Monastrol
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MedKoo CAT#: 406240

CAS#: 254753-54-3

Description: Monastrol is a kinesin Eg5 inhibitor. Induction of apoptosis by monastrol is independent of the spindle checkpoint. Monastrol binds to the KSP-ADP complex, forming a KSP-ADP- monastrol ternary complex, which cannot bind to microtubules productively and cannot undergo further ATP-driven conformational changes.


Price and Availability

Size
Price

100mg
USD 650
1g
USD 2250
Size
Price

200mg
USD 950
2g
USD 3250
Size
Price

500mg
USD 1650
5g
USD 5650

Monastrol, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 406240
Name: Monastrol
CAS#: 254753-54-3
Chemical Formula: C14H16N2O3S
Exact Mass: 292.08816
Molecular Weight: 292.35
Elemental Analysis: C, 57.52; H, 5.52; N, 9.58; O, 16.42; S, 10.97


Related CAS #: 254753-54-3   329689-23-8  

Synonym: Monastrol

IUPAC/Chemical Name: ethyl 4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

InChi Key: LOBCDGHHHHGHFA-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H16N2O3S/c1-3-19-13(18)11-8(2)15-14(20)16-12(11)9-5-4-6-10(17)7-9/h4-7,12,17H,3H2,1-2H3,(H2,15,16,20)

SMILES Code: O=C(C1=C(C)NC(NC1C2=CC=CC(O)=C2)=S)OCC


Technical Data

Appearance:
Solid powder

Purity:
>98%

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:
>5 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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Kaur J, Dutta S, Chang KP, Singh N. A member of the Ras oncogene family, RAP1A, mediates antileishmanial activity of monastrol. J Antimicrob Chemother. 2013 Jan 4. [Epub ahead of print] PubMed PMID: 23292345.

2: Sashidhara KV, Avula SR, Sharma K, Palnati GR, Bathula SR. Discovery of coumarin-monastrol hybrid as potential antibreast tumor-specific agent. Eur J Med Chem. 2013 Feb;60:120-7. doi: 10.1016/j.ejmech.2012.11.044. Epub 2012 Dec 8. PubMed PMID: 23287057.

3: Soumyanarayanan U, Bhat VG, Kar SS, Mathew JA. Monastrol mimic Biginelli dihydropyrimidinone derivatives: synthesis, cytotoxicity screening against HepG2 and HeLa cell lines and molecular modeling study. Org Med Chem Lett. 2012 Jun 12;2(1):23. doi: 10.1186/2191-2858-2-23. PubMed PMID: 22691177; PubMed Central PMCID: PMC3518143.

4: Kamal A, Shaheer Malik M, Bajee S, Azeeza S, Faazil S, Ramakrishna S, Naidu VG, Vishnuwardhan MV. Synthesis and biological evaluation of conformationally flexible as well as restricted dimers of monastrol and related dihydropyrimidones. Eur J Med Chem. 2011 Aug;46(8):3274-81. doi: 10.1016/j.ejmech.2011.04.048. Epub 2011 May 5. PubMed PMID: 21620531.

5: Zhang Z, Ge Y, Zhang D, Zhou X. High-content analysis in monastrol suppressor screens. A neural network-based classification approach. Methods Inf Med. 2011;50(3):265-72. doi: 10.3414/ME09-01-0030. Epub 2010 Jul 5. PubMed PMID: 20602002.

6: Blasco MA, Thumann S, Wittmann J, Giannis A, Gröger H. Enantioselective biocatalytic synthesis of (S)-monastrol. Bioorg Med Chem Lett. 2010 Aug 1;20(15):4679-82. doi: 10.1016/j.bmcl.2010.05.063. Epub 2010 May 25. PubMed PMID: 20566290.

7: Svetlik J, Veizerová L, Mayer TU, Catarinella M. Monastrol analogs: a synthesis of pyrazolopyridine, benzopyranopyrazolopyridine, and oxygen-bridged azolopyrimidine derivatives and their biological screening. Bioorg Med Chem Lett. 2010 Jul 15;20(14):4073-6. doi: 10.1016/j.bmcl.2010.05.085. Epub 2010 May 26. PubMed PMID: 20542426.

8: Kaur J, Sundar S, Singh N. Molecular docking, structure-activity relationship and biological evaluation of the anticancer drug monastrol as a pteridine reductase inhibitor in a clinical isolate of Leishmania donovani. J Antimicrob Chemother. 2010 Aug;65(8):1742-8. doi: 10.1093/jac/dkq189. Epub 2010 Jun 2. PubMed PMID: 20519355.

9: Lakämper S, Thiede C, Düselder A, Reiter S, Korneev MJ, Kapitein LC, Peterman EJ, Schmidt CF. The effect of monastrol on the processive motility of a dimeric kinesin-5 head/kinesin-1 stalk chimera. J Mol Biol. 2010 May 28;399(1):1-8. doi: 10.1016/j.jmb.2010.03.009. Epub 2010 Mar 19. PubMed PMID: 20227420.

10: Tcherniuk S, van Lis R, Kozielski F, Skoufias DA. Mutations in the human kinesin Eg5 that confer resistance to monastrol and S-trityl-L-cysteine in tumor derived cell lines. Biochem Pharmacol. 2010 Mar 15;79(6):864-72. doi: 10.1016/j.bcp.2009.11.001. Epub 2009 Nov 6. PubMed PMID: 19896928.

11: Kulkarni MG, Chavhan SW, Shinde MP, Gaikwad DD, Borhade AS, Dhondge AP, Shaikh YB, Ningdale VB, Desai MP, Birhade DR. Zeolite catalyzed solvent-free one-pot synthesis of dihydropyrimidin-2(1H)-ones--a practical synthesis of monastrol. Beilstein J Org Chem. 2009;5:4. doi: 10.3762/bjoc.5.4. Epub 2009 Feb 4. PubMed PMID: 19259340; PubMed Central PMCID: PMC2649439.

12: Dallinger D, Kappe CO. Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave-assisted synthesis. Nat Protoc. 2007;2(2):317-21. PubMed PMID: 17406591.

13: Garcia-Saez I, DeBonis S, Lopez R, Trucco F, Rousseau B, Thuéry P, Kozielski F. Structure of human Eg5 in complex with a new monastrol-based inhibitor bound in the R configuration. J Biol Chem. 2007 Mar 30;282(13):9740-7. Epub 2007 Jan 23. PubMed PMID: 17251189.

14: Bevan DR, Garst JF, Osborne CK, Sims AM. Application of molecular modeling to analysis of inhibition of kinesin motor proteins of the BimC subfamily by monastrol and related compounds. Chem Biodivers. 2005 Nov;2(11):1525-32. PubMed PMID: 17191952.

15: Chin GM, Herbst R. Induction of apoptosis by monastrol, an inhibitor of the mitotic kinesin Eg5, is independent of the spindle checkpoint. Mol Cancer Ther. 2006 Oct;5(10):2580-91. PubMed PMID: 17041103.

16: Russowsky D, Canto RF, Sanches SA, D'Oca MG, de Fátima A, Pilli RA, Kohn LK, Antônio MA, de Carvalho JE. Synthesis and differential antiproliferative activity of Biginelli compounds against cancer cell lines: Monastrol, oxo-monastrol and oxygenated analogues. Bioorg Chem. 2006 Aug;34(4):173-82. Epub 2006 Jun 12. PubMed PMID: 16765411.

17: Müller C, Gross D, Sarli V, Gartner M, Giannis A, Bernhardt G, Buschauer A. Inhibitors of kinesin Eg5: antiproliferative activity of monastrol analogues against human glioblastoma cells. Cancer Chemother Pharmacol. 2007 Feb;59(2):157-64. Epub 2006 May 16. PubMed PMID: 16703323.

18: Krzysiak TC, Wendt T, Sproul LR, Tittmann P, Gross H, Gilbert SP, Hoenger A. A structural model for monastrol inhibition of dimeric kinesin Eg5. EMBO J. 2006 May 17;25(10):2263-73. Epub 2006 Apr 27. PubMed PMID: 16642039; PubMed Central PMCID: PMC1462975.

19: Maliga Z, Mitchison TJ. Small-molecule and mutational analysis of allosteric Eg5 inhibition by monastrol. BMC Chem Biol. 2006 Feb 27;6:2. PubMed PMID: 16504166; PubMed Central PMCID: PMC1448180.

20: Maliga Z, Xing J, Cheung H, Juszczak LJ, Friedman JM, Rosenfeld SS. A pathway of structural changes produced by monastrol binding to Eg5. J Biol Chem. 2006 Mar 24;281(12):7977-82. Epub 2006 Jan 23. PubMed PMID: 16434397.