Copyright © 2007 Elsevier Ltd All rights reserved.
Synthesis of neutral and cationic tripyridylporphyrin-d-galactose conjugates and the photoinactivation of HSV-1
Received 7 December 2006;
References and further reading may be available for this article. To view references and further reading you must purchase this article.
Abstract
Neutral and cationic tripyridylporphyrin-d-galactose conjugates were synthesized and their antiviral activity against herpes simplex virus type 1 (HSV-1) was evaluated. At non-cytotoxic concentrations the studied compounds show significant antiviral activity after photoactivation. The influence of photoactivation on drug treated cells was also analyzed, at different times of infection with HSV-1, for a neutral (1b) and a cationic glycoporphyrin (3b) derivative. The results show that the inhibition of the viral yield is more dependent on photoactivation for compound 1b than for compound 3b. These two compounds also differ in the inhibitory effect during the viral replicative cycle: while compound 3b inhibits the viral yield at all the addition times assayed, compound 1b is more efficient in later times of infection.
Keywords: Cationic porphyrins; Sugars; Antiviral compounds; HSV-1
Article Outline
- 1. Introduction
- 2. Chemistry
- 3. Photophysical studies
- 4. Biological evaluation
- 4.1. Photocytotoxicity studies
- 4.2. Virucidal effect
- 4.3. Influence of the drug addition time on virus yield during infection
- 5. Discussion and conclusions
- 6. Experimental
- 6.1. General
- 6.2. Synthesis
- 6.2.1. 5-[4-(1,2:3,4-Di-O-isopropylidene-α-d-galactopyranosyl-6-oxycarbonyl)phenyl]-10,15,20-tri(4-pyridyl)porphyrin (1a)
- 6.2.2. 5-[4-(α/β-d-Galactopyranosyl-6-oxycarbonyl)phenyl]-10,15,20-tri(4-pyridyl)porphyrin (1b)
- 6.2.3. Methylation of porphyrins 1a and 1b
- 6.2.4. 5-[4-(1,2:3,4-Di-O-isopropylidene-α-d-galactopyranosyl-6-oxycarbonyl)phenyl]-10,15,20-Tris(N-methylpyridinium-4-yl)porphyrin tri-iodide (3a)
- 6.2.5. 5-[4-(α/β-d-Galactopyranosyl-6-oxycarbonyl)phenyl]-10,15,20-Tris(N-methylpyridinium-4-yl)porphyrin tri-iodide (3b)
- 6.3. Photostability of the porphyrin derivatives
- 6.4. Singlet oxygen generation
- 6.5. Photosensitizers
- 6.6. Cells and virus
- 6.7. Photocytotoxicity
- 6.8. Virucidal effect
- 6.9. Influence of the drug addition time on virus yield during infection
- Acknowledgements
- References







E-mail Article
Add to my Quick Links

Cited By in Scopus (2)







