((addition))-Apogossypol

Cat No:	I013850
Cas No:	66389-74-0
Product-Name:	((addition))-Apogossypol
IUPAC Name:	3-methyl-5-propan-2-yl-2-(1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)naphthalene-1,6,7-triol;sulfane
InChI:	InChI=1S/C28H30O6.H2S/c1-11(2)21-15-7-13(5)23(25(31)17(15)9-19(29)27(21)33)24-14(6)8-16-18(26(24)32)10-20(30)28(34)22(16)12(3)4;/h7-12,29-34H,1-6H3;1H2
InChIKey:	MEOWTYRKWJLKKQ-UHFFFAOYSA-N
SMILES:	CC1=C(C(=C2C=C(C(=C(C2=C1)C(C)C)O)O)O)C3=C(C=C4C(=C3O)C=C(C(=C4C(C)C)O)O)C.S

(+)-Apogossypol(Apogossypol; NSC736630) is a potent inhibitor of Bcl-2 family proteins; competing with the BH3 peptide-binding sites on Bcl-2, Bcl-XL, Mcl-1, Bcl-W, and Bcl-B, but not Bfl-1, with IC50s of 0.5 to 2 μM. IC50 value: 0.5- 2 uM [1] Target: Bcl-2 inhibitor in vitro: Bcl-2-expressing B cells from transgenic mice were more sensitive to cytotoxicity induced by apogossypol than gossypol, with LD50 values of 3 to 5 microM and 7.5 to 10 microM, respectively [1]. in vivo: Using the maximum tolerated dose of gossypol for sequential daily dosing, apogossypol displayed superior activity to gossypol in terms of reducing splenomegaly and reducing B-cell counts in spleens of Bcl-2-transgenic mice [1]. Apogossypol is capable of binding and inhibiting Bcl-2 and Bcl-X(L) with high affinity and induces apoptosis of tumor cell lines [2].

[1]. Kitada S, et al. Bcl-2 antagonist apogossypol (NSC736630) displays single-agent activity in Bcl-2-transgenic mice and has superior efficacy with less toxicity compared with gossypol (NSC19048). Blood. 2008 Mar 15;111(6):3211-9.
[2]. Becattini B, et al. Rational design and real time, in-cell detection of the proapoptotic activity of a novel compound targeting Bcl-X(L). Chem Biol. 2004 Mar;11(3):389-95.