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The Immobilization of Gossypol Derivative on N-Polyvinylpyrrolidone Increases its Water Solubility and Modifies Membrane-Active Properties
- Source :
- Journal of Medicinal Chemistry. 52:4119-4125
- Publication Year :
- 2009
- Publisher :
- American Chemical Society (ACS), 2009.
-
Abstract
- The conjugate of the gossypol derivative megosin (1) with N-polyvinylpyrrolidone named rometin (2) was synthesized. The effects of 1 and 2 on the structure and permeability of human erythrocytes and rat liver mitochondria were compared. Compound 1 induced dose-dependent erythrocyte hemolysis and increased mitochondrial permeability, with concomitant changes in membrane structure as determined by ESR and fluorescence anisotropy methods. Immobilization of 1 on N-polyvinylpyrrolidone (compound 2) increased its water solubility and reduced the intensity of its effects on erythrocyte membrane integrity and mitochondrial permeability, which correlated with a decrease in the membranes structural changes induced by the compound. Although the same concentrations of free and N-polyvinylpyrrolidone bound 1 were used, far less (14)C-labeled 1 was incorporated into the membranes from complex than free 1. The increase in water solubility and the reduction of membrane-active properties of 1 after immobilization on N-polyvinylpyrrolidone could explain our previous observation of the decreased toxicity of 1.
- Subjects :
- Male
Cell Membrane Permeability
Erythrocytes
chemistry.chemical_compound
Drug Discovery
Animals
Humans
Organic chemistry
Rats, Wistar
Aqueous solution
Staining and Labeling
Cell Membrane
Gossypol
Membrane structure
Povidone
Water
Biological membrane
Rats
Membrane
Solubility
chemistry
Permeability (electromagnetism)
Mitochondrial Membranes
Biophysics
Molecular Medicine
Fluorescence anisotropy
Derivative (chemistry)
Subjects
Details
- ISSN :
- 15204804 and 00222623
- Volume :
- 52
- Database :
- OpenAIRE
- Journal :
- Journal of Medicinal Chemistry
- Accession number :
- edsair.doi.dedup.....2210074f999bc8acfa8dee787352b98a