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Gossypol Acetic Acid

Gossypol Acetic Acid

Product ID G5875
Cas No. 12542-36-8
Purity ≥98%
Product Unit SizeCostQuantityStock
250 mg $110.30 In stock
1 g $325.30 In stock
Bulk Quote

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  • Product Info
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  • References
  • Description
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Description

Gossypol acetic acid (GA) exhibits anticancer chemotherapeutic, pro-oxidative, antioxidative, and antibacterial activities. GA inhibits Bcl-2/Bcl-xl, enhancing TRAIL/mitochondria-induced apoptosis in breast cancer cells. In animal models, GA delayed the onset of androgen-independent prostate cancer. In macrophages, GA increases production of ROS, upregulates expression of caspases 3 and 9, and decreases the mitochondrial membrane potential, inducing apoptosis. GA increases activity of glutathione peroxidase and inhibits lipid peroxidation but also increases generation of ROS and induces DNA damage. This compound also exhibits antibiotic activity, inhibiting growth of gram negative bacteria such as Edwardsiella. Additionally, GA has been studied as a male contraceptive; it inhibits sialyl transferase activity in seminal plasma, decreases tubulin content and spermatocyte mobility, and reversibly inhibits spermatogenesis in vivo.

Product Info

Cas No.

12542-36-8

Purity

≥98%

Formula

C30H30O8 • C2H4O2

Formula Wt.

578.61

Chemical Name

1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1- methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde-acetic acid

IUPAC Name

acetic acid;7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde

Synonym

Gossypol acetate

Melting Point

184

Solubility

Soluble in DMSO, methanol or ethanol. Insoluble in water.

Appearance

Yellow Powder

Shipping and Storage

Store Temp

4°C

Ship Temp

Ambient

Downloads

MSDS

G5875 MSDS PDF

Info Sheet

G5875 Info Sheet PDF

References

Deng S, Yuan H, Yi J, et al. Gossypol acetic acid induces apoptosis in RAW264.7 cells via a caspase-dependent mitochondrial signaling pathway. J Vet Sci. 2013;14(3):281-9. PMID: 23820203.

Hall C, Troutman SM, Price DK, et al. Bcl-2 family of proteins as therapeutic targets in genitourinary neoplasms. Clin Genitourin Cancer. 2013 Mar;11(1):10-9. PMID: 23083798.

Kisim A, Atmaca H, Cakar B, et al. Pretreatment with AT-101 enhances tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-induced apoptosis of breast cancer cells by inducing death receptors 4 and 5 protein levels. J Cancer Res Clin Oncol. 2012 Jul;138(7):1155-63. PMID: 22411600.

El-Sharaky AS, Wahby MM, Bader El-Dein MM, et al. Mutual anti-oxidative effect of gossypol acetic acid and gossypol-iron complex on hepatic lipid peroxidation in male rats. Food Chem Toxicol. 2009 Nov;47(11):2735-41. PMID: 19665044.

Loberg RD, McGregor N, Ying C, et al. In vivo evaluation of AT-101 (R-(-)-gossypol acetic acid) in androgen-independent growth of VCaP prostate cancer cells in combination with surgical castration. Neoplasia. 2007 Dec;9(12):1030-7. PMID: 18084610.

Yildirim-Aksoy M, Lim C, Dowd MK, et al. In vitro inhibitory effect of gossypol from gossypol-acetic acid, and (+)- and (-)-isomers of gossypol on the growth of Edwardsiella ictaluri. J Appl Microbiol. 2004;97(1):87-92. PMID: 15186445.

Sharma S, Kumar M, Goyal RB, et al. Reversible antispermatogenic effect of gossypol in langur monkeys (Presbytis entellus entellus). Adv Contracept. 1999;15(1):15-27. PMID: 10794043.

Teng CS. Reversible changes in the content of cellular and microtubular tubulin in spermatogenic cells after gossypol treatment. Contraception. 1997 Jan;55(1):41-6. PMID: 9013060.

Levinsky H, Singer R, Sagiv M, et al. Inhibition of sialyl transferase activity by gossypol acetic acid in human seminal plasma. Andrologia. 1991 Mar-Apr;23(2):159-61. PMID: 1952122.

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