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

doi:10.1021/np049955b

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

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19 Scopus citations

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 language	English (US)
Pages (from-to)	1325-1331
Number of pages	7
Journal	Journal of Natural Products
Volume	67
Issue number	8
DOIs	https://doi.org/10.1021/np049955b
State	Published - Aug 1 2004

All Science Journal Classification (ASJC) codes

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

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10.1021/np049955b

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AU - Terracciano, Stefania

AU - Bruno, Ines

AU - Bifulco, Giuseppe

AU - Copper, Jean E.

AU - Smith, Charles

AU - Gomez-Paloma, Luigi

AU - Riccio, Raffaele

PY - 2004/8/1

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AB - 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.

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

Abstract

All Science Journal Classification (ASJC) codes

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