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| Product Name: | KT5823 | | Synonyms: | PROTEIN KINASE INHIBITOR KT 5823;9,12-Epoxy-1H-diindolo[1,2,3-fg:3',2',1'-kl]pyrrolo[3,4-i][1,6]benzodiazocine-10-carboxylic acid, 2,3,9,10,11,12-hexahydro-10-methoxy-2,9-dimethyl-1-oxo-, methyl ester, (9S,10R,12R)-;(9S, 10R, 12R)-2,3,9,10,11,12-HEXAHYDRO-10-METHOXY-2,9-DIMETHYL-1-OXO-9,12-EPOXY-1H-DIINDOLO[1,2,3-FG:3',2',1'-KL]PYRROLO[3,4-I][1,6]BENZODIAZOCINE-10-CARBOXYLIC ACID, METHYL ESTER;KT5823;(9S,10R,12R)-2,3,9,10,11,12-Hexahydro-10-methoxy-2,9-dimethyl-1-oxo-9,12-epoxy-1H-diindolo[1,2,3-fg:3',2',1'-kl]pyrrolo[3,4-i][1,6]benzodiazocine-10-carboxylic acid, methyl ester;(9R)-2,3,9,10,11,12-Hexahydro-10β-methoxy-2,9-dimethyl-1-oxo-9α,12α-epoxy-1H-diindolo[1,2,3-fg:3',2',1'-kl]pyrrolo[3,4-i][1,6]benzodiazocine-10-carboxylic acid methyl ester;9,12-Epoxy-1H-diindolo(1,2,3-fg:3',2',1'-kl)pyrrolo(3,4-I)(1,6)benzodiazocine-10-carboxylic acid, 2,3,9,10,11,12-hexahydro-10-methoxy-2,9-dimethyl-1-oxo-, methyl ester, (9R-(9alpha,10beta,12alpha))-;9,12-Epoxy-1H-diindolo(1,2,3-fg:3',2',1'-kl)pyrrolo(3,4-I)(1,6)benzodiazocine-10-carboxylic acid, 2,3,9,10,11,12-hexahydro-10-methoxy-2,9-dimethyl-1-oxo-, methyl ester, (9R,10R,12R)- | | CAS: | 126643-37-6 | | MF: | C29H25N3O5 | | MW: | 495.53 | | EINECS: | 603-150-0 | | Product Categories: | Cyclic Nucleotide related;antibiotic;Protein Kinase G (PKG)Cell Signaling and Neuroscience;Enzyme Inhibitors by Enzyme;Kinase/Phosphatase Biology;P to;Protein kinase CSerine/Threonine Kinase Biology;Protein Kinase Inhibitors;Serine/Threonine Kinase Inhibitors | | Mol File: | 126643-37-6.mol |  |
| | KT5823 Chemical Properties |
| Boiling point | 629.2±55.0 °C(Predicted) | | density | 1.52±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | ethyl acetate: 5 mg/mL | | pka | -1.01±0.60(Predicted) | | form | lyophilized powder | | color | white | | Stability: | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or DMF may be stored at -20° for up to 3 months. | | InChIKey | XCMSIGRHKNQVBF-UDUFFBJHNA-N | | SMILES | N12C3=C(C4=C1C1=C(C5=C(N1[C@]1([H])O[C@@]2(C)[C@](C)(C(OOC)=O)C1)C=CC=C5)C1C(=O)N(C)CC=14)C=CC=C3 |&1:10,13,15,r| |
| Hazard Codes | Xi | | WGK Germany | 3 | | F | 10 | | HS Code | 29349990 | | Storage Class | 11 - Combustible Solids |
| | KT5823 Usage And Synthesis |
| Description | KT5823 (126643-37-6) is a selective protein kinase G inhibitor (K>i =0.23, 4 and >10 μM for PKG, PKC and PKA respectively.1Arrests human skin fibroblast cell cycle after the G0/G1 boundary.2 KT5823 abolishes the cGMP-induced relaxation in smooth muscle cells (IC50=60 nM).3Cell permeable. | | Chemical Properties | Yellow powder | | Uses | KT 5823 is a protein kinase inhibitor shown to increase TSH-induced NIS expression, and thus iodide uptake, in thyroid cells. | | Uses | KT 5823 has been used as cyclic guanosine monophosphate (cGMP)-dependent protein kinase (PKG) inhibitor in cortical cultures, cortical neurons and in mouse brain capillary endothelial cells. | | Definition | ChEBI: KT 5823 is an organic heterooctacyclic compound that is 1H,1'H-2,2'-biindole in which the nitrogens have undergone formal oxidative coupling to positions 2 and 5 of methyl (3R)-3-methoxy-2-methyltetrahydrofuran-3-carboxylate (the 2S,3R,5R product), and in which the 3 and 3' positions of the biindole moiety have also undergone formal oxidative coupling to positions 3 and 4 of 1-methyl-1,5-dihydro-2H-pyrrol-2-one. It has a role as an EC 2.7.11.12 (cGMP-dependent protein kinase) inhibitor. It is a gamma-lactam, an organic heterooctacyclic compound, a methyl ester, a hemiaminal and an indolocarbazole. | | General Description | Highly specific cell-permeable, reversible, and ATP-competitive inhibitor of protein kinase G (Ki = 234 nM). Inhibits protein kinase C (Ki = 4.0 μM) and protein kinase A (Ki >10.0 μM) at higher concentrations. | | Biological Activity | Selective inhibitor of protein kinase G (K i values are 0.23, 4 and > 10 μ M for inhibition of PKG, PKC and PKA respectively). Inhibits SNP-stimulated PKG activity with an IC 50 of 60 nM in dispersed smooth muscle cells and has little effect on PKA activity at concentrations of up to 10 μ M. Also available as part of the Mixed Kinase Inhibitor Tocriset™ . | | Biochem/physiol Actions | Cell permeable: yes | | storage | -20°C (desiccate) | | References | [1] HIROSHI KASE. K-252 compounds, novel and potent inhibitors of protein kinase C and cyclic nucleotide-dependent protein kinases[J]. Biochemical and biophysical research communications, 1987, 142 2: Pages 436-440. DOI:10.1016/0006-291x(87)90293-2
[2] D M GADBOIS. Multiple kinase arrest points in the G1 phase of nontransformed mammalian cells are absent in transformed cells.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1992, 89 18: 8626-8630. DOI:10.1073/pnas.89.18.8626
[3] K S MURTHY G M M. Interaction of cA-kinase and cG-kinase in mediating relaxation of dispersed smooth muscle cells.[J]. American Journal of Physiology, 1995, 268 1 Pt 1: C171-80. DOI:10.1152/ajpcell.1995.268.1.c171 |
| | KT5823 Preparation Products And Raw materials |
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