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475848

Sigma-Aldrich

MIF Antagonist V, p425

The MIF Antagonist V, p425, also referenced under CAS 2610-05-1, controls the biological activity of MIF. This small molecule/inhibitor is primarily used for Cell Structure applications.

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Synonym(s):
MIF Antagonist V, p425, Sodium 6,6ʹ-(1 E,1ʹ E)-(3,3ʹ-dimethoxybiphenyl-4,4ʹ-diyl) bis(diazene-2,1-diyl) bis(4-amino-5-hydroxynaphthalene-1,3-disulfonate), Sodium 6,6ʹ-(1E,1ʹE)-(3,3ʹ-dimethoxybiphenyl-4,4ʹ-diyl)bis(diazene-2,1-diyl)bis(4-amino-5-hydroxynaphthalene-1,3-disulfonate)
Empirical Formula (Hill Notation):
C34H24N6Na4O16S4
CAS Number:
2610-05-1
Molecular Weight:
992.80
MDL number:
MFCD00004020
UNSPSC Code:
12171500
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)
protect from light

color

blue

solubility

water: 25 mg/mL

shipped in

ambient

storage temp.

2-8°C

SMILES string

OC1=C(C=CC(C(S(=O)(O[Na])=O)=C2)=C1C(N)=C2S(=O)(O[Na])=O)/N=N/C3=CC=C(C=C3OC)C4=CC(OC)=C(/N=N/C5=C(O)C6=C(C(S(=O)(O[Na])=O)=CC(S(=O)(O[Na])=O)=C6N)C=C5)C=C4

InChI

1S/C34H28N6O16S4.4Na/c1-55-23-11-15(3-7-19(23)37-39-21-9-5-17-25(57(43,44)45)13-27(59(49,50)51)31(35)29(17)33(21)41)16-4-8-20(24(12-16)56-2)38-40-22-10-6-18-26(58(46,47)48)14-28(60(52,53)54)32(36)30(18)34(22)42;;;;/h3-14,37-38H,35-36H2,1-2H3,(H,43,44,45)(H,46,47,48)(H,49,50,51)(H,52,53,54);;;;/q;4*+1/p-4/b39-21-,40-22+;;;;

InChI key

UPKAWFACSJWKND-ZXFFUEEESA-J

General description

A symmetrical bis-(amino, hydroxynaphthalenedisulfonate) compound that antagonizes macrophage migration inhibitory factor against receptor binding (IC50 = 810 nM against hMIF and CD74 interaction) and is more potent than ISO-1 (Cat. No. 475837) in suppressing MIF-induced cytokines and MMP-3 productions in human fibroblasts cultures (IC50 = ≤0.7 µM vs >5 µM). Unlike MIF Antagonists I-IV, p425 targets an area at the interface of two MIF trimers, distal to the active site.
A symmetrical bis-(amino, hydroxynaphthalenedisulfonate) compound that antagonizes macrophage migration inhibitory factor against receptor binding (IC50 = 810 nM against hMIF and CD74 interaction) and is more potent than ISO-1 (Cat. No. 475837) in suppressing both MIF-induced IL-6 and IL-8 production in human foreskin fibroblasts (IC50 = 0.6 - 0.7 µM vs >5 µM) and MIF-induced MMP-3 production in human synovial fibroblasts (IC50 = 0.1 µM vs >10 µM). Shown to exhibit little cytotoxicity in human foreskin fibroblast cultures even at concentrations as high as 100 µM. Unlike MIF Antagonists I-IV, p425 targets an area at the interface of two MIF trimers, distal to the active site.

Biochem/physiol Actions

Primary Target
MIF
Reversible: yes

Packaging

Packaged under inert gas

Warning

Toxicity: Harmful (C)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Bai, F., et al. 2012. J. Biol. Chem.287, 30653.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H350

Hazard Classifications

Carc. 1B

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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