Synonym
Stauprimide; N-Benzoyl-7-oxostaurosporine;
IUPAC/Chemical Name
N-[(2S,3R,4R,6R)-3-Methoxy-2-methyl-16,18-dioxo-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-nonaen-4-yl]-N-methylbenzamide
InChi Key
MQCCJEYZKWZQHU-MPRCCEKMSA-N
InChi Code
InChI=1S/C35H28N4O5/c1-35-31(43-3)23(37(2)34(42)18-11-5-4-6-12-18)17-24(44-35)38-21-15-9-7-13-19(21)25-27-28(33(41)36-32(27)40)26-20-14-8-10-16-22(20)39(35)30(26)29(25)38/h4-16,23-24,31H,17H2,1-3H3,(H,36,40,41)/t23-,24-,31-,35+/m1/s1
SMILES Code
O=C(N([C@H](C[C@](O1)([H])N2C3=CC=CC=C3C4=C5C(N6)=O)[C@@H](OC)[C@@]1(C)N(C7=C42)C8=CC=CC=C8C7=C5C6=O)C)C9=CC=CC=C9
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
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
Biological target:
Stauprimide increases the efficiency of mouse and human embryonic stem cell differentiation in conjunction with lineage specification cues (EC50 = 0.3 μM). It specifically inhibits the nuclear localization of NME2, resulting in the suppression of c-Myc.
In vitro activity:
In small cell lung carcinoma (SCLC) cells, albeit a higher substrate specificity, staurosporine analogs can induce staurosporine-comparable effects. In H1184 cells, process formation was predominantly induced by staurosporine and, to lesser extent, in lestaurtinib-, stauprimide-, and UCN-01-treated cells. There was induction of polyploidy in all staurosporine and in two out of four stauprimide-treated SCLC cell lines.
Reference: Tumour Biol. 2015 Apr;36(4):2725-35. https://pubmed.ncbi.nlm.nih.gov/25487614/
In vivo activity:
Stauprimide has potential as a putative therapeutic agent in triple-negative breast cancer. Orthotopic MDA-MB-231 xenograft and 4T1 syngeneic models suggested an effect of stauprimide in vivo, increasing the necrotic core of tumors and reducing metastasis in lung and liver of mice.
Reference: Biomed Pharmacother. 2023 Feb;158:114070. https://pubmed.ncbi.nlm.nih.gov/36526536/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
25.0 |
42.76 |
| DMSO |
10.0 |
17.10 |
| Ethanol |
0.2 |
0.34 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
584.63
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.
| 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. Gallala H, Winter J, Veit N, Nowak M, Perner S, Courts C, Kraus D, Janzen V, Probstmeier R. Staurosporine analogs promote distinct patterns of process outgrowth and polyploidy in small cell lung carcinoma cells. Tumour Biol. 2015 Apr;36(4):2725-35. doi: 10.1007/s13277-014-2897-6. Epub 2014 Dec 7. PMID: 25487614.
2. Zhu S, Wurdak H, Wang J, Lyssiotis CA, Peters EC, Cho CY, Wu X, Schultz PG. A small molecule primes embryonic stem cells for differentiation. Cell Stem Cell. 2009 May 8;4(5):416-26. doi: 10.1016/j.stem.2009.04.001. PMID: 19427291.
3. Carrillo P, Bernal M, Téllez-Quijorna C, Marrero AD, Vidal I, Castilla L, Caro C, Domínguez A, García-Martín ML, Quesada AR, Medina MA, Martínez-Poveda B. The synthetic molecule stauprimide impairs cell growth and migration in triple-negative breast cancer. Biomed Pharmacother. 2023 Feb;158:114070. doi: 10.1016/j.biopha.2022.114070. Epub 2022 Dec 14. PMID: 36526536.
4. Bouvard C, Lim SM, Ludka J, Yazdani N, Woods AK, Chatterjee AK, Schultz PG, Zhu S. Small molecule selectively suppresses MYC transcription in cancer cells. Proc Natl Acad Sci U S A. 2017 Mar 28;114(13):3497-3502. doi: 10.1073/pnas.1702663114. Epub 2017 Mar 14. PMID: 28292893; PMCID: PMC5380033.
In vitro protocol:
1. Gallala H, Winter J, Veit N, Nowak M, Perner S, Courts C, Kraus D, Janzen V, Probstmeier R. Staurosporine analogs promote distinct patterns of process outgrowth and polyploidy in small cell lung carcinoma cells. Tumour Biol. 2015 Apr;36(4):2725-35. doi: 10.1007/s13277-014-2897-6. Epub 2014 Dec 7. PMID: 25487614.
2. Zhu S, Wurdak H, Wang J, Lyssiotis CA, Peters EC, Cho CY, Wu X, Schultz PG. A small molecule primes embryonic stem cells for differentiation. Cell Stem Cell. 2009 May 8;4(5):416-26. doi: 10.1016/j.stem.2009.04.001. PMID: 19427291.
In vivo protocol:
1. Carrillo P, Bernal M, Téllez-Quijorna C, Marrero AD, Vidal I, Castilla L, Caro C, Domínguez A, García-Martín ML, Quesada AR, Medina MA, Martínez-Poveda B. The synthetic molecule stauprimide impairs cell growth and migration in triple-negative breast cancer. Biomed Pharmacother. 2023 Feb;158:114070. doi: 10.1016/j.biopha.2022.114070. Epub 2022 Dec 14. PMID: 36526536.
2. Bouvard C, Lim SM, Ludka J, Yazdani N, Woods AK, Chatterjee AK, Schultz PG, Zhu S. Small molecule selectively suppresses MYC transcription in cancer cells. Proc Natl Acad Sci U S A. 2017 Mar 28;114(13):3497-3502. doi: 10.1073/pnas.1702663114. Epub 2017 Mar 14. PMID: 28292893; PMCID: PMC5380033.
1: Carrillo P, Bernal M, Téllez-Quijorna C, Marrero AD, Vidal I, Castilla L, Caro C, Domínguez A, García-Martín ML, Quesada AR, Medina MA, Martínez-Poveda B. The synthetic molecule stauprimide impairs cell growth and migration in triple- negative breast cancer. Biomed Pharmacother. 2023 Feb;158:114070. doi: 10.1016/j.biopha.2022.114070. Epub 2022 Dec 14. PMID: 36526536.
2: Bouvard C, Lim SM, Ludka J, Yazdani N, Woods AK, Chatterjee AK, Schultz PG, Zhu S. Small molecule selectively suppresses MYC transcription in cancer cells. Proc Natl Acad Sci U S A. 2017 Mar 28;114(13):3497-3502. doi: 10.1073/pnas.1702663114. Epub 2017 Mar 14. PMID: 28292893; PMCID: PMC5380033.
3: Gallala H, Winter J, Veit N, Nowak M, Perner S, Courts C, Kraus D, Janzen V, Probstmeier R. Staurosporine analogs promote distinct patterns of process outgrowth and polyploidy in small cell lung carcinoma cells. Tumour Biol. 2015 Apr;36(4):2725-35. doi: 10.1007/s13277-014-2897-6. Epub 2014 Dec 7. PMID: 25487614.
4: Tahamtani Y, Azarnia M, Farrokhi A, Moradmand A, Mirshahvaladi S, Aghdami N, Baharvand H. Stauprimide Priming of Human Embryonic Stem Cells toward Definitive Endoderm. Cell J. 2014 Feb 3;16(1):63-72. Epub 2014 Feb 3. PMID: 24518969; PMCID: PMC3933440.
5: Tahamtani Y, Azarnia M, Farrokhi A, Sharifi-Zarchi A, Aghdami N, Baharvand H. Treatment of human embryonic stem cells with different combinations of priming and inducing factors toward definitive endoderm. Stem Cells Dev. 2013 May 1;22(9):1419-32. doi: 10.1089/scd.2012.0453. Epub 2013 Feb 1. PMID: 23249309.
6: Zhu S, Wurdak H, Wang J, Lyssiotis CA, Peters EC, Cho CY, Wu X, Schultz PG. A small molecule primes embryonic stem cells for differentiation. Cell Stem Cell. 2009 May 8;4(5):416-26. doi: 10.1016/j.stem.2009.04.001. PMID: 19427291.
