MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 592148 | Name: Gossypolone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Gossypolone, a polyphenolic compound derived from gossypol, exhibits potent bioactivity as an inhibitor of anti-apoptotic Bcl-2 family proteins, particularly Bcl-2 and Bcl-xL. It binds to the BH3-binding groove of these proteins with low micromolar affinity (IC₅₀ ~0.5–2 μM), disrupting their interaction with pro-apoptotic partners like Bax and Bak, thereby promoting apoptosis in cancer cells. In vitro studies show that gossypolone induces caspase-dependent cell death in multiple tumor cell lines, including leukemia and hepatocellular carcinoma, while demonstrating lower toxicity toward normal cells. Additionally, it has been reported to sensitize cancer cells to chemotherapeutic agents such as cisplatin and doxorubicin, suggesting a synergistic potential.

Chemical Structure

Gossypolone
Gossypolone
CAS#4547-72-2

Theoretical Analysis

MedKoo Cat#: 592148

Name: Gossypolone

CAS#: 4547-72-2

Chemical Formula: C30H26O10

Exact Mass: 546.1526

Molecular Weight: 546.53

Elemental Analysis: C, 65.93; H, 4.80; O, 29.27

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Gossypolone,
IUPAC/Chemical Name
(2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',4,4'-tetrahydro-6,6',7,7'-tetrahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-1,1',4,4'-tetraoxo-
InChi Key
YSPBCFMMSKAENM-UHFFFAOYSA-N
InChi Code
InChI=1S/C30H26O10/c1-9(2)15-21-19(13(7-31)25(35)29(15)39)27(37)17(11(5)23(21)33)18-12(6)24(34)22-16(10(3)4)30(40)26(36)14(8-32)20(22)28(18)38/h7-10,35-36,39-40H,1-6H3
SMILES Code
O=CC1=C(O)C(O)=C(C(C)C)C2=C1C(C(C(C3=O)=C(C)C(C4=C3C(C=O)=C(O)C(O)=C4C(C)C)=O)=C(C)C2=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 546.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Adamski V, Schmitt C, Ceynowa F, Adelung R, Lucius R, Synowitz M, Hattermann K, Held-Feindt J. Effects of sequentially applied single and combined temozolomide, hydroxychloroquine and AT101 treatment in a long-term stimulation glioblastoma in vitro model. J Cancer Res Clin Oncol. 2018 Jun 1. doi: 10.1007/s00432-018-2680-y. [Epub ahead of print] PubMed PMID: 29858681. 2: Li X, He J, Li B, Gao M, Zeng Y, Lian J, Shi C, Huang Y, He F. The PPARγ agonist rosiglitazone sensitizes the BH3 mimetic (-)-gossypol to induce apoptosis in cancer cells with high level of Bcl-2. Mol Carcinog. 2018 Jun 1. doi: 10.1002/mc.22837. [Epub ahead of print] PubMed PMID: 29856104. 3: Saleh SR, Attia R, Ghareeb DA. The Ameliorating Effect of Berberine-Rich Fraction against Gossypol-Induced Testicular Inflammation and Oxidative Stress. Oxid Med Cell Longev. 2018 Apr 3;2018:1056173. doi: 10.1155/2018/1056173. eCollection 2018. PubMed PMID: 29849861; PubMed Central PMCID: PMC5903196. 4: Sarosiek B, Dryl K, Palińska-Żarska K, Żarski D. The influence of inhibition of acid phosphatase, β-N-acetylglucosaminidase and lactate dehydrogenase present in the sperm of ide (Leuciscus idus) on the percentage of fertilised eggs. Anim Reprod Sci. 2018 May 17. pii: S0378-4320(18)30046-0. doi: 10.1016/j.anireprosci.2018.05.011. [Epub ahead of print] PubMed PMID: 29807827. 5: Cao H, Sethumadhavan K. Cottonseed Extracts and Gossypol Regulate Diacylglycerol Acyltransferase Gene Expression in Mouse Macrophages. J Agric Food Chem. 2018 Jun 20;66(24):6022-6030. doi: 10.1021/acs.jafc.8b01240. Epub 2018 Jun 8. PubMed PMID: 29807418. 6: Judge JL, Nagel DJ, Owens KM, Rackow A, Phipps RP, Sime PJ, Kottmann RM. Prevention and treatment of bleomycin-induced pulmonary fibrosis with the lactate dehydrogenase inhibitor gossypol. PLoS One. 2018 May 24;13(5):e0197936. doi: 10.1371/journal.pone.0197936. eCollection 2018. PubMed PMID: 29795645; PubMed Central PMCID: PMC5967738. 7: Conceição AA, Soares Neto CB, Ribeiro JAA, Siqueira FG, Miller RNG, Mendonça S. Development of an RP-UHPLC-PDA method for quantification of free gossypol in cottonseed cake and fungal-treated cottonseed cake. PLoS One. 2018 May 23;13(5):e0196164. doi: 10.1371/journal.pone.0196164. eCollection 2018. PubMed PMID: 29791447; PubMed Central PMCID: PMC5965856. 8: Tian X, Ruan JX, Huang JQ, Yang CQ, Fang X, Chen ZW, Hong H, Wang LJ, Mao YB, Lu S, Zhang TZ, Chen XY. Characterization of gossypol biosynthetic pathway. Proc Natl Acad Sci U S A. 2018 Jun 5;115(23):E5410-E5418. doi: 10.1073/pnas.1805085115. Epub 2018 May 21. PubMed PMID: 29784821. 9: Zhi K, Wang L, Zhang Y, Jiang Y, Zhang L, Yasin A. Influence of Size and Shape of Silica Supports on the Sol⁻Gel Surface Molecularly Imprinted Polymers for Selective Adsorption of Gossypol. Materials (Basel). 2018 May 11;11(5). pii: E777. doi: 10.3390/ma11050777. PubMed PMID: 29751648; PubMed Central PMCID: PMC5978154. 10: Cao T, Kong Y, Luo K, Chen L, Zhu S. Cascade Claisen Rearrangement: Rapid Synthesis of Polysubstituted Salicylaldehydes and Total Syntheses of Hemigossypol and Gossypol. Angew Chem Int Ed Engl. 2018 Jul 9;57(28):8702-8707. doi: 10.1002/anie.201801612. Epub 2018 May 27. PubMed PMID: 29697177. 11: Theis T, Johal AS, Kabat M, Basak S, Schachner M. Enhanced Neuronal Survival and Neurite Outgrowth Triggered by Novel Small Organic Compounds Mimicking the LewisX Glycan. Mol Neurobiol. 2018 Mar 8. doi: 10.1007/s12035-018-0953-8. [Epub ahead of print] PubMed PMID: 29520715. 12: Luz VB, Gadelha ICN, Cordeiro LAV, Melo MM, Soto-Blanco B. In vitro study of gossypol's ovarian toxicity to rodents and goats. Toxicon. 2018 Apr;145:56-60. doi: 10.1016/j.toxicon.2018.02.051. Epub 2018 Mar 2. PubMed PMID: 29501827. 13: Chen CY, Lin WC, Wong KL, Cheng KS, Leung YM, Yang SE. Gossypol stimulates opening of a Ca(2+) - and Na(+) -permeable but Ni(2+) - and Co(2+) -impermeable pore in bEND.3 endothelial cells. Clin Exp Pharmacol Physiol. 2018 Mar 1. doi: 10.1111/1440-1681.12929. [Epub ahead of print] PubMed PMID: 29498086. 14: Zhu J, Guo M, Ban L, Song LM, Liu Y, Pelosi P, Wang G. Niemann-Pick C2 Proteins: A New Function for an Old Family. Front Physiol. 2018 Jan 31;9:52. doi: 10.3389/fphys.2018.00052. eCollection 2018. PubMed PMID: 29472868; PubMed Central PMCID: PMC5810286. 15: Amano Y, Nakamura M, Shiraishi S, Chigira N, Shiozawa N, Hagio M, Yano T, Hasegawa T. Preparation and functional analysis of gossypols having two carbohydrate appendages with enaminooxy linkages. Carbohydr Res. 2018 Mar 22;458-459:67-76. doi: 10.1016/j.carres.2018.02.001. Epub 2018 Feb 14. PubMed PMID: 29466762. 16: Hatamoto-Zervoudakis LK, Duarte Júnior MF, Zervoudakis JT, Motheo TF, Silva-Marques RP, Tsuneda PP, Nichi M, Santo BSE, Almeida RD. Free gossypol supplementation frequency and reproductive toxicity in young bulls. Theriogenology. 2018 Apr 1;110:153-157. doi: 10.1016/j.theriogenology.2018.01.003. Epub 2018 Jan 9. PubMed PMID: 29407896. 17: Wen N, Dong Y, Song R, Zhang W, Sun C, Zhuang X, Guan Y, Meng Q, Zhang Y. Zero-Order Release of Gossypol Improves Its Antifertility Effect and Reduces Its Side Effects Simultaneously. Biomacromolecules. 2018 Jun 11;19(6):1918-1925. doi: 10.1021/acs.biomac.7b01648. Epub 2018 Jan 22. PubMed PMID: 29355309. 18: Adamski V, Hempelmann A, Flüh C, Lucius R, Synowitz M, Hattermann K, Held-Feindt J. Dormant glioblastoma cells acquire stem cell characteristics and are differentially affected by Temozolomide and AT101 treatment. Oncotarget. 2017 Nov 18;8(64):108064-108078. doi: 10.18632/oncotarget.22514. eCollection 2017 Dec 8. PubMed PMID: 29296224; PubMed Central PMCID: PMC5746126. 19: Park J, Shim JK, Kang JH, Choi J, Chang JH, Kim SY, Kang SG. Regulation of bioenergetics through dual inhibition of aldehyde dehydrogenase and mitochondrial complex I suppresses glioblastoma tumorspheres. Neuro Oncol. 2018 Jun 18;20(7):954-965. doi: 10.1093/neuonc/nox243. PubMed PMID: 29294080; PubMed Central PMCID: PMC6007558. 20: Tang C, Meng Q, Zhang K, Zhan T, Zhao Q, Zhang S, Zhang J. Multi-omics analyses of red blood cell reveal antioxidation mechanisms associated with hemolytic toxicity of gossypol. Oncotarget. 2017 Oct 10;8(61):103693-103709. doi: 10.18632/oncotarget.21779. eCollection 2017 Nov 28. PubMed PMID: 29262594; PubMed Central PMCID: PMC5732760.