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30891

Sigma-Aldrich

Biliverdin hydrochloride

≥97.0% (TLC)

Synonyme(s) :

Biliverdin

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About This Item

Formule empirique (notation de Hill):
C33H34N4O6 · HCl
Numéro CAS:
856699-18-8
Poids moléculaire :
619.11
Code UNSPSC :
12352204
ID de substance PubChem :
329753599
Nomenclature NACRES :
NA.32

Pureté

≥97.0% (TLC)

Forme

powder or crystals

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

Chaîne SMILES 

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-;

Clé InChI

KTRFJVRKVQROKS-UJCZHUFNSA-N

Catégories apparentées

Description générale

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

Actions biochimiques/physiologiques

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Marking cells with infrared fluorescent proteins to preserve photoresponsiveness in the retina
Fyk-Kolodziej B, et al.
Biotechniques, 57(5), 245-253 (2014)
Min-Hyung Ryu et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(28), 10167-10172 (2014-07-02)
Bacteriophytochromes sense light in the near-infrared window, the spectral region where absorption by mammalian tissues is minimal, and their chromophore, biliverdin IXα, is naturally present in animal cells. These properties make bacteriophytochromes particularly attractive for optogenetic applications. However, the lack
Hakan Dortay et al.
PloS one, 6(4), e18900-e18900 (2011-05-05)
Protein expression in heterologous hosts for functional studies is a cumbersome effort. Here, we report a superior platform for parallel protein expression in vivo and in vitro. The platform combines highly efficient ligation-independent cloning (LIC) with instantaneous detection of expressed
Self-Assembling Endogenous Biliverdin as a Versatile Near-Infrared Photothermal Nanoagent for Cancer Theranostics
Xing R, et al.
Advanced Materials, 1900822-1900822 (2019)
Biliverdin in biological systems
Cornelius, C. E. et al.
One Medicine: A Tribute to Kurt Benirschkle, 321-334 (1984)
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