Compounds > isoindigotin
Page last updated: 2024-11-08

isoindigotin

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Description

isoindigotin: used in treatment of chronic granulocytic leukemia; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID164610
CHEMBL ID515155
SCHEMBL ID9899740
SCHEMBL ID9899736
SCHEMBL ID12386233
MeSH IDM0140700

Synonyms (39)

Synonym
nsc-717810
nsc717810
NCI60_040614
OPREA1_712169
isoindigotin
CHEMBL515155 ,
isoindigo
(3e)-3-(2-oxo-1h-indol-3-ylidene)-1h-indol-2-one
AKOS001588195
(e)-[3,3''-biindolinylidene]-2,2''-dione
bdbm50342561
(2-oxoindolin-3-ylidene)indolin-2-one
2h-indol-2-one, 3-(1,2-dihydro-2-oxo-3h-indol-3-ylidene)-1,3-dihydro-
476-34-6
6ue33xxj1y ,
unii-6ue33xxj1y
(3e)-3-(2-oxoindolin-3-ylidene)indolin-2-one
MLCPSWPIYHDOKG-BUHFOSPRSA-N
SCHEMBL9899740
SCHEMBL9899736
SCHEMBL12386233
.delta.3,3'-bioxindole
3-(1,2-dihydro-2-oxo-3h-indol-3-ylidene)-1,3-dihydro-2h-indol-2-one
180479-95-2
(.delta.3,3'-biindoline)-2,2'-dione
SR-01000390554-1
sr-01000390554
3-(2-oxo-2,3-dihydro-1h-indol-3-ylidene)-2,3-dihydro-1h-indol-2-one
3-(2-hydroxy-1h-indol-3-yl)indol-2-one
AKOS032947324
[3,3'-biindolinylidene]-2,2'-dione
(e)-[3,3'-biindolinylidene]-2,2'-dione
isoindigo;(e)-[3,3'-biindolinylidene]-2,2'-dione
BCP32739
Q27265545
AS-82948
3,3'-biindole 2,2'(1h,1'h)-dione
CS-0030758
HY-107869
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Protein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)IC50 (µMol)8.00000.04502.67428.0000AID594815
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (24)

Processvia Protein(s)Taxonomy
gene expressionProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
dopamine secretionProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
chromatin remodelingProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
proteolysisProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
peptide cross-linkingProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
protein deaminationProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
negative regulation of endoplasmic reticulum calcium ion concentrationProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
regulation of apoptotic processProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
positive regulation of apoptotic processProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
apoptotic cell clearanceProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
positive regulation of GTPase activityProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
positive regulation of cell adhesionProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
positive regulation of neurogenesisProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
positive regulation of small GTPase mediated signal transductionProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
positive regulation of mitochondrial calcium ion concentrationProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
bone developmentProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
branching involved in salivary gland morphogenesisProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
salivary gland cavitationProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
cellular response to cocaineProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
cellular response to dopamineProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
positive regulation of sprouting angiogenesisProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
cellular response to serotoninProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
regulation of apoptotic cell clearanceProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
protein-glutamine gamma-glutamyltransferase activityProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
calcium ion bindingProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
protein bindingProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
GTP bindingProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
peptidase activityProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
protein-glutamine glutaminase activityProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
histone serotonyltransferase activityProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
histone dopaminyltransferase activityProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
peptide noradrenalinyltransferase activityProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
peptide histaminyltransferase activityProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
collagen-containing extracellular matrixProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
nucleusProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
mitochondrionProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
endoplasmic reticulumProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
cytosolProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
plasma membraneProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
focal adhesionProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
extracellular matrixProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
perinuclear region of cytoplasmProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
collagen-containing extracellular matrixProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
extracellular exosomeProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
chromatinProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
nucleosomeProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
mitochondrionProtein-glutamine gamma-glutamyltransferase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID453304Antiproliferative activity against human HuH7 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Nov-01, Volume: 17, Issue:21
Synthesis and evaluation of functionalized isoindigos as antiproliferative agents.
AID417758Induction of CYP1A1 activity in mouse Hepa-1c1c7 cells assessed as induction ratio at 0.1 uM after 48 hrs by EROD assay relative to control2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Functionalized 3-benzylidene-indolin-2-ones: inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity.
AID417741Cytotoxicity against mouse Hepa-1c1c7 cells after 48 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Functionalized 3-benzylidene-indolin-2-ones: inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity.
AID453303Antiproliferative activity against human HCT116 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Nov-01, Volume: 17, Issue:21
Synthesis and evaluation of functionalized isoindigos as antiproliferative agents.
AID594815Inhibition of human transglutaminase 2 using Cbz-Gln-Gly as a substrate by GDH-coupled assay2011Bioorganic & medicinal chemistry letters, May-01, Volume: 21, Issue:9
Acylideneoxoindoles: a new class of reversible inhibitors of human transglutaminase 2.
AID1061106Antimicrobial activity against Mycobacterium tuberculosis H37Rv infected in african green monkey Vero cells2014Bioorganic & medicinal chemistry letters, Jan-01, Volume: 24, Issue:1
A novel indigoid anti-tuberculosis agent.
AID384103Antiproliferative activity against human K562 cells at 10 uM after 72 hrs by MTS test2008European journal of medicinal chemistry, Apr, Volume: 43, Issue:4
Synthesis and antiproliferative activities of isoindigo and azaisoindigo derivatives.
AID453559Inhibition of CDK2/cyclin A at 10 uM by IMAP assay2009Bioorganic & medicinal chemistry, Nov-01, Volume: 17, Issue:21
Synthesis and evaluation of functionalized isoindigos as antiproliferative agents.
AID384100Antiproliferative activity against human KB cells at 10 uM after 72 hrs by MTS test2008European journal of medicinal chemistry, Apr, Volume: 43, Issue:4
Synthesis and antiproliferative activities of isoindigo and azaisoindigo derivatives.
AID384102Antiproliferative activity against human HL60 cells at 10 uM after 72 hrs by MTS test2008European journal of medicinal chemistry, Apr, Volume: 43, Issue:4
Synthesis and antiproliferative activities of isoindigo and azaisoindigo derivatives.
AID453305Antiproliferative activity against human IMR90 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Nov-01, Volume: 17, Issue:21
Synthesis and evaluation of functionalized isoindigos as antiproliferative agents.
AID453302Antiproliferative activity against human HL60 cells after 5 days by MTT assay2009Bioorganic & medicinal chemistry, Nov-01, Volume: 17, Issue:21
Synthesis and evaluation of functionalized isoindigos as antiproliferative agents.
AID384101Antiproliferative activity against human KB cells after 72 hrs by MTS test2008European journal of medicinal chemistry, Apr, Volume: 43, Issue:4
Synthesis and antiproliferative activities of isoindigo and azaisoindigo derivatives.
AID417768Ratio of induction of CYP1 activity to induction of NQO1 activity Hepa-1c1c7 cells at 0.1 uM after 48 hrs2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Functionalized 3-benzylidene-indolin-2-ones: inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity.
AID453301Antiproliferative activity against human K562 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Nov-01, Volume: 17, Issue:21
Synthesis and evaluation of functionalized isoindigos as antiproliferative agents.
AID417749Induction of NQO1 activity in mouse Hepa-1c1c7 cells assessed as induction ratio at 0.1 uM after 48 hrs by MTT assay relative to control2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Functionalized 3-benzylidene-indolin-2-ones: inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity.
AID417740Induction of NQO1 activity in mouse Hepa-1c1c7 cells assessed as drug level required to double basal enzyme activity after 48 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Functionalized 3-benzylidene-indolin-2-ones: inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.85)18.7374
1990's0 (0.00)18.2507
2000's6 (23.08)29.6817
2010's15 (57.69)24.3611
2020's4 (15.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.13

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 Index31.13 (24.57)
Research Supply Index3.30 (2.92)
Research Growth Index4.75 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.13)

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%
Other26 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
beta-naphthoflavone
beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.		2.0510extended flavonoid;
naphtho-gamma-pyrone;
organic heterotricyclic compound		aryl hydrocarbon receptor agonist
indirubin-3'-monoxime
indirubin-3'-monoxime: has antiangiogenic activity. indirubin-3'-monoxime : A member of the class of biindoles that is indirubin in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime.		2.0510
isoniazid
Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).		2.110carbohydrazideantitubercular agent;
drug allergen
sulforaphane
sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.		2.0510isothiocyanate;
sulfoxide		antineoplastic agent;
antioxidant;
EC 3.5.1.98 (histone deacetylase) inhibitor;
plant metabolite
5-bromoisatin
[no description available]		2.0610indolesanticoronaviral agent
quinoxalines
quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.		2.0810mancude organic heterobicyclic parent;
naphthyridine;
ortho-fused heteroarene
isatin
tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal;		2.0610indoledioneEC 1.4.3.4 (monoamine oxidase) inhibitor;
plant metabolite
benzothiophene
[no description available]		2.17101-benzothiophenes;
benzothiophene
thiophenes
Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.		3.0940mancude organic heteromonocyclic parent;
monocyclic heteroarene;
thiophenes;
volatile organic compound		non-polar solvent
indirubin
[no description available]		8.1250
indigo
[no description available]		2.110hydroxyindoles
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.1110acetylcysteine;
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
2-piperidone
2-piperidone: structure given in first source. piperidin-2-one : A delta-lactam that is piperidine which is substituted by an oxo group at position 2.		2.0410delta-lactam;
piperidones		EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor
fluorine
Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.		2.0810diatomic fluorine;
gas molecular entity		NMR chemical shift reference compound
pyrrolidine dithiocarbamate
pyrrolidine dithiocarbamic acid: spelled pyrolidine in J Nutr 1979 reference; RN given refers to parent cpd. pyrrolidine dithiocarbamate : A member of the class of dithiocarbamic acids that is the N-dithiocarboxy derivative of pyrrolidine.		2.1110dithiocarbamic acids;
pyrrolidines		anticonvulsant;
antineoplastic agent;
geroprotector;
neuroprotective agent;
NF-kappaB inhibitor;
radical scavenger
5-Chloro-1H-indole-2,3-dione
[no description available]		2.0610indolesanticoronaviral agent
5-iodoisatin
5-iodoisatin: structure in first source		2.0610indolesanticoronaviral agent
n-methylisoindigotin
N-methylisoindigotin: used in therapy of Lewis lung carcinoma; structure given in first source		2.4620
docetaxel
[no description available]		2.0410hydrate;
secondary alpha-hydroxy ketone		antineoplastic agent
indigoidine
indigoidine: structure in first source. indigoidine : A member of the class of pyridone that is a dimeric blue pigment biosynthesised from L-glutamine.		2.0410
2-oxindole
2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.		2.110gamma-lactam;
indolinone
6-bromoindirubin-3'-oxime
6-bromoindirubin-3'-oxime: structure in first source. 6-bromoindirubin-3'-oxime : A member of the class of biindoles that is indirubin substituted at position 6 by a bromo group and in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime.		2.0510
glycosides
[no description available]		2.0810
indigo carmine
Indigo Carmine: Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.. indigo carmine : An organic sodium salt resulting from the formal condensation of indigo carmine (acid form) with two equivalents of sodium hydroxide. It is an indicator at pH 11.5-14, changing from blue to yellow.		2.3920
cytochrome c-t
Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.		2.1110
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor		2.1110
rifampin
Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)		2.110cyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion		angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Mouth
[description not available]		02.0410
Mouth Neoplasms
Tumors or cancer of the MOUTH.		02.0410
Plasmodium falciparum Malaria
[description not available]		02.110
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.110
Benign Neoplasms
[description not available]		02.8630
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.		02.8630
Acute Myelogenous Leukemia
[description not available]		02.1110
Leukemia, Myeloid, Acute
Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.		02.1110
Acute Promyelocytic Leukemia
[description not available]		02.5220
Leukemia, Promyelocytic, Acute
An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.		02.5220
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0310
Hepatocellular Carcinoma
[description not available]		02.0410
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.0410
Granulocytic Leukemia
[description not available]		01.9610
Leukemia, Myeloid
Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.		01.9610