WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 205865
Description: PRI-724, an isomer or enantiomer of ICG-001, is a potent, specific inhibitor of the canonical Wnt signaling pathway in cancer stem cells with potential antineoplastic activity. Wnt signaling pathway inhibitor PRI-724 specifically inhibits the recruiting of beta-catenin with its coactivator CBP (the binding protein of the cAMP response element-binding protein CREB); together with other transcription factors beta-catenin/CBP binds to WRE (Wnt-responsive element) and activates transcription of a wide range of target genes of Wnt/beta-catenin signaling. Note: ICG-001 and PRR-724 are not the same molecule, which are enantiomer isomers. Many vendors confused them.
MedKoo Cat#: 205865
Chemical Formula: C33H32N4O4
Exact Mass: 548.24236
Molecular Weight: 548.63
Elemental Analysis: C, 72.24; H, 5.88; N, 10.21; O, 11.66
Related CAS #: 847591-62-2 (PRI-724); 780757-88-2 (ICG-001).
Synonym: PRI724; PRI-724; PRI 724; ICG001 isomer; ICG-001 isomer; ICG 001 isomer.
IUPAC/Chemical Name: (6S,9aS)-N-benzyl-6-(4-hydroxybenzyl)-8-(naphthalen-1-ylmethyl)-4,7-dioxooctahydro-1H-pyrazino[1,2-a]pyrimidine-1-carboxamide
InChi Key: HQWTUOLCGKIECB-XZWHSSHBSA-N
InChi Code: InChI=1S/C33H32N4O4/c38-27-15-13-23(14-16-27)19-29-32(40)35(21-26-11-6-10-25-9-4-5-12-28(25)26)22-30-36(18-17-31(39)37(29)30)33(41)34-20-24-7-2-1-3-8-24/h1-16,29-30,38H,17-22H2,(H,34,41)/t29-,30+/m0/s1
SMILES Code: O=C(N(CC1)[C@](CN(CC2=C3C=CC=CC3=CC=C2)C([C@@H]4CC5=CC=C(O)C=C5)=O)([H])N4C1=O)NCC6=CC=CC=C6
Note: There was confusion on between IGC001 and PRI-724.
1. Sci Rep. 2015 Apr 21;5:9979. doi: 10.1038/srep09979.
In this paper, tt was described: "PRI724 is the second generation of ICG-001 and is 20 times more potent than ICG001". Based on this statement, IGC001 and PRI-724 are not the same molecule.
2. Oncotarget. 2015 Sep 15;6(27):23720-34.
In the abstract section: "therapeutic targeting of this pathway with iCG-001/PRI-724, which has been shown to be well tolerated in Phase I trials, may be an effective treatment option" Based on this statement, IGC001 and PRI-724 are the same molecule.
3. Sci-finder Database, listed below (searched date: 6/16/2016).
PRI-724, CAS# 847591-62-2, chemical name: (6S,9aS)-6-(4-Hydroxybenzyl)-8-[(naphthalen-1-yl)methyl]-4,7-dioxohexahydropyrazino[1,2-a]pyrimidine-1-carboxylic acid N-benzylamide.
ICG-001, CAS#780757-88-2, chemical name: rel-(6R,9aR)-Hexahydro-6-[(4-hydroxyphenyl)methyl]-8-(1-naphthalenylmethyl)-4,7-dioxo-N-(phenylmethyl)-2H-pyrazino[1,2-a]pyrimidine-1(6H)-carboxamide.
Based on Sci-finder, IGC001 and PRI-724 are enantiomers: IGC001 has (R,R)-configuration, while PRI-724 has (S,S)-confirmation.
We believe Sci-finder is more reliable. Thus,we believe that IGC001 and PRI-724 are different molecules. PRI-724 has CAS# 847591-62-2; while ICG-001h as CAS#780757-88-2
1: Lenz HJ, Kahn M. Safely targeting cancer stem cells via selective catenin coactivator antagonism. Cancer Sci. 2014 Sep;105(9):1087-92. doi: 10.1111/cas.12471. Epub 2014 Sep 6. PubMed PMID: 24975284; PubMed Central PMCID: PMC4175086.