ICG-001

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 206608

CAS#: 780757-88-2

Description: ICG-001, an isomer or enantiomer of PRI-724, is a potent and selective Wnt signaling modulator. ICG-001 modulates Wnt signaling and increased the expression of genes beneficial for cardiac regeneration in epicardial cells. ICG-001 binds cAMP-responsive element binding (CREB)-binding protein (CBP) to disrupt its interaction with β-catenin and inhibit CBP function as a coactivator of Wnt/β-catenin-mediated transcription. ICG-001 induces cytotoxicity of multiple myeloma cells in Wnt-independent manner. Note: ICG-001 and PRR-724 are not the same molecule, which are enantiomer isomers. Many vendors confused them.


Price and Availability

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ICG-001 is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206608
Name: ICG-001
CAS#: 780757-88-2
Chemical Formula: C33H32N4O4
Exact Mass: 548.2424
Molecular Weight: 548.643
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: ICG-001; ICG 001; ICG001. PRI-724 isomer; PRI 724 isomer; PRI724 isomer;

IUPAC/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.

InChi Key: HQWTUOLCGKIECB-IHLOFXLRSA-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+/m1/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


Technical Data

Appearance:
Solid powder

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

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Note: There was confusion on between IGC001 and PRI-724.
1. Sci Rep. 2015 Apr 21;5:9979. doi: 10.1038/srep09979.
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4404684/pdf/srep09979.pdf
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


References

1: Grigson ER, Ozerova M, Pisklakova A, Liu H, Sullivan DM, Nefedova Y. Canonical
Wnt pathway inhibitor ICG-001 induces cytotoxicity of multiple myeloma cells in
Wnt-independent manner. PLoS One. 2015 Jan 30;10(1):e0117693. doi:
10.1371/journal.pone.0117693. eCollection 2015. PubMed PMID: 25635944; PubMed
Central PMCID: PMC4311909.

2: Arensman MD, Telesca D, Lay AR, Kershaw KM, Wu N, Donahue TR, Dawson DW. The
CREB-binding protein inhibitor ICG-001 suppresses pancreatic cancer growth. Mol
Cancer Ther. 2014 Oct;13(10):2303-14. doi: 10.1158/1535-7163.MCT-13-1005. Epub
2014 Jul 31. PubMed PMID: 25082960; PubMed Central PMCID: PMC4188417.

3: Sasaki T, Hwang H, Nguyen C, Kloner RA, Kahn M. The small molecule Wnt
signaling modulator ICG-001 improves contractile function in chronically
infarcted rat myocardium. PLoS One. 2013 Sep 12;8(9):e75010. doi:
10.1371/journal.pone.0075010. eCollection 2013. PubMed PMID: 24069374; PubMed
Central PMCID: PMC3771968.

4: Eguchi M, Nguyen C, Lee SC, Kahn M. ICG-001, a novel small molecule regulator
of TCF/beta-catenin transcription. Med Chem. 2005 Sep;1(5):467-72. PubMed PMID:
16787331.