MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 145139 | Name: Staurosporinone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Staurosporinone is a bioactive indolocarbazole alkaloid and is also known as K-252c. Staurosporinone is a natural product derived from Streptomyces staurosporeus.

Chemical Structure

Staurosporinone
Staurosporinone
CAS#85753-43-1

Theoretical Analysis

MedKoo Cat#: 145139

Name: Staurosporinone

CAS#: 85753-43-1

Chemical Formula: C20H13N3O

Exact Mass: 311.1059

Molecular Weight: 311.34

Elemental Analysis: C, 77.16; H, 4.21; N, 13.50; O, 5.14

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Staurosporinone; Staurosporine Aglycon; K-252c;
IUPAC/Chemical Name
6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one
InChi Key
MEXUTNIFSHFQRG-UHFFFAOYSA-N
InChi Code
1S/C20H13N3O/c24-20-17-12(9-21-20)15-10-5-1-3-7-13(10)22-18(15)19-16(17)11-6-2-4-8-14(11)23-19/h1-8,22-23H,9H2,(H,21,24)
SMILES Code
O=C1NCC2=C3C4=CC=CC=C4NC3=C5NC6=CC=CC=C6C5=C12
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 311.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Singh S, Samineni R, Pabbaraja S, Mehta G. A General Carbazole Synthesis via Stitching of Indole-Ynones with Nitromethanes: Application to Total Synthesis of Carbazomycin A, Calothrixin B, and Staurosporinone. Org Lett. 2019 May 3;21(9):3372-3376. doi: 10.1021/acs.orglett.9b01111. Epub 2019 Apr 23. PMID: 31013110. 2: Fox JC, Gilligan RE, Pitts AK, Bennett HR, Gaunt MJ. The total synthesis of K-252c (staurosporinone) via a sequential C-H functionalisation strategy. Chem Sci. 2016 Apr 21;7(4):2706-2710. doi: 10.1039/c5sc04399a. Epub 2016 Jan 21. PMID: 28660044; PMCID: PMC5477024. 3: Kaneko M, Saito Y, Saito H, Matsumoto T, Matsuda Y, Vaught JL, Dionne CA, Angeles TS, Glicksman MA, Neff NT, Rotella DP, Kauer JC, Mallamo JP, Hudkins RL, Murakata C. Neurotrophic 3,9-bis[(alkylthio)methyl]-and-bis(alkoxymethyl)-K-252a derivatives. J Med Chem. 1997 Jun 6;40(12):1863-9. doi: 10.1021/jm970031d. PMID: 9191963. 4: Peruzzi B, Bottaro DP. Targeting the c-Met signaling pathway in cancer. Clin Cancer Res. 2006 Jun 15;12(12):3657-60. doi: 10.1158/1078-0432.CCR-06-0818. PMID: 16778093. 5: Wada Y, Nagasaki H, Tokuda M, Orito K. Synthesis of N-protected staurosporinones. J Org Chem. 2007 Mar 16;72(6):2008-14. doi: 10.1021/jo062184r. Epub 2007 Feb 20. PMID: 17309305. 6: Oga S, Goto K, Sakamoto J, Honda Y, Sasaki R, Ishikawa K, Kataoka H, Nakano J, Origuchi T, Okita M. Mechanisms underlying immobilization-induced muscle pain in rats. Muscle Nerve. 2020 May;61(5):662-670. doi: 10.1002/mus.26840. Epub 2020 Mar 8. PMID: 32083755. 7: Tamaki K, Shotwell JB, White RD, Drutu I, Petsch DT, Nheu TV, He H, Hirokawa Y, Maruta H, Wood JL. Efficient syntheses of novel C2'-alkylated (+/-)-K252a analogues. Org Lett. 2001 May 31;3(11):1689-92. doi: 10.1021/ol015894m. PMID: 11405687. 8: Zhang GY, Zhang QG. Agents targeting c-Jun N-terminal kinase pathway as potential neuroprotectants. Expert Opin Investig Drugs. 2005 Nov;14(11):1373-83. doi: 10.1517/13543784.14.11.1373. PMID: 16255677. 9: Rüegg UT, Burgess GM. Staurosporine, K-252 and UCN-01: potent but nonspecific inhibitors of protein kinases. Trends Pharmacol Sci. 1989 Jun;10(6):218-20. doi: 10.1016/0165-6147(89)90263-0. PMID: 2672462. 10: Mahboobi S, Eibler E, Koller M, Kumar KC S, Popp A, Schollmeyer D. Synthesis of Pyrrolidin-2-ones and of Staurosporine Aglycon (K-252c) by Intermolecular Michael Reaction. J Org Chem. 1999 Jun 25;64(13):4697-4704. doi: 10.1021/jo9825106. PMID: 11674542. 11: Lazarovici P, Rasouly D, Friedman L, Tabekman R, Ovadia H, Matsuda Y. K252a and staurosporine microbial alkaloid toxins as prototype of neurotropic drugs. Adv Exp Med Biol. 1996;391:367-77. doi: 10.1007/978-1-4613-0361-9_31. PMID: 8726076. 12: Liu X, Ye K, Weinshenker D. Norepinephrine Protects against Amyloid-β Toxicity via TrkB. J Alzheimers Dis. 2015;44(1):251-60. doi: 10.3233/JAD-141062. PMID: 25208620; PMCID: PMC4714587. 13: Knüsel B, Hefti F. K-252 compounds: modulators of neurotrophin signal transduction. J Neurochem. 1992 Dec;59(6):1987-96. doi: 10.1111/j.1471-4159.1992.tb10085.x. PMID: 1431889. 14: Tran TD, Cartner LK, Bokesch HR, Henrich CJ, Wang XW, Mahidol C, Ruchirawat S, Kittakoop P, O'Keefe BR, Gustafson KR. NMR characterization of rearranged staurosporine aglycone analogues from the marine sponge Damiria sp. Magn Reson Chem. 2021 May;59(5):534-539. doi: 10.1002/mrc.4932. Epub 2019 Sep 9. PMID: 31379005; PMCID: PMC7428849. 15: Nick TA, Ribera AB. Synaptic activity modulates presynaptic excitability. Nat Neurosci. 2000 Feb;3(2):142-9. doi: 10.1038/72082. PMID: 10649569. 16: Dankwa S, Dols MM, Wei L, Glennon EKK, Kain HS, Kaushansky A, Smith JD. Exploiting polypharmacology to dissect host kinases and kinase inhibitors that modulate endothelial barrier integrity. Cell Chem Biol. 2021 Dec 16;28(12):1679-1692.e4. doi: 10.1016/j.chembiol.2021.06.004. Epub 2021 Jul 2. PMID: 34216546; PMCID: PMC8688180. 17: Kafitz KW, Rose CR, Thoenen H, Konnerth A. Neurotrophin-evoked rapid excitation through TrkB receptors. Nature. 1999 Oct 28;401(6756):918-21. doi: 10.1038/44847. PMID: 10553907. 18: Cherubini E, Mariotta S, Scozzi D, Mancini R, Osman G, D'Ascanio M, Bruno P, Cardillo G, Ricci A. BDNF/TrkB axis activation promotes epithelial-mesenchymal transition in idiopathic pulmonary fibrosis. J Transl Med. 2017 Sep 22;15(1):196. doi: 10.1186/s12967-017-1298-1. PMID: 28938915; PMCID: PMC5610541. 19: Oyama Y, Nagao S, Na L, Yanai K, Umebayashi M, Nakamura K, Nagai S, Fujimura A, Yamasaki A, Nakayama K, Morisaki T, Onishi H. TrkB/BDNF Signaling Could Be a New Therapeutic Target for Pancreatic Cancer. Anticancer Res. 2021 Aug;41(8):4047-4052. doi: 10.21873/anticanres.15205. PMID: 34281873. 20: Diniz CRAF, da Silva LA, Domingos LB, Sonego AB, Moraes LRB, Joca S. Fluoxetine acts concomitantly on dorsal and ventral hippocampus to Trk- dependently modulate the extinction of fear memory. Prog Neuropsychopharmacol Biol Psychiatry. 2022 Mar 8;113:110451. doi: 10.1016/j.pnpbp.2021.110451. Epub 2021 Oct 4. PMID: 34619303.

View History

Coumermycin sodium

Coumermycin sodium