[Membrane protective properties of diastereomers of methylpheophorbide a 13(2)-n-n-octyl-N-(2-hydroxy-3-isobornyl-5-methylbenzyl)amide]

E V Buravlev; D V Belykh; I Iu Chukicheva; I S Tarabukina; O G Shevchenko; A V Kutchin

doi:10.1134/s1068162013040055

[Membrane protective properties of diastereomers of methylpheophorbide a 13(2)-n-n-octyl-N-(2-hydroxy-3-isobornyl-5-methylbenzyl)amide]

Bioorg Khim. 2013 Jul-Aug;39(4):486-90. doi: 10.1134/s1068162013040055.

[Article in Russian]

Authors

E V Buravlev, D V Belykh, I Iu Chukicheva, I S Tarabukina, O G Shevchenko, A V Kutchin

PMID: 24707730
DOI: 10.1134/s1068162013040055

Abstract

Two diastereomers of methylpheophorbide a 13(2)-N-n-octyl-N-(2-hydroxy-3-isobornyl-5-methylbenzyl)amide were obtained from (+)- and (-)-enantiomers of 2-isobornyl-4-methylphenol. Evaluation of membrane protective and antioxidant activity of individual diastereomers on the model of H2O2-induced hemolysis of blood erythrocytes showed that the stereochemistry of isobornyl substituent in the synthesized conjugates has no effect on their biological activity.

MeSH terms

Animals
Camphanes / chemistry*
Chlorophyll / analogs & derivatives*
Chlorophyll / chemical synthesis
Chlorophyll / chemistry
Chlorophyll / pharmacology
Chromatography, High Pressure Liquid
Cresols / chemistry
Erythrocytes / drug effects
Hydrogen Peroxide / chemistry
Membranes / drug effects*
Mice
Molecular Structure
Protective Agents / chemical synthesis
Protective Agents / chemistry*
Protective Agents / pharmacology
Stereoisomerism

Substances

13(2)-n-n-octyl-N-(2-hydroxy-3-isobornyl-5-methylbenzyl)amide
Camphanes
Cresols
Protective Agents
Chlorophyll
4-cresol
methylpheophorbide
Hydrogen Peroxide