7-bromoindirubin-3'-oxime: has mild protein kinase inhibitory activity; induces caspase-independent cell death; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 135423792 |
| CHEMBL ID | 373834 |
| CHEMBL ID | 1092509 |
| MeSH ID | M0504141 |
| Synonym |
|---|
| nsc-737346 |
| 7-bromo-indirubin-3'-oxime |
| nsc737346 |
| UNM-0000305775 , |
| 7-bromo-3-[3-(hydroxyamino)-1h-indol-2-yl]indol-2-one |
| bdbm50191405 |
| (2''z,3''e)-7-bromoindirubin-3''-oxime |
| CHEMBL373834 , |
| 7-bromoindirubin-3'oxime |
| 7bio |
| CHEMBL1092509 , |
| bdbm50012184 |
| 7-bromoindirubin-3'-oxime |
| 7-bromanyl-3-[3-(oxidanylamino)-1h-indol-2-yl]indol-2-one |
| 7-bromo-3-[3-(hydroxyamino)-1h-indol-2-yl]-2-indolone |
| cid_11846148 |
| bdbm54685 |
| 916440-85-2 |
| 7-bromo-3-(3-nitroso-1h-indol-2-yl)-1h-indol-2-ol |
| EX-A5481 |
| F81812 |
| MS-25568 |
| cid 11846148 |
| HY-121035 |
| CS-0079342 |
| PD017146 |
| PD044752 |
| 7'-bromo-3-(hydroxyimino)-[2,3'-biindolinylidene]-2'-one |
| AKOS040744967 |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Glycogen synthase kinase-3 beta | Sus scrofa (pig) | IC50 (µMol) | 21.0000 | 0.0050 | 1.8419 | 10.0000 | AID1895346; AID727166 |
| [Tau protein] kinase | Sus scrofa (pig) | IC50 (µMol) | 32.0000 | 0.0050 | 1.9832 | 10.0000 | AID1895346 |
| Aurora kinase A | Homo sapiens (human) | IC50 (µMol) | 51.0000 | 0.0000 | 0.4620 | 8.6000 | AID1895347; AID297163 |
| Casein kinase I isoform alpha | Sus scrofa (pig) | IC50 (µMol) | 10.0000 | 1.2000 | 1.2000 | 1.2000 | AID727165 |
| Cyclin-dependent kinase 1 | Homo sapiens (human) | IC50 (µMol) | 22.0000 | 0.0004 | 1.3452 | 10.0000 | AID469484 |
| Polyunsaturated fatty acid 5-lipoxygenase | Homo sapiens (human) | IC50 (µMol) | 3.7000 | 0.0001 | 1.6847 | 9.3200 | AID1139553; AID1139554; AID1139555 |
| Aryl hydrocarbon receptor | Homo sapiens (human) | IC50 (µMol) | 20.0000 | 0.0280 | 0.0280 | 0.0280 | AID266519 |
| Glycogen synthase kinase-3 alpha | Homo sapiens (human) | IC50 (µMol) | 32.0000 | 0.0010 | 1.2249 | 9.1000 | AID266509 |
| Glycogen synthase kinase-3 beta | Homo sapiens (human) | IC50 (µMol) | 32.0000 | 0.0006 | 0.8013 | 10.0000 | AID266509 |
| Cyclin-dependent-like kinase 5 | Homo sapiens (human) | IC50 (µMol) | 27.2500 | 0.0002 | 1.1832 | 10.0000 | AID1895345; AID266508; AID469486; AID727167 |
| Cyclin-dependent kinase 5 activator 1 | Homo sapiens (human) | IC50 (µMol) | 33.0000 | 0.0010 | 1.2898 | 10.0000 | AID1895345; AID266508 |
| Dual specificity tyrosine-phosphorylation-regulated kinase 1A | Rattus norvegicus (Norway rat) | IC50 (µMol) | 1.9000 | 0.0100 | 0.5741 | 2.8000 | AID727164 |
| Dual specificity tyrosine-phosphorylation-regulated kinase 2 | Homo sapiens (human) | IC50 (µMol) | 1.3000 | 0.0140 | 0.9744 | 3.0000 | AID727163 |
| Aurora kinase B | Homo sapiens (human) | IC50 (µMol) | 4.6000 | 0.0003 | 0.9634 | 9.8000 | AID1895352; AID297164 |
| Aurora kinase C | Homo sapiens (human) | IC50 (µMol) | 0.4000 | 0.0010 | 0.4137 | 8.6000 | AID1895353; AID297165 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| GTP-binding protein (rab7) | Canis lupus familiaris (dog) | EC50 (µMol) | 30.0000 | 0.0220 | 1.2146 | 6.4190 | AID2036 |
| ras protein, partial | Homo sapiens (human) | EC50 (µMol) | 33.7485 | 0.0200 | 0.2237 | 1.9660 | AID2038; AID2043 |
| Rac1 protein | Homo sapiens (human) | EC50 (µMol) | 30.0000 | 0.0202 | 5.9860 | 29.5100 | AID2039; AID2040 |
| cell division cycle 42 (GTP binding protein, 25kDa), partial | Homo sapiens (human) | EC50 (µMol) | 42.5405 | 0.0563 | 3.0554 | 13.5100 | AID2021; AID2022 |
| Ras-related protein Rab-2A | Canis lupus familiaris (dog) | EC50 (µMol) | 65.7660 | 0.1580 | 0.3777 | 0.7042 | AID2046 |
| Sigma non-opioid intracellular receptor 1 | Rattus norvegicus (Norway rat) | EC50 (µMol) | 33.7485 | 0.1060 | 1.0765 | 1.7000 | AID2038; AID2043 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1895346 | Inhibition of porcine brain GSK-3alpha/beta incubated for 30 mins in presence of [33p]-gamma ATP by scintillation counter analysis | 2021 | European journal of medicinal chemistry, Nov-05, Volume: 223 | Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship. |
| AID1139554 | Inhibition of 5-LO in human neutrophils assessed as product formation by cell-intact assay relative to control in presence of 2.5 uM A23187 ionophore | 2014 | Journal of medicinal chemistry, May-08, Volume: 57, Issue:9 | Indirubin core structure of glycogen synthase kinase-3 inhibitors as novel chemotype for intervention with 5-lipoxygenase. |
| AID1293545 | Antiproliferative activity against apoptosis resistant human A549 cells after 72 hrs by MTT assay | 2016 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 26, Issue:6 | Isatin derivatives with activity against apoptosis-resistant cancer cells. |
| AID1139551 | Inhibition of human recombinant 5-LO assessed as product formation at 3 uM by cell-free assay relative to control | 2014 | Journal of medicinal chemistry, May-08, Volume: 57, Issue:9 | Indirubin core structure of glycogen synthase kinase-3 inhibitors as novel chemotype for intervention with 5-lipoxygenase. |
| AID1139558 | Anticancer activity against human SH-SY5Y cells assessed as reduction in cell viability | 2014 | Journal of medicinal chemistry, May-08, Volume: 57, Issue:9 | Indirubin core structure of glycogen synthase kinase-3 inhibitors as novel chemotype for intervention with 5-lipoxygenase. |
| AID1293544 | Antiproliferative activity against apoptosis resistant human U373 cells after 72 hrs by MTT assay | 2016 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 26, Issue:6 | Isatin derivatives with activity against apoptosis-resistant cancer cells. |
| AID1293543 | Antiproliferative activity against human LoVo cells after 72 hrs by MTT assay | 2016 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 26, Issue:6 | Isatin derivatives with activity against apoptosis-resistant cancer cells. |
| AID1293551 | Antiproliferative activity against apoptosis sensitive human MCF7 cells after 72 hrs by MTT assay | 2016 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 26, Issue:6 | Isatin derivatives with activity against apoptosis-resistant cancer cells. |
| AID1895352 | Inhibition of Aurora B (unknown origin) | 2021 | European journal of medicinal chemistry, Nov-05, Volume: 223 | Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship. |
| AID1895345 | Inhibition of GST-fused CDK5/p25 (unknown origin) | 2021 | European journal of medicinal chemistry, Nov-05, Volume: 223 | Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship. |
| AID1895353 | Inhibition of Aurora C (unknown origin) | 2021 | European journal of medicinal chemistry, Nov-05, Volume: 223 | Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship. |
| AID1895348 | Antiproliferative activity against human TT cells assessed as cell growth inhibition measured after 48 hrs by Cell titer-Glo assay | 2021 | European journal of medicinal chemistry, Nov-05, Volume: 223 | Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship. |
| AID1293550 | Antiproliferative activity against apoptosis sensitive human PC3 cells after 72 hrs by MTT assay | 2016 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 26, Issue:6 | Isatin derivatives with activity against apoptosis-resistant cancer cells. |
| AID1293549 | Antiproliferative activity against apoptosis sensitive mouse B16F10 cells after 72 hrs by MTT assay | 2016 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 26, Issue:6 | Isatin derivatives with activity against apoptosis-resistant cancer cells. |
| AID1459473 | Cytotoxicity against human KCL22 cells harboring ABL1 T315I mutant assessed as reduction in cell viability at 1 uM after 48 hrs by MTS assay | 2016 | Journal of natural products, 10-28, Volume: 79, Issue:10 | Natural-Based Indirubins Display Potent Cytotoxicity toward Wild-Type and T315I-Resistant Leukemia Cell Lines. |
| AID1293547 | Antiproliferative activity against apoptosis resistant human SK-MEL-28 cells after 72 hrs by MTT assay | 2016 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 26, Issue:6 | Isatin derivatives with activity against apoptosis-resistant cancer cells. |
| AID1293548 | Antiproliferative activity against apoptosis sensitive human Hs683 cells after 72 hrs by MTT assay | 2016 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 26, Issue:6 | Isatin derivatives with activity against apoptosis-resistant cancer cells. |
| AID1139552 | Inhibition of 5-LO in human neutrophils assessed as product formation at 3 uM by cell-intact assay relative to control in presence of 2.5 uM A23187 ionophore | 2014 | Journal of medicinal chemistry, May-08, Volume: 57, Issue:9 | Indirubin core structure of glycogen synthase kinase-3 inhibitors as novel chemotype for intervention with 5-lipoxygenase. |
| AID1139553 | Inhibition of human recombinant 5-LO assessed as product formation by cell-free assay relative to control | 2014 | Journal of medicinal chemistry, May-08, Volume: 57, Issue:9 | Indirubin core structure of glycogen synthase kinase-3 inhibitors as novel chemotype for intervention with 5-lipoxygenase. |
| AID1293546 | Antiproliferative activity against apoptosis resistant human OE21 cells after 72 hrs by MTT assay | 2016 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 26, Issue:6 | Isatin derivatives with activity against apoptosis-resistant cancer cells. |
| AID1895288 | Inhibition of starfish oocyte CDK1/Cyclin B using histone H1 as substrate incubated for 10 mins in presence of [gamma-32P]ATP by scintillation counter analysis | 2021 | European journal of medicinal chemistry, Nov-05, Volume: 223 | Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship. |
| AID1459472 | Cytotoxicity against human KCL22 cells assessed as reduction in cell viability at 1 uM after 48 hrs by MTS assay | 2016 | Journal of natural products, 10-28, Volume: 79, Issue:10 | Natural-Based Indirubins Display Potent Cytotoxicity toward Wild-Type and T315I-Resistant Leukemia Cell Lines. |
| AID1895347 | Inhibition of Aurora A (unknown origin) | 2021 | European journal of medicinal chemistry, Nov-05, Volume: 223 | Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship. |
| AID1461889 | Cytotoxicity against human HepG2 cells assessed as cell growth inhibition after 24 hrs by alamar blue assay | |||
| AID1139555 | Inhibition of 5-LO in human neutrophils assessed as product formation by cell-intact assay relative to control in presence of 20 uM A23187/AA ionophore | 2014 | Journal of medicinal chemistry, May-08, Volume: 57, Issue:9 | Indirubin core structure of glycogen synthase kinase-3 inhibitors as novel chemotype for intervention with 5-lipoxygenase. |
| AID727164 | Inhibition of rat recombinant GST-fused DYRK1A expressed in Escherichia coli using KKISGRLSPIMTEQ as substrate after 30 mins by scintillation counting analysis in presence of [gamma-33P]-ATP | 2013 | ACS medicinal chemistry letters, Jan-10, Volume: 4, Issue:1 | Novel Inverse Binding Mode of Indirubin Derivatives Yields Improved Selectivity for DYRK Kinases. |
| AID266522 | Survival of human Huh7 cells after 48 hrs by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID297165 | Inhibition of human recombinant aurora C kinase | 2007 | Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17 | An integrated computational approach to the phenomenon of potent and selective inhibition of aurora kinases B and C by a series of 7-substituted indirubins. |
| AID266509 | Inhibition of porcine brain GSK3alpha/beta | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID266507 | Inhibition of starfish CDK1/cyclin B in presence of 15 uM ATP | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID297163 | Inhibition of human recombinant aurora A kinase | 2007 | Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17 | An integrated computational approach to the phenomenon of potent and selective inhibition of aurora kinases B and C by a series of 7-substituted indirubins. |
| AID727165 | Inhibition of porcine brain CK1 using RRKHAAIGpSAYSITA as substrate | 2013 | ACS medicinal chemistry letters, Jan-10, Volume: 4, Issue:1 | Novel Inverse Binding Mode of Indirubin Derivatives Yields Improved Selectivity for DYRK Kinases. |
| AID266525 | Death of human SH-SY5Y cells in presence of 20 uM Q-VD-OPh by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID727166 | Inhibition of porcine brain GSK3beta using YRRAAVPPSPSLSRHSSPHQSpEDEEE as substrate | 2013 | ACS medicinal chemistry letters, Jan-10, Volume: 4, Issue:1 | Novel Inverse Binding Mode of Indirubin Derivatives Yields Improved Selectivity for DYRK Kinases. |
| AID266512 | Survival of human SH-SY5Y cells after 48 hrs by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID266518 | Survival of human PC3 cells after 48 hrs by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID266510 | Survival of human SH-SY5Y cells at 25 uM by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID266514 | Survival of human HT29 cells after 48 hrs by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID469485 | Inhibition of GSK3 | 2009 | Journal of natural products, Dec, Volume: 72, Issue:12 | Synthesis and antiproliferative activity of 7-azaindirubin-3'-oxime, a 7-aza isostere of the natural indirubin pharmacophore. |
| AID469486 | Inhibition of CDK5 | 2009 | Journal of natural products, Dec, Volume: 72, Issue:12 | Synthesis and antiproliferative activity of 7-azaindirubin-3'-oxime, a 7-aza isostere of the natural indirubin pharmacophore. |
| AID266520 | Survival of mouse AhR -/- BP8 cells after 48 hrs by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID266516 | Survival of human MDA-MB-231 cells after 48 hrs by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID727167 | Inhibition of human recombinant CDK5 | 2013 | ACS medicinal chemistry letters, Jan-10, Volume: 4, Issue:1 | Novel Inverse Binding Mode of Indirubin Derivatives Yields Improved Selectivity for DYRK Kinases. |
| AID297164 | Inhibition of human recombinant aurora B kinase | 2007 | Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17 | An integrated computational approach to the phenomenon of potent and selective inhibition of aurora kinases B and C by a series of 7-substituted indirubins. |
| AID266517 | Survival of human A549 cells after 48 hrs by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID266508 | Inhibition of mammalian CDK5/p25 | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID266519 | Survival of mouse AhR +/+ 5L cells after 48 hrs by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID266521 | Survival of mouse F1 cells after 48 hrs by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID727163 | Inhibition of human recombinant GST-fused DYRK2 expressed in Escherichia coli using KKISGRLSPIMTEQ as substrate after 30 mins by scintillation counting analysis in presence of [gamma-33P]-ATP | 2013 | ACS medicinal chemistry letters, Jan-10, Volume: 4, Issue:1 | Novel Inverse Binding Mode of Indirubin Derivatives Yields Improved Selectivity for DYRK Kinases. |
| AID469484 | Inhibition of CDK1 | 2009 | Journal of natural products, Dec, Volume: 72, Issue:12 | Synthesis and antiproliferative activity of 7-azaindirubin-3'-oxime, a 7-aza isostere of the natural indirubin pharmacophore. |
| AID266515 | Survival of human HCT116 cells after 48 hrs by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID266511 | Survival of human SH-SY5Y cells after 24 hrs by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID266524 | Death of human SH-SY5Y cells in absence of 20 uM Q-VD-OPh by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID266513 | Death of human SH-SY5Y cells at 25 uM after 48 hrs by LDH release assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| AID266523 | Survival of human HEK293 cells after 48 hrs by MTS reduction assay | 2006 | Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15 | 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 6 (40.00) | 29.6817 |
| 2010's | 8 (53.33) | 24.3611 |
| 2020's | 1 (6.67) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (6.67%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 14 (93.33%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||