Deoxy cholic acid

Jenkins et al. demonstrated that the secondary bile acid, deoxycholic acid could induce micronuclei formation in the oesophageal adenocarcinoma cell line, OE33. The induction of micronuclei demonstrated a dose-dependent effect and occurred under both neutral and acidic pH conditions. An example of a micronucleus induced by treatment of the OE33 oesophageal adenocarcinoma cell line with deoxy cholic acid is shown in Figure 4.3. 

Thomas LA, Veysey MJ, Murphy GM, Russell-Jones D, French GL, Wass JAH, Dowling RH. Octreotide induced prolongation of colonic transit increases fecal anaerobic bacteria, bile acid metabolizing enzymes, and serum deoxy-cholic acid in patients with acromegaly. Gut 2005 54 630-5. 

In addition to the use of penetration enhancers in eye solutions, both for improving the corneal and the conjunctival (systemic) delivery of drugs, the use of these agents has also been extended to their incorporation into other ocular delivery systems. For example, solid ocular inserts made of polyvinylalcohol (PVA) containing sulfadicramide and some absorption promoters, e.g., polyoxyethylene-9-lauryl ether, L-(lysophosphatidylocholine), and deoxy-cholic acid sodium salt, have been reported. Such inserts showed an increase in the penetration of the drug through the animal cornea in in vitro studies [108]. 

The secondary bile acids result from the activity of anaerobic intestinal microorganisms in the ileum, caecum and colon, (s. fig. 3.3) Deconjugation, with the subsequent release of free bile acids, is a prerequisite for these reactions. This is followed by 7a-dehydroxylation of cholic acid and chenodeoxycholic acid to yield deoxy-cholic acid and lithocholic acid, respectively. 7a-de-hydrogenation and oxidation of chenodeoxycholic acid also yield ketolithocholic acid ... 

There are four major bile acids (see Figures 47-5 to 47-7). Cholic acid and chenodeoxycholic acid, the primary bile acids, are synthesized in the liver. Bacteria metabolize these primary bile acids to the secondary bile acids—deoxy-cholic acid and lithocholic acid, respectively. Bile acids are conjugated in the liver with the amino acids glycine or taurine. This decreases passive absorption in the biliary tree and proximal small intestine, but permits conservation through active transport in the terminal ileum. This combi-... 

Derivation From bile and gallstones, from deoxy-cholic acid or cholic acid. 

As well as the enzyme 3a-hydroxysteroid dehydrogenase, a 7a-enzyme has been isolated from E. coli and a 12a enzyme from a strain of Clostridium (Ml). These group-specific enzymes can be used to measure the amounts and ratios of the three main bile acids (cholic, chenodeoxycholic, and deoxy-cholic acids) in bile specimens. Bioluminescent assays suitable for serum bile acid analysis have been described using 7a-hydroxysteroid dehydrogenase (R6) and 12a-hydroxysteroid dehydn enase (S12), as well as for the 3a enzyme (S13, S44). 

A chiral host could readily be available from a naturally occurring compound. The use of steroidal acid, deoxycholic acid (Fig. 3d), yielded coinprehensive polymers, particularly, optically active polymers from pro-chiral monomers. Many derivatives of deoxy cholic acid have the corresponding characteristic inclusion abilities. For example, use of apocholic acid (Fig. 3e), cholic acid (Fig. 3f), and chenodeoxycholic acid (Fig. 3g) enabled us to perform one-dimensional inclusion polymerization of various diene and vinyl monomers. 

Triamine 24 and relatives permeabilize the membranes of gram-negative bacteria and possess antibiotic activity. A series of poly amines derived from deoxy cholic acid, lithocholic acid, or cholesterol were shown to strongly bind Especially effective was 25,... 

Little information exists on the influence of bile acids on electrolyte and water movements in the small intestine. Forth et al. (107) noted that deoxy-cholic acid, but not conjugated bile acids, inhibited water and electrolyte absorption systematic examination of the effect of nucleus substitution and presence and type of conjugation was not carried out. No information is available at present on the influence of bile acids on water movements in the human jejunum and ileum. 

These studies were followed by the asymmetric polymerization of similar trans- and cis-l,3-pentadienes within the channels of two steroids of deoxy-cholic acid (DCA) and apocholic acid (ACA) [12-14]. The packing of the two... 

The three main bile acids are cholic acid, lithocholic acid and deoxy-cholic acid. 

This keto acid was first identified in beef bile by Wieland and Kishi (36). It had been obtained earlier as a molecular complex with chenodeoxycholic acid (152). 12-Ketolithocholic acid has been identified as a fecal acid in several species (4). The acid may be prepared by direct oxidation of deoxy-cholic acid (153) but better overall yields are obtained by protection of the hydroxyl group at carbon 3 (154). 

The crystalline structure of cholanic acids and their alkaline metal salts has unfortunately been neglected. The major crystallographic work was carried oUt by Kratky, Giacomello, and co-workers (76-79) 30 years ago and was oriented toward solving the structure of the choleic acids. These substances, isolated by Wieland and Sorge (80), are mixed crystals of deoxy-cholic acids (or certain other bile acids such as a and apocholic acids) obtained on crystallization from organic solvents. A summary of the work on choleic acid appears in Sobotka (28). 

The most important end products in mammalian cholesterol metabolism are the bile acids. The parent C24-acid is cholanic acid with a ring structure identical to that of coprostanol (A/B cis). The bile acids are hydroxylated cholanic acids, all hydroxyl-groups have a-orientation. Consequently, they do not form digi-tonides. The principal acids are cholic acid (3a, 7a, 12a-trihydroxy-cholanic acid), chenodeoxycholic acid (3a, 7a-dihydroxycholanic acid) and deoxy-cholic acid (3a, 12a-dihydroxycholanic acid). Lithocholic acid (3a-hydroxycholanic acid) also occurs in human bile, but only in small amounts. 

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