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Titolo:
Synthesis and biological evaluation of nonylprodigiosin and macrocyclic prodigiosin analogues
Autore:
Furstner, A; Grabowski, J; Lehmann, CW; Kataoka, T; Nagai, K;
Indirizzi:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany Max Planck Inst Kohlenforsch Mulheim Germany D-45470 70 Mulheim, Germany Tokyo Inst Technol, Dept Bioengn, Yokohama, Kanagawa 2268501, Japan Tokyo Inst Technol Yokohama Kanagawa Japan 2268501 anagawa 2268501, Japan
Titolo Testata:
CHEMBIOCHEM
fascicolo: 1, volume: 2, anno: 2001,
pagine: 60 - 68
SICI:
1439-4227(20010108)2:1<60:SABEON>2.0.ZU;2-O
Fonte:
ISI
Lingua:
ENG
Soggetto:
RING-CLOSING-METATHESIS; CROSS-COUPLING REACTIONS; CTL-MEDIATED CYTOTOXICITY; H+-ATPASE INHIBITORS; OLEFIN METATHESIS; CONCANAMYCIN-A; LYTIC GRANULES; T-CELLS; MURINE SPLENOCYTES; RESIN GLYCOSIDES;
Keywords:
alkaloids; immunosuppression; metathesis; prodigiosins; Suzuki reaction;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
74
Recensione:
Indirizzi per estratti:
Indirizzo: Furstner, A Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany Max Planck Inst Kohlenforsch Kaiser Wilhelm Pl 1 Mulheim Germany D-45470
Citazione:
A. Furstner et al., "Synthesis and biological evaluation of nonylprodigiosin and macrocyclic prodigiosin analogues", CHEMBIOCHEM, 2(1), 2001, pp. 60-68

Abstract

Nonylprodigiosin (4) and various of its analogues have been prepared by Suzuki cross-coupling reactions of a well accessible pyrrolyl triflate with (hetero)aryl boronic acid derivatives bearing alkenyl side chains. The resulting alkenes or dienes were subjected to metathesis dimerization or ring-closing metathesis (RCM) reactions, respectively, by using a ruthenium indenylidene complex as the catalyst. The biological activity of the products thus obtained was tested in two different assays monitoring ii the proliferation of murine spleen cells induced by lipopolysaccharides (LPS) and concanavalin A (Con A), and iii the vacuolar acidification of baby hamster kidney (BHK) cells. Compounds 4 and 21 suppressed Con A-induced T-cell proliferation much more potently than LPS-induced B-cell proliferation. Furthermore, compounds 4 and 26 : markedly inhibited vacuolar acidification, although other compounds exhibited no or only marginal effects. Thus, the immunosuppressive activity of prodigiosins toward T-cell proliferation seems to be mediated through cellular targets distinct from vacuolar acidification, and the prodigiosin analogues might be powerful tools to dissect these biological responses. The X-ray crystal structure of the macrocyclic product 25 has beendetermined, showing that the replacement of one pyrrole ring of the parentcompound 4 by a phenyl group does not alter the overall electronic features of the remaining heterocyclic ring system of these alkaloids.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 14/07/20 alle ore 07:55:19