MedKoo Cat#: 464395 | Name: BIM-46174

Description:

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

BIM-46174 is a New Inhibitor of the Heterotrimeric Gα/Gβγ Protein Complex. BIM-46174 acts as a selective inhibitor of heterotrimeric G-protein complex. BIM-46174 prevents the heterotrimeric G-protein signaling linked to several GPCRs mediating (a) cyclic AMP generation (Gαs), (b) calcium release (Gαq), and (c) cancer cell invasion by Wnt-2 frizzled receptors and high-affinity neurotensin receptors (Gαo/i and Gαq). BIM-46174 inhibits the growth of a large panel of human cancer cell lines, including anticancer drug-resistant cells. Exposure of cancer cells to BIM-46174 leads to caspase-3-dependent apoptosis and poly(ADP-ribose) polymerase cleavage.

Chemical Structure

BIM-46174
BIM-46174
CAS#195450-11-4

Theoretical Analysis

MedKoo Cat#: 464395

Name: BIM-46174

CAS#: 195450-11-4

Chemical Formula: C22H30N4OS

Exact Mass: 398.2140

Molecular Weight: 398.57

Elemental Analysis: C, 66.30; H, 7.59; N, 14.06; O, 4.01; S, 8.04

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
BIM-46174; BIM46174; BIM 46174;
IUPAC/Chemical Name
(R)-2-amino-1-((S)-8-(cyclohexylmethyl)-2-phenyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)-3-mercaptopropan-1-one
InChi Key
HVSILNVTAWKPSC-ICSRJNTNSA-N
InChi Code
InChI=1S/C22H30N4OS/c23-18(15-28)22(27)26-12-11-25-14-19(17-9-5-2-6-10-17)24-21(25)20(26)13-16-7-3-1-4-8-16/h2,5-6,9-10,14,16,18,20,28H,1,3-4,7-8,11-13,15,23H2/t18-,20-/m0/s1
SMILES Code
O=C([C@H](CS)N)N1CCN2C([C@@H]1CC3CCCCC3)=NC(C4=CC=CC=C4)=C2
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 398.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Küppers J, Benkel T, Annala S, Kimura K, Reinelt L, Fleischmann BK, Kostenis E, Gütschow M. Tetrahydroimidazo[1,2-a]pyrazine Derivatives: Synthesis and Evaluation as Gαq -Protein Ligands. Chemistry. 2020 Oct 1;26(55):12615-12623. doi: 10.1002/chem.202001446. Epub 2020 Sep 7. PMID: 32428383; PMCID: PMC7590114. 2: Küppers J, Benkel T, Annala S, Schnakenburg G, Kostenis E, Gütschow M. BIM-46174 fragments as potential ligands of G proteins. Medchemcomm. 2019 Aug 21;10(10):1838-1843. doi: 10.1039/c9md00269c. PMID: 32180917; PMCID: PMC7053702. 3: Gilmour AM, Abdulkhalek S, Cheng TS, Alghamdi F, Jayanth P, O'Shea LK, Geen O, Arvizu LA, Szewczuk MR. A novel epidermal growth factor receptor-signaling platform and its targeted translation in pancreatic cancer. Cell Signal. 2013 Dec;25(12):2587-603. doi: 10.1016/j.cellsig.2013.08.008. Epub 2013 Aug 30. PMID: 23993964. 4: Abdulkhalek S, Szewczuk MR. Neu1 sialidase and matrix metalloproteinase-9 cross-talk regulates nucleic acid-induced endosomal TOLL-like receptor-7 and -9 activation, cellular signaling and pro-inflammatory responses. Cell Signal. 2013 Nov;25(11):2093-105. doi: 10.1016/j.cellsig.2013.06.010. Epub 2013 Jul 1. PMID: 23827939. 5: Sabbah M, Emami S, Redeuilh G, Julien S, Prévost G, Zimber A, Ouelaa R, Bracke M, De Wever O, Gespach C. Molecular signature and therapeutic perspective of the epithelial-to-mesenchymal transitions in epithelial cancers. Drug Resist Updat. 2008 Aug-Oct;11(4-5):123-51. doi: 10.1016/j.drup.2008.07.001. Epub 2008 Aug 20. PMID: 18718806. 6: Prévost GP, Lonchampt MO, Holbeck S, Attoub S, Zaharevitz D, Alley M, Wright J, Brezak MC, Coulomb H, Savola A, Huchet M, Chaumeron S, Nguyen QD, Forgez P, Bruyneel E, Bracke M, Ferrandis E, Roubert P, Demarquay D, Gespach C, Kasprzyk PG. Anticancer activity of BIM-46174, a new inhibitor of the heterotrimeric Galpha/Gbetagamma protein complex. Cancer Res. 2006 Sep 15;66(18):9227-34. doi: 10.1158/0008-5472.CAN-05-4205. PMID: 16982767.