Butaprost

Butaprost is a selective prostaglandin E receptor (EP2) agonist with an EC50 of 33 nM and a Ki of 2.4 μM for murine EP2 receptor. Butaprost is less activity against murine EP1, EP3 and EP4 receptors. Butaprost attenuates fibrosis by hampering TGF-β/Smad2 signalling.

Product information

CAS Number: 69685-22-9

Molecular Weight: 408.57

Formula: C24H40O5

Chemical Name: methyl 7-[(1R, 2R, 3R)-3-hydroxy-2-[(1E, 4S)-4-hydroxy-4-(1-propylcyclobutyl)but-1-en-1-yl]-5-oxocyclopentyl]heptanoate

Smiles: CCCC1(CCC1)[C@@H](O)C/C=C/[C@@H]1[C@@H](CCCCCCC(=O)OC)C(=O)C[C@H]1O

InChiKey: XRISENIKJUKIHD-IOOSKWMSSA-N

InChi: InChI=1S/C24H40O5/c1-3-14-24(15-9-16-24)22(27)12-8-11-19-18(20(25)17-21(19)26)10-6-4-5-7-13-23(28)29-2/h8,11,18-19,21-22,26-27H,3-7,9-10,12-17H2,1-2H3/b11-8+/t18-,19-,21-,22+/m1/s1

Technical Data

Appearance: Solid Power

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

Solubility: Soluble in DMSO

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:

Butaprost (1-100 nM; 0.5-24 hours) induces about a five-fold upregulation of Nur77 mRNA expression in hEP2-HEK293/EBNA cells in a dose- and time-dependent. Butaprost upregulated Nur77 gene expression through the PKC pathway. Butaprost (50 μM; 24 hours) reduces TGF-β-induced fibronectin (FN) expression, Smad2 phosphorylation and epithelial-mesenchymal transition in Madin-Darby Canine Kidney (MDCK) cells.

In Vivo:

Butaprost (1-4 mg/kg; intraperitoneal injection; twice daily; for 7 days) treatment attenuates the development of fibrosis in mice that underwent unilateral ureteral obstruction surgery, as illustrated by a reduction in the gene and protein expression of α-smooth muscle actin, fibronectin and collagen 1A1.

References:

1. Yanbin Liang, et al. Upregulation of orphan nuclear receptor Nur77 following PGF(2alpha), Bimatoprost, and Butaprost treatments. Essential role of a protein kinase C pathway involved in EP(2) receptor activated Nur77 gene transcription. Br J Pharmacol. 2004 Jun;142(4):737-48.
2. Michael Schou Jensen, et al. Activation of the prostaglandin E 2 EP 2 receptor attenuates renal fibrosis in unilateral ureteral obstructed mice and human kidney slices. Acta Physiol (Oxf). 2019 Sep;227(1):e13291.

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