Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands (Articolo in rivista)

Type

• Articolo in rivista (Classe)
• Prodotto della ricerca (Classe)

Label

• Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands (Articolo in rivista) (literal)

Anno

• 2014-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1039/c4ob02002b (literal)

Alternative label

• Zanato, Chiara; Watson, Sonia; Bewick, Guy S.; Harrison, William T. A.; Zanda, Matteo (2014)
  Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands
  in Organic & biomolecular chemistry
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Zanato, Chiara; Watson, Sonia; Bewick, Guy S.; Harrison, William T. A.; Zanda, Matteo (literal)

Pagina inizio

• 9638 (literal)

Pagina fine

• 9643 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 12 (literal)

Rivista

• Organic & biomolecular chemistry (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali

• 6 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo

• 47 (literal)

Note

• ISI Web of Science (WoS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• University of Aberdeen; University of Aberdeen; University of Aberdeen; Consiglio Nazionale delle Ricerche (CNR) (literal)

Titolo

• Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands (literal)

Abstract

• (-)-Kainic acid potently increases stretch-induced afferent firing in muscle spindles, probably acting through a hitherto uncloned phospholipase D (PLD)-coupled mGlu receptor. Structural modification of (-)-kainic acid was undertaken to explore the C-4 substituent effect on the pharmacology related to muscle spindle firing. Three analogues 1a-c were synthesised by highly stereoselective additions of a CF3, a hydride and an alkynyl group to the Re face of the key pyrrolidin-4-one intermediate 5a followed by further structural modifications. Only the 4-(1,2,3-triazolyl)-kainate derivative 1c retained the kainate-like agonism, increasing firing in a dose-dependent manner. Further modification of 1c by introduction of a PEG-biotin chain on the 1,2,3-triazole fragment afforded compound 14 which retained robust agonism at 1 mu M and appears to be suitable for future use in pull-down assays and far western blotting for PLD-mGluR isolation. (literal)

Prodotto di

• Istituto di chimica del riconoscimento molecolare (ICRM) (Istituto)
• Targeting e inibizione dell'angiogenesi per la terapia anti-cancro (PM.P01.021.004) (Modulo)

Autore CNR

• MATTEO ZANDA (Persona)

Incoming links:

Autore CNR di

• MATTEO ZANDA (Persona)

Prodotto

• Istituto di chimica del riconoscimento molecolare (ICRM) (Istituto)
• Targeting e inibizione dell'angiogenesi per la terapia anti-cancro (PM.P01.021.004) (Modulo)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Organic & biomolecular chemistry (Rivista)