http://www.cnr.it/ontology/cnr/individuo/prodotto/ID169950

Chemical synthesis, pharmacological characterization, and possible formation in unicellular fungi of 3-hydroxy-anandamide (Articolo in rivista)

Type

Label

Chemical synthesis, pharmacological characterization, and possible formation in unicellular fungi of 3-hydroxy-anandamide (Articolo in rivista) (literal)

Anno

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

Alternative label

De Petrocellis L, Deva R, Mainieri F, Schaefer M, Bisogno T, Ciccoli R, Ligresti A, Hill K, Nigam S, Appendino G, Di Marzo V. (2009)
Chemical synthesis, pharmacological characterization, and possible formation in unicellular fungi of 3-hydroxy-anandamide
in Journal of lipid research (Print); American Society Of Biochemistry And Molecular Biology Inc. (ASBMB), Rockville (Stati Uniti d'America)
(literal)

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

De Petrocellis L, Deva R, Mainieri F, Schaefer M, Bisogno T, Ciccoli R, Ligresti A, Hill K, Nigam S, Appendino G, Di Marzo V. (literal)

Pagina inizio

Pagina fine

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

Rivista

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

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

Note

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

Endocannabinoid Research Group, Institutes of Cybernetics Consiglio Nazionale delle Ricerche, Pozzuoli (Napoli), Italy Eicosanoid & Lipid Research Division & Experimental Gynecology and Breast Research, Department of Gynecology & Obstetrics, Charité Medical School Benjamin Franklin, Berlin, Germany Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Novara, Italy Molekulare Pharmakologie und Zellbiologie, Neurowissenschaftliches Forschungszentrum, Charité-Universitätsmedizin Berlin, Germany Biomolecular Chemistry, Consiglio Nazionale delle Ricerche, Pozzuoli (Napoli), Italy Ente per le Nuove Tecnologie, l'Energia e l'Ambiente Centro Ricerche Casaccia, Rome, Italy (literal)

Titolo

Chemical synthesis, pharmacological characterization, and possible formation in unicellular fungi of 3-hydroxy-anandamide (literal)

Abstract

The fungal pathogen Candida albicans transforms arachidonic acid (AA) into 3-hydroxyarachidonic acid [3(R)HETE], and we investigated if its nonpathogenic and 3(R)HETE-producing close relative, Dipodascopsis uninucleata, could similarly transform the endocannabinoid/endovanilloid anandamide into 3-hydroxyanandamide (3-HAEA). We found that D. uninucleata converts anandamide into 3-HAEA, and we therefore developed an enantiodivergent synthesis for this compound to study its pharmacological activity. Both enantiomers of 3-HAEA were as active as anandamide at elevating intracellular Ca(2+) via TRPV1 receptors overexpressed in HEK-293 cells, while a similar to 70-90-fold and similar to 45-60-fold lower affinity at cannabinoid CB(1) and CB(2) receptors was instead observed. Patch clamp recordings showed that 3(R)-HAEA activates a TRPV1-like current in TRPV1-expressing HEK-293 cells. Thus, 3(R)-HETE-producing yeasts might convert anandamide released by host cells at the site of infection into 3(R)-HAEA, and this event might contribute to the inflammatory and algogenous responses associated to fungal diseases.-De Petrocellis, L., R. Deva, F. Mainieri, M. Schaefer, T. Bisogno, R. Ciccoli, A. Ligresti, K. Hill, S. Nigam, G. Appendino, and V. Di Marzo. Chemical synthesis, pharmacological characterization, and possible formation in unicellular fungi of 3-hydroxyanandamide. (literal)

Editore