7-Oxostaurosporine
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04193 |
| CAS | 141196-69-2 |
| Molecular Weight | 480.52 |
| Molecular Formula | C28H24N4O4 |
| Purity | >98% by HPLC |
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Description
It is the oxidised and highly fluorescent analogue of Antibiotic UCN-01 and UCN-02. It is a potent inhibitor of protein kinase C and formation of cellular blebs induced by phorbols. It inhibits the cell cycle at the G2 stage with the accumulation of 4C DNA cells and possesses comparable activity against tumour cells lines to UCN-01.
Specification
| Synonyms | 7-Oxostaurosporine; BMY 41950; RK 1409; (9S,10R,11R,13R)-10,11,12,13-Tetrahydro-10-methoxy-9-methyl-11-(methylamino)-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonine-1,3(2H)-dione; 10,11,12,13-Tetrahydro-10-methoxy-9-methyl-11-(methylamino)-[9S-(9α,10β,11β,13α)]-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonine-1,3(2H)-dione |
| Storage | Store at -20°C |
| IUPAC Name | (2S,3R,4R,6R)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaene-16,18-dione |
| Canonical SMILES | CC12C(C(CC(O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)C(=O)NC6=O)NC)OC |
| InChI | InChI=1S/C28H24N4O4/c1-28-25(35-3)15(29-2)12-18(36-28)31-16-10-6-4-8-13(16)19-21-22(27(34)30-26(21)33)20-14-9-5-7-11-17(14)32(28)24(20)23(19)31/h4-11,15,18,25,29H,12H2,1-3H3,(H,30,33,34)/t15-,18-,25-,28+/m1/s1 |
| InChI Key | POTTVLREWUNNRO-UGZRAAABSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Yellow Solid |
| Density | 1.62 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Antikinetoplastid Activity of Indolocarbazoles from Streptomyces sanyensis
José E Piñero, José J Fernández, Ines Sifaoui, Desirée San Nicolás-Hernández, Luis Cartuche, Ana R Díaz-Marrero, Carlos J Bethencourt-Estrella, Atteneri López-Arencibia, Jacob Lorenzo-Morales Biomolecules . 2020 Apr 24;10(4):657. doi: 10.3390/biom10040657.
Chagas disease and leishmaniasis are neglected tropical diseases caused by kinetoplastid parasites ofTrypanosomaandLeishmaniagenera that affect poor and remote populations in developing countries. These parasites share similar complex life cycles and modes of infection. It has been demonstrated that the particular group of phosphorylating enzymes, protein kinases (PKs), are essential for the infective mechanisms and for parasite survival. The natural indolocarbazole staurosporine (STS,1) has been extensively used as a PKC inhibitor and its antiparasitic effects described. In this research, we analyze the antikinetoplastid activities of three indolocarbazole (ICZs) alkaloids of the family of staurosporine STS,2-4, and the commercial ICZs rebeccamycin (5), K252a (6), K252b (7), K252c (8), and arcyriaflavin A (9) in order to establish a plausive approach to the mode of action and to provide a preliminary qualitative structure-activity analysis. The most active compound was 7-oxostaurosporine (7OSTS,2) that showed IC50values of 3.58 ± 1.10; 0.56 ± 0.06 and 1.58 ± 0.52 µM againstL. amazonensis; L. donovaniandT. cruzi,and a Selectivity Index (CC50/IC50) of 52 against amastigotes ofL. amazonensiscompared to the J774A.1 cell line of mouse macrophages.
2. A new inhibitor of protein kinase C, RK-1409 (7-oxostaurosporine). II. Fermentation, isolation, physico-chemical properties and structure
H Osada, H Koshino, K Isono J Antibiot (Tokyo) . 1992 Feb;45(2):195-8. doi: 10.7164/antibiotics.45.195.
RK-1409, a new inhibitor of protein kinase C, was isolated from the culture broth of Streptomyces platensis subsp. malvinus RK-1409. The structure was elucidated as 7-oxostaurosporine on the basis of spectroscopic analyses and oxidation of staurosporine.
3. Effect of staurosporine derivatives on protein kinase activity and vinblastine accumulation in mouse leukaemia P388/ADR cells
M Koyama, S Kajita, S Wakusawa, K Ikeda, K Miyamoto, K Inoko, K Takagi, T Hasegawa J Pharm Pharmacol . 1993 Jan;45(1):43-7. doi: 10.1111/j.2042-7158.1993.tb03677.x.
Inhibition by staurosporine derivatives of cyclic AMP-dependent protein kinase (A-kinase) and protein kinase C (C-kinase), and drug resistance has been investigated. The substitution of an acetyl or an ethoxycarbonyl group for the amine N-ethoxycarbonyl-7-oxostaurosporine moiety on the tetrahydropyran ring of staurosporine decreased inhibition of both protein kinases, but increased selectivity for C-kinase by further modification of the lactam moiety to the imide (NA-382). The activities of SF-2370 on protein kinases were decreased by decarboxylation and hydroxyalkylation. These staurosporine derivatives enhanced accumulation of vinblastine in adriamycin-resistant P388 (P388/ADR) cells in a dose-dependent manner. The potency for the drug accumulation of these compounds was correlated with their inhibitory activity on the drug efflux, but was not correlated with their activity on protein kinases. Staurosporine and NA-382, with high potency for vinblastine accumulation, inhibited the photolabelling of [3H]azidopine on 140 kDa P-glycoprotein in the plasma membrane. The tetrahydrofuran compounds and NA-357, which had low potency for the drug accumulation, hardly interacted with azidopine on P-glycoprotein. Most of these compounds were highly cytotoxic by themselves, and only NA-382 was less cytotoxic among them and completely reversed the vinblastine-resistance of P388/ADR cells at a non-cytotoxic concentration. These results suggest that staurosporine derivatives can enhance drug accumulation and inhibit drug resistance through their direct action on the P-glycoprotein.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
