Synthesis, solution structure, and bioactivity of six new simplified analogues of the natural cyclodepsipeptide jaspamide

Stefania Terracciano; Ines Bruno; Giuseppe Bifulco; Elvira Avallone; Charles D. Smith; Luigi Gomez-Paloma; Raffaele Riccio

doi:10.1016/j.bmc.2005.05.042

Synthesis, solution structure, and bioactivity of six new simplified analogues of the natural cyclodepsipeptide jaspamide

Stefania Terracciano
, Ines Bruno
, Giuseppe Bifulco
, Elvira Avallone
, Charles D. Smith
, Luigi Gomez-Paloma
, Raffaele Riccio

Research output: Contribution to journal › Article › peer-review

23 Citations (SciVal)

Abstract

Recently, we described the synthesis and the biological evaluation of three modified analogues of jaspamide (1), a natural cyclodepsipeptide possessing a potent antitumor activity as a consequence of its ability to interfere with actin cytoskeleton. To obtain additional information on the potential pharmacophoric core of the target molecule, which is of fundamental importance to discover new and more effective anticancer products, we decided to explore the biological effects of further structural modifications carried out on the parent molecule. The synthesis and the chemical characterization of six jaspamide analogues (2-7) are reported and their conformational and biological properties are described.

Original language	English (US)
Pages (from-to)	5225-5239
Number of pages	15
Journal	Bioorganic and Medicinal Chemistry
Volume	13
Issue number	17
DOIs	https://doi.org/10.1016/j.bmc.2005.05.042
State	Published - Sep 1 2005

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1016/j.bmc.2005.05.042

Cite this

@article{e8eb0d4baf6f443d8d1fbe026a370d7d,

title = "Synthesis, solution structure, and bioactivity of six new simplified analogues of the natural cyclodepsipeptide jaspamide",

abstract = "Recently, we described the synthesis and the biological evaluation of three modified analogues of jaspamide (1), a natural cyclodepsipeptide possessing a potent antitumor activity as a consequence of its ability to interfere with actin cytoskeleton. To obtain additional information on the potential pharmacophoric core of the target molecule, which is of fundamental importance to discover new and more effective anticancer products, we decided to explore the biological effects of further structural modifications carried out on the parent molecule. The synthesis and the chemical characterization of six jaspamide analogues (2-7) are reported and their conformational and biological properties are described.",

author = "Stefania Terracciano and Ines Bruno and Giuseppe Bifulco and Elvira Avallone and Smith, \{Charles D.\} and Luigi Gomez-Paloma and Raffaele Riccio",

note = "Funding Information: The University of Salerno and the Ministry of Instruction, University and Research (MIUR, Rome), are gratefully acknowledged for financial support of this project through the funds ex-60\% and PRIN 2001, 2003 programs, respectively. The use of instrumental facilities of the Competence Center for Diagnostics and Molecular Pharmaceutics, sponsored by Regione Campania POR funds, is gratefully acknowledged. Finally, we thank Prof. Caterina Turco and Ms. Rita Di Giacomo (University of Salerno) for performing apoptosis assays on Jurkat cells.",

year = "2005",

month = sep,

day = "1",

doi = "10.1016/j.bmc.2005.05.042",

language = "English (US)",

volume = "13",

pages = "5225--5239",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd",

number = "17",

}

TY - JOUR

T1 - Synthesis, solution structure, and bioactivity of six new simplified analogues of the natural cyclodepsipeptide jaspamide

AU - Terracciano, Stefania

AU - Bruno, Ines

AU - Bifulco, Giuseppe

AU - Avallone, Elvira

AU - Smith, Charles D.

AU - Gomez-Paloma, Luigi

AU - Riccio, Raffaele

N1 - Funding Information: The University of Salerno and the Ministry of Instruction, University and Research (MIUR, Rome), are gratefully acknowledged for financial support of this project through the funds ex-60% and PRIN 2001, 2003 programs, respectively. The use of instrumental facilities of the Competence Center for Diagnostics and Molecular Pharmaceutics, sponsored by Regione Campania POR funds, is gratefully acknowledged. Finally, we thank Prof. Caterina Turco and Ms. Rita Di Giacomo (University of Salerno) for performing apoptosis assays on Jurkat cells.

PY - 2005/9/1

Y1 - 2005/9/1

N2 - Recently, we described the synthesis and the biological evaluation of three modified analogues of jaspamide (1), a natural cyclodepsipeptide possessing a potent antitumor activity as a consequence of its ability to interfere with actin cytoskeleton. To obtain additional information on the potential pharmacophoric core of the target molecule, which is of fundamental importance to discover new and more effective anticancer products, we decided to explore the biological effects of further structural modifications carried out on the parent molecule. The synthesis and the chemical characterization of six jaspamide analogues (2-7) are reported and their conformational and biological properties are described.

AB - Recently, we described the synthesis and the biological evaluation of three modified analogues of jaspamide (1), a natural cyclodepsipeptide possessing a potent antitumor activity as a consequence of its ability to interfere with actin cytoskeleton. To obtain additional information on the potential pharmacophoric core of the target molecule, which is of fundamental importance to discover new and more effective anticancer products, we decided to explore the biological effects of further structural modifications carried out on the parent molecule. The synthesis and the chemical characterization of six jaspamide analogues (2-7) are reported and their conformational and biological properties are described.

UR - https://www.scopus.com/pages/publications/22844445699

UR - https://www.scopus.com/pages/publications/22844445699#tab=citedBy

U2 - 10.1016/j.bmc.2005.05.042

DO - 10.1016/j.bmc.2005.05.042

M3 - Article

C2 - 16023351

AN - SCOPUS:22844445699

SN - 0968-0896

VL - 13

SP - 5225

EP - 5239

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 17

ER -

Synthesis, solution structure, and bioactivity of six new simplified analogues of the natural cyclodepsipeptide jaspamide

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this