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Evans blue (dye)

From Wikipedia, the free encyclopedia
Evans blue
Space-filling model of the Evans blue molecule, sodium salt
Names
IUPAC name
tetrasodium (6E,6'E)-6,6-[(3,3'-dimethylbiphenyl-4,4'-diyl)di(1E)hydrazin-2-yl-1-ylidene]bis(4-amino-5-oxo-5,6-dihydronaphthalene-1,3-disulfonate)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.005.676Edit this at Wikidata
KEGG
MeSHEvans+blue
UNII
  • 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+;;;;
    Key: KBNIFDASRCWYGC-KUDYKLHASA-J
  • [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)c6cc(c(N)c5c6C=C/C(=N\Nc1ccc(cc1C)c4ccc(N\N=C3/C=Cc2c(cc(c(N)c2C3=O)S([O-])(=O)=O)S([O-])(=O)=O)c(C)c4)C5=O)S([O-])(=O)=O
Properties
C34H24N6Na4O14S4
Molar mass960.809
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

T-1824 orEvans blue, often incorrectly rendered asEvan's blue, is anazo dye that has a very high affinity forserum albumin. Because of this, it can be useful inphysiology in estimating the proportion ofbody water contained inblood plasma.[1] It fluoresces with excitation peaks at 470 and 540 nm and an emission peak at 680 nm.[2]

Evans blue dye has been used as aviability assay on the basis of its penetration into non-viable cells, although the method is subject to error because it assumes that damaged or otherwise altered cells are not capable of repair and therefore are not viable.[3]

Evans blue is also used to assess the permeability of theblood–brain barrier to macromolecules. Because serum albumin cannot cross the barrier and virtually all Evans blue is bound to albumin, normally the neural tissue remains unstained.[4] When the blood–brain barrier has been compromised, albumin-bound Evans blue enters the CNS.

Evans blue is pharmacologically active, acting as anegative allosteric modulator of theAMPA andkainate receptors and as aninhibitor ofvesicular glutamate transporters.[5][6] It also acts onP2 receptors.[7]

It was named afterHerbert McLean Evans, an American anatomist.[8]

References

[edit]
  1. ^Nosek, Thomas M."Section 7/7ch02/7ch02p17".Essentials of Human Physiology. Archived fromthe original on 2016-03-24.
  2. ^Hed J, Dahlgren C, Rundquist I (1983). "A Simple Fluorescence Technique to Stain the Plasma Membrane of Human Neutrophils".Histochemistry.79 (1):105–10.doi:10.1007/BF00494347.PMID 6196326.S2CID 785829.
  3. ^Crutchfield A, Diller K, Brand J (1999). "Cryopreservation of Chlamydomonas reinhardtii (Chlorophyta)".European Journal of Phycology.34 (1):43–52.doi:10.1080/09670269910001736072.
  4. ^Hawkins BT, Egleton RD (2006). "Fluorescence imaging of blood–brain barrier disruption".Journal of Neuroscience Methods.151 (2):262–7.doi:10.1016/j.jneumeth.2005.08.006.PMID 16181683.S2CID 31154215.
  5. ^Schürmann, B.; Wu, X.; Dietzel, I. D.; Lessmann, V. (May 1997)."Differential modulation of AMPA receptor mediated currents by evans blue in postnatal rat hippocampal neurones".British Journal of Pharmacology.121 (2):237–247.doi:10.1038/sj.bjp.0701125.ISSN 0007-1188.PMC 1564681.PMID 9154333.
  6. ^Price, C. J.; Raymond, L. A. (December 1996). "Evans blue antagonizes both alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate and kainate receptors and modulates receptor desensitization".Molecular Pharmacology.50 (6):1665–1671.doi:10.1016/S0026-895X(25)09628-2.ISSN 0026-895X.PMID 8967991.
  7. ^Wittenburg, H.; Bültmann, R.; Pause, B.; Ganter, C.; Kurz, G.; Starke, K. (October 1996). "P2-purinoceptor antagonists: II. Blockade of P2-purinoceptor subtypes and ecto-nucleotidases by compounds related to Evans blue and trypan blue".Naunyn-Schmiedeberg's Archives of Pharmacology.354 (4):491–497.doi:10.1007/bf00168441.ISSN 0028-1298.PMID 8897453.S2CID 22823820.
  8. ^Venes, Donald. "Evans Blue".Taber's Cyclopedic Medical Dictionary.21: 818.


External links

[edit]
  • el-Sayed H, Goodall S, Hainsworth R (1995). "Re-evaluation of Evans blue dye dilution method of plasma volume measurement".Clin Lab Haematol.17 (2):189–94.PMID 8536425.
GABATooltip γ-Aminobutyric acidmetabolism andtransportmodulators
Transporter
GATTooltip GABA transporter
VIAATTooltip Vesicular inhibitory amino acid transporter
Enzyme
GADTooltip Glutamate decarboxylase
GABA-TTooltip γ-Aminobutyrate aminotransferase
Other
Antivitamin B6
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Transporter
EAATsTooltip Excitatory amino acid transporters
vGluTsTooltip Vesicular glutamate transporters
Enzyme
GAHTooltip Glutamine aminohydrolase (glutaminase)
ASTTooltip Aspartate aminotransferase
ALTTooltip Alanine aminotransferase
GDHTooltip Glutamate dehydrogenase
GSTooltip Glutamine synthetase
GADTooltip Glutamate decarboxylase
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others
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