Staurosporine
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MedKoo CAT#: 206463

CAS#: 62996-74-1

Description: Staurosporine, also known as antibiotic AM-2282 or STS, is a potent, non-selective inhibitor of protein kinases, including protein kinase C with promising anti-cancer activity. Staurosporine is a natural product originally isolated in 1977 from the bacterium Streptomyces staurosporeus. Staurosporine was discovered to have biological activities ranging from anti-fungal to anti-hypertensive. Staurosporine induces apoptosis in pancreatic carcinoma cells via the intrinsic signaling pathway. Staurosporine synergizes with the HER2 inhibitor lapatinib to restore sensitivity toward HER2 inhibition in a HER2 inhibitor resistant breast cancer model.


Chemical Structure

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Staurosporine
CAS# 62996-74-1

Theoretical Analysis

MedKoo Cat#: 206463
Name: Staurosporine
CAS#: 62996-74-1
Chemical Formula: C28H26N4O3
Exact Mass: 466.20
Molecular Weight: 466.541
Elemental Analysis: C, 72.09; H, 5.62; N, 12.01; O, 10.29

Price and Availability

Size Price Availability Quantity
5mg USD 150 Ready to ship
10mg USD 250 Ready to Ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to Ship
500mg USD 2450 Ready to Ship
1g USD 3850 Ready to Ship
2g USD 6450 Ready to ship
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Synonym: AM-2282; AM2282; AM 2282; STS; Antibiotic 230; CGP 41251; CGP41251; CGP-41251; CGP-39360; CGP39360; CGP 39360; Staurosporine; Staurosporin.

IUPAC/Chemical Name: (5S,6R,7R,9R)-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-5H,14H-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[e]-as-indacen-14-one

InChi Key: HKSZLNNOFSGOKW-FYTWVXJKSA-N

InChi Code: InChI=1S/C28H26N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20-,26-,28+/m1/s1

SMILES Code: CO[C@@H]1[C@@H](C[C@@H]2N3C4=C(N(C5=CC=CC=C56)[C@@]1(C)O2)C6=C7CNC(C7=C4C8=CC=CC=C83)=O)NC

Appearance: Solid powder

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: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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:

Biological target: Staurosporine is a potent, ATP-competitive and non-selective inhibitor of protein kinases with IC50s of 6 nM, 15 nM, 2 nM, and 3 nM for PKC, PKA, c-Fgr, and Phosphorylase kinase respectively. Staurosporine also inhibits TAOK2 with an IC50 of 3 μM.
In vitro activity: The gene expression analysis through RT-qPCR (list of primers are provided in Table 1) shows that staurosporine treatment significantly induces the mRNA levels of ERN1, MOAP1, BAK1, Caspase-3, and Caspase 7 when compared to the untreated control group. These results suggest that staurosporine-mediated apoptosis in HEK293T cells largely depends upon ERN1, MOAP1, and BAK1, which may be the key initiator molecules for the apoptosis pathway in our model. Reference: PLoS One. 2022 Sep 26;17(9):e0275072. https://pubmed.ncbi.nlm.nih.gov/36156601/
In vivo activity: PBS-injected non-ONI (optic nerve injury) control mouse retina had an average RGC cell number of 151.75 ± 12.01 in captured photos. In comparison with the control, this study found that by 30 days after the ONI, there was substantial reduction in the number of retinal ganglion cells. PBS-injected ONI retinas had an approximate 63.59% loss of RGC (remaining RGC 36.4 ± 9.55%; P<0.001). In contrast, STS (staurosporine) injection significantly promoted RGC survival by an approximate 25.54% compared with PBS injection (remaining RGC approximately 61.94 ± 6.91%; P<0.01). The above results prove that STS can act as a neuroprotectant for ganglion cells that would otherwise die from ONI-induced neurotoxicity. Reference: Int J Clin Exp Pathol. 2017 Jul 1;10(7):7920-7928. https://pubmed.ncbi.nlm.nih.gov/31966642/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 43.9 94.19
Methanol 2.0 4.29

Preparing Stock Solutions

The following data is based on the product molecular weight 466.54 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
Formulation protocol: 1. Pandeya A, Khalko RK, Singh S, Kumar M, Gosipatala SB. Hcmv-miR-UL148D regulates the staurosporine-induced apoptosis by targeting the Endoplasmic Reticulum to Nucleus signaling 1(ERN1). PLoS One. 2022 Sep 26;17(9):e0275072. doi: 10.1371/journal.pone.0275072. PMID: 36156601; PMCID: PMC9512192. 2. Brunelli F, Torosantucci L, Gelmetti V, Franzone D, Grünewald A, Krüger R, Arena G, Valente EM. PINK1 Protects against Staurosporine-Induced Apoptosis by Interacting with Beclin1 and Impairing Its Pro-Apoptotic Cleavage. Cells. 2022 Feb 15;11(4):678. doi: 10.3390/cells11040678. PMID: 35203326; PMCID: PMC8870463. 3. Kim YH, Gum SI, Lee TY, Shin JY, Ma JY, Kim I, Park YJ, Jung JC. The neuroprotective effect of staurosporine on mouse retinal ganglion cells after optic nerve injury. Int J Clin Exp Pathol. 2017 Jul 1;10(7):7920-7928. PMID: 31966642; PMCID: PMC6965234. 4. Tagliati F, Gagliano T, Gentilin E, Minoia M, Molè D, Delgi Uberti EC, Zatelli MC. Magmas overexpression inhibits staurosporine induced apoptosis in rat pituitary adenoma cell lines. PLoS One. 2013 Sep 17;8(9):e75194. doi: 10.1371/journal.pone.0075194. Erratum in: PLoS One. 2013 Sep 27;8(9):null. PMID: 24069394; PMCID: PMC3775776.
In vitro protocol: 1. Pandeya A, Khalko RK, Singh S, Kumar M, Gosipatala SB. Hcmv-miR-UL148D regulates the staurosporine-induced apoptosis by targeting the Endoplasmic Reticulum to Nucleus signaling 1(ERN1). PLoS One. 2022 Sep 26;17(9):e0275072. doi: 10.1371/journal.pone.0275072. PMID: 36156601; PMCID: PMC9512192. 2. Brunelli F, Torosantucci L, Gelmetti V, Franzone D, Grünewald A, Krüger R, Arena G, Valente EM. PINK1 Protects against Staurosporine-Induced Apoptosis by Interacting with Beclin1 and Impairing Its Pro-Apoptotic Cleavage. Cells. 2022 Feb 15;11(4):678. doi: 10.3390/cells11040678. PMID: 35203326; PMCID: PMC8870463.
In vivo protocol: 1. Kim YH, Gum SI, Lee TY, Shin JY, Ma JY, Kim I, Park YJ, Jung JC. The neuroprotective effect of staurosporine on mouse retinal ganglion cells after optic nerve injury. Int J Clin Exp Pathol. 2017 Jul 1;10(7):7920-7928. PMID: 31966642; PMCID: PMC6965234. 2. Tagliati F, Gagliano T, Gentilin E, Minoia M, Molè D, Delgi Uberti EC, Zatelli MC. Magmas overexpression inhibits staurosporine induced apoptosis in rat pituitary adenoma cell lines. PLoS One. 2013 Sep 17;8(9):e75194. doi: 10.1371/journal.pone.0075194. Erratum in: PLoS One. 2013 Sep 27;8(9):null. PMID: 24069394; PMCID: PMC3775776.

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1: Cheshenko N, Bonanno JB, Hoffmann HH, Jangra RK, Chandran K, Rice CM, Almo SC, Herold BC. Cell-impermeable staurosporine analog targets extracellular kinases to inhibit HSV and SARS-CoV-2. Commun Biol. 2022 Oct 16;5(1):1096. doi: 10.1038/s42003-022-04067-4. PMID: 36245045; PMCID: PMC9569420.


2: Pandeya A, Khalko RK, Singh S, Kumar M, Gosipatala SB. Hcmv-miR-UL148D regulates the staurosporine-induced apoptosis by targeting the Endoplasmic Reticulum to Nucleus signaling 1(ERN1). PLoS One. 2022 Sep 26;17(9):e0275072. doi: 10.1371/journal.pone.0275072. PMID: 36156601; PMCID: PMC9512192.


3: Stevanovic M, D'Agostino PM, Mojicevic M, Gulder TAM, Nikodinovic-Runic J, Vojnovic S. Streptomyces sp. BV410: Interspecies cross-talk for staurosporine production. J Appl Microbiol. 2022 Oct;133(4):2560-2568. doi: 10.1111/jam.15726. Epub 2022 Aug 1. PMID: 35880373.


4: Chakraborty M, Rabby SMF, Gupta DR, Rahman M, Paul SK, Mahmud NU, Rahat AAM, Jankuloski L, Islam T. Natural Protein Kinase Inhibitors, Staurosporine, and Chelerythrine Suppress Wheat Blast Disease Caused by Magnaporthe oryzae Triticum. Microorganisms. 2022 Jun 9;10(6):1186. doi: 10.3390/microorganisms10061186. PMID: 35744705; PMCID: PMC9230996.


5: Brunelli F, Torosantucci L, Gelmetti V, Franzone D, Grünewald A, Krüger R, Arena G, Valente EM. PINK1 Protects against Staurosporine-Induced Apoptosis by Interacting with Beclin1 and Impairing Its Pro-Apoptotic Cleavage. Cells. 2022 Feb 15;11(4):678. doi: 10.3390/cells11040678. PMID: 35203326; PMCID: PMC8870463.


6: Luo Y, Tian L, Liang C, Xu Y. KLHL38 facilitates staurosporine-induced apoptosis in HL-1 cells via myocardin degradation. IUBMB Life. 2022 May;74(5):446-462. doi: 10.1002/iub.2602. Epub 2022 Feb 22. PMID: 35112472.


7: Conte M, Palumbo R, Monti A, Fontana E, Nebbioso A, Ruvo M, Altucci L, Doti N. Relevance of AIF/CypA Lethal Pathway in SH-SY5Y Cells Treated with Staurosporine. Int J Mol Sci. 2021 Dec 27;23(1):265. doi: 10.3390/ijms23010265. PMID: 35008690; PMCID: PMC8745523.


8: Meyer FAH, Kraus D, Glassmann A, Veit N, Winter J, Probstmeier R. The Presence of Yin-Yang Effects in the Migration Pattern of Staurosporine-Treated Single versus Collective Breast Carcinoma Cells. Int J Mol Sci. 2021 Nov 4;22(21):11961. doi: 10.3390/ijms222111961. PMID: 34769389; PMCID: PMC8584475.


9: Bassiouni W, Seubert JM, Schulz R. Staurosporine-induced cleavage of apoptosis-inducing factor in human fibrosarcoma cells is independent of matrix metalloproteinase-2. Can J Physiol Pharmacol. 2022 Feb;100(2):184-191. doi: 10.1139/cjpp-2021-0199. Epub 2021 Oct 1. PMID: 34597523.


10: Ren Z, Li Q, Shen Y, Meng L. Intrinsic relative preference profile of pan- kinase inhibitor drug staurosporine towards the clinically occurring gatekeeper mutations in Protein Tyrosine Kinases. Comput Biol Chem. 2021 Oct;94:107562. doi: 10.1016/j.compbiolchem.2021.107562. Epub 2021 Aug 12. PMID: 34428735.


11: Cai ZP, Cao C, Guo Z, Yu Y, Zhong SJ, Pan RY, Liang H, Lan R, Qin XY. Coeloglossum viride var. bracteatum extract attenuates staurosporine induced neurotoxicity by restoring the FGF2-PI3K/Akt signaling axis and Dnmt3. Heliyon. 2021 Jul 7;7(7):e07503. doi: 10.1016/j.heliyon.2021.e07503. PMID: 34401557; PMCID: PMC8353313.


12: Bustamante HA, Ehrich MF, Klein BG. Intracellular potassium depletion enhances apoptosis induced by staurosporine in cultured trigeminal satellite glial cells. Somatosens Mot Res. 2021 Sep;38(3):194-201. doi: 10.1080/08990220.2021.1941843. Epub 2021 Jun 30. PMID: 34187291.


13: Gayler KM, Kong K, Reisenauer K, Taube JH, Wood JL. Staurosporine Analogs Via C-H Borylation. ACS Med Chem Lett. 2020 Oct 30;11(12):2441-2445. doi: 10.1021/acsmedchemlett.0c00420. PMID: 33335665; PMCID: PMC7734790.


14: Chen P, Wang J, Wang X, Wang Y, Xu C, Ji C. Porcine ubiquitin-like protein MNSFβ promotes cell apoptosis and covalently binds to BCL-G to enhance staurosporine-induced apoptosis. Ann Transl Med. 2020 Oct;8(20):1306. doi: 10.21037/atm-20-6348. PMID: 33209886; PMCID: PMC7661876.


15: Voss TD, Gerget M, Linkus B, von Einem B, Landwehrmeyer GB, Lewerenz J. Ubiquitination and the proteasome rather than caspase-3-mediated C-terminal cleavage are involved in the EAAT2 degradation by staurosporine-induced cellular stress. J Neurochem. 2021 May;157(4):1284-1299. doi: 10.1111/jnc.15237. Epub 2020 Dec 3. PMID: 33180957.


16: Khosravi Babadi Z, Ebrahimipour G, Wink J, Narmani A, Risdian C. Isolation and identification of Streptomyces sp. Act4Zk, a good producer of Staurosporine and some derivatives. Lett Appl Microbiol. 2021 Feb;72(2):206-218. doi: 10.1111/lam.13415. Epub 2020 Nov 10. PMID: 33058293.


17: Musaogullari A, Mandato A, Chai YC. Role of Glutathione Depletion and Reactive Oxygen Species Generation on Caspase-3 Activation: A Study With the Kinase Inhibitor Staurosporine. Front Physiol. 2020 Aug 28;11:998. doi: 10.3389/fphys.2020.00998. PMID: 32982774; PMCID: PMC7485172.


18: Ren TT, Fan SR, Lang XY, Yu Y, Lan R, Qin XY. 2,3,5,4'-tetrahydoxystilbene-2-O-β-D-glucoside eliminates staurosporine-induced cytotoxicity by restoring BDNF-TrkB/Akt signaling axis. Int J Med Sci. 2020 Aug 19;17(14):2207-2213. doi: 10.7150/ijms.47919. PMID: 32922183; PMCID: PMC7484659.


19: Kido M, Idogaki H, Nishikawa K, Omasa T. Low-concentration staurosporine improves recombinant antibody productivity in Chinese hamster ovary cells without inducing cell death. J Biosci Bioeng. 2020 Nov;130(5):525-532. doi: 10.1016/j.jbiosc.2020.07.005. Epub 2020 Aug 12. PMID: 32800439.


20: Schwarz N, Tumpara S, Wrenger S, Ercetin E, Hamacher J, Welte T, Janciauskiene S. Alpha1-antitrypsin protects lung cancer cells from staurosporine-induced apoptosis: the role of bacterial lipopolysaccharide. Sci Rep. 2020 Jun 12;10(1):9563. doi: 10.1038/s41598-020-66825-w. PMID: 32533048; PMCID: PMC7293251.