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Titolo:
STABILIZATION OF THE HYDROPHILIC SPHERE OF IOBITRIDOL, A NEW NONIONICIODINATED CONTRAST AGENT
Autore:
MEYER D; PETTA M; FOUCHET MH; VADEL M; SCHAEFER M; DUGASTZRIHEN M; GUILLEMOT M;
Indirizzi:
GUERBET GCA,POB 50400 F-95943 ROISSY FRANCE
Titolo Testata:
Acta radiologica
, volume: 37, anno: 1996, supplemento:, 400
pagine: 8 - 16
SICI:
0284-1851(1996)37:<8:SOTHSO>2.0.ZU;2-F
Fonte:
ISI
Lingua:
ENG
Soggetto:
MEDIA;
Keywords:
IODINATED CONTRAST MEDIA, IOBITRIDOL; MOLECULAR FLEXIBILITY; X-RAYS IMAGING;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
21
Recensione:
Indirizzi per estratti:
Citazione:
D. Meyer et al., "STABILIZATION OF THE HYDROPHILIC SPHERE OF IOBITRIDOL, A NEW NONIONICIODINATED CONTRAST AGENT", Acta radiologica, 37, 1996, pp. 8-16

Abstract

The chemotoxicity of iodinated contrast agents is essentially relatedto the spatial accessibility of lipophilic and polarizable iodine atoms. This accessibility was examined in iobitridol by HPLC and H-1- andC-13-NMR Spectroscopy, taking into account both the static distribution of the hydrophilic groups around the triiodinated benzene ring and in particular the dynamic modulation of this distribution. The aim of this latter parameter is to prevent distortion of the hydrophilic sphere of nonionic agents when faced with a hydrophobic environment. Iobitridol is characterized by 2 tertiary carbamoyl substituents whose highrotation barriers (Delta G(353)(double dagger)=27.6 kcal for E/Z-rotation and Delta G(345)(double dagger)=17.3 kcal for syn/anti-rotation) stabilize the hydrophilic sphere. The 3rd dihydroxylated anilide substituent does not undergo SMILES rearrangement and provides iobitridol with its even hydrophilic distribution. Iobitridol presents remarkable chemical solubility (>140% m/v) and stability. The iobitridol moleculewas specifically designed with the aim of stabilizing the hydrophilicsphere around the triiodinated benzene ring, thereby permanently masking access to the iodine atoms. This new concept represents a further step forward towards the synthesis of new iodinated contrast agents which should be totally inert vis-a-vis biological membranes and proteins.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 29/09/20 alle ore 15:49:48