Cholylglycyltyrosine

For research use only. Not for therapeutic Use.

  • CAT Number: I024615
  • CAS Number: 67319-56-6
  • Molecular Formula: C35H52N2O8
  • Molecular Weight: 628.80
  • Purity: 98%
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Cholylglycyltyrosine(Cat No.:I024615)is a conjugate of cholyl acid (a bile acid) with glycyl and tyrosine residues. This compound is of interest in the field of drug delivery and biochemistry, as bile acids play a role in emulsifying fats and aiding in absorption in the gastrointestinal system. Cholylglycyltyrosine has been explored for its potential to enhance the solubility and bioavailability of drugs, particularly in treating liver and gastrointestinal disorders. Additionally, its structure may be useful in the design of therapeutic agents that interact with bile acid transport systems, promoting targeted delivery in specific tissues.


Catalog Number I024615
CAS Number 67319-56-6
Synonyms

Cholylglycyltyrosine; Chol-gly-tyr; 125I-Cgtyr; Cholyl-glycyl-tyrosine; I-Cholylglycyltyrosine;

Molecular Formula C35H52N2O8
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name (2S)-3-(4-hydroxyphenyl)-2-[[2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetyl]amino]propanoic acid
InChI InChI=1S/C35H52N2O8/c1-19(4-11-30(42)36-18-31(43)37-27(33(44)45)14-20-5-7-22(38)8-6-20)24-9-10-25-32-26(17-29(41)35(24,25)3)34(2)13-12-23(39)15-21(34)16-28(32)40/h5-8,19,21,23-29,32,38-41H,4,9-18H2,1-3H3,(H,36,42)(H,37,43)(H,44,45)/t19-,21+,23-,24-,25+,26+,27+,28-,29+,32+,34+,35-/m1/s1
InChIKey HERYPGYAYHTUGY-KFNBCNGZSA-N
SMILES C[C@H](CCC(=O)NCC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)O)[C@H]2CC[C@@H]3[C@@]2([C@H](C[C@H]4[C@H]3[C@@H](C[C@H]5[C@@]4(CC[C@H](C5)O)C)O)O)C
Reference

1: Clements D, Mills C, Iqbal S, Chandler S, Elias E. Iodinated cholylglycyltyrosine: a new agent for hepatobiliary imaging. Eur J Nucl Med. 1986;11(10):401-4. PubMed PMID: 3699064.
2: Mills CO, Freeman JF, Salt PJ, Elias E. Effect of anaesthetic agents on bile flow and biliary excretion of 131I-cholylglycyltyrosine in the rat. Br J Anaesth. 1989 Mar;62(3):311-5. PubMed PMID: 2784686.
3: Suchy FJ, Balistreri WF, Hung J, Miller P, Garfield SA. Intracellular bile acid transport in rat liver as visualized by electron microscope autoradiography using a bile acid analogue. Am J Physiol. 1983 Nov;245(5 Pt 1):G681-9. PubMed PMID: 6638192.
4: Miller P, Weiss S, Cornell M, Dockery J. Specific 125I-radioimmunoassay for cholyglycine, a bile acid, in serum. Clin Chem. 1981 Oct;27(10):1698-703. PubMed PMID: 7285320.
5: Suchy FJ, Balistreri WF, Breslin JS, Dumaswala R, Setchell KD, Garfield SA. Absence of an acinar gradient for bile acid uptake in developing rat liver. Pediatr Res. 1987 Apr;21(4):417-21. PubMed PMID: 3574993.
6: Mills CO, Iqbal S, Elias E. Ileal absorption of tyrosine-conjugated bile acids in Wistar rats. Biochim Biophys Acta. 1987 Nov 6;926(2):154-9. PubMed PMID: 3663709.
7: Al-Jabri AA, Wigg MD, Elias E, Lambkin R, Mills CO, Oxford JS. In vitro anti-HIV-1 virucidal activity of tyrosine-conjugated tri- and dihydroxy bile salt derivatives. J Antimicrob Chemother. 2000 May;45(5):617-21. PubMed PMID: 10797083.
8: Deutsch JC, Iwahashi MM, Sutherland EM, Mapoles J, Simon FR. Characterization of the transport of a synthetic bile salt, iodinated cholyl-glycyl-tyrosine, in isolated cultured rat hepatocytes. Hepatology. 1992 May;15(5):917-22. PubMed PMID: 1314773.
9: Mills CO, Iqbal S, Elias E. Synthesis and biliary excretion of tyrosine-conjugated bile salts in Wistar rats. Biochim Biophys Acta. 1986 May 21;876(3):667-76. PubMed PMID: 3707990.
10: Mills CO, Martin GH, Elias E. The effect of tyrosine conjugation on the critical micellar concentration of free and glycine-conjugated bile salts. Biochim Biophys Acta. 1986 May 21;876(3):677-83. PubMed PMID: 3707991.

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