improved remarkably. Electron paramagnetic resonance spin‐trapping measurements were used to investigate the photodynamic action of the three compounds in the presence of oxygen. Singlet oxygen (1O2) and superoxide anion radical (O2•−) generated by illuminating the hypocrellin derivatives in aerobic solution were observed.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Three Novel Amphiphilic Aminated Hypocrellins as Photodynamic Therapeutic Agents¶

Chen

Zhang

et al. 2007

Photochemistry and Photobiology

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“…However, the naturally occurring compounds are only lipid soluble and exhibit little absorption in the photodynamic window (600-900 nm), which limits their application in PDT. To improve water solubility and red absorptivity of hypocrellins, a series of hypocrellin derivatives have been synthesized in the last 20 years (10)(11)(12)(13)(14)(15)(16)(17), among which are the amino-substituted hypocrellins (5,18,19). Their photoresponse was enhanced remarkably, and they possessed higher photodynamic activity than the other derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Three Novel Amphiphilic Aminated Hypocrellins as Photodynamic Therapeutic Agents¶

Xu¹,

Chen²,

Zhang³

et al. 2003

Photochem Photobiol

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To improve the amphiphilicities and red absorption of the hypocrellins, three novel 2-amino-2-demethoxy-hypocrellins were synthesized by the mild reactions of hypocrellin B with 4-(2-amino-ethyl)morpholine, N,N-dimethylethylenediamine and 1-(2-amino-ethyl)piperazine, respectively. The structures of these derivatives were characterized with proton nuclear magnetic resonance, infrared and mass spectra (MS). The ultraviolet-visible absorption and fluorescence spectra of the derivatives were measured and the new amino-substituted hypocrellins showed strong absorption in the domain of the phototherapeutic window (600-900 nm). Their amphiphilicities evaluated via the partition coefficients between n-octanol and phosphate-buffered saline buffer improved remarkably. Electron paramagnetic resonance spin-trapping measurements were used to investigate the photodynamic action of the three compounds in the presence of oxygen. Singlet oxygen (1O2) and superoxide anion radical (O2.-) generated by illuminating the hypocrellin derivatives in aerobic solution were observed.

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“…For hypocrellins are hydrophobic compounds and tend to aggregate into clusters in blood which may block the vascular system, during the past decade, main attention has been paid to improving their water solubility and enhancing the red absorption by chemical modifications [5][6][7][8][9][10] . Among these derivatives, some aminated ones become even more lipophilic [8,11,12] , while water-soluble ones, such as the sulfonation and glycoside substituted hypocrellin B, lose their biological activity completely due to poor cell-uptakes [6,13,14] .…”

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confidence: 99%