81-24-3Relevant articles and documents
Use of the intestinal bile acid transporter for the uptake of cholic acid conjugates with HIV-1-protease inhibitory activity
Kagedahl, Matts,Swaan, Peter W.,Redemann, Carl T.,Tang, Mary,Craik, Charles S.,Szoka Jr., Francis C.,ie, Svein
, p. 176 - 180 (1997)
Purpose. To investigate the ability of the human intestinal bile acid transporter to transport cholic acid conjugates with potential HIV-1 protease inhibitory activity. Methods. Cholic acid was conjugated at the 24 position of the sterol nucleus with various amino acids and amino acid analogs. The CaCo2 cell line was used as a model to investigate the interaction of these bile acid conjugates with the human intestinal bile acid transporter. Interaction between the carrier and the conjugates was quantified by inhibition of taurocholic acid transport and confirmed by transport of radiolabelled conjugates in this cell line. Results. The highest interaction with the transporter, as quantified by inhibition of taurocholic acid transport, occurred when a single negative charge was present around the 24 to 29 region of the sterol nucleus. A second negative charge or a positive charge significantly reduced the interaction. Transport of radiolabelled cholyl-L-Lys-ε-tBOC ester and cholyl-D-Asp-β-benzyl ester was inhibited by taurocholic acid. Of all tested compounds, only cholyl-D-Asp-β-benzyl ester showed modest HIV-1 protease inhibitory activity with an IC50 of 125 μM Conclusions. Cholic acid-amino acid conjugates with appropriate stereochemistry are recognized and transported by the human bile acid transporter and show modest HIV-1 protease inhibitory activity. Transport of these conjugates by the bile acid carrier is influenced by charge and hydrophobicity around the 24 position of the sterol nucleus.
OPHTHALMIC COMPOSITIONS COMPRISING dDC
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, (2010/04/23)
A composition comprising dDC and a polymer, wherein the composition is an aqueous liquid with a viscosity which increases upon contact with a surface of an eye is disclosed herein. An aqueous composition comprising a therapeutically effective concentration of dDC, wherein the concentration of dDC is less than 1% is also disclosed. An eye drop comprising a therapeutically effective amount of dDC, wherein the amount of dDC is less than 300 μg is also disclosed. A method comprising administering an effective amount of dDC topically to an eye of a person suffering from viral conjunctivitis a viral infection, wherein less than 300 μL of dDC is administered to said eye is also disclosed. A kit comprising a composition and a dispenser, wherein said dispenser dispenses a drop comprising a therapeutically effective amount of dDC, wherein the amount of dDC is less than 300 μg is also disclosed.
Chemical modifications of bile acids under high-intensity ultrasound or microwave irradiation
Cravotto, Giancarlo,Boffa, Luisa,Turello, Marta,Parenti, Massimo,Barge, Alessandro
, p. 77 - 83 (2007/10/03)
High-intensity ultrasound (HIU) and microwave (MW) irradiation, having emerged as effective promoters of organic reactions, were exploited for the synthesis of bile acids derivatives. Esterification, amidation, hydrolysis, oxidation, and reduction were investigated. Compared to conventional methods, both techniques proved much more efficient, increasing product yields and dramatically cutting down reaction times. Scaled-up studies are now under way.
An improved procedure for the synthesis of glycine and taurine conjugates of bile acids
Tserng,Hachey,Klein
, p. 404 - 407 (2007/10/06)
Glycine and taurine conjugates of 5β cholanic acids have been synthesized using improved procedures based on the peptide coupling reagent, N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline. The conjugates are obtained in chromatographically pure form in yields higher than 90%. The use of this procedure in the large scale preparation of choly[1,2 13C2]glycine is described.
