Gossypol

Gossypol is a lipid of Prenol Lipids (PR) class. Gossypol is associated with abnormalities such as Paralytic Ileus, PARKINSON DISEASE, LATE-ONSET, Fibrillation, Hepatic necrosis and Lymphopenia. The involved functions are known as Atrophic, Ulcer, Necrosis, Apoptosis and antagonists. Gossypol often locates in Mucous Membrane, Epithelium, Blood, Microsomes, Liver and Autophagic vacuole. The associated genes with Gossypol are BCL2A1 gene, BCL2 gene, Transgenes, IGH@ gene cluster and Bax protein (53-86). The related lipids are Promega, proteoliposomes, Phosphatidylserines and Liposomes. The related experimental models are Transgenic Model and Xenograft Model.

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Introduction

To understand associated biological information of Gossypol, we collected biological information of abnormalities, associated pathways, cellular/molecular locations, biological functions, related genes/proteins, lipids and common seen animal/experimental models with organized paragraphs from literatures.

What diseases are associated with Gossypol?

Gossypol is suspected in Severe Combined Immunodeficiency, Aortic Valve Insufficiency, PARKINSON DISEASE, LATE-ONSET, Infertility, CLEFT LIP, CONGENITAL HEALED, Pulmonary Fibrosis and other diseases in descending order of the highest number of associated sentences.

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Disease Cross reference Weighted score Related literature
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Possible diseases from mapped MeSH terms on references

We collected disease MeSH terms mapped to the references associated with Gossypol

MeSH term MeSH ID Detail
Abnormalities, Drug-Induced D000014 10 associated lipids
Adenocarcinoma D000230 166 associated lipids
Body Weight D001835 333 associated lipids
Carcinoma, Non-Small-Cell Lung D002289 72 associated lipids
Cattle Diseases D002418 24 associated lipids
Cell Transformation, Neoplastic D002471 126 associated lipids
Colonic Neoplasms D003110 161 associated lipids
Edema D004487 152 associated lipids
Endometriosis D004715 29 associated lipids
Genital Neoplasms, Male D005834 3 associated lipids
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PubChem Associated disorders and diseases

What pathways are associated with Gossypol

Lipid pathways are not clear in current pathway databases. We organized associated pathways with Gossypol through full-text articles, including metabolic pathways or pathways of biological mechanisms.

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Pathway name Related literatures
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PubChem Biomolecular Interactions and Pathways

Link to PubChem Biomolecular Interactions and Pathways

What cellular locations are associated with Gossypol?

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Location Cross reference Weighted score Related literatures
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What functions are associated with Gossypol?


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Function Cross reference Weighted score Related literatures

What lipids are associated with Gossypol?

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Lipid concept Cross reference Weighted score Related literatures
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What genes are associated with Gossypol?

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Gene Cross reference Weighted score Related literatures

What common seen animal models are associated with Gossypol?

Xenograft Model

Xenograft Model are used in the study 'Gossypol induces apoptosis by activating p53 in prostate cancer cells and prostate tumor-initiating cells.' (Volate SR et al., 2010), Xenograft Model are used in the study 'Sorafenib sensitizes (-)-gossypol-induced growth suppression in androgen-independent prostate cancer cells via Mcl-1 inhibition and Bak activation.' (Lian J et al., 2012), Xenograft Model are used in the study 'Natural BH3 mimetic (-)-gossypol chemosensitizes human prostate cancer via Bcl-xL inhibition accompanied by increase of Puma and Noxa.' (Meng Y et al., 2008), Xenograft Model are used in the study '(-)-Gossypol suppresses the growth of human prostate cancer xenografts via modulating VEGF signaling-mediated angiogenesis.' (Pang X et al., 2011) and Xenograft Model are used in the study 'Gossypol induces death receptor-5 through activation of the ROS-ERK-CHOP pathway and sensitizes colon cancer cells to TRAIL.' (Sung B et al., 2010).

Transgenic Model

Transgenic Model are used in the study '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).' (Kitada S et al., 2008).

Related references are published most in these journals:

Model Cross reference Weighted score Related literatures
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NCBI Entrez Crosslinks

All references with Gossypol

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Per page 10 20 50 100 | Total 1511
Authors Title Published Journal PubMed Link
Schteingart DE et al. Expression of anti-apoptosis genes determines the response of adrenal cancer to apoptosis-inducing chemotherapy. 2010 Anticancer Res. pmid:21187456
Cengiz E et al. Overcoming drug resistance in hormone- and drug-refractory prostate cancer cell line, PC-3 by docetaxel and gossypol combination. 2010 Mol. Biol. Rep. pmid:19288219
Fulda S Modulation of apoptosis by natural products for cancer therapy. 2010 Planta Med. pmid:20486070
Ionov M et al. The interaction of PVP complexes of gossypol and its derivatives with an artificial membrane lipid matrix. 2010 Cell. Mol. Biol. Lett. pmid:19936629
Wu G et al. Responses of three successive generations of beet armyworm, Spodoptera exigua, fed exclusively on different levels of gossypol in cotton leaves. 2010 J. Insect Sci. pmid:21067414
Wei J et al. Synthesis and biological evaluation of Apogossypolone derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. 2010 J. Med. Chem. pmid:21033669
ZHU Y et al. Involvement of Bcl-2, Src, and ERα in gossypol-mediated growth inhibition and apoptosis in human uterine leiomyoma and myometrial cells. 2010 Acta Pharmacol. Sin. pmid:21102482
Zhan WH et al. [Studies on the killing effect of gamma ray irradiated peripheral blood mononuclear cells combined with (-)-gossypol on human prostate cancer LNCaP cells]. 2010 Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi pmid:21319440
Sung B et al. Gossypol induces death receptor-5 through activation of the ROS-ERK-CHOP pathway and sensitizes colon cancer cells to TRAIL. 2010 J. Biol. Chem. pmid:20837473
Chang Q et al. Effects of combined administration of low-dose gossypol with steroid hormones on the mitotic phase of spermatogenesis of rat. 2010 J Exp Zool A Ecol Genet Physiol pmid:20839281
Uzunoglu S et al. Comparison of XTT and Alamar blue assays in the assessment of the viability of various human cancer cell lines by AT-101 (-/- gossypol). 2010 Toxicol. Mech. Methods pmid:20843265
Przybylski P et al. The influence of protonation on molecular structure and physico-chemical properties of gossypol Schiff bases. 2010 Org. Biomol. Chem. pmid:20959900
Vizirianakis IS et al. Toward the development of innovative bifunctional agents to induce differentiation and to promote apoptosis in leukemia: clinical candidates and perspectives. 2010 J. Med. Chem. pmid:20925433
Zwitter M Combining cytotoxic and targeted therapies for lung cancer. 2010 J Thorac Oncol pmid:20871258
Lian J et al. The Bcl-2-Beclin 1 interaction in (-)-gossypol-induced autophagy versus apoptosis in prostate cancer cells. 2010 Autophagy pmid:20930561
Moretti L et al. AT-101, a pan-Bcl-2 inhibitor, leads to radiosensitization of non-small cell lung cancer. 2010 J Thorac Oncol pmid:20354451
Priyadarshi A et al. Structural insights into mouse anti-apoptotic Bcl-xl reveal affinity for Beclin 1 and gossypol. 2010 Biochem. Biophys. Res. Commun. pmid:20206602
Reddish JM et al. (-)-Gossypol containing hen sera and a myosin (-)-gossypol conjugate reduces the proliferation of MCF-7 cells. 2010 Anticancer Res. pmid:20332451
Banerjee S et al. Preclinical studies of apogossypolone, a novel pan inhibitor of bcl-2 and mcl-1, synergistically potentiates cytotoxic effect of gemcitabine in pancreatic cancer cells. 2010 Pancreas pmid:19823097
Goldsmith KC et al. BH3 response profiles from neuroblastoma mitochondria predict activity of small molecule Bcl-2 family antagonists. 2010 Cell Death Differ. pmid:19893570
Wei J et al. BI-97C1, an optically pure Apogossypol derivative as pan-active inhibitor of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. 2010 J. Med. Chem. pmid:20443627
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McGregor N et al. AT-101 (R-(-)-gossypol acetic acid) enhances the effectiveness of androgen deprivation therapy in the VCaP prostate cancer model. 2010 J. Cell. Biochem. pmid:20589722
Zhang XQ et al. Apogossypolone, a novel inhibitor of antiapoptotic Bcl-2 family proteins, induces autophagy of PC-3 and LNCaP prostate cancer cells in vitro. 2010 Asian J. Androl. pmid:20657602
Huang LH et al. Gossypol inhibits phosphorylation of Bcl-2 in human leukemia HL-60 cells. 2010 Eur. J. Pharmacol. pmid:20633548
Liu YX Temperature control of spermatogenesis and prospect of male contraception. 2010 Front Biosci (Schol Ed) pmid:20036980
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Wang H et al. Inhibition of calcineurin by quercetin in vitro and in Jurkat cells. 2010 J. Biochem. pmid:19880376
Anuja MN et al. Spermatotoxicity of a protein isolated from the root of Achyranthes aspera: a comparative study with gossypol. 2010 Contraception pmid:20851234
Li G et al. [Effect of testosterone on the expression of CMTM family of the male spermatogenesis suppression rats]. 2010 Yao Xue Xue Bao pmid:21351585
Karaca B et al. Enhancement of taxane-induced cytotoxicity and apoptosis by gossypol in human breast cancer cell line MCF-7. 2009 Jul-Sep J BUON pmid:19810142
Pankajakshy A and Madambath I Spermatotoxic effects of Cananga odorata (Lam): a comparison with gossypol. 2009 Fertil. Steril. pmid:18692834
Wei J et al. Synthesis and evaluation of Apogossypol atropisomers as potential Bcl-xL antagonists. 2009 Cancer Lett. pmid:18782651
Azmi AS and Mohammad RM Non-peptidic small molecule inhibitors against Bcl-2 for cancer therapy. 2009 J. Cell. Physiol. pmid:18767026
Kang MH and Reynolds CP Bcl-2 inhibitors: targeting mitochondrial apoptotic pathways in cancer therapy. 2009 Clin. Cancer Res. pmid:19228717
Lin J et al. [Effect of apogossypolone on induction apoptosis in multiple myeloma cells and its mechanisms]. 2009 Zhongguo Shi Yan Xue Ye Xue Za Zhi pmid:19236755
Przybylski P et al. Complexes of heterocyclic aza-derivatives of phytoalexin from cotton plant-gossypol with alkali metal cations and perchlorate anion studied by ESI mass spectrometric method in the positive and negative modes. 2009 J Mass Spectrom pmid:19189269
Przybylski P et al. Antifungal activity of alkyl and heterocyclic aza-derivatives of gossypol as well as their complexes with NaClO4 against Fusarium oxysporum f. sp. lupini. 2009 Bioorg. Med. Chem. Lett. pmid:19264482
Balakrishnan K et al. AT-101 induces apoptosis in CLL B cells and overcomes stromal cell-mediated Mcl-1 induction and drug resistance. 2009 Blood pmid:18836097
Liu G et al. An open-label, multicenter, phase I/II study of single-agent AT-101 in men with castrate-resistant prostate cancer. 2009 Clin. Cancer Res. pmid:19366825
Wei J et al. Apogossypol derivatives as antagonists of antiapoptotic Bcl-2 family proteins. 2009 Mol. Cancer Ther. pmid:19372563
Xu WB et al. The immunosuppressive effect of gossypol in mice is mediated by inhibition of lymphocyte proliferation and by induction of cell apoptosis. 2009 Acta Pharmacol. Sin. pmid:19363517
Zhan Y et al. Design and synthesis of a gossypol derivative with improved antitumor activities. 2009 Arch. Pharm. (Weinheim) pmid:19340835
Verma PC et al. Efficient production of gossypol from hairy root cultures of cotton (Gossypium hirsutum L.). 2009 Curr Pharm Biotechnol pmid:19751178
Sanli UA et al. Targeting apoptosis in the hormone- and drug-resistant prostate cancer cell line, DU-145, by gossypol/zoledronic acid combination. 2009 Cell Biol. Int. pmid:19716895
Das SG et al. Structure-activity relationship and molecular mechanisms of ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6-phenyl-4h-chromene-3-carboxylate (sha 14-1) and its analogues. 2009 J. Med. Chem. pmid:19743858
Hu ZY et al. ApoG2 induces cell cycle arrest of nasopharyngeal carcinoma cells by suppressing the c-Myc signaling pathway. 2009 J Transl Med pmid:19698176
Kilic A et al. Efficacy of signal pathway inhibitors alone and in combination with Cisplatin varies between human non-small cell lung cancer lines. 2009 J. Surg. Res. pmid:19084241
Chen BB et al. The (+)- and (-)-gossypols potently inhibit human and rat 11beta-hydroxysteroid dehydrogenase type 2. 2009 J. Steroid Biochem. Mol. Biol. pmid:19150652
Stipanovic RD et al. Total and percent atropisomers of gossypol and gossypol-6-methyl ether in seeds from pima cottons and accessions of Gossypium barbadense L. 2009 J. Agric. Food Chem. pmid:19113939
Zhang L et al. Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling. 2009 Eur J Med Chem pmid:19447525
Sun J et al. Apogossypolone inhibits cell growth by inducing cell cycle arrest in U937 cells. 2009 Oncol. Rep. pmid:19513523
Jiang J et al. Gossypol inhibits the growth of MAT-LyLu prostate cancer cells by modulation of TGFbeta/Akt signaling. 2009 Int. J. Mol. Med. pmid:19513537
Przybylski P et al. Synthesis, crystal structures and antibacterial activity studies of aza-derivatives of phytoalexin from cotton plant--gossypol. 2009 Eur J Med Chem pmid:19577825
Wei J et al. Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. 2009 J. Med. Chem. pmid:19555126
Lestini BJ et al. Mcl1 downregulation sensitizes neuroblastoma to cytotoxic chemotherapy and small molecule Bcl2-family antagonists. 2009 Cancer Biol. Ther. pmid:19556859
Ionov M et al. The immobilization of gossypol derivative on N-polyvinylpyrrolidone increases its water solubility and modifies membrane-active properties. 2009 J. Med. Chem. pmid:19603832
Anilkumar KJ et al. Synergistic interactions between Cry1Ac and natural cotton defenses limit survival of Cry1Ac-resistant Helicoverpa zea (Lepidoptera: Noctuidae) on Bt cotton. 2009 J. Chem. Ecol. pmid:19588197
Huang YW et al. (-)-Gossypol reduces invasiveness in metastatic prostate cancer cells. 2009 Anticancer Res. pmid:19528479
Yurekli B et al. Can gossypol be a hope for transsexual patients (male to female) before sex reassignment surgery? Just for adjusting the body to mind. 2009 Med. Hypotheses pmid:19647947
El-Sharaky AS et al. Mutual anti-oxidative effect of gossypol acetic acid and gossypol-iron complex on hepatic lipid peroxidation in male rats. 2009 Food Chem. Toxicol. pmid:19665044
Hu GX et al. The (+)- and (-)-gossypols potently inhibit both 3beta-hydroxysteroid dehydrogenase and 17beta-hydroxysteroid dehydrogenase 3 in human and rat testes. 2009 J. Steroid Biochem. Mol. Biol. pmid:19429456
Barba-Barajas M et al. Gossypol induced apoptosis of polymorphonuclear leukocytes and monocytes: involvement of mitochondrial pathway and reactive oxygen species. 2009 Immunopharmacol Immunotoxicol pmid:19235535
Basini G et al. Gossypol, a polyphenolic aldehyde from cotton plant, interferes with swine granulosa cell function. 2009 Domest. Anim. Endocrinol. pmid:19342192
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Atmaca H et al. Combined gossypol and zoledronic acid treatment results in synergistic induction of cell death and regulates angiogenic molecules in ovarian cancer cells. 2009 Eur. Cytokine Netw. pmid:19825521
Zerp SF et al. AT-101, a small molecule inhibitor of anti-apoptotic Bcl-2 family members, activates the SAPK/JNK pathway and enhances radiation-induced apoptosis. 2009 Radiat Oncol pmid:19852810
Varol U et al. The effect of racemic gossypol and at-101 on angiogenic profile of ovcar-3 cells: a preliminary molecular framework for gossypol enantiomers. 2009 Exp. Oncol. pmid:20010531
Wu G et al. Temporal allocation of metabolic tolerance in the body of beet armyworm in response to three gossypol-cotton cultivars. 2009 Sci. China, C, Life Sci. pmid:20016971
Roychoudhury S et al. In vitro gossypol induced spermatozoa motility alterations in rabbits. 2009 J Environ Sci Health B pmid:20183084
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Macoska JA et al. -(-)Gossypol promotes the apoptosis of bladder cancer cells in vitro. 2008 Nov-Dec Pharmacol. Res. pmid:18840529
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Politzer WM Long-term clinical remission of a patient with chronic lymphocytic leukemia using alternative treatment option: cottonseed oil (gossypol). 2008 Phytomedicine pmid:18573644
Shaaban WF et al. Reproductive toxicologic effects of gossypol on male rabbits: biochemical, enzymatic, and electrolytic properties of seminal plasma. 2008 Fertil. Steril. pmid:17953964
Li ZM et al. Synergistic cytotoxicity of Bcl-xL inhibitor, gossypol and chemotherapeutic agents in non-Hodgkin's lymphoma cells. 2008 Cancer Biol. Ther. pmid:17938578
Tang G et al. Acylpyrogallols as inhibitors of antiapoptotic Bcl-2 proteins. 2008 J. Med. Chem. pmid:18237106
Kline MP et al. R-(-)-gossypol (AT-101) activates programmed cell death in multiple myeloma cells. 2008 Exp. Hematol. pmid:18346839
Gao F et al. Interactive effects of elevated CO2 and cotton cultivar on tri-trophic interaction of Gossypium hirsutum, Aphis gossyppii, and Propylaea japonica. 2008 Environ. Entomol. pmid:18348793
Moon DO et al. Gossypol suppresses NF-kappaB activity and NF-kappaB-related gene expression in human leukemia U937 cells. 2008 Cancer Lett. pmid:18314260
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Paoluzzi L 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. 2008 Blood pmid:18292288
Przybylski P et al. CP/MAS spectroscopy in the determination of the tautomeric forms of gossypol, its Schiff bases and hydrazones in the solid state. 2008 Magn Reson Chem pmid:18338327
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Arnold AA et al. Preclinical studies of Apogossypolone: a new nonpeptidic pan small-molecule inhibitor of Bcl-2, Bcl-XL and Mcl-1 proteins in Follicular Small Cleaved Cell Lymphoma model. 2008 Mol. Cancer pmid:18275607
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Sun Y et al. Apogossypolone, a nonpeptidic small molecule inhibitor targeting Bcl-2 family proteins, effectively inhibits growth of diffuse large cell lymphoma cells in vitro and in vivo. 2008 Cancer Biol. Ther. pmid:18769131
Moon DO et al. Gossypol suppresses telomerase activity in human leukemia cells via regulating hTERT. 2008 FEBS Lett. pmid:18775705
Przybylski P et al. Molecular structures and stability constants of gossypol and its aza-derivative complexes with silver(I) cations studied by potentiometric, ESI MS, NMR, and AM1d semiempirical methods. 2008 J Phys Chem A pmid:18698745
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Zhou DR et al. Gossypol repressed the gap junctional intercellular communication between Sertoli cells by decreasing the expression of Connexin43. 2008 Toxicol In Vitro pmid:18706992
Trischitta F and Faggio C Gossypol affects ion transport in the isolated intestine of the seawater adapted eel, Anguilla anguilla. 2008 Comp. Biochem. Physiol., Part A Mol. Integr. Physiol. pmid:18606239
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Gong YZ et al. Cinnamyl-3,4-dihydroxy-alpha-cyanocinnamate and nordihydroguaiaretic acid inhibit human Kv1.5 currents independently of lipoxygenase. 2008 Eur. J. Pharmacol. pmid:18930721