Compounds > gossypolone
Page last updated: 2024-12-08

gossypolone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

gossypolone: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID197045
CHEMBL ID575828
SCHEMBL ID2622243
MeSH IDM0127392

Synonyms (19)

Synonym
NCI60_018178
(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'-tetroxo-
gossypolone
(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-
(+-)-gossypolone
nsc-651924
nsc651924
6,6',7,7'-tetrahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-8,8'-diformyl(2,2'-binaphthalene)-1,1'4,4'-tetrone
7-(8-formyl-6,7-dihydroxy-5-isopropyl-3-methyl-1,4-dioxo-2-naphthyl)-2,3-dihydroxy-4-isopropyl-6-methyl-5,8-dioxo-naphthalene-1-carbaldehyde
glossypol tetrone deriv.
CHEMBL575828
4547-72-2
7-[8-formyl-6,7-dihydroxy-3-methyl-5-(methylethyl)-1,4-dioxo(2-naphthyl)]-2,3- dihydroxy-6-methyl-4-(methylethyl)-5,8-dioxonaphthalenecarbaldehyde
ST069298
SCHEMBL2622243
AKOS024283484
DTXSID30196521
gossypolone, ~98%
7-(8-formyl-3-methyl-1,4,6,7-tetraoxo-5-propan-2-ylnaphthalen-2-yl)-2,3,5,8-tetrahydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Gossypolone was also observed to be more toxic than gossypol against both cell lines."( Cytotoxicity of enantiomers of gossypol Schiff's bases and optical stability of gossypolone.
Dao, VT; Dowd, MK; Gaspard, C; Martin, MT; Mayer, M; Michelot, RJ, 2004)		1.46

Bioavailability

ExcerptReferenceRelevance
"Our data suggest that PEGylation improved the bioavailability of Gn as well as achieved tumor-targeted delivery and controlled release of Gn, which enhanced its overall biocompatibility and drug efficacy in vivo."( Natural product derivative Gossypolone inhibits Musashi family of RNA-binding proteins.
Appelman, C; Aubé, J; De Guzman, RN; Gao, P; Gowthaman, R; Karanicolas, J; Lan, L; Larsen, S; Liu, FY; Liu, H; Marquez, RT; Neufeld, KL; Rogers, S; Smith, AR; Wu, X; Xu, L; Yu, J, 2018)		0.78

Dosage Studied

ExcerptRelevanceReference
" Long-term daily dosing with gossypol is associated with minimal side effects and no myelosuppression."( Stereo-specific cytotoxic effects of gossypol enantiomers and gossypolone in tumour cell lines.
Evans, A; Fish, RG; Groundwater, P; Hartley, L; Mason, M; Morgan, JJ; Mort, D; Shelley, MD, 1999)		0.54
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID437154Anticancer activity against human HeLa cells after 48 hrs by MTT assay2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling.
AID437158Ratio of compound IC50 to (-)-gossypol IC50 for human U87 cells2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling.
AID437155Anticancer activity against human U87 cells after 48 hrs by MTT assay2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling.
AID437162Ratio of compound IC50 to cisplatin IC50 for human M85 cells2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling.
AID437156Anticancer activity against human M85 cells after 48 hrs by MTT assay2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling.
AID437160Ratio of compound IC50 to cisplatin IC50 for human HeLa cells2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling.
AID437157Ratio of compound IC50 to (-)-gossypol IC50 for human HeLa cells2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling.
AID437159Ratio of compound IC50 to (-)-gossypol IC50 for human M85 cells2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling.
AID437161Ratio of compound IC50 to cisplatin IC50 for human U87 cells2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (4.55)18.7374
1990's7 (31.82)18.2507
2000's6 (27.27)29.6817
2010's7 (31.82)24.3611
2020's1 (4.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.38

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.38 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index5.33 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.38)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other22 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
gossypol
Gossypol: A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.		4.46220
corticosterone
[no description available]		6.971011beta-hydroxy steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
C21-steroid;
glucocorticoid;
primary alpha-hydroxy ketone		human metabolite;
mouse metabolite
thymidine
[no description available]		1.9810pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
mannitol
[no description available]		210mannitolallergen;
antiglaucoma drug;
compatible osmolytes;
Escherichia coli metabolite;
food anticaking agent;
food bulking agent;
food humectant;
food stabiliser;
food thickening agent;
hapten;
metabolite;
osmotic diuretic;
sweetening agent
ethylamine
ethylamine : A two-carbon primary aliphatic amine.		2.0210primary aliphatic aminehuman metabolite
pregnenolone
[no description available]		1.971020-oxo steroid;
3beta-hydroxy-Delta(5)-steroid;
C21-steroid		human metabolite;
mouse metabolite
25-hydroxycholesterol
[no description available]		1.971025-hydroxy steroid;
oxysterol		human metabolite
apogossypol
apogossypol: structure in first source		2.0510
luteolin
[no description available]		7.6103'-hydroxyflavonoid;
tetrahydroxyflavone		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist
agar
Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.		2.0810
apogossypolone
apogossypolone: has antineoplastic activity; structure in first source		7.9940
ConditionIndicatedRelationship StrengthStudiesTrials
Acquired Form of Epidermolysis Bullosa
[description not available]		02.610
Epidermolysis Bullosa Acquisita
Form of epidermolysis bullosa characterized by trauma-induced, subepidermal blistering with no family history of the disease. Direct immunofluorescence shows IMMUNOGLOBULIN G deposited at the dermo-epidermal junction.		02.610
Cancer of Lung
[description not available]		02.1710
Malignant Melanoma
[description not available]		02.4420
B16 Melanoma
[description not available]		02.1710
Cancer of Skin
[description not available]		02.1710
Lung Neoplasms
Tumors or cancer of the LUNG.		02.1710
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		07.4420
Skin Neoplasms
Tumors or cancer of the SKIN.		02.1710
Cancer of Colon
[description not available]		02.1710
Colonic Neoplasms
Tumors or cancer of the COLON.		02.1710
Breast Cancer
[description not available]		07.6930
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.6930
Hormone-Dependent Neoplasms
[description not available]		01.9810