A polyphenol with spermicidal and anticancer activities
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Isomer(s)
14482Gossypol
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(−)-Gossypol (acetate)

Item No. 42421

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R)-1,1′,6,6′,7,7′-hexahydroxy-3,3′-dimethyl-5,5′-bis(1-methylethyl)-[2,2′-binaphthalene]-8,8′-dicarboxaldehyde, compd. with acetic acid (1:1)
CAS Number
866541-93-7
Synonyms
  • AT-101
Molecular Formula
C30H30O8 • C2H4O2
Formula Weight
578.6
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥10 mg/mlEthanol: Soluble: ≥10 mg/ml
SMILES
O=CC1=C(C(O)=C(C(C)C)C2=CC(C)=[C@@]([C@@]3=C(C4=C(C(O)=C(C(C(C)C)=C4C=C3C)O)C=O)O)C(O)=C12)O.CC(O)=O
InChi Code
InChI=1S/C30H30O8.C2H4O2/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36;1-2(3)4/h7-12,33-38H,1-6H3;1H3,(H,3,4)
InChi Key
NIOHNDKHQHVLKA-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Cayman Chemical
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    Product Description

    (−)-Gossypol is a polyphenol that has been found in Gossypium and has diverse biological activities.1,2,3,4,5 It induces complete immobilization of isolated human sperm within 3 minutes when used at a concentration of 5 mg/ml.2 (−)-Gossypol inhibits Bcl-2, Bcl-xL, and myeloid cell leukemia-1 (Mcl-1; Kis = 0.32, 0.48, and 0.18 µM, respectively).3 It induces apoptosis in patient-derived B cell chronic lymphocytic leukemia (B-CLL) cells when used at a concentration of 20 µM.4 (−)-Gossypol (35 mg/kg), in combination with rituximab and cyclophosphamide (Item No. 13849), induces tumor regression in an RL diffuse large B-cell lymphoma (DLBCL) mouse xenograft model.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Robinson, P.H., Getachew, G., De Peters, E.J., et al. Influence of variety and storage for up to 22 days on nutrient composition and gossypol level of Pima cottonseed (Gossypium spp.). Anim. Feed Sci. Technol. 91(3-4), 149-156 (2001).

    2. Kim, I.C., Waller, D.P., Marcelle, G.B., et al. Comparative in vitro spermicidal effects of (+)-gossypol, (+)-gossypol, (−)-gossypol and gossypolone. Contraception 30(3), 253-259 (1984).

    3. Wang, G., Nikolovska-Coleska, Z., Yang, C.Y., et al. Structure-based design of potent small-molecule inhibitors of anti-apoptotic Bcl-2 proteins. J. Med. Chem. 49(21), 6139-6142 (2006).

    4. Balakrishnan, K., Burger, J.A., Wierda, W.G., et al. AT-101 induces apoptosis in CLL B cells and overcomes stromal cell-mediated Mcl-1 induction and drug resistance. Blood 113(1), 149-153 (2009).

    5. Paoluzzi, L., Gonen, M., Gardner, J.R., et al. Targeting Bcl-2 family members with the BH3 mimetic AT-101 markedly enhances the therapeutic effects of chemotherapeutic agents in in vitro and in vivo models of B-cell lymphoma. Blood 111(11), 5350-5358 (2008).