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R0382

Sigma-Aldrich

Retrorsine

≥90% (HPLC), powder, retronecine-type pyrrolizidine alkaloid

Sinonimo/i:

Retrorsin, Senecionan-11,16-Dione, 12,18-Dihydroxy- (9CI), β-Longilobine, 12,18-Dihydroxysenecionan-11,16-dione

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About This Item

Formula empirica (notazione di Hill):
C18H25NO6
Numero CAS:
480-54-6
Peso molecolare:
351.39
Codice UNSPSC:
12352200
ID PubChem:
24899338
NACRES:
NA.77

Nome del prodotto

Retrorsine, ≥90% (HPLC)

Livello qualitativo

100

Saggio

≥90% (HPLC)

Punto di fusione

208-211 °C (lit.)

Stringa SMILE

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
BCJMNZRQJAVDLD-CQRYIUNCSA-N

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Applicazioni

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

Azioni biochim/fisiol

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.

Pittogrammi

Skull and crossbones
GHS06

Avvertenze

Danger

Indicazioni di pericolo

H300 + H310 + H330

Classi di pericolo

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

Codice della classe di stoccaggio

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
BCCG3827
BCCC7869
BCCC4967
BCBZ7529
BCBZ3777

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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
Mabel Fragoso-Serrano et al.
Journal of natural products, 75(5), 890-895 (2012-05-04)
Commercial preparations of the Mexican herbal drug known as "miracle tea" (Packera candidissima and P. bellidifolia) have been profiled qualitatively by HPLC and GC-MS. Eremophilanes (3-7) were the major components found in the hexane-soluble fraction, while pyrrolizidine alkaloids (PAs) were
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
Gary E Martin et al.
Magnetic resonance in chemistry : MRC, 50(8), 563-568 (2012-07-19)
ADEQUATE experiments provide an alternative to the more commonly employed GHMBC experiment for the establishment of long-range heteronuclear connectivities. The 1,1-ADEQUATE experiment allows the unequivocal identification of both protonated and non-protonated carbon resonances adjacent to a protonated carbon. The 1,n-ADEQUATE
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