Evans blue, L-glutamate uptake inhibitor

Key facts

Purity

> 95%

Form

Solid

Molecular weight

960.8 Da

Molecular formula

C₃₄H₂₄N₆Na₄O₁₄S₄

PubChem identifier

9566057

Nature

Synthetic

Biochemical name

tetrasodium;(6E)-4-amino-6-[[4-[4-[(2E)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methylphenyl]-2-methylphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate

Biological description

Potent inhibitor of L-glutamate uptake via the membrane bound excitatory amino acid transporter (EAAT). Able to antagonize AMPA and kainate receptor mediated currents (IC₅₀ values are 220 and 150 nM, respectively). Binds with high affinity to serum albumin.

Canonical SMILES

CC1=C(C=CC(=C1)C2=CC(=C(C=C2)NN=C3C=CC4=C(C3=O)C(=C(C=C4S(=O)(=O)[O-])S(=O)(=O)[O-])N)C)NN=C5C=CC6=C(C5=O)C(=C(C=C6S(=O)(=O)[O-])S(=O)(=O)[O-])N.[Na+].[Na+].[Na+].[Na+]

Isomeric SMILES

CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N/N=C\3/C(=O)C4=C(C(=CC(=C4N)S(=O)(=O)[O-])S(=O)(=O)[O-])C=C3)C)N/N=C\5/C(=O)C6=C(C(=CC(=C6N)S(=O)(=O)[O-])S(=O)(=O)[O-])C=C5.[Na+].[Na+].[Na+].[Na+]

InChI

InChI=1S/C34H28N6O14S4.4Na/c1-15-11-17(3-7-21(15)37-39-23-9-5-19-25(55(43,44)45)13-27(57(49,50)51)31(35)29(19)33(23)41)18-4-8-22(16(2)12-18)38-40-24-10-6-20-26(56(46,47)48)14-28(58(52,53)54)32(36)30(20)34(24)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/b39-23+,40-24+;;;;

InChIKey

KBNIFDASRCWYGC-GXNXWABVSA-J

IUPAC name

tetrasodium;(6E)-4-amino-6-[[4-[4-[(2E)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methylphenyl]-2-methylphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate