Abstract

Studies on the synthesis, structural elucidation, and antiviral evaluation of several carbohydrate-substituted meso-tetraarylporphyrins against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) are described. The potential of those photosensitizers, and of their precursors, on the photoinactivation of HSV-1 and HSV-2 was examined in Vero cells. Their virucidal and viral replication effects were assessed under white light, at their maximum noncytotoxic concentrations. The highest inhibitory effects on viral replication, for both viruses, were obtained with the glycoporphyrins where the sugar moiety bears unprotected hydroxyl groups. Strong inhibition of virus yield was observed even at concentrations much lower than their maximum noncytotoxic concentrations. These compounds can be postulated to be useful as potential drugs for the treatment of herpes simplex viruses infections.

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Keywords: Porphyrins; Sugars; Antiviral compounds; HSV-1; HSV-2

Article Outline

1. Introduction

2. Results and discussion

2.1. Chemistry

3. Biological evaluation

3.1. Results and discussion

4. Conclusion

5. Experimental

5.1. General

5.2. Synthesis

5.2.1. 5-(4-Hydroxyphenyl)-10,15,20-triphenylporphyrin (1)

5.2.2. 5-[4-(Pentafluorophenyloxy)phenyl]-10,15,20-triphenylporphyrin (2)

5.2.3. meso-Tetrakis(pentafluorophenyl)porphyrin (3)

5.2.4. 5-(4-Carboxyphenyl)-10,15,20-triphenylporphyrin (4)

5.2.5. 5-[4-(2,3,4,6-Tetra-O-acetyl-β-d-glucopyranosyloxy)phenyl]-10,15,20-triphenylporphyrin (1a)

5.2.6. 5-(4-β-d-Glucopyranosyloxyphenyl)-10,15,20-triphenylporphyrin (1b)

5.2.7. 5-{4-[4-(1,2:3,4-Di-O-isopropylidene-α-d-galactopyranosyl-6-oxy)tetrafluorophenyloxy]phenyl}-10,15,20-triphenylporphyrin (2a)

5.2.8. 5-{4-[4-(α/β-d-Galactopyranosyl-6-oxy)tetrafluorophenyloxy]phenyl}-10,15,20-triphenylporphyrin (2b)

5.2.9. 5-[4-(1,2:3,4-Di-O-isopropylidene-α-d-galactopyranosyl-6-oxy)tetrafluorophenyl]-10,15,20-tris(pentafluorophenyl)porphyrin (3a)

5.2.10. 5-[4-(α/β-d-Galactopyranosyl-6-oxy)tetrafluorophenyl]-10,15,20-tris(pentafluorophenyl)porphyrin (3b)

5.2.11. 5-[4-(1,2:3,4-Di-O-isopropylidene-α-d-galactopyranosyl-6-oxycarbonyl)phenyl]-10,15,20-triphenylporphyrin (4a)

5.2.12. 5-[4-(α/β-d-Galactopyranosyl-6-oxycarbonyl)phenyl]-10,15,20-triphenylporphyrin (4b)

5.2.13. 5-[4-(α-Methyl-d-galactopyranosyl-6-oxycarbonyl)phenyl]-10,15,20-triphenylporphyrin (α-4c) and 5-[4-(β-methyl-d-galactopyranosyl-6-oxycarbonyl)phenyl]-10,15,20-triphenylporphyrin (β-4c)

5.2.14. Photosensitizers

5.2.15. Photostability of the compounds

5.2.16. Cells and virus

5.2.17. Photocytotoxicity

5.2.18. Virucidal effect

5.2.19. Viral replication effect

5.2.20. Effect of glycoporphyrin 1b on viral adsorption and post-adsorption

Acknowledgements

References