Retrorsine

Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes. Retrorsine can be used for the research of hepatocellular injury.

Product information

CAS Number: 480-54-6

Molecular Weight: 351.39

Formula: C18H25NO6

Chemical Name: (1R,4Z,6R,7S,17R)-4-ethylidene-1,17-dihydrogenio-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

Smiles: C[C@@H]1C/C(=C/C)/C(=O)O[C@@H]2CCN3CC=C(COC(=O)[C@@]1(O)CO)[C@@H]32

InChiKey: BCJMNZRQJAVDLD-CQRYIUNCSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Retrorsine (60-240 μM; 24 hours) significantly reduces HSEC-CYP3A4 cells viability and GSH levels, and increases formation of pyrrole-protein adducts.

In Vivo:

Retrorsine (30 mg/kg; i.p.; twice) impairs liver regeneration in the PBL model not only by an S or G2/M phase block, but also by a block located before the G1/S transition of the cell cycle.

References:

1. F J Cubero, et al. Hepatic proliferation in Gunn rats transplanted with hepatocytes: effect of retrorsine and tri-iodothyronine. Cell Prolif. 2005 Jun;38(3):137-46.
2. S Laconi, et al. Liver regeneration in response to partial hepatectomy in rats treated with retrorsine: a kinetic study. J Hepatol. 1999 Dec;31(6):1069-74.
3. Yao Lu, et al. Establishment of a novel CYP3A4-transduced human hepatic sinusoidal endothelial cell model and its application in screening hepatotoxicity of pyrrolizidine alkaloids. J Environ Sci Health C Toxicol Carcinog. 2020;38(2):169-185.

Products are for research use only. Not for human use.