Bilirubin diglucuronide

Bilirubin diglucuronide
Names
IUPAC name
(2,17-Diethenyl-3,7,13,18-tetramethyl-1,19-dioxo-10,19,21,22,23,24-hexahydro-1H-biline-8,12-diyl)bis(1-oxopropane-3,1-diyl) di(β-D-glucopyranosiduronic acid)
Systematic IUPAC name
(12S,13R,14S,15S,16S,132S,133R,134S,135S,136S)-65-[(Z)-(3-Ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-85-[(Z)-(4-ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-13,14,15,133,134,135-hexahydroxy-64,84-dimethyl-3,11-dioxo-61H,81H-2,12-dioxa-6(3,2),8(2,3)-dipyrrola-1,13(2)-bis(oxana)tridecaphane-16,136-dicarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
MeSH bilirubin+diglucuronide
UNII
  • InChI=1S/C45H52N4O18/c1-7-20-19(6)40(58)49-27(20)14-25-18(5)23(10-12-31(51)65-45-37(57)33(53)35(55)39(67-45)43(62)63)29(47-25)15-28-22(17(4)24(46-28)13-26-16(3)21(8-2)41(59)48-26)9-11-30(50)64-44-36(56)32(52)34(54)38(66-44)42(60)61/h7-8,13-14,32-39,44-47,52-57H,1-2,9-12,15H2,3-6H3,(H,48,59)(H,49,58)(H,60,61)(H,62,63)/b26-13+,27-14+/t32-,33-,34-,35-,36+,37+,38-,39-,44+,45+/m0/s1 X markN
    Key: SCJLWMXOOYZBTH-SDXZDYKGSA-N X markN
  • InChI=1/C45H52N4O18/c1-7-20-19(6)40(58)49-27(20)14-25-18(5)23(10-12-31(51)65-45-37(57)33(53)35(55)39(67-45)43(62)63)29(47-25)15-28-22(17(4)24(46-28)13-26-16(3)21(8-2)41(59)48-26)9-11-30(50)64-44-36(56)32(52)34(54)38(66-44)42(60)61/h7-8,13-14,32-39,44-47,52-57H,1-2,9-12,15H2,3-6H3,(H,48,59)(H,49,58)(H,60,61)(H,62,63)/b26-13+,27-14+/t32-,33-,34-,35-,36+,37+,38-,39-,44+,45+/m0/s1
    Key: SCJLWMXOOYZBTH-SDXZDYKGBT
  • Cc1c(c([nH]c1/C=C/2\C(=C(C(=O)N2)C=C)C)Cc3c(c(c([nH]3)/C=C/4\C(=C(C(=O)N4)C)C=C)C)CCC(=O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O)CCC(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O
Properties
C45H52N4O18
Molar mass 936.911 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)
Infobox references

Bilirubin di-glucuronide is a conjugated form of bilirubin formed in bilirubin metabolism.[1] The hydrophilic character of bilirubin diglucuronide enables it to be water-soluble. It is pumped across the hepatic canalicular membrane into the bile by the transporter MRP2.[2]

Bilirubin molecular species play an important role in early diagnosis, prognosis and prevention of liver diseases.[3] Measuring the levels of unconjugated bilirubin, monoglucuronide and diglucuronide is done by using a high performance liquid chromotography method to determine bilirubin fractions in blood of patients.[4] Unconjugated bilirubin has to convert to water soluble monoglucuronide and diglucuronide so the levels of these show a correlation between them and inflammation in liver disease.[3]

See also

References

  1. ↑ Chowdhury, J. R.; Chowdhury, N. R.; Wu, G.; Shouval, R.; Arias, I. M. (1981). "Bilirubin mono- and diglucuronide formation by human liver in vitro: Assay by high-pressure liquid chromatography". Hepatology. 1 (6): 622–7. doi:10.1002/hep.1840010610. PMID 6796486.
  2. ↑ Lengyel, G.; et al. (2007-08-29). "Modulation of sinusoidal and canalicular elimination of bilirubin-glucuronides by rifampicin and other cholestatic drugs in a sandwich culture of rat hepatocytes". Hepatology Research. 38 (3). Wiley: 300–309. doi:10.1111/j.1872-034X.2007.00255.x. PMID 17760873.
  3. 1 2 Castillo-Castañeda, Stephany M.; Cordova-Gallardo, Jacqueline; Rivera-Espinosa, Liliana; Chavez-Pacheco, Juan L.; Ramírez-Mejía, Mariana M.; Méndez-Sánchez, Nahum (2024-07-26). "Bilirubin Molecular Species Play an Important Role in the Pathophysiology of Acute-on-Chronic Liver Failure". International Journal of Molecular Sciences. 25 (15): 8181. doi:10.3390/ijms25158181. ISSN 1422-0067. PMC 11311833. PMID 39125751.
  4. ↑ Nielsen, Morten Hjuler; Mørk, Morten; Madsen, Poul; Brock, Axel (2023-02-01). "A simplified HPLC-based method for measuring unconjugated bilirubin, bilirubin-monoglucuronide, bilirubin-diglucuronide, and delta-bilirubin in plasma with increased conjugated bilirubin". Scandinavian Journal of Clinical and Laboratory Investigation. 83 (1): 64–67. doi:10.1080/00365513.2022.2155989. ISSN 0036-5513. PMID 36534490.


This page is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.