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| Isatin, also known as tribulin, is an organic compound derived from indole with formula C8H5NO2. The compound was first obtained by Otto Linné Erdman and Auguste Laurent in 1840 as a product from the oxidation of indigo dye by nitric acid and chromic acids.
Isatin is a well-known natural product which can be found in plants of the genus Isatis, in Couroupita guianensis, and also in humans, as a metabolic derivative of adrenaline.
It looks like a red-orange powder, and it is usually employed as building block for the synthesis of a wide variety of biologically active compounds including antitumorals, antivirals, anti-HIVs, and antituberculars.
The isatin core is also responsible for the color of “Maya blue” and “Maya yellow” dyes. |
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Read full article at Wikipedia
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| InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11) |
| JXDYKVIHCLTXOP-UHFFFAOYSA-N |
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EC 1.4.3.4 (monoamine oxidase) inhibitor
An EC 1.4.3.* (oxidoreductase acting on donor CH-NH2 group, oxygen as acceptor) inhibitor that interferes with the action of monoamine oxidase (EC 1.4.3.4).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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View more via ChEBI Ontology
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indole-2,3-dione
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NIST Chemistry WebBook
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Isatin
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KEGG COMPOUND
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ISATIN
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PDBeChem
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isatin
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UniProt
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C00026981
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KNApSAcK
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C11129
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KEGG COMPOUND
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DB02095
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DrugBank
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Isatin
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Wikipedia
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ISATIN
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MetaCyc
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ISN
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PDBeChem
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| View more database links |
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165206
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Gmelin Registry Number
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Gmelin
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383659
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Reaxys Registry Number
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Reaxys
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91-56-5
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CAS Registry Number
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KEGG COMPOUND
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91-56-5
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CAS Registry Number
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NIST Chemistry WebBook
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91-56-5
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CAS Registry Number
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ChemIDplus
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Xu P, Hou L, Ju C, Zhang Z, Sun W, Zhang L, Song J, Lv Y, Liu L, Chen Z, Wang Y (2016)
Isatin inhibits the proliferation and invasion of SH-SY5Y neuroblastoma cells.
Molecular medicine reports 13, 2757-2762 [PubMed:26846278]
[show Abstract]
Isatin has been shown to initiate apoptotic processes in SH‑SY5Y neuroblastoma cells. The aim of the present study was to investigate whether isatin is also able to alter the proliferation and migratory ability of SH‑SY5Y cells. The results demonstrated that the proportion of SH‑SY5Y cells in G1 phase was significantly increased following treatment with isatin for 48 h with simultaneous downregulation of cyclin D1 expression. In addition, isatin significantly inhibited cell migration and invasion, along with decreases in matrix metalloproteinase (MMP)2 and MMP9 expression. In addition, isatin reduced the levels of phosphorylated signal transducer and activator of transcription 3 (p‑STAT3) in a concentration-dependent manner. These results demonstrated that isatin induces G1‑phase arrest in SH‑SY5Y cells, possibly by decreasing cyclin D1 expression as well as inhibiting their migration and invasiveness, probably by reducing MMP2 and MMP9. These effects may be exerted by isatin via a downregulating the levels of pSTAT3. | Pakravan P, Kashanian S, Khodaei MM, Harding FJ (2013)
Biochemical and pharmacological characterization of isatin and its derivatives: from structure to activity.
Pharmacological reports : PR 65, 313-335 [PubMed:23744416]
[show Abstract]
Isatin, 1H-indole-2,3-dione, is a heterocyclic compound of significant importance in medicinal chemistry. It is a synthetically versatile molecule, a precursor for a large number of pharmacologically active compounds. Isatin and its derivatives have aroused great attention in recent years due to their wide variety of biological activities, relevant to application as insecticides and fungicides and in a broad range of drug therapies, including anticancer drugs, antibiotics and antidepressants. The purpose of this review is to provide an overview of the pharmacological activities of isatin and its synthetic and natural derivatives. Molecular modifications to tailor the properties of isatin and its derivatives are also discussed. | Buneeva O, Gnedenko O, Zgoda V, Kopylov A, Glover V, Ivanov A, Medvedev A, Archakov A (2010)
Isatin-binding proteins of rat and mouse brain: proteomic identification and optical biosensor validation.
Proteomics 10, 23-37 [PubMed:19834914]
[show Abstract]
Isatin (indole-2,3-dione) is an endogenous indole that has a distinct and discontinuous distribution in the brain and in other mammalian tissues and body fluids. Its output is increased under conditions of stress and anxiety. Isatin itself and its analogues exhibit a wide range of pharmacological activities but its specific biological targets still are not well characterized. Affinity chromatography of Triton X-100 lysates of soluble and particulate fractions of mouse and rat whole brain homogenates on 5-aminocaproyl-isatin-Sepharose followed by subsequent proteomic analysis resulted in identification of 65 and 64 individual proteins, respectively. Isatin-binding capacity of some of the identified proteins has been validated in an optical biosensor study using a Biacore 3000 optical biosensor, 5-aminocarproyl-isatin, and 5-aminoisatin as the affinity ligands. The K(d) values (of 0.1-20 microM) obtained during the optical biosensor experiments were consistent with the range of K(d) values recently reported for [(3)H]isatin binding to brain sections. Although the number of isatin-binding proteins identified in the mouse and rat brain was similar, only 21 proteins (about one-third) were identical in the two species. This may be one reason for the differences in isatin effects in rats and mice reported in the literature. | Zou P, Koh HL (2007)
Determination of indican, isatin, indirubin and indigotin in Isatis indigotica by liquid chromatography/electrospray ionization tandem mass spectrometry.
Rapid communications in mass spectrometry : RCM 21, 1239-1246 [PubMed:17330218]
[show Abstract]
The roots and leaves of Isatis indigotica, named 'Ban-Lan-Gen' and 'Da-Qing-Ye', respectively, are widely used for the treatment of influenza, viral pneumonia, mumps, pharyngitis, and hepatitis. The indoxyl derivatives detected in the roots and leaves of I. indigotica have been reported to be biologically active. In the present study, a liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) method was developed to determine indican, isatin, indirubin and indigotin in the roots and leaves of I. indigotica. The method has been validated for linearity, precision and accuracy. Using multiple reaction monitoring (MRM), the limits of detection (LODs) were determined as 0.004 ng for indican, 0.01 ng for isatin, 0.01 ng for indrubin and 0.03 ng for indigotin, while the limits of quantitation (LOQs) were 0.015 ng for indican, 0.04 ng for isatin, 0.04 ng for indirubin and 0.1 ng for indigotin. Compared with previously reported methods, the current method is more rapid, selective and sensitive. This is the first report of the LC/MS/MS determination of indican, isatin, indirubin and indigotin. | Minami M, Hamaue N, Hirafuji M, Saito H, Hiroshige T, Ogata A, Tashiro K, Parvez SH (2006)
Isatin, an endogenous MAO inhibitor, and a rat model of Parkinson's disease induced by the Japanese encephalitis virus.
Journal of neural transmission. Supplementum87-95 [PubMed:17447419]
[show Abstract]
A single dose of isatin (indole-2,3-dione)(i.p.), an endogenous MAO inhibitor, significantly increased norepinephrine and 5-hydroxytryptamine concentrations in the rat brain and also significantly increased acetylcholine and dopamine (DA) levels in the rat striatum. Urinary isatin concentrations in patients with Parkinson's disease tend to increase according to the severity of disease. We have developed a rat model of Parkinson's disease induced by the Japanese encephalitis virus (JEV). The distribution of the pathological lesions of JEV-rats resemble those found in Parkinson's disease. Significant behavioral improvement was observed in JEV-rats after isatin, L-DOPA and selegiline administration using a pole test. Both isatin and selegiline prevented the decrease in striatum DA levels of JEV-rats. The increased turnover of DA (DOPAC/DA) induced by JEV was significantly inhibited by isatin, but not selegiline. These findings suggest that JEV-infected rats may serve as a model of Parkinson's disease and that exogenously administered isatin and selegiline can improve JEV-induced parkinsonism by increasing DA concentrations in the striatum. | Igosheva N, Lorz C, O'Conner E, Glover V, Mehmet H (2005)
Isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells.
Neurochemistry international 47, 216-224 [PubMed:15876476]
[show Abstract]
Isatin is an endogenous indole that is increased in stress, inhibits monoamine oxidase (MAO) B and improves bradykinesia and striatal dopamine levels in rat models of Parkinson's disease. Consequently, it has been suggested that isatin might be a possible treatment for Parkinson's disease although little is known about its effects on neural cell growth and survival. The aim of this study was to investigate the survival of dopaminergic human neuroblastoma (SH-SY5Y) cells following treatment with increasing concentrations of isatin. SH-SY5Y cells were exposed to isatin for defined time points, after which cell survival was determined by MTT assay. A combination of Annexin V binding and propidium iodide (PI) exclusion was used to distinguish apoptosis from necrosis in flow cytometry experiments and FACS profiles of permeabilised PI-labelled cells were employed for the assessment of cell cycle distribution. Isatin treatment (1-400 microM) for 24h induced a significant dose-dependent increase in MTT metabolism by SH-SY5Y cells in culture, but this was not due to an increase in cell division. At the higher concentrations (200-400 microm) isatin triggered cell death, although MTT metabolism was still increased in the culture, suggesting that surviving cells were hypermetabolic. Following a longer (48 h) exposure, isatin was found to cause cell death in a dose-dependent manner; at lower concentrations (50 microM), the predominant mode of cell death was apoptosis while at the highest concentration (400 microm) increasing numbers of necrotic cells were also evident. Thus, in dopaminergic SH-SY5Y cells isatin induces cell death in dose- and time-dependent manner. This death occurred as a continuum of survival, apoptosis and necrosis. Our results re-emphasise that caution should be exercised when considering high doses of isatin as a putative anti-Parkinson's disease therapeutic. | Medvedev A, Igosheva N, Crumeyrolle-Arias M, Glover V (2005)
Isatin: role in stress and anxiety.
Stress (Amsterdam, Netherlands) 8, 175-183 [PubMed:16236622]
[show Abstract]
(Indoledione 2,3) isatin is an endogenous indole found both in mammalian brain and peripheral tissues. Isatin concentration in blood can exceed 1 microM and tissue concentrations vary from < 0.1 to 10 microM. Its level in the brain and periphery is increased by stress. Isatin has a wide spectrum of behavioural and metabolic effects. It is anxiogenic at lower doses and sedative at higher doses. Its most potent known in vitro actions are as an antagonist of atrial natriuretic peptide (ANP) function and NO signaling. In this review, we discuss isatin and stress in animal models, the few human studies, and also what it is known to date about the molecular mechanisms of its action. We suggest the possibility that isatin and its analogues may be interesting new pharmacological agents; Isatin antagonists may be anxiolytic, and isatin agonists may activate the HPA axis. | Hamaue N, Yamazaki N, Minami M, Endo T, Hirahuji M, Monma Y, Togashi H (1998)
Determination of isatin, an endogenous monoamine oxidase inhibitor, in urine and tissues of rats by HPLC.
General pharmacology 30, 387-391 [PubMed:9510091]
[show Abstract]
1. We have previously identified isatin as one of the endogenous monoamine oxidase (MAO) inhibitors in the urine and the brain of stroke-prone spontaneously hypertensive rats (SHRSP), using gas chromatography-mass spectrometry (GC-MS). 2. In this study, we attempted to develop a convenient assay to determine isatin using high performance liquid chromatography with an ultraviolet detector (HPLC-UV). The standard curve for authentic isatin was linear at a range from 2 to 20 nmol per ml. The coefficient of variance was within 3% for both intra-assay and inter-assay. The sensitivity was 20 pmol per 10 microl of urine sample. 3. Isatin concentration correlated significantly and positively with endogenous MAO activity (tribulin-like activity) in both urine (r=0.924, P<0.001) and kidney extracts (r=0.862, P<0.01). There was a significant difference in urinary isatin between Wistar Kyoto rats (WKY) and SHRSP. Oral administration of isatin increased urinary isatin concentration and systolic blood pressure in WKY. 4. Determination of isatin using HPLC-UV may be useful for elucidating role of isatin in various conditions of stress and disease. | Varga JM, Kalchschmid G, Klein GF, Fritsch P (1991)
Mechanism of allergic cross-reactions--I. Multispecific binding of ligands to a mouse monoclonal anti-DNP IgE antibody.
Molecular immunology 28, 641-654 [PubMed:1650428]
[show Abstract]
A recently developed solid-phase binding assay was used to investigate the specificity of ligand binding to a mouse monoclonal anti-dinitrophenyl IgE [IgE(aDNP)]. All DNP-amino acids, that were tested, inhibited the binding of radio-labeled IgE(aDNP) to DNP covalently attached to polystyrene microtiter plates; however, the concentration for 50% inhibition varied within four orders of magnitude, DNP-L-serine being the most, DNP-proline the least potent inhibitor. In addition to DNP analogues a large number (2074) of drugs and other compounds were tested for their ability to compete with DNP for the binding site of IgE(aDNP). At the concentrations used for screening 59% of the compounds had no significant inhibition; 19% inhibited the binding of IgE(aDNP) more than 50%. Several families of compounds (tetracyclines, polymyxines, phenotiazines, salicylates and quinones) of effective competitors were found. Within these families change in the functional groups attached to the "family stem" had major effects on the affinity of ligand binding. The occurrence frequencies of interactions of ligands with IgE(aDNP) is in good agreement with a semi-empirical model for multispecific antibody-ligand interactions. |
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