Page last updated: 2024-12-05

anthrone

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

Description

Anthrone is a synthetic organic compound, a derivative of anthracene. It is a pale yellow crystalline solid with a melting point of 153–156 °C. Anthrone is used as a reagent in analytical chemistry for the determination of carbohydrates, such as glucose, fructose, and sucrose. Anthrone is synthesized by the reduction of anthraquinone with zinc dust and sodium hydroxide. Anthrone reacts with carbohydrates to form a colored solution, which can be measured spectrophotometrically. The color intensity is proportional to the concentration of the carbohydrate present. The reaction is specific for carbohydrates, and it is not affected by other organic compounds. The anthrone reagent is therefore a valuable tool for the quantitative determination of carbohydrates in biological samples. Anthrone is also used in the synthesis of other organic compounds, such as anthracene and anthraquinone. The compound has also been studied for its potential as a fluorescent probe for the detection of biomolecules, such as proteins and nucleic acids. Anthrone has also been investigated for its potential anticancer activity.'

anthrone: used in colorimetric determination of sugar & animal starch in body fluids; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

anthrone : A member of the class of anthracenes that is 9,10-dihydroanthracene carrying an oxo group at C-9. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID7018
CHEMBL ID124440
CHEBI ID33835
SCHEMBL ID18143
MeSH IDM0045611

Synonyms (60)

Synonym
nsc 1965
hsdb 2158
ccris 3175
anthracene, 9,10-dihydro-9-oxo-
ai3-11256
einecs 201-994-0
9(10h)-anthracenone
anthrone
nsc-1965
carbothrone
anthracene,10-dihydro-9-oxo-
nsc1965
90-44-8
CHEBI:33835 ,
9,10-dihydro-9-oxoanthracene
9-oxoanthracene
anthracen-9(10h)-one
anthranone
az-o
AP-065/41069590
inchi=1/c14h10o/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-8h,9h
anthrone, acs reagent, 97%
A-8100
A0509
AKOS000118893
10h-anthracen-9-one
CHEMBL124440 ,
bdbm50060860
dtxcid0029391
cas-90-44-8
dtxsid1049431 ,
tox21_202949
NCGC00260495-01
fp0fj7k744 ,
unii-fp0fj7k744
FT-0622426
BBL019139
EPITOPE ID:116188
dithranol impurity a [ep impurity]
anthrone [mi]
9-anthrone
SCHEMBL18143
9,10-dihydroanthracen-9-one
STR00681
(10h)-9-anthracenone
mfcd00001187
F0001-2207
anthrone, 96%
anthrone, analytical standard
anthrone, acs grade
SY010357
Q411768
STL199162
H10720
9 10-dihydro-9-ketoanthracene
anthracen-9(10h)-one; dithranol imp. a (ep); anthrone; dithranol impurity a
anthracen-9(10h)-one (anthrone)
CS-W010654
EN300-19192
HY-W009938

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" So far, detailed information concerning their metabolism and pharmacokinetic characteristics is available only in a few cases."( Metabolism and pharmacokinetics of anthranoids.
de Witte, P, 1993
)
0.29

Bioavailability

ExcerptReferenceRelevance
" In the present study we formulated liposomes to increase the bioavailability of 1,9-P in the brain and developed a simple, sensitive and selective high performance liquid chromatographic method and validated for the estimation of 1,9-P in Wistar rat plasma and tissue samples."( Pharmacokinetic and tissue distribution studies of 1,9-pyrazoloanthrone, a c-Jun-N-terminal kinase inhibitor in Wistar rats by a simple and sensitive HPLC method.
Ambhore, NS; Elango, K; Mohire, S; Mulukutla, S; Murthy, V; Raju, KR; Tondhawada, M; Yamjala, K, 2016
)
0.67
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
radical scavengerA role played by a substance that can react readily with, and thereby eliminate, radicals.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
anthracenoneAny member of the class of anthracenes in which the anthracene moiety is substituted by an oxo group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (19)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RAR-related orphan receptor gammaMus musculus (house mouse)Potency9.22030.006038.004119,952.5996AID1159521; AID1159523
SMAD family member 2Homo sapiens (human)Potency15.60770.173734.304761.8120AID1346859
SMAD family member 3Homo sapiens (human)Potency15.60770.173734.304761.8120AID1346859
caspase 7, apoptosis-related cysteine proteaseHomo sapiens (human)Potency69.07820.013326.981070.7614AID1346978
estrogen receptor 2 (ER beta)Homo sapiens (human)Potency69.07820.000657.913322,387.1992AID1259378
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency13.24480.001022.650876.6163AID1224838; AID1224839; AID1224893
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency9.82230.003041.611522,387.1992AID1159552; AID1159555
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency62.48270.001530.607315,848.9004AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403
pregnane X nuclear receptorHomo sapiens (human)Potency27.50050.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency11.78760.000229.305416,493.5996AID1259244; AID1259248; AID743069; AID743075; AID743077; AID743078; AID743079; AID743080; AID743091
caspase-3Homo sapiens (human)Potency69.07820.013326.981070.7614AID1346978
nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_aHomo sapiens (human)Potency0.001419.739145.978464.9432AID1159509
histone deacetylase 9 isoform 3Homo sapiens (human)Potency6.80770.037617.082361.1927AID1259364; AID1259388
Voltage-dependent calcium channel gamma-2 subunitMus musculus (house mouse)Potency27.50050.001557.789015,848.9004AID1259244
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency27.50050.001551.739315,848.9004AID1259244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thioredoxin reductase 1, cytoplasmicRattus norvegicus (Norway rat)IC50 (µMol)200.00000.27201.82606.0000AID551520
Amine oxidase [flavin-containing] AHomo sapiens (human)IC50 (µMol)1.89000.00002.37899.7700AID1888748
5-lipoxygenase Bos taurus (cattle)IC50 (µMol)2.00000.18001.75824.0000AID160507
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
biogenic amine metabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
positive regulation of signal transductionAmine oxidase [flavin-containing] AHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
protein bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] AHomo sapiens (human)
cytosolAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID1605075-LO inhibitory activity was determined by inhibition of LTB4 biosynthesis in bovine polymorphonuclear leukocytes (PMNL)1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
AID233179Antioxidant potential was assessed from reducing activity against 2,2,di-phenyl-1-picrylhydrazyl.1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
AID551520Inhibition of rat liver cytosolic TrxR1 by spectrophotometry2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Hypericins and thioredoxin reductase: Biochemical and docking studies disclose the molecular basis for effective inhibition by naphthodianthrones.
AID231071Peroxidant property was expressed as ratio of uMol of malondialdehyde and mMol of deoxyribose released by 75 uM test compound1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
AID85489Induction of Keratinocyte Differentiation in cross-linked envelope assay at 1 uM expressed as difference of the amount of cross-linked protein as a measure of HaCaT keratinocyte differentiation2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antipsoriatic anthrones with modulated redox properties. 5. Potent inhibition of human keratinocyte growth, induction of keratinocyte differentiation, and reduced membrane damage by novel 10-arylacetyl-1,8-dihydroxy-9(10H)-anthracenones.
AID85482Antiproliferative (inhibition of cell growth) activity against HaCaT cells (human keratinocyte line)1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
AID85490Induction of Keratinocyte Differentiation in cross-linked envelope assay at 10 uM expressed as difference of the amount of cross-linked protein as a measure of HaCaT keratinocyte differentiation2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antipsoriatic anthrones with modulated redox properties. 5. Potent inhibition of human keratinocyte growth, induction of keratinocyte differentiation, and reduced membrane damage by novel 10-arylacetyl-1,8-dihydroxy-9(10H)-anthracenones.
AID475504Binding affinity to amyloid beta (1 to 42) fibrils by change in fluorescence at 100 uM after 10 mins2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.
AID19630Partition coefficient (logP)1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
AID475505Binding affinity to amyloid beta (1 to 42) oligomers by change in fluorescence at 100 uM after 10 mins2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.
AID85486Cytotoxic activity (2 uM) was measured by the amount of LDH (mU) release in HaCaT cells.1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
AID1888748Inhibition of recombinant human MAO-A expressed in baculovirus infected BTI insect cells using kynuramine as substrate after 20 mins by fluorescence spectrophotometric assay2022Bioorganic & medicinal chemistry, 01-15, Volume: 54Phenothiazine, anthraquinone and related tricyclic derivatives as inhibitors of monoamine oxidase.
AID85491Induction of Keratinocyte Differentiation in cross-linked envelope assay at 5 uM expressed as difference of the amount of cross-linked protein as a measure of HaCaT keratinocyte differentiation2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antipsoriatic anthrones with modulated redox properties. 5. Potent inhibition of human keratinocyte growth, induction of keratinocyte differentiation, and reduced membrane damage by novel 10-arylacetyl-1,8-dihydroxy-9(10H)-anthracenones.
AID551521Inhibition of rat liver mitochondrial TrxR2 by spectrophotometry2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Hypericins and thioredoxin reductase: Biochemical and docking studies disclose the molecular basis for effective inhibition by naphthodianthrones.
AID1888752Inhibition of recombinant human MAO-B expressed in baculovirus infected BTI insect cells using kynuramine as substrate at 100 uM after 20 mins by fluorescence spectrophotometric assay2022Bioorganic & medicinal chemistry, 01-15, Volume: 54Phenothiazine, anthraquinone and related tricyclic derivatives as inhibitors of monoamine oxidase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (141)

TimeframeStudies, This Drug (%)All Drugs %
pre-199079 (56.03)18.7374
1990's16 (11.35)18.2507
2000's21 (14.89)29.6817
2010's20 (14.18)24.3611
2020's5 (3.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 52.90

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index52.90 (24.57)
Research Supply Index5.04 (2.92)
Research Growth Index4.43 (4.65)
Search Engine Demand Index85.03 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (52.90)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (2.60%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other150 (97.40%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]