Novel bile acid derivatives (BANBs) with cytostatic activity obtained by conjugation of their side chain with nitrogenated bases

2007 ◽  
Vol 73 (9) ◽  
pp. 1394-1404 ◽  
Author(s):  
Marta Vallejo ◽  
Maria A. Castro ◽  
Manuel Medarde ◽  
Rocio I.R. Macias ◽  
Marta R. Romero ◽  
...  
Keyword(s):  
Bile Acid ◽  
Cytostatic Activity ◽  
Side Chain ◽  
Bile Acid Derivatives

Systematic Structural Study of Asymmetric Supramolecular Assembly by a Series of Bile Acid Derivatives with Different Side-Chain Lengths

2004 ◽  
Vol 4 (2) ◽  
pp. 263-272 ◽  
Author(s):  
Kazuaki Kato ◽  
Michihiro Sugahara ◽  
Norimitsu Tohnai ◽  
Kazuki Sada ◽  
Mikiji Miyata
Keyword(s):  
Bile Acid ◽  
Structural Study ◽  
Supramolecular Assembly ◽  
Side Chain ◽  
Bile Acid Derivatives ◽  
Chain Lengths

Influence of side-chain charge on hepatic transport of bile acids and bile acid analogues

1985 ◽  
Vol 249 (4) ◽  
pp. G479-G488 ◽  
Author(s):  
M. S. Anwer ◽  
E. R. O'Maille ◽  
A. F. Hofmann ◽  
R. A. DiPietro ◽  
E. Michelotti
Keyword(s):  
Bile Acid ◽  
Bile Acids ◽  
Liver Cell ◽  
Hepatic Uptake ◽  
Biliary Secretion ◽  
Side Chain ◽  
Bile Fistula ◽  
Bile Acid Derivatives ◽  
Derivatives Of ◽  
Secretion Rates

The importance of side-chain charge on hepatic uptake and biliary secretion of bile acids and analogues was studied using the isolated, perfused rat liver and the anesthetized rat with a bile fistula. Derivatives of cholic acid with negative, neutral, zwitterionic, or positive charges on the side chain were synthesized and studied. Hepatic uptake by the isolated perfused liver, determined by measuring the rate of disappearance of a single 20-mumol bolus added to the perfusate, was strongly influenced by side-chain charge. A fully positively charged bile acid derivative (cholylcholamine) and two fully zwitterionic bile acid derivatives (CHAPS and cholyllysine) showed no appreciable uptake (less than 1% of the uptake rate of cholyltaurine). Bile acid derivatives existing mostly in cationic form (cholylamine) at pH 7.4, in neutral form (cholylglycylhistamine), or in divalent anion form (cholylaspartate and cholylcysteate) had an uptake rate that was greater but only 7-19% that of cholyltaurine. Side-chain charge also appeared to influence the rate of secretion into bile. Bile acids existing in mono- or dianionic form were well secreted (greater than 95% of dose in 2 h) into the bile, but all other derivatives had much lower secretion rates (less than 20% of dose in 2 h). When the biliary secretion of each bile acid derivative was expressed in relation to the amount that had entered the liver, relative secretion rates (presumably from liver cell) into bile decreased in the following order: cholyltaurine greater than cholylaspartate and cholylcysteate greater than CHAPS greater than cholyllysine greater than cholylglycylhistamine approximately equal to cholylamine. In bile fistula rats, cholylaspartate was quantitatively secreted into bile when infused at rates below its secretory maximum, whereas only very low biliary secretion rates of CHAPS were observed even during relatively high infusion rates; cholylamine was cholestatic. The above data show that, although uncharged and anionic derivatives of cholic acid may be taken up by the liver at a moderate rate, only anionic derivatives (both monovalent and divalent) are well secreted from within the liver cell into bile. A single negative charge on the side chain appears to be required for optimal transport of a bile acid from sinusoidal blood to bile.

scholarly journals DEGRADATION OF THE BILE ACID SIDE CHAIN

1946 ◽  
Vol 164 (1) ◽  
pp. 451-453
Author(s):  
Martin G. Ettlinger ◽  
Louis F. Fieser
Keyword(s):  
Bile Acid ◽  
Side Chain

Control of the enantioselectivity by keto bile acid derivatives in the epoxidation of alkenes with Oxone

2004 ◽  
Vol 15 (24) ◽  
pp. 3831-3833 ◽  
Author(s):  
Olga Bortolini ◽  
Giancarlo Fantin ◽  
Marco Fogagnolo ◽  
Lara Mari
Keyword(s):  
Bile Acid ◽  
Bile Acid Derivatives ◽  
Epoxidation Of Alkenes

scholarly journals Resolution of organic racemates via host-guest enantioselective inclusion complexation in bile acid derivatives

ARKIVOC ◽  
2006 ◽  
Vol 2006 (6) ◽  
pp. 40-48 ◽  
Author(s):  
O. Bortolini ◽  
G. Fantin ◽  
M. Fogagnolo ◽  
S. Maietti
Keyword(s):  
Bile Acid ◽  
Inclusion Complexation ◽  
Bile Acid Derivatives

Protective effect of bile acid derivatives in phalloidin-induced rat liver toxicity

2009 ◽  
Vol 239 (1) ◽  
pp. 21-28 ◽  
Author(s):  
Elisa Herraez ◽  
Rocio I.R. Macias ◽  
Jose Vazquez-Tato ◽  
Carlos Hierro ◽  
Maria J. Monte ◽  
...  
Keyword(s):  
Bile Acid ◽  
Protective Effect ◽  
Rat Liver ◽  
Liver Toxicity ◽  
Bile Acid Derivatives
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