WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H529008
CAS#: 12542-36-8 (acetic acid)
Description: Gossypol is an orally-active polyphenolic aldehyde with potential antineoplastic activity. Derived primarily from unrefined cottonseed oil, gossypol induces cell cycle arrest at the G0/G1 phase, thereby inhibiting DNA replication and inducing apoptosis. This agent also inhibits cell-signaling enzymes, resulting in inhibition of cell growth, and may act as a male contraceptive.
Hodoodo Cat#: H529008
Name: Gossypol acetic acid
CAS#: 12542-36-8 (acetic acid)
Chemical Formula: C32H34O10
Exact Mass: 578.22
Molecular Weight: 578.614
Elemental Analysis: C, 66.43; H, 5.92; O, 27.65
Related CAS #: 12542-36-8 (acetic acid) 303-45-7 (free) 812542-36-8 (R-isomer acetic acid)
Synonym: Gossypol acetate; Gossypol acetic acid; Acetic acid Gossypol.
IUPAC/Chemical Name: acetic acid compound with (S)-1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2'-binaphthalene]-8,8'-dicarbaldehyde (1:1)
InChi Key: NIOHNDKHQHVLKA-UHFFFAOYSA-N
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)
SMILES Code: O=CC1=C(O)C(O)=C(C(C)C)C2=CC(C)=[C@@]([C@@]3=C(C)C=C4C(C(C)C)=C(O)C(O)=C(C=O)C4=C3O)C(O)=C12.CC(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: >2 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:
| Biological target: | Gossypol acetic acid ((±)-Gossypol-acetic acid) binds to Bcl-xL protein and Bcl-2 protein with Kis of 0.5-0.6 μM and 0.2-0.3 mM, respectively. |
| In vitro activity: | Treatment with 10 μM gossypol for 24 and 48 h induced drastic morphological changes in both pancreatic cancer cell lines (Fig. 1B). While the hMSCs revealed shrunken morphology, the cancer cells exhibited a reduced cell volume and appeared buoyant. These surface structural changes induced via gossypol treatment preceded apoptosis. Thus, these results confirmed that gossypol may effectively inhibit the proliferation of pancreatic cancer cells. Reference: J Microbiol Biotechnol. 2022 May 28;32(5):645-656. https://pubmed.ncbi.nlm.nih.gov/35283426/ |
| In vivo activity: | This study examined isolated Langendorff-perfused hearts that were subjected to 30 min of no-flow ischemia followed by 2 h reperfusion. TTC staining was used to assess myocardial tissue viability and determine myocardial infarct size. These results showed that post-treatment with GAA (gossypol acetic acid) (5 μM) significantly attenuated I/R-induced cardiac infarct size in ex vivo rat hearts (Figure 7A). Reference: Biomolecules. 2021 Nov 10;11(11):1667. https://pubmed.ncbi.nlm.nih.gov/34827665/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 62.5 | 108.02 | |
| Ethanol | 12.0 | 20.74 |
The following data is based on the product molecular weight 578.61 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.
| 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 |
| Formulation protocol: | 1. Lee S, Hong E, Jo E, Kim ZH, Yim KJ, Woo SH, Choi YS, Jang HJ. Gossypol Induces Apoptosis of Human Pancreatic Cancer Cells via CHOP/Endoplasmic Reticulum Stress Signaling Pathway. J Microbiol Biotechnol. 2022 May 28;32(5):645-656. doi: 10.4014/jmb.2110.10019. PMID: 35283426. 2. Martínez-Escardó L, Alemany M, Sánchez-Osuna M, Sánchez-Chardi A, Roig-Martínez M, Suárez-García S, Ruiz-Molina D, Vidal N, Plans G, Majós C, Ribas J, Baltrons MA, Bayascas JR, Barcia C, Bruna J, Yuste VJ. Gossypol Treatment Restores Insufficient Apoptotic Function of DFF40/CAD in Human Glioblastoma Cells. Cancers (Basel). 2021 Nov 8;13(21):5579. doi: 10.3390/cancers13215579. PMID: 34771741; PMCID: PMC8583586. 3. Lin JH, Yang KT, Ting PC, Luo YP, Lin DJ, Wang YS, Chang JC. Gossypol Acetic Acid Attenuates Cardiac Ischemia/Reperfusion Injury in Rats via an Antiferroptotic Mechanism. Biomolecules. 2021 Nov 10;11(11):1667. doi: 10.3390/biom11111667. PMID: 34827665; PMCID: PMC8615989. 4. Zhu X, Wu Y, Pan J, Li C, Huang J, Cui E, Chen Z, Zhou W, Chai X, Zhao S. Neuroinflammation Induction and Alteration of Hippocampal Neurogenesis in Mice Following Developmental Exposure to Gossypol. Int J Neuropsychopharmacol. 2021 May 18;24(5):419-433. doi: 10.1093/ijnp/pyaa093. PMID: 33283869; PMCID: PMC8130202. |
| In vitro protocol: | 1. Lee S, Hong E, Jo E, Kim ZH, Yim KJ, Woo SH, Choi YS, Jang HJ. Gossypol Induces Apoptosis of Human Pancreatic Cancer Cells via CHOP/Endoplasmic Reticulum Stress Signaling Pathway. J Microbiol Biotechnol. 2022 May 28;32(5):645-656. doi: 10.4014/jmb.2110.10019. PMID: 35283426. 2. Martínez-Escardó L, Alemany M, Sánchez-Osuna M, Sánchez-Chardi A, Roig-Martínez M, Suárez-García S, Ruiz-Molina D, Vidal N, Plans G, Majós C, Ribas J, Baltrons MA, Bayascas JR, Barcia C, Bruna J, Yuste VJ. Gossypol Treatment Restores Insufficient Apoptotic Function of DFF40/CAD in Human Glioblastoma Cells. Cancers (Basel). 2021 Nov 8;13(21):5579. doi: 10.3390/cancers13215579. PMID: 34771741; PMCID: PMC8583586. |
| In vivo protocol: | 1. Lin JH, Yang KT, Ting PC, Luo YP, Lin DJ, Wang YS, Chang JC. Gossypol Acetic Acid Attenuates Cardiac Ischemia/Reperfusion Injury in Rats via an Antiferroptotic Mechanism. Biomolecules. 2021 Nov 10;11(11):1667. doi: 10.3390/biom11111667. PMID: 34827665; PMCID: PMC8615989. 2. Zhu X, Wu Y, Pan J, Li C, Huang J, Cui E, Chen Z, Zhou W, Chai X, Zhao S. Neuroinflammation Induction and Alteration of Hippocampal Neurogenesis in Mice Following Developmental Exposure to Gossypol. Int J Neuropsychopharmacol. 2021 May 18;24(5):419-433. doi: 10.1093/ijnp/pyaa093. PMID: 33283869; PMCID: PMC8130202. |
1: Krempl C, Sporer T, Reichelt M, Ahn SJ, Heidel-Fischer H, Vogel H, Heckel DG, Joußen N. Potential detoxification of gossypol by UDP-glycosyltransferases in the two Heliothine moth species Helicoverpa armigera and Heliothis virescens. Insect Biochem Mol Biol. 2016 Apr;71:49-57. doi: 10.1016/j.ibmb.2016.02.005. PubMed PMID: 26873292.
2: Chen G, Wang R, Chen H, Wu L, Ge RS, Wang Y. Gossypol ameliorates liver fibrosis in diabetic rats induced by high-fat diet and streptozocin. Life Sci. 2016 Mar 15;149:58-64. doi: 10.1016/j.lfs.2016.02.044. PubMed PMID: 26883980.
3: Tian X, Ruan J, Huang J, Fang X, Mao Y, Wang L, Chen X, Yang C. Gossypol: phytoalexin of cotton. Sci China Life Sci. 2016 Feb;59(2):122-9. doi: 10.1007/s11427-016-5003-z. Review. PubMed PMID: 26803304.
4: Lin QR, Li CG, Zha QB, Xu LH, Pan H, Zhao GX, Ouyang DY, He XH. Gossypol induces pyroptosis in mouse macrophages via a non-canonical inflammasome pathway. Toxicol Appl Pharmacol. 2016 Feb 1;292:56-64. doi: 10.1016/j.taap.2015.12.027. PubMed PMID: 26765310.
5: Li L, Li Z, Wang K, Liu Y, Li Y, Wang Q. Synthesis and antiviral, insecticidal, and fungicidal activities of gossypol derivatives containing alkylimine, oxime or hydrazine moiety. Bioorg Med Chem. 2016 Feb 1;24(3):474-83. doi: 10.1016/j.bmc.2015.08.015. PubMed PMID: 26337022.
6: Kim NY, Han BI, Lee M. Cytoprotective role of autophagy against BH3 mimetic gossypol in ATG5 knockout cells generated by CRISPR-Cas9 endonuclease. Cancer Lett. 2016 Jan 1;370(1):19-26. doi: 10.1016/j.canlet.2015.10.008. PubMed PMID: 26476415.
7: Tomoda K, Chiang C, Kozak KR, Kwon GS. Examination of Gossypol-Pluronic Micelles as Potential Radiosensitizers. AAPS J. 2015 Nov;17(6):1369-75. doi: 10.1208/s12248-015-9809-6. PubMed PMID: 26246329; PubMed Central PMCID: PMC4627454.
8: Wagner TA, Liu J, Puckhaber LS, Bell AA, Williams H, Stipanovic RD. RNAi construct of a cytochrome P450 gene CYP82D109 blocks an early step in the biosynthesis of hemigossypolone and gossypol in transgenic cotton plants. Phytochemistry. 2015 Jul;115:59-69. doi: 10.1016/j.phytochem.2015.02.016. PubMed PMID: 25794893.
9: Dong Y, Mao B, Li L, Guan H, Su Y, Li X, Lian Q, Huang P, Ge RS. Gossypol enantiomers potently inhibit human placental 3β-hydroxysteroid dehydrogenase 1 and aromatase activities. Fitoterapia. 2016 Mar;109:132-7. doi: 10.1016/j.fitote.2015.12.014. PubMed PMID: 26709042.
10: Li C, Zhao T, Li C, Mei L, Yu E, Dong Y, Chen J, Zhu S. Determination of gossypol content in cottonseeds by near infrared spectroscopy based on Monte Carlo uninformative variable elimination and nonlinear calibration methods. Food Chem. 2017 Apr 15;221:990-996. doi: 10.1016/j.foodchem.2016.11.064. PubMed PMID: 27979304.
11: Zeng QF, Bai P, Wang JP, Ding XM, Luo YH, Bai SP, Xuan Y, Su ZW, Lin SQ, Zhao LJ, Zhang KY. The response of meat ducks from 15 to 35 d of age to gossypol from cottonseed meal. Poult Sci. 2015 Jun;94(6):1277-86. doi: 10.3382/ps/pev070. PubMed PMID: 25834247; PubMed Central PMCID: PMC4988552.
12: Câmara AC, Gadelha IC, Borges PA, de Paiva SA, Melo MM, Soto-Blanco B. Toxicity of Gossypol from Cottonseed Cake to Sheep Ovarian Follicles. PLoS One. 2015 Nov 24;10(11):e0143708. doi: 10.1371/journal.pone.0143708. PubMed PMID: 26600470; PubMed Central PMCID: PMC4658018.
13: Effenberger I, Zhang B, Li L, Wang Q, Liu Y, Klaiber I, Pfannstiel J, Wang Q, Schaller A. Dirigent Proteins from Cotton (Gossypium sp.) for the Atropselective Synthesis of Gossypol. Angew Chem Int Ed Engl. 2015 Dec 1;54(49):14660-3. doi: 10.1002/anie.201507543. PubMed PMID: 26460165.
14: Gong Y, Ni ZH, Zhang X, Chen XH, Zou ZM. Valproic Acid Enhances the Anti-tumor Effect of (-)-gossypol to Burkitt Lymphoma Namalwa Cells. Biomed Environ Sci. 2015 Oct;28(10):773-7. doi: 10.3967/bes2015.108. PubMed PMID: 26582100.
15: He T, Zhang HJ, Wang J, Wu SG, Yue HY, Qi GH. Application of low-gossypol cottonseed meal in laying hens' diet. Poult Sci. 2015 Oct;94(10):2456-63. doi: 10.3382/ps/pev247. PubMed PMID: 26287003.
16: Yang D, Qu J, Qu X, Cao Y, Xu L, Hou K, Feng W, Liu Y. Gossypol sensitizes the antitumor activity of 5-FU through down-regulation of thymidylate synthase in human colon carcinoma cells. Cancer Chemother Pharmacol. 2015 Sep;76(3):575-86. doi: 10.1007/s00280-015-2749-0. PubMed PMID: 26208739.
17: Santana AT, Guelfi M, Medeiros HC, Tavares MA, Bizerra PF, Mingatto FE. Mechanisms involved in reproductive damage caused by gossypol in rats and protective effects of vitamin E. Biol Res. 2015 Jul 31;48:43. doi: 10.1186/s40659-015-0026-7. PubMed PMID: 26227499; PubMed Central PMCID: PMC4521381.
18: Zeng QF, Yang GL, Liu GN, Wang JP, Bai SP, Ding XM, Luo YH, Zhang KY. Effects of dietary gossypol concentration on growth performance, blood profiles, and hepatic histopathology in meat ducks. Poult Sci. 2014 Aug;93(8):2000-9. doi: 10.3382/ps.2013-03841. PubMed PMID: 24902707; PubMed Central PMCID: PMC4988539.
19: Mani J, Vallo S, Rakel S, Antonietti P, Gessler F, Blaheta R, Bartsch G, Michaelis M, Cinatl J, Haferkamp A, Kögel D. Chemoresistance is associated with increased cytoprotective autophagy and diminished apoptosis in bladder cancer cells treated with the BH3 mimetic (-)-Gossypol (AT-101). BMC Cancer. 2015 Apr 7;15:224. doi: 10.1186/s12885-015-1239-4. PubMed PMID: 25885284; PubMed Central PMCID: PMC4409725.
20: Liu H, Sun H, Lu D, Zhang Y, Zhang X, Ma Z, Wu B. Identification of glucuronidation and biliary excretion as the main mechanisms for gossypol clearance: in vivo and in vitro evidence. Xenobiotica. 2014 Aug;44(8):696-707. doi: 10.3109/00498254.2014.891780. PubMed PMID: 24555821.
