aminoflavone

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

Description

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

Cross-References

ID Source	ID
PubMed CID	389710
CHEMBL ID	62006
SCHEMBL ID	2411480
MeSH ID	M0370428

Synonyms (19)

Synonym
5-amino-2-(4-amino-3-fluorophenyl)-6,8-difluoro-7-methyl-4h-chromen-4-one
nsc-686288
4h-1-benzopyran-4-one,8-difluoro-7-methyl-
NSC686288 ,
NCI60_031035
NCIMECH_000858
165179-35-1
aminoflavone
CHEMBL62006
5-amino-2-(4-amino-3-fluorophenyl)-6,8-difluoro-7-methylchromen-4-one
5-amino-2-(4-amino-3-fluorophenyl)-6,8-difluoro-7-methyl-4h-1-benzopyran-4-one
CCG-35825
2exs38428u ,
4h-1-benzopyran-4-one, 5-amino-2-(4-amino-3-fluorophenyl)-6,8-difluoro-7-methyl-
unii-2exs38428u
RTUZVPPGTJRELI-UHFFFAOYSA-N
SCHEMBL2411480
DTXSID50167854
Q27254640

Research Excerpts

Overview

Aminoflavone (AF) acts as a ligand of the aryl hydrocarbon receptor (AhR) It is a promising therapeutic agent for breast cancer due to its unique mechanism of action.

Excerpt	Reference	Relevance
"Aminoflavone (AF) acts as a ligand of the aryl hydrocarbon receptor (AhR). "	( Reactivation of estrogen receptor α by vorinostat sensitizes mesenchymal-like triple-negative breast cancer to aminoflavone, a ligand of the aryl hydrocarbon receptor. Burger, A; Li, J; Polin, L; Shelton, P; Stark, K; Wu, J, 2013)	2.04
"Aminoflavone is a unique DNA damaging agent currently undergoing phase I evaluation in a prodrug form (AFP464). "	( Synergistic interactions between aminoflavone, paclitaxel and camptothecin in human breast cancer cells. Ames, MM; Goetz, MP; Kuffel, MJ; Reinicke, KE, 2010)	2.08
"Aminoflavone is a promising therapeutic agent for breast cancer due to its unique mechanism of action compared to commonly used drugs. "	( Synergistic interactions between aminoflavone, paclitaxel and camptothecin in human breast cancer cells. Ames, MM; Goetz, MP; Kuffel, MJ; Reinicke, KE, 2010)	2.08
"Aminoflavone (AF) is an anticancer drug in early clinical trials, and its antiproliferative activity involves the induction of DNA-protein cross-links. "	( Cytokeratin-RNA cross-linking mediated by the antitumor aminoflavone, 5-amino-2,3-fluorophenyl-6,8-difluoro-7-methyl-4H-1-benzopyran-4-one. Meng, LH; Meng, Z; Miao, ZH; Pommier, Y; Veenstra, TD, 2008)	2.03

Effects

Excerpt	Reference	Relevance
"Aminoflavone has a unique activity profile in the NCI 60 cell lines (COMPARE analysis; http://www.dtp.nci.nih.gov/docs/dtp_search.html), and exhibits potent cellular and animal antitumor activity."	( DNA-protein cross-links and replication-dependent histone H2AX phosphorylation induced by aminoflavone (NSC 686288), a novel anticancer agent active against human breast cancer cells. Antony, S; Kohlhagen, G; Liao, ZY; Meng, LH; Pommier, Y; Sausville, E, 2005)	1.27
"Aminoflavone has a unique activity profile in the NCI 60 cell lines (COMPARE analysis; http://www.dtp.nci.nih.gov/docs/dtp_search.html), and exhibits potent cellular and animal antitumor activity."	( DNA-protein cross-links and replication-dependent histone H2AX phosphorylation induced by aminoflavone (NSC 686288), a novel anticancer agent active against human breast cancer cells. Antony, S; Kohlhagen, G; Liao, ZY; Meng, LH; Pommier, Y; Sausville, E, 2005)	1.27

Treatment

Excerpt	Reference	Relevance
"Aminoflavone treatment causes a translocation of the AhR from the cytoplasm to the nucleus with subsequent formation of AhR-XRE protein DNA complexes."	( Aryl hydrocarbon receptor activation of an antitumor aminoflavone: basis of selective toxicity for MCF-7 breast tumor cells. Alley, MC; Boswell, J; Ciolino, HP; Hollingshead, M; Hose, C; Kenney, S; Loaiza-Pérez, AI; Sausville, EA; Trepel, JB; Vistica, DT; Yeh, GC, 2004)	1.29

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (6)

Assay ID	Title	Year	Journal	Article
AID121547	Ratio of tumor growth rate of the drug-treated group relative to that of the control group at a dose of 6.3 mg/kg	1998	Journal of medicinal chemistry, Jun-04, Volume: 41, Issue:12	Structure-activity relationships of the 7-substituents of 5,4'-diamino-6,8,3'-trifluoroflavone, a potent antitumor agent.
AID103910	In vitro cytotoxicity against MCF-7 cell lines, treated for 3 days then uptake of neutral red dye was measured	1998	Journal of medicinal chemistry, Jun-04, Volume: 41, Issue:12	Structure-activity relationships of the 7-substituents of 5,4'-diamino-6,8,3'-trifluoroflavone, a potent antitumor agent.
AID121542	Ratio of tumor growth rate of the drug-treated group relative to that of the control group at a dose of 12.5 mg/kg	1998	Journal of medicinal chemistry, Jun-04, Volume: 41, Issue:12	Structure-activity relationships of the 7-substituents of 5,4'-diamino-6,8,3'-trifluoroflavone, a potent antitumor agent.
AID87594	In vitro cytotoxicity against HeLa S3 cell lines, treated for 3 days then uptake of neutral red dye was measured	1998	Journal of medicinal chemistry, Jun-04, Volume: 41, Issue:12	Structure-activity relationships of the 7-substituents of 5,4'-diamino-6,8,3'-trifluoroflavone, a potent antitumor agent.
AID110267	Compound was tested for percentage Body weight change in vivo against MCF-7 cells implanted into Nude Mice, Dosage 6.3(mg/kg)	1998	Journal of medicinal chemistry, Jun-04, Volume: 41, Issue:12	Structure-activity relationships of the 7-substituents of 5,4'-diamino-6,8,3'-trifluoroflavone, a potent antitumor agent.
AID110142	Compound was tested for percentage Body weight change in vivo against MCF-7 cells implanted into Nude Mice, Dosage 12.5(mg/kg)	1998	Journal of medicinal chemistry, Jun-04, Volume: 41, Issue:12	Structure-activity relationships of the 7-substituents of 5,4'-diamino-6,8,3'-trifluoroflavone, a potent antitumor agent.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (38)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	1 (2.63)	18.2507
2000's	11 (28.95)	29.6817
2010's	18 (47.37)	24.3611
2020's	8 (21.05)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.16

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.

Metric	This Compound (vs All)
Research Demand Index	22.16 (24.57)
Research Supply Index	3.69 (2.92)
Research Growth Index	5.26 (4.65)
Search Engine Demand Index	21.17 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (22.16)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	3 (7.69%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	36 (92.31%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
melatonin [no description available]	3.15	1	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	3.15	1	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
arecoline Arecoline: An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands.. arecoline : A tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine.	3.15	1	enoate ester; methyl ester; pyridine alkaloid; tetrahydropyridine	metabolite; muscarinic agonist
caffeine [no description available]	2.03	1	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	7.08	1	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	2.03	1	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
benzothiazole benzothiazole: structure. benzothiazole : An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.	3.35	1	benzothiazoles	environmental contaminant; plant metabolite; xenobiotic
acetic anhydride acetic anhydride: RN given refers to unlabeled cpd; structure. acetic anhydride : An acyclic carboxylic anhydride derived from acetic acid.	2.13	1	acyclic carboxylic anhydride	metabolite; reagent
thiazoles [no description available]	2.52	2	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.04	1	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	2.31	1	titanium group element atom
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	7.51	2	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2	1	dihydrogen
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	7.05	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
topotecan Topotecan: An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.. topotecan : A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.	2.21	1	pyranoindolizinoquinoline	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor
irinotecan [no description available]	2.05	1	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug
6-hydroxyflavone 6-hydroxyflavone: antioxidant; structure in first source	2.13	1	hydroxyflavonoid
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	2.31	1	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
pyropheophorbide a pyropheophorbide a: RN given refers to (3S-trans)-isomer	2.31	1
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	2.21	1	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
wortmannin [no description available]	2.03	1	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
2,5-bis(5-hydroxymethyl-2-thienyl)furan [no description available]	2.25	1	thiophenes
5f-203 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole: structure in first source	2.52	2
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	2.04	1	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
oncrasin-1 oncrasin-1: an antineoplastic agent; structure in first source. oncrasin-1 : A member of the class of indoles that is 1H-indole substituted by 4-chlorobenzyl and formyl groups at positions 1 and 3, respectively. It is an anti-cancer agent that is active against lung cancer cells with K-Ras mutations.	2.25	1	arenecarbaldehyde; indoles; monochlorobenzenes	antineoplastic agent; apoptosis inducer
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	2.21	1	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
tamoxifen [no description available]	7.17	1	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
px 478 2-amino-3-(4'-N,N-bis(2-chloroethyl)amino)phenylpropionic acid N-oxide: inhibits hypoxia-inducible factor-1alpha	2.21	1
oligonucleotides [no description available]	2.21	1
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	2.13	1	glycoside
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	2.31	1	chlorophyll; methyl ester	cofactor

Condition	Relationship Strength	Studies
Breast Cancer [description not available]	4.77	11
Breast Neoplasms Tumors or cancer of the human BREAST.	4.77	11
Cancer of Kidney [description not available]	3.74	3
Kidney Neoplasms Tumors or cancers of the KIDNEY.	3.74	3
Benign Neoplasms [description not available]	3.21	5
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.21	5
Adenocarcinoma Of Kidney [description not available]	2.51	2
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	2.51	2
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.51	2
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	2.51	2
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.11	1
Experimental Neoplasms [description not available]	2.11	1
Experimental Mammary Neoplasms [description not available]	2.13	1
Animal Mammary Carcinoma [description not available]	2.15	1
Carcinoma, Papillary A malignant neoplasm characterized by the formation of numerous, irregular, finger-like projections of fibrous stroma that is covered with a surface layer of neoplastic epithelial cells. (Stedman, 25th ed)	2.07	1
Adenocarcinoma, Basal Cell [description not available]	2.03	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.03	1

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