Antiviral Activities of Photoactive Perylenequinones

Nine perylenequinones (PQ), including some familiar naturally occurring pigments, were compared for their light‐mediated antiviral efficacies. Calphostin C was the most active compound against the two target viruses, herpes simplex virus type 1 and Sindbis virus. Hypo‐crellins A and B were also very active. However, three cercosporin‐like PQ were substantially less active in spite of their high quantum yields of singlet oxygen, whereas phleichrome, another efficient singlet oxygen producer, showed no detectable antiviral activity. One other PQ, which was a very weak singlet oxygen producer, also showed no antiviral activity. None of the active compounds showed significant antiviral activity in the dark. Thus, for some groups of PQ there was correlation between quantum yield of singlet oxygen C02) and antiviral efficacy, but there are evidently other structural features of PQ that influence activity.

[1]  S. Yamazaki,et al.  The Chemistry and Stereochemistry of Cercosporin , 1972 .

[2]  J. Hudson Antiviral Compounds From Plants , 1989 .

[3]  T. Tamaoki,et al.  Calphostins (UCN-1028), novel and specific inhibitors of protein kinase C. I. Fermentation, isolation, physico-chemical properties and biological activities. , 1989, The Journal of antibiotics.

[4]  J. Lown,,et al.  HYPOCRELLINS and THEIR USE IN PHOTOSENSITIZATION * , 1990, Photochemistry and photobiology.

[5]  S. Carpenter,et al.  PHOTOSENSITIZATION IS REQUIRED FOR INACTIVATION OF EQUINE INFECTIOUS ANEMIA VIRUS BY HYPERICIN , 1991, Photochemistry and photobiology.

[6]  J. Hudson,et al.  ANTIVIRAL ACTIVITY OF THE PHOTOACTIVE PLANT PIGMENT HYPERICIN , 1991, Photochemistry and photobiology.

[7]  Zhenjun Diwu,et al.  Photosensitization by anticancer agents 12. Perylene quinonoid pigments, a novel type of singlet oxygen sensitizer , 1992 .

[8]  R. Marles,et al.  STRUCTURE‐ACTIVITY STUDIES OF PHOTOACTIVATED ANTIVIRAL AND CYTOTOXIC TRICYCLIC THIOPHENES , 1992, Photochemistry and photobiology.

[9]  J. Lown,,et al.  A simple high-yielding approach to perylenequinone from the novel one-step double coupling reaction of 1,2-naphtoquinone , 1992 .

[10]  J. Lenard,et al.  Antiretroviral activities of hypericin and rose bengal: photodynamic effects on Friend leukemia virus infection of mice. , 1993, Antiviral research.

[11]  J. Hudson,et al.  The importance of light in the anti-HIV effect of hypericin. , 1993, Antiviral research.

[12]  T. Meyer,et al.  Design, synthesis and investigation of mechanisms of action of novel protein kinase C inhibitors: perylenequinonoid pigments. , 1994, Biochemical pharmacology.

[13]  J. Hudson,et al.  HYPOCRELLIN, FROM HYPOCRELLA BAMBUASE, IS PHOTOTOXIC TO HUMAN IMMUNODEFICIENCY VIRUS , 1994, Photochemistry and photobiology.

[14]  J. Lown,,et al.  Phototherapeutic potential of alternative photosensitizers to porphyrins. , 1994, Pharmacology & therapeutics.

[15]  PHOTOACTIVE TERTHIOPHENES: THE INFLUENCE OF SERUM ON ANTI‐HIV (HUMAN IMMUNODEFICIENCY VIRUS) ACTIVITIES , 1994, Photochemistry and photobiology.

[16]  J. Hudson,et al.  Antiviral assays on phytochemicals: the influence of reaction parameters. , 1994, Planta medica.