Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Experiment Videos

Quantitative structure-activity relationships in amphotericin B derivatives.

M Chéron1, B Cybulska, J Mazerski

  • 1Laboratoire de Physique et Chimie Biomoléculaire, CNRS (U.A. 198), Université Pierre et Marie Curie, Paris, France.

Biochemical Pharmacology
|March 1, 1988
PubMed
Summary

Quantitative structure-activity relationships of amphotericin B derivatives show a positive charge is essential for activity and sterol interaction. Lack of a carboxyl group helps differentiate cell types.

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Community-acquired Clostridium difficile infections in emergency departments.

Medecine et maladies infectieuses·2016
Same author

STEM study of Li4 Ti5 O12 anode material modified with Ag nanoparticles.

Journal of microscopy·2016
Same author

Thin layer spectroelectrochemical (RVC-OTTLE) studies of pertechnetate reduction in acidic media.

Journal of radioanalytical and nuclear chemistry·2015
Same author

Development of antileishmanial lipid nanocomplexes.

Biochimie·2014
Same author

High order kinoforms as a broadband achromatic diffractive optics for terahertz beams.

Optics express·2014
Same author

Modeling of the optical system illuminated by quasi-monochromatic spatially incoherent light: new numerical approach.

Optics letters·2012

Area of Science:

  • Medicinal Chemistry
  • Pharmacology
  • Biochemistry

Background:

  • Amphotericin B is a vital antifungal agent.
  • Understanding structure-activity relationships (SAR) is key to developing improved antifungals.
  • Modifications to amphotericin B can alter its efficacy and selectivity.

Purpose of the Study:

  • To investigate the quantitative structure-activity relationships (QSAR) of amphotericin B and its semisynthetic derivatives.
  • To correlate molecular modifications with biological activity and target interaction.
  • To elucidate the role of specific functional groups in amphotericin B's mechanism of action.

Main Methods:

  • Synthesis of 16 semisynthetic derivatives of amphotericin B.
  • Quantitative structure-activity relationship (QSAR) analysis using five biological tests.

Related Experiment Videos

  • Principal Component Analysis (PCA) for data analysis.
  • Spectroscopic investigation of compound interaction with lipidic vesicles.

    • Main Results:

    • A positively charged nitrogen atom (protonable or fixed) is indispensable for both biological activity and antibiotic-sterol interaction.
    • The absence of a free carboxyl group enhances the molecule's ability to differentiate between cholesterol and ergosterol.
    • QSAR models were developed to predict the activity of amphotericin B derivatives.

    Conclusions:

    • The positive charge on the nitrogen atom is a critical pharmacophore for amphotericin B.
    • Modifications at the carboxyl group can tune the selectivity of amphotericin B towards different sterols.
    • These findings provide a basis for designing novel amphotericin B analogs with improved therapeutic profiles.