Hypericin, the Photodynamic Pigment from St. John'swort

Pace, Natalie A.; Mackinney, G.

doi:10.1021/ja01855a009

Cited by 52 publications

(30 citation statements)

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“…Both reagents induced direct photodynamic hemolysis (data not shown), confirming previous reports (10)(11)(12)(13). 150 values were much higher than those for viral inactivation of hemolysis, however (Table 1).…”

Section: Resultssupporting

confidence: 91%

“…Hypericin's photodynamic activity against membranes in vitro was also noted very early, when it was found to be a promoter of light-induced hemolysis (H. F. Blum, quoted in ref. 10). In this regard it resembled rose bengal, another potent inducer of photodynamic hemolysis (11)(12)(13).…”

mentioning

confidence: 99%

“…In this regard, hypericin has been regarded as a promising potential anti-AIDS drug since 1988, when it was reported that a single injection of this compound prevented splenomegaly and death in mice infected with Friend leukemia virus. Hypericin was "coadministered" with the virus; 50% survival was conferred by 10 jig of hypericin, whereas 150 Ag was needed for complete protection (1,2). In addition, biweekly injections of hypericin into mice greatly reduced the viremia resulting from infection with the slower acting LP-BM5 murine leukemia virus (2).…”

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confidence: 99%

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Photodynamic inactivation of infectivity of human immunodeficiency virus and other enveloped viruses using hypericin and rose bengal: inhibition of fusion and syncytia formation.

Lenard¹,

Rabson

Vanderoef³

1993

Proc. Natl. Acad. Sci. U.S.A.

227

160

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The mechanism of the antiviral activity of hypericin was characterized and compared with that of rose bengal. Both compounds inactivate enveloped (but not unenveloped) viruses upon illumination by visible light. Human immunodeficiency and vesicular stomatitis viruses were photodynamically inactivated by both dyes at nanomolar concentrations. Photodynamic inactivation of fusion (hemolysis) by vesicular stomatitis, influenza, and Sendai viruses was induced by both dyes under similar conditions (e.g., I50 = 20-50 nM for vesicular stomatitis virus), suggesting that loss of infectivity resulted from inactivation of fusion. Syncytium formation, between cells activated to express human immunodeficiency virus gpl20 on their surfaces and CD4+ cells, was inhibited by illumination in the presence of 1 ,uM hypericin. Hypericin and rose bengal thus exert similar virucidal effects. Both presumably act by the same mechanism-namely, the inactivation of the viral fusion function by singlet oxygen produced upon illumination. The implications of this photodynamic antiviral action for the potential therapeutic usefulness of both hypericin and rose bengal are discussed.

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Section: Resultssupporting

confidence: 91%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Photodynamic inactivation of infectivity of human immunodeficiency virus and other enveloped viruses using hypericin and rose bengal: inhibition of fusion and syncytia formation.

Lenard¹,

Rabson

Vanderoef³

1993

Proc. Natl. Acad. Sci. U.S.A.

227

160

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“…Hypericism is oxygen dependent, and it is thus recognized as a photodynamic action by hypericin (Pace and Mackinney, 1941). Interestingly, hypericin is also a potent antidepressant, although it is no longer widely used as a drug.…”

Section: Ohmentioning

confidence: 99%

Hypericin and Its Photodynamic Action

Durán

Song

1986

Photochem & Photobiology

270

171

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“…Inhibition of DNA polymerases by the other phenalenones have been reported, but they did not inhibit HIV reverse transcriptase [19]. A plant metabolite, hypericin [20], is the only orthoand peri-fused aromatic compound reported to show integrase inhibition [21]. …”

mentioning

confidence: 99%