ML188


Catalog No. size PriceQuantity
M7138-2 2mg solid $151
M7138-10 10mg solid $603

Description

Cas:1417700-13-0 (R-isomer)

Product Information

ML188 is a Potent Noncovalent Small Molecule Inhibitor of the Severe Acute Respiratory Syndrome Coronavirus (SARS-CoV) 3CL Protease. The X-ray structure of SARS-CoV 3CLpro bound with ML188 was instrumental in guiding subsequent rounds of chemistry optimization. ML188 provides an excellent starting point for the further design and refinement of 3CLpro inhibitors that act by a noncovalent mechanism of action.

 

Chemical Formula: C26H31N3O3

 

Exact Mass: 433.2365

 

Molecular Weight: 433.552

 

Elemental Analysis: C, 72.03; H, 7.21; N, 9.69; O, 11.07

 

Synonym: 

 

ML188

ML-188

ML 188

 

Chemical Name: N-[(1R)-2-(tert-Butylamino)-2-oxo-1-pyridin-3-ylethyl]-N-(4-tert-butylphenyl)furan-2-carboxamide

 

InChi Key: 

JXGIYKRRPGCLFV-JOCHJYFZSA-N

 

InChi Code: InChI=1S/C26H31N3O3/c1-25(2,3)19-11-13-20(14-12-19)29(24(31)21-10-8-16-32-21)22(18-9-7-15-27-17-18)23(30)28-26(4,5)6/h7-17,22H,1-6H3,(H,28,30)/t22-/m1/s1

 

Smiles Code:

O=C(C1=CC=CO1)N([C@H](C2=CC=CN=C2)C(NC(C)(C)C)=O)C3=CC=C(C(C)(C)C)C=C3

 

 

Technical Data:

 

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

Shelf Life: >3 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

 

In Vitro

ML188 (0-30 μM; 48 hours) effectively inhibit SARS-CoV replication in cell culture.

Probe ML188 is a modest molecular weight SARS-CoV 3CLpro inhibitor with demonstrated antiviral activity and a non-covalent mechanism of action. ML188 yields an antiviral EC50 value ranging from 12.9 to 13.4 μM in mock-infected and SARS-CoV infected cells

 

 

References

 

  1. Berry M, Fielding B, Gamieldien J. Human coronavirus OC43 3CL protease and the potential of ML188 as a broad-spectrum lead compound: homology modelling and molecular dynamic studies. BMC Struct Biol. 2015 Apr 28;15:8. doi: 10.1186/s12900-015-0035-3. PMID: 25928480; PMCID: PMC4411765.

 

  1. Turlington M, Chun A, Tomar S, Eggler A, Grum-Tokars V, Jacobs J, Daniels JS, Dawson E, Saldanha A, Chase P, Baez-Santos YM, Lindsley CW, Hodder P, Mesecar AD, Stauffer SR. Discovery of N-(benzo[1,2,3]triazol-1-yl)-N-(benzyl)acetamido)phenyl) carboxamides as severe acute respiratory syndrome coronavirus (SARS-CoV) 3CLpro inhibitors: identification of ML300 and noncovalent nanomolar inhibitors with an induced-fit binding. Bioorg Med Chem Lett. 2013 Nov 15;23(22):6172-7. doi: 10.1016/j.bmcl.2013.08.112. Epub 2013 Sep 7. PMID: 24080461; PMCID: PMC3878165.

 

  1. Turlington M, Chun A, Jacobs J, Dawson E, Daniels JS, Saldanha A, Chase P, Hodder P, Eggler A, Tokars V, Mesecar A, Lindsley CW, Stauffer SR. Non-covalent triazole-based inhibitors of the SARS main proteinase 3CLpro. 2012 Apr 9 [updated 2013 Mar 14]. In: Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010–. PMID: 23762941.

 

  1. Jacobs J, Zhou S, Dawson E, Daniels JS, Hodder P, Tokars V, Mesecar A, Lindsley CW, Stauffer SR. Discovery of non-covalent inhibitors of the SARS main proteinase 3CLpro. 2010 Oct 30 [updated 2013 Feb 28]. In: Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010–. PMID: 23658941.

 

  1. Jacobs J, Grum-Tokars V, Zhou Y, Turlington M, Saldanha SA, Chase P, Eggler A, Dawson ES, Baez-Santos YM, Tomar S, Mielech AM, Baker SC, Lindsley CW, Hodder P, Mesecar A, Stauffer SR. Discovery, synthesis, and structure-based optimization of a series of N-(tert-butyl)-2-(N-arylamido)-2-(pyridin-3-yl) acetamides (ML188) as potent noncovalent small molecule inhibitors of the severe acute respiratory syndrome coronavirus (SARS-CoV) 3CL protease. J Med Chem. 2013 Jan 24;56(2):534-46. doi: 10.1021/jm301580n. Epub 2013 Jan 3. PMID: 23231439; PMCID: PMC3569073.

 

Products are for research use only. Not for human use.

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