30891
Biliverdin hydrochloride
≥97.0% (TLC)
Synonym(s):
Biliverdin
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About This Item
Empirical Formula (Hill Notation):
C33H34N4O6 · HCl
CAS Number:
Molecular Weight:
619.11
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32
Quality Level
assay
≥97.0% (TLC)
form
powder or crystals
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
storage temp.
−20°C
SMILES string
Cl.CC1=C(C=C)C(\NC1=O)=C\c2[nH]c(/C=C3\N=C(\C=C4/NC(=O)C(C=C)=C4C)C(C)=C3CCC(O)=O)c(CCC(O)=O)c2C
InChI
1S/C33H34N4O6.ClH/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26;/h7-8,13-15,35H,1-2,9-12H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41);1H/b26-13-,27-14-,28-15-;
InChI key
KTRFJVRKVQROKS-UJCZHUFNSA-N
General description
Biliverdin (BV) is considered as a near-infrared (NIR)-absorbing pigment, that is endogenic. It is a linear tetrapyrrolic intermediate of heme degradation (heme catabolism) to bilirubin. The bile of amphibia and birds contains only biliverdine, no bilirubin.
Application
Biliverdin hydrochloride has been used:
- as a treatment to J774A.1 cells to study its role in alternation of beta (β)-endorphins level
- as a commercial standard for the detection of biliverdin in mouse unstable and stable plaques tissues using liquid chromatography-tandem mass spectrometry (LC-MS-MS)
- to add to Fucci-containing cells to improve the mIFP signal
- to examine its impact on infrared fluorescent protein (iRFP) in some retinal preparations
Biochem/physiol Actions
Biliverdin (BV) is an excellent anti-inflammatory agent that protects against lipopolysaccharides (LPS)-induced lung injury in mouse endothelial cells. It aids protection in polymicrobial sepsis. Biliverdin has cytoprotective effects on rat livers and protects from prolonged ischemia and reperfusion injury. It also shows antioxidant activities.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Constantino Fondevila et al.
Hepatology (Baltimore, Md.), 40(6), 1333-1341 (2004-11-27)
Heme oxygenase (HO-1) provides a cellular defense mechanism during oxidative stress and catalyzes the rate-limiting step in heme metabolism that produces biliverdin (BV). The role of BV and its potential use in preventing ischemia/reperfusion injury (IRI) had never been studied.
Biological implications of heme metabolism.
Sassa, S.
Journal of Clinical Biochemistry and Nutrition, 38, 138-155 (2006)
Tracking multiple genomic elements using correlative CRISPR imaging and sequential DNA FISH
Guan J, et al.
Biophysical Journal, 112(6), 1077-1084 (2017)