Combining NMR and molecular modelling in a drug delivery context: investigation of the multi-mode inclusion of a new NPY-5 antagonist bromobenzenesulfonamide into beta-cyclodextrin.
NMR spectroscopic and molecular modelling methods have been employed to describe the complexation of trans-N-4-[N'-(4-chlorobenzoyl)hydrazinocarbonyl]cyclohexylmethyl-4-bromobenzenesulfonamide, a new chemotype of NPY-5 antagonist, and beta-cyclodextrin, revealing the coexistence of two different kinds of 1:1 complexes where conformational changes of the guest compound with respect to the free state are also detected.
Uccello-Barretta
Gloria
G
Dipartimento di Chimica e Chimica Industriale, Università degli Studi di Pisa, via Risorgimento 35, 56126 Pisa, Italy. gub@dcci.unipi.it
Balzano
Federica
F
Sicoli
Giuseppe
G
Fríglola
Carmen
C
Aldana
Ignacio
I
Monge
Antonio
A
Paolino
Donatella
D
Guccione
Salvatore
S
D001671:Biochemistry / Q000379:methods; D001969:Bromobenzenes / Q000737:chemistry*; D003505:Cyclodextrins / Q000737:chemistry*; D003510:Cyclohexanes / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D004337:Drug Carriers / Q000737:chemistry; D004353:Drug Evaluation, Preclinical / Q000379:methods; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D017476:Receptors, Neuropeptide Y / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D047392:beta-Cyclodextrins; D000096926:Benzenesulfonamides
D001969:Bromobenzenes; D003505:Cyclodextrins; D003510:Cyclohexanes; D004337:Drug Carriers; D017476:Receptors, Neuropeptide Y; D013449:Sulfonamides; D047392:beta-Cyclodextrins; C100568:neuropeptide Y5 receptor; C492876:trans-N-4-(N'-(4-chlorobenzoyl)hydrazinocarbonyl)cyclohexylmethyl-4-bromobenzenesulfonamide; D000096926:Benzenesulfonamides; C086996:4-bromobenzenesulfonamide; C031215:betadex