Merck
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R0382

Sigma-Aldrich

Retrorsine

≥90% (HPLC)

Sinónimos:
β-Longilobine, 12,18-Dihydroxysenecionan-11,16-dione, Retrorsin, Senecionan-11,16-Dione, 12,18-Dihydroxy- (9CI)
Empirical Formula (Hill Notation):
C18H25NO6
Número de CAS:
Peso molecular:
351.39
ID de la sustancia en PubChem:
NACRES:
NA.77

Nivel de calidad

100

ensayo

≥90% (HPLC)

mp

208-211 °C (lit.)

SMILES string

C\C=C1\C[C@@H](C)[C@](O)(CO)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23

InChI

1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-/m1/s1

InChI key

BCJMNZRQJAVDLD-CQRYIUNCSA-N

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Aplicación

Retrorsine has been used:
  • as a mito-inhibitory pyrrolizidine alkaloid compound to induce necrotic liver injury in rats
  • to induce hepatocellular injury in rats
  • to arrest endogenous hepatocyte growth in mice

Acciones bioquímicas o fisiológicas

Retrorsine (RTS) is a retronecine-type pyrrolizidine alkaloid associated with Senecio and Crotalaria species. It belongs to the pyrrolizidine alkaloid family with mito-inhibitory property and elicits hepatotoxicity. It mediates the inactivation of cytochrome P450 3A4. Retrorsine also inhibits replication of fully differentiated hepatocytes.

pictogramas

Skull and crossbones

Palabra de señalización

Danger

Frases de peligro

Clasificaciones de peligro

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Código de clase de almacenamiento

6.1B - Non-combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Punto de inflamabilidad F

Not applicable

Punto de inflamabilidad C

Not applicable

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificado de Análisis

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Certificado de origen

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Valerie Gouon-Evans et al.
Nature biotechnology, 24(11), 1402-1411 (2006-11-07)
When differentiated in the presence of activin A in serum-free conditions, mouse embryonic stem cells efficiently generate an endoderm progenitor population defined by the coexpression of either Brachyury, Foxa2 and c-Kit, or c-Kit and Cxcr4. Specification of these progenitors with
Suchitra Sumitran-Holgersson et al.
Cell transplantation, 18(2), 183-193 (2009-06-09)
Although the appearance of hepatic foci in the pancreas has been described in animal experiments and in human pathology, evidence for the conversion of human pancreatic cells to liver cells is still lacking. We therefore investigated the developmental plasticity between
Chun-Hsien Yu et al.
Cell transplantation, 18(10), 1081-1092 (2009-08-05)
Efficient repopulation by transplanted hepatocytes in the severely injured liver is essential for their clinical application in the treatment of acute hepatic failure. We studied here whether and how the transplanted hepatocytes are able to efficiently repopulate the toxin-induced acute
Biao Zhang et al.
The Journal of surgical research, 157(1), 71-80 (2009-04-07)
The therapeutic effects of bone marrow and hepatocyte transplantation were investigated regarding the treatment of retrorsine-partial hepatectomy-induced liver injury. Analbuminemic F344alb rats were given two doses of retrorsine 2 wk apart, followed 4 wk later by transplantation with F344 rat
Kate E Brilliant et al.
Transplantation, 88(4), 486-495 (2009-08-22)
Pretreatment with retrorsine crosslinks host hepatocyte DNA and prevents proliferation after partial hepatectomy (PH), allowing selective expansion of transplanted progenitors. Shortcomings are length of protocol and carcinogenicity of retrorsine. This report describes a rapid liver repopulation protocol using mitomycin C

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