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Conjugates of gadolinium complexes to bile acids as hepatocyte-directed contrast agents for magnetic resonance imaging.

Abstract：

:A series of structurally different Gd(III) conjugates incorporating a bile acid moiety have been prepared. Polyaminopolycarboxylic ligands such as diethylenetriaminepentaacetic acid (DTPA) and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic acid (DOTA) have been selected as chelating subunit for the Gd(III) ion. Cholic acid, cholylglycine, and cholyltaurine have been incorporated as the bile acid moieties. In first generation conjugates the Gd(III) complex is linked to the carboxyl group of cholic acid. Second generation conjugates feature the attachment of the Gd(III) complex to the 3 position of the steroidic backbone of the bile acid. Finally, in third generation conjugates the Gd(III) complex is attached to the epsilon nitrogen atom of cholyllysine. The conjugates are eliminated through the biliary route to a various extent (7.5 to 77% in rats) according to their structural features. Among the most promising terms, a second generation conjugate in which the Gd(III) complex is linked to cholic acid through the 3alpha hydroxy group seems to enter hepatocytes using the Na(+)/taurocholate transporter. Noticeably, some of the second generation conjugates are characterized by very high tolerabilities (LD(50) up to 9.5 mmol/kg) after intravenous administration in mice.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Anelli PL,Lattuada L,Lorusso V,Lux G,Morisetti A,Morosini P,Serleti M,Uggeri F

doi

10.1021/jm0310683

keywords:

subject

Has Abstract

pub_date

2004-07-01 00:00:00

pages

3629-41

issue

14

eissn

0022-2623

issn

1520-4804

journal_volume

47

pub_type

杂志文章

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