View source for 5-Bromo-4-chloro-3-indolyl phosphate

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 445341734
|   Name = BCIP
|   ImageFile = BCIP.svg
|   ImageSize = 200px
|   ImageAlt = Skeletal formula of BCIP
|   ImageFile1 = 5-Bromo-4-chloro-3-indolyl-phosphate-3D-balls.png
|   ImageSize1 = 220
|   ImageAlt1 = Ball-and-stick model of the BCIP molecule
|   PIN = 5-Bromo-4-chloro-1''H''-indol-3-yl dihydrogen phosphate
|   OtherNames = BCIP
| Section1 = {{Chembox Identifiers
|   SMILES = C1=CC(=C(C2=C1NC=C2OP(=O)(O)O)Cl)Br
|   CASNo = 38404-93-2
|   CASNo_Ref = {{cascite|correct|??}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BZ64NZV99J
|   PubChem = 65409
|   RTECS =
|  ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 58873
|  InChI = 1/C8H6BrClNO4P/c9-4-1-2-5-7(8(4)10)6(3-11-5)15-16(12,13)14/h1-3,11H,(H2,12,13,14)
|  InChIKey = QRXMUCSWCMTJGU-UHFFFAOYAN
|  StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C8H6BrClNO4P/c9-4-1-2-5-7(8(4)10)6(3-11-5)15-16(12,13)14/h1-3,11H,(H2,12,13,14)
|  StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = QRXMUCSWCMTJGU-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
|   C=8|H=6|Br=1|Cl=1|N=1|O=4|P=1
|   Appearance = Colorless
|   Density =
|   Solubility = soluble in [[water]] (sodium salt)
|   MeltingPt =
}}
}}
'''5-Bromo-4-chloro-3-indolyl phosphate''' (BCIP, X-phosphate, XP) is an artificial chromogenic [[Substrate (biochemistry)|substrate]] used for the sensitive [[colorimetric]] detection of [[alkaline phosphatase]] activity. It is, for example, used in [[immunoblotting]], [[in situ hybridization]], and [[immunohistochemistry]], often in combination with [[nitro blue tetrazolium chloride]] (NBT).<ref>{{cite web|url=http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/B1026|title=5-Bromo-4-chloro-3-indolyl phosphate disodium salt|website=Millipore Sigma}}</ref><ref>
Alkaline phosphatase hydrolyses BCIP to 5-bromo-4-chloro-3-indoxyl<JP Horwitz J. Med. Chem., 1966, 9 (3), pp 447–447 and inorganic [[phosphate]]</ref> 5-bromo-4-chloro-3-indoxyl is oxidized by atmospheric oxygen to form the blue dye 5,5′-dibromo-4,4′-dichloro-indigo. It is also oxidized by nitroblue tetrazolium (NBT), which forms an insoluble dark blue diformazan precipitate after reduction. Alkaline phosphatase is commonly conjugated to [[secondary antibodies]].
==References==
{{reflist}}
{{DEFAULTSORT:Bromo-4-Chloro-3-Indolyl Phosphate, 5-}}
[[Category:Biochemistry detection reactions]]
[[Category:Indoles]]
[[Category:Organophosphates]]
[[Category:Chloroarenes]]
[[Category:Bromoarenes]]