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30891

Sigma-Aldrich

Biliverdin hydrochloride

≥97.0% (TLC)

Empirical Formula (Hill Notation):
C33H34N4O6 · HCl
Molecular Weight:
619.11
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥97.0% (TLC)

form

powder or crystals

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

Related Categories

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Biological implications of heme metabolism.
Sassa, S.
Journal of Clinical Biochemistry and Nutrition, 38, 138-155 (2006)
Nader G Abraham et al.
Pharmacological reviews, 60(1), 79-127 (2008-03-08)
This review is intended to stimulate interest in the effect of increased expression of heme oxygenase-1 (HO-1) protein and increased levels of HO activity on normal and pathological states. The HO system includes the heme catabolic pathway, comprising HO and
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.
Tracking multiple genomic elements using correlative CRISPR imaging and sequential DNA FISH
Guan J, et al.
Biophysical Journal, 112(6), 1077-1084 (2017)
Linear tetrapyrroles as functional pigments in chemistry and biology.
Mizutani, T. and Yagi, S.
Journal of Porphyrins and Phthalocyanines, 8, 226-237 (2004)

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