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.

Cross Reference

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.

Related references are mostly published in these journals:

Disease Cross reference Weighted score Related literature
Loading... please refresh the page if content is not showing up.

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
Hemolysis D006461 131 associated lipids
Neovascularization, Pathologic D009389 39 associated lipids
Adenocarcinoma D000230 166 associated lipids
Lung Neoplasms D008175 171 associated lipids
Pancreatic Neoplasms D010190 77 associated lipids
Colonic Neoplasms D003110 161 associated lipids
Cattle Diseases D002418 24 associated lipids
Infertility, Male D007248 11 associated lipids
Mammary Neoplasms, Experimental D008325 67 associated lipids
Body Weight D001835 333 associated lipids
Per page 10 20 50 100 | Total 52

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.

Related references are published most in these journals:

Pathway name Related literatures
Loading... please refresh the page if content is not showing up.

PubChem Biomolecular Interactions and Pathways

Link to PubChem Biomolecular Interactions and Pathways

What cellular locations are associated with Gossypol?

Related references are published most in these journals:

Location Cross reference Weighted score Related literatures
Loading... please refresh the page if content is not showing up.

What functions are associated with Gossypol?


Related references are published most in these journals:

Function Cross reference Weighted score Related literatures

What lipids are associated with Gossypol?

Related references are published most in these journals:

Lipid concept Cross reference Weighted score Related literatures
Loading... please refresh the page if content is not showing up.

What genes are associated with Gossypol?

Related references are published most in these journals:


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
Loading... please refresh the page if content is not showing up.

NCBI Entrez Crosslinks

All references with Gossypol

Download all related citations
Per page 10 20 50 100 | Total 1511
Authors Title Published Journal PubMed Link
Kennedy WP et al. Gossypol inhibition of acrosin and proacrosin, and oocyte penetration by human spermatozoa. 1983 Biol. Reprod. pmid:6416323
Shandilya L et al. Effects of gossypol on reproductive and endocrine functions of male cynomolgus monkeys (Macaca fascicularis). 1982 Biol. Reprod. pmid:7115850
Dabrowski K et al. Effects of diets containing gossypol on reproductive capacity of rainbow trout (Oncorhynchus mykiss). 2000 Biol. Reprod. pmid:10642557
Hoffer AP et al. Ultrastructural, fertility, and spermicidal studies with isomers and derivatives of gossypol in male hamsters. 1987 Biol. Reprod. pmid:3689857
Tanphaichitr N et al. Direct effect of gossypol on TR-ST cells: perturbation of rhodamine 123 accumulation in mitochondria. 1984 Biol. Reprod. pmid:6518226
Shi QX and Friend DS Gossypol-induced inhibition of guinea pig sperm capacitation in vitro. 1983 Biol. Reprod. pmid:6640034
Olgiati KL et al. Gossypol modulation of nucleotide metabolizing enzymes in the reproductive tract of male rats. 1984 Biol. Reprod. pmid:6095938
Hoffer AP and Hinton BT Morphological evidence for a blood-epididymis barrier and the effects of gossypol on its integrity. 1984 Biol. Reprod. pmid:6733204
Oko R and Hrudka F Comparison of the effects of gossypol, estradiol-17 beta and testosterone compensation on male rat reproductive organs. 1984 Biol. Reprod. pmid:6733210
Hoffer AP Effects of gossypol on the seminiferous epithelium in the rat: a light and electron microscope study. 1983 Biol. Reprod. pmid:6860736
Santana AT et al. Mechanisms involved in reproductive damage caused by gossypol in rats and protective effects of vitamin E. 2015 Biol. Res. pmid:26227499
Gu ZW et al. Studies on fertility control-the formation and antifertility effect of polyvinyl-pyrolidone-gossypol complex. 1984 Biomater Med Devices Artif Organs pmid:6532483
Li K et al. Mulberry-like dual-drug complicated nanocarriers assembled with apogossypolone amphiphilic starch micelles and doxorubicin hyaluronic acid nanoparticles for tumor combination and targeted therapy. 2015 Biomaterials pmid:25477180
Zhang H et al. Canonical Wnt signaling acts synergistically on BMP9-induced osteo/odontoblastic differentiation of stem cells of dental apical papilla (SCAPs). 2015 Biomaterials pmid:25468367
Xu R et al. Proteomic analysis of gossypol induces necrosis in multiple myeloma cells. 2014 Biomed Res Int pmid:25197664
Jin L et al. Phosphoproteomic analysis of gossypol-induced apoptosis in ovarian cancer cell line, HOC1a. 2014 Biomed Res Int pmid:25180175
Gong Y et al. Valproic Acid Enhances the Anti-tumor Effect of (-)-gossypol to Burkitt Lymphoma Namalwa Cells. 2015 Biomed. Environ. Sci. pmid:26582100
Xin J et al. ApoG2 as the most potent gossypol derivatives inhibits cell growth and induces apoptosis on gastric cancer cells. 2013 Biomed. Pharmacother. pmid:23201009
Tiliabaev KZ et al. [Synthesis, structures, and acute toxicity of gossypol nonsymmetrical aldehyde derivatives]. 2010 May-Jun Bioorg. Khim. pmid:20644599
Dao VT et al. New thioderivatives of gossypol and gossypolone, as prodrugs of cytotoxic agents. 2003 Bioorg. Med. Chem. pmid:12670651
Dodou K et al. Synthesis of gossypol atropisomers and derivatives and evaluation of their anti-proliferative and anti-oxidant activity. 2005 Bioorg. Med. Chem. pmid:15878283
Xing C et al. Development of selective inhibitors for anti-apoptotic Bcl-2 proteins from BHI-1. 2007 Bioorg. Med. Chem. pmid:17227711
Li HQ et al. Structure-based design of rhodanine-based acylsulfonamide derivatives as antagonists of the anti-apoptotic Bcl-2 protein. 2012 Bioorg. Med. Chem. pmid:22739087
Song T et al. 3-Thiomorpholin-8-oxo-8H-acenaphtho [1,2-b] pyrrole-9-carbonitrile (S1) derivatives as pan-Bcl-2-inhibitors of Bcl-2, Bcl-xL and Mcl-1. 2013 Bioorg. Med. Chem. pmid:23206987
Liu F et al. Pharmacophore identification of KSP inhibitors. 2007 Bioorg. Med. Chem. Lett. pmid:17095225
Yang J et al. Synthesis and antiviral activities of novel gossypol derivatives. 2012 Bioorg. Med. Chem. Lett. pmid:22226654
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
Janssen CO et al. Interaction of kendomycin and semi-synthetic analogues with the anti-apoptotic protein Bcl-xl. 2008 Bioorg. Med. Chem. Lett. pmid:18845435
Hamdy R et al. Synthesis and evaluation of 3-(benzylthio)-5-(1H-indol-3-yl)-1,2,4-triazol-4-amines as Bcl-2 inhibitory anticancer agents. 2013 Bioorg. Med. Chem. Lett. pmid:23474389
Yang J et al. Synthesis and anti-H5N1 activity of chiral gossypol derivatives and its analogs implicated by a viral entry blocking mechanism. 2013 Bioorg. Med. Chem. Lett. pmid:23538114
Wu Y et al. Changes in membrane properties during energy depletion-induced cell injury studied with fluorescence microscopy. 1996 Biophys. J. pmid:8804592
Przybylski P et al. Spectroscopic studies and PM5 semiempirical calculations of new Schiff bases of gossypol with polyoxaalkylamines. 2002 Biopolymers pmid:12209461
Przybylski P et al. Schiff base of gossypol with 3,6,9-trioxa-decylamine complexes with monovalent cations studied by mass spectrometry, (1)H-NMR, FTIR, and PM5 semiempirical methods. 2004 Biopolymers pmid:14991665
Przybylski P et al. 1H- and 13C-NMR, FTIR, UV-VIS, ESI-MS, and PM5 studies as well as emission properties of a new Schiff base of gossypol with 5-methoxytryptamine and a new hydrazone of gossypol with dansylhydrazine. 2006 Biopolymers pmid:16538663
Przybylski P et al. Multinuclear magnetic resonance, electrospray ionization-mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2-thiophenecarbohydrazide as well as its complexes with LI+, Na+, K+, RB+, and Cs+ cations. 2006 Biopolymers pmid:16741985
Przybylski P et al. The schiff base of gossypol with 3,6,9,12,15,18,21,24-octaoxa-pentacosylamine complexes and monovalent cations studied by electrospray ionization-mass spectrometry, (1)H nuclear magnetic resonance, Fourier transform infrared, as well as PM5 semiempirical methods. 2004 Biopolymers pmid:15211497
Przybylski P and Brzezinski B Spectroscopic studies and PM3 semiempirical calculations of Schiff bases of gossypol with L-amino acid methyl esters. 2002 Biopolymers pmid:11842415
Shibatani M et al. Accumulation of Isohemigossypolone and Its Related Compounds in the Inner Bark and Heartwood of Diseased Pachira aquatica. 1999 Biosci. Biotechnol. Biochem. pmid:26300168
Sagach VF and Kindybaliuk AM [The role of the endothelium in the development of functional hyperemia of the skeletal muscles]. 1991 Biull Eksp Biol Med pmid:1810472
Sonpavde G et al. Radiographic progression by Prostate Cancer Working Group (PCWG)-2 criteria as an intermediate endpoint for drug development in metastatic castration-resistant prostate cancer. 2014 BJU Int. pmid:24298897
Kitada S et al. 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). 2008 Blood pmid:18202226
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
Balakrishnan K et al. Gossypol, a BH3 mimetic, induces apoptosis in chronic lymphocytic leukemia cells. 2008 Blood pmid:18566329
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
Pan R et al. Inhibition of Mcl-1 with the pan-Bcl-2 family inhibitor (-)BI97D6 overcomes ABT-737 resistance in acute myeloid leukemia. 2015 Blood pmid:26045609
Sipkema P et al. Does the endothelium play a role in flow-dependent constriction? A study in the isolated rabbit femoral artery. 1989 Blood Vessels pmid:2641926
Zhao R et al. AT-101 enhances gefitinib sensitivity in non-small cell lung cancer with EGFR T790M mutations. 2016 BMC Cancer pmid:27431492
Mani J et al. Chemoresistance is associated with increased cytoprotective autophagy and diminished apoptosis in bladder cancer cells treated with the BH3 mimetic (-)-Gossypol (AT-101). 2015 BMC Cancer pmid:25885284
Celorio-Mancera Mde L et al. Transcriptional responses underlying the hormetic and detrimental effects of the plant secondary metabolite gossypol on the generalist herbivore Helicoverpa armigera. 2011 BMC Genomics pmid:22111916
Wang J et al. Reversal of a full-length mutant huntingtin neuronal cell phenotype by chemical inhibitors of polyglutamine-mediated aggregation. 2005 BMC Neurosci pmid:15649316
Andrade AT [Information on advances in sciences and technology. Advances in contraceptive technology]. 1993 Bol Cent Biol Reprod pmid:12345521
Joseph AE et al. Cytotoxicity of enantiomers of gossypol. 1986 Br. J. Cancer pmid:3756086
Ligueros M et al. Gossypol inhibition of mitosis, cyclin D1 and Rb protein in human mammary cancer cells and cyclin-D1 transfected human fibrosarcoma cells. 1997 Br. J. Cancer pmid:9218727
Jarzabek MA et al. Interrogation of gossypol therapy in glioblastoma implementing cell line and patient-derived tumour models. 2014 Br. J. Cancer pmid:25375271
Spagnuolo C et al. Quercetin downregulates Mcl-1 by acting on mRNA stability and protein degradation. 2011 Br. J. Cancer pmid:21750559
Masood A et al. Downregulation of BCL2 by AT-101 enhances the antileukaemic effect of lenalidomide both by an immune dependant and independent manner. 2012 Br. J. Haematol. pmid:22171982
Paulus A et al. AT-101 downregulates BCL2 and MCL1 and potentiates the cytotoxic effects of lenalidomide and dexamethasone in preclinical models of multiple myeloma and Waldenström macroglobulinaemia. 2014 Br. J. Haematol. pmid:24236538
Paulus A et al. The investigational agent MLN2238 induces apoptosis and is cytotoxic to CLL cells in vitro, as a single agent and in combination with other drugs. 2014 Br. J. Haematol. pmid:24467634
Bertrand V and Belleville J Effect of refeeding diets containing cottonseed flour with traces of gossypol on rat liver and testis. 1991 Br. J. Nutr. pmid:1760445
Sarwar Gilani G et al. Impact of antinutritional factors in food proteins on the digestibility of protein and the bioavailability of amino acids and on protein quality. 2012 Br. J. Nutr. pmid:23107545
Inoue H et al. Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema. 1993 Br. J. Pharmacol. pmid:7508328
Warner TD Simultaneous perfusion of rat isolated superior mesenteric arterial and venous beds: comparison of their vasoconstrictor and vasodilator responses to agonists. 1990 Br. J. Pharmacol. pmid:2328405
Alheid U et al. Selective inhibition by gossypol of endothelium-dependent relaxations augments relaxations to glyceryl trinitrate in rabbit coeliac artery. 1987 Br. J. Pharmacol. pmid:2444300
Gschwentner M et al. Blockade of swelling-induced chloride channels by phenol derivatives. 1996 Br. J. Pharmacol. pmid:8733574
Burton GA et al. Cyclic GMP release and vasodilatation induced by EDRF and atrial natriuretic factor in the isolated perfused kidney of the rat. 1990 Br. J. Pharmacol. pmid:2158376
Panigrahi S et al. Effects of dietary cottonseed meal, with and without iron treatment, on laying hens. 1989 Br. Poult. Sci. pmid:2819506
Mandal AB et al. Comparison of broiler chicken performance when fed diets containing meals of Bollgard II hybrid cotton containing Cry-X gene (Cry1Ac and Cry2ab gene), parental line or commercial cotton. 2004 Br. Poult. Sci. pmid:15623220
Phillis JW et al. Effects of immunosuppressants, calcineurin inhibition, and blockade of endoplasmic reticulum calcium channels on free fatty acid efflux from the ischemic/reperfused rat cerebral cortex. 2002 Brain Res. pmid:12443975
Mego M Telomerase inhibitors in anticancer therapy: gossypol as a potential telomerase inhibitor. 2002 Bratisl Lek Listy pmid:12583508
Medeiros YS et al. Gossypol affects the responsiveness of isolated rat myometrium and vas deferens. 1989 Braz. J. Med. Biol. Res. pmid:2638200
Van Poznak C et al. Oral gossypol in the treatment of patients with refractory metastatic breast cancer: a phase I/II clinical trial. 2001 Breast Cancer Res. Treat. pmid:11510695
Ogot JO The performance of pigs in Kenya fed cottonseed meal in mixtures of concentrate supplements. 1973 Bull Epizoot Dis Afr pmid:4808120
Sokolova TM et al. Ridostin induces transcription of a wide spectrum of interferon genes in human cells. 2013 Bull. Exp. Biol. Med. pmid:24319751
Waites GM Male fertility regulation: recent advances. 1986 Bull. World Health Organ. pmid:3091279
Majumdar SK et al. Gossypol--an effective male contraceptive was not mutagenic in sperm head abnormality assay in mice. 1982 Can. J. Genet. Cytol. pmid:7182060
Tam SC Acute hypokalemic effect of gossypol. 1986 Can. J. Physiol. Pharmacol. pmid:3768796
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
Sikora MJ et al. Anti-oxidant treatment enhances anti-tumor cytotoxicity of (-)-gossypol. 2008 Cancer Biol. Ther. pmid:18376141
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
Lestini BJ et al. Mcl1 downregulation sensitizes neuroblastoma to cytotoxic chemotherapy and small molecule Bcl2-family antagonists. 2009 Cancer Biol. Ther. pmid:19556859
Stein RC et al. A preliminary clinical study of gossypol in advanced human cancer. 1992 Cancer Chemother. Pharmacol. pmid:1394805
Jia L et al. Comparison of pharmacokinetic and metabolic profiling among gossypol, apogossypol and apogossypol hexaacetate. 2008 Cancer Chemother. Pharmacol. pmid:17356822
Rao PN et al. Antitumor effects of gossypol on murine tumors. 1985 Cancer Chemother. Pharmacol. pmid:4006045
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
Tso WW Gossypol inhibits Ehrlich ascites tumor cell proliferation. 1984 Cancer Lett. pmid:6498805
Wei J et al. Synthesis and evaluation of Apogossypol atropisomers as potential Bcl-xL antagonists. 2009 Cancer Lett. pmid:18782651
Hu YF et al. Presence of antitumor activities in the milk collected from gossypol-treated dairy cows. 1994 Cancer Lett. pmid:7954365
Shidaifat F et al. Inhibition of human prostate cancer cells growth by gossypol is associated with stimulation of transforming growth factor-beta. 1996 Cancer Lett. pmid:8913264
Ford JM et al. Modulation of resistance to alkylating agents in cancer cell by gossypol enantiomers. 1991 Cancer Lett. pmid:2004358
Shelley MD et al. Stereo-specific cytotoxic effects of gossypol enantiomers and gossypolone in tumour cell lines. 1999 Cancer Lett. pmid:10096426
Xin J et al. ApoG2 induces ER stress-dependent apoptosis in gastric cancer cells in vitro and its real-time evaluation by bioluminescence imaging in vivo. 2013 Cancer Lett. pmid:23523614
Kim SH et al. Gossypol, a hyperthermic sensitizer of HeLa cells. 1985 Cancer Res. pmid:4063984
Imai A et al. Metronomic dosing of BH3 mimetic small molecule yields robust antiangiogenic and antitumor effects. 2012 Cancer Res. pmid:22158856
Jarvis WD et al. Induction of apoptotic DNA fragmentation and cell death in HL-60 human promyelocytic leukemia cells by pharmacological inhibitors of protein kinase C. 1994 Cancer Res. pmid:7511048
Jaroszewski JW et al. Action of gossypol and rhodamine 123 on wild type and multidrug-resistant MCF-7 human breast cancer cells: 31P nuclear magnetic resonance and toxicity studies. 1990 Cancer Res. pmid:2208159
Wang Y and Rao PN Effect of gossypol on DNA synthesis and cell cycle progression of mammalian cells in vitro. 1984 Cancer Res. pmid:6690046
Tuszynski GP and Cossu G Differential cytotoxic effect of gossypol on human melanoma, colon carcinoma, and other tissue culture cell lines. 1984 Cancer Res. pmid:6581864
Mazumder S et al. Mcl-1 Phosphorylation defines ABT-737 resistance that can be overcome by increased NOXA expression in leukemic B cells. 2012 Cancer Res. pmid:22525702
Adlakha RC et al. Modulation of 4'-(9-acridinylamino)methanesulfon-m-anisidide-induced, topoisomerase II-mediated DNA cleavage by gossypol. 1989 Cancer Res. pmid:2539251
Wu YW et al. An in vitro and in vivo study of antitumor effects of gossypol on human SW-13 adrenocortical carcinoma. 1989 Cancer Res. pmid:2736516