3α-AMINOCHOLESTANE (3AC)

Description: 3alpha-Aminocholestane (also known as 3AC) is a potent and selective SH2 domain-containing inositol-5?-phosphatase 1 (SHIP1) inhibitor with an IC50 of ca.2.5 uM. It shows no inhibition on SHIP2 or PTEN. Many tumors present with increased activation of the phosphatidylinositol 3-kinase (PI3K)-PtdIns(3, 4, 5)P(3)-protein kinase B (PKB/Akt) signaling pathway. It has long been thought that the lipid phosphatases SH2 domain-containing inositol-5'-phosphatase 1 (SHIP1) and SHIP2 act as tumor suppressors by counteracting with the survival signal induced by this pathway through hydrolysis or PtdIns(3, 4, 5)P(3) to PtdIns(3, 4)P(2). However, a growing body of evidence suggests that PtdInd(3, 4)P(2) is capable of, and essential for, Akt activation, thus suggesting a potential role for SHIP1/2 enzymes as proto-oncogenes. 3AC is capable of killing malignant hematologic cells. In vivo growth of MM cells is blocked by treatment of mice with the SHIP1 inhibitor 3AC.

References: Mol Med. 2012 Feb 10; 18:65-75; Nature. 2015 May 21; 521(7552):357-61.

3alpha-Aminocholestane; 3AC, 3-AC, 3 AC

Chemical Name: (3R, 8R, 9S, 10S, 13R, 14S, 17R)-10, 13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-amine

SMILES Code: CC(C)CCC[CH](C)[CH]1CC[C]2([H])[C]3([H])CCC4C[CH](N)CC[C]4(C)[C]3([H])CC[C]12C