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SML2139

Sigma-Aldrich

MDL-860

≥98% (HPLC)

Synonym(s):

2-(3,4-Dichlorophenoxy)-5-nitrobenzonitrile

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5 MG
CZK 1,720.00
25 MG
CZK 6,910.00

CZK 1,720.00

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5 MG
CZK 1,720.00
25 MG
CZK 6,910.00

About This Item

Empirical Formula (Hill Notation):
C13H6Cl2N2O3
CAS Number:
78940-62-2
Molecular Weight:
309.10
MDL number:
MFCD07832293
UNSPSC Code:
12352200
NACRES:
NA.77

CZK 1,720.00

Please contact Customer Service for Availability

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

ClC1=CC=C(OC2=CC=C([N+]([O-])=O)C=C2C#N)C=C1Cl

InChI

1S/C13H6Cl2N2O3/c14-11-3-2-10(6-12(11)15)20-13-4-1-9(17(18)19)5-8(13)7-16/h1-6H

InChI key

QAYKDRUKUZJJSO-UHFFFAOYSA-N

Biochem/physiol Actions

MDL-860 is a 5-nitro-2-phenoxybenzonitrile that exerts broad-spectrum antipicornaviral activity (MIC50 from 0.1-1.5 μg/mL in HeLa cultures) by acting as an irreversible inhibitor against host phosphatidylinositol-4 kinase beta (PI4KB; PtdIns 4-kinase beta; PI4Kbeta; NPIK; PI4K92) via covalent modification of Cys646 located at the bottom of a surface pocket apart from the PI4KB active site. MCL-860 (MIC50 from 0.1-1.5 μg/mL in HeLa cultures). A pleconaril/MDL-860/oxoglaucine consecutive alternating administration (CAA), but not simultaneous daily treatment, is reported to be effective against coxsackievirus B1 infection without the development of drug resistance in newborn mice (75 mg/kg MDL-860 via s.c. every third day on the day following pleconaril and prior to oxoglaucine).
Phosphatidylinositol 4-kinase Beta (PI4KB) inhibitor with broad-spectrum antipicornavirus activity.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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H L Torney et al.
Antimicrobial agents and chemotherapy, 22(4), 635-638 (1982-10-01)
A nitrobenzene derivative, MDL-860, was found to inhibit plaque formation, cytopathic effect, or both in 11 of 12 picornaviruses at concentrations which did not affect cell growth. The compound did not directly inactivate the virus. MDL-860 inhibited actinomycin D-resistant [3H]uridine
Minetaro Arita et al.
ACS infectious diseases, 3(8), 585-594 (2017-06-13)
MDL-860 is a broad-spectrum antipicornavirus compound discovered in 1982 and one of the few promising candidates effective in in vivo virus infection. Despite the effectiveness, the target and the mechanism of action of MDL-860 remain unknown. Here, we have characterized
Georgi M Dobrikov et al.
Bioorganic & medicinal chemistry letters, 27(19), 4540-4543 (2017-09-06)
A series of twelve novel compounds, analogues of antiviral agent MDL-860 were synthesized and their antiviral activity was evaluated in vitro against enteroviruses poliovirus 1 (PV1), Coxsackieviruses B1 (CVB1) and Coxsackieviruses B3 (CVB3). Compounds 14, 24 and 25 manifested strong
R D Powers et al.
Antimicrobial agents and chemotherapy, 22(4), 639-642 (1982-10-01)
The newly synthesized compound 2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile (MDL-860) has been found to inhibit picornavirus replication. In multiple growth cycle experiments, 1 microgram of MDL-860 per ml caused a reduction in virus yield of at least 1.0 log10 50% tissue culture infectious doses

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