Synthesis, conformational analysis, and cytotoxicity of new analogues of the natural cyclodepsipeptide jaspamide

Stefania Terracciano, Ines Bruno, Giuseppe Bifulco, Jean E. Copper, Charles Smith, Luigi Gomez-Paloma, Raffaele Riccio

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Three analogues of the natural bioactive cyclodepsipeptide jaspamide (3-5) were efficiently synthesized using a combination of solid and solution phase techniques. The preliminary design of the molecules has involved the rational substitution and/or simplification of the most critical structural features of the lead compound. The synthetic products were subjected to pharmacological assays, and the conformational properties were investigated by MM (molecular mechanics) and MD (molecular dynamics) calculations, to describe the potential pharmacophoric core responsible for the observed activities.

Original languageEnglish (US)
Pages (from-to)1325-1331
Number of pages7
JournalJournal of Natural Products
Volume67
Issue number8
DOIs
StatePublished - Aug 1 2004

Fingerprint

jasplakinolide
synthetic products
Depsipeptides
Lead compounds
Molecular mechanics
molecular dynamics
Molecular Dynamics Simulation
Cytotoxicity
Mechanics
mechanics
Molecular dynamics
cytotoxicity
Assays
Substitution reactions
Pharmacology
Molecules
synthesis
assays
methodology
Lead

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Terracciano, S., Bruno, I., Bifulco, G., Copper, J. E., Smith, C., Gomez-Paloma, L., & Riccio, R. (2004). Synthesis, conformational analysis, and cytotoxicity of new analogues of the natural cyclodepsipeptide jaspamide. Journal of Natural Products, 67(8), 1325-1331. https://doi.org/10.1021/np049955b
Terracciano, Stefania ; Bruno, Ines ; Bifulco, Giuseppe ; Copper, Jean E. ; Smith, Charles ; Gomez-Paloma, Luigi ; Riccio, Raffaele. / Synthesis, conformational analysis, and cytotoxicity of new analogues of the natural cyclodepsipeptide jaspamide. In: Journal of Natural Products. 2004 ; Vol. 67, No. 8. pp. 1325-1331.
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Terracciano, S, Bruno, I, Bifulco, G, Copper, JE, Smith, C, Gomez-Paloma, L & Riccio, R 2004, 'Synthesis, conformational analysis, and cytotoxicity of new analogues of the natural cyclodepsipeptide jaspamide', Journal of Natural Products, vol. 67, no. 8, pp. 1325-1331. https://doi.org/10.1021/np049955b

Synthesis, conformational analysis, and cytotoxicity of new analogues of the natural cyclodepsipeptide jaspamide. / Terracciano, Stefania; Bruno, Ines; Bifulco, Giuseppe; Copper, Jean E.; Smith, Charles; Gomez-Paloma, Luigi; Riccio, Raffaele.

In: Journal of Natural Products, Vol. 67, No. 8, 01.08.2004, p. 1325-1331.

Research output: Contribution to journalArticle

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AU - Terracciano, Stefania

AU - Bruno, Ines

AU - Bifulco, Giuseppe

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AU - Smith, Charles

AU - Gomez-Paloma, Luigi

AU - Riccio, Raffaele

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