IMC-76

• CAT Number: I029249
• CAS Number: 98129-27-2
• Molecular Formula: C30H45NO3
• Molecular Weight: 467.69
• Purity: 98%
• Synonyms: IMC-76; IMC 76; IMC76; NSC-59276; NSC 59276; NSC59276
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (3S,5S,8S,9S,10R,13R,14R,17R)-17-[(1R)-1-(6-Methoxy-2,4-dihydro-1,3-benzoxazin-3-yl)ethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• InChI: InChI=1S/C30H45NO3/c1-19(31-17-20-15-23(33-4)6-10-28(20)34-18-31)25-8-9-26-24-7-5-21-16-22(32)11-13-29(21,2)27(24)12-14-30(25,26)3/h6,10,15,19,21-22,24-27,32H,5,7-9,11-14,16-18H2,1-4H3/t19-,21+,22+,24-,25+,26-,27+,29-,30+/m1/s1
• InChIKey: JVEDHWWWBFCUKI-JVULLFNSSA-N
• SMILES: O[C@H]1CC[C@@]2(C)[C@@]3([H])CC[C@@]4(C)[C@H]([C@H](N5COC6=CC=C(OC)C=C6C5)C)CC[C@]4([H])[C@@]3([H])CC[C@@]2([H])C1

IMC-76 is a BCL2 i-motif-interactive compound that acts by destabilizing or unfolding the i-motif.

Reference

1: Kendrick S, Muranyi A, Gokhale V, Hurley LH, Rimsza LM. Simultaneous Drug Targeting of the Promoter MYC G-Quadruplex and BCL2 i-Motif in Diffuse Large B-Cell Lymphoma Delays Tumor Growth. J Med Chem. 2017 Aug 10;60(15):6587-6597. doi: 10.1021/acs.jmedchem.7b00298. Epub 2017 Jul 25. PubMed PMID: 28605593.
2: Cui Y, Koirala D, Kang H, Dhakal S, Yangyuoru P, Hurley LH, Mao H. Molecular population dynamics of DNA structures in a bcl-2 promoter sequence is regulated by small molecules and the transcription factor hnRNP LL. Nucleic Acids Res. 2014 May;42(9):5755-64. doi: 10.1093/nar/gku185. Epub 2014 Mar 7. PubMed PMID: 24609386; PubMed Central PMCID: PMC4027204.
3: Kang HJ, Kendrick S, Hecht SM, Hurley LH. The transcriptional complex between the BCL2 i-motif and hnRNP LL is a molecular switch for control of gene expression that can be modulated by small molecules. J Am Chem Soc. 2014 Mar 19;136(11):4172-85. doi: 10.1021/ja4109352. Epub 2014 Mar 7. PubMed PMID: 24559432; PubMed Central PMCID: PMC3985447.