Editing DAPI (section)

{{short description|Fluorescent stain}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 443556310
| ImageFile=DAPI.svg
| ImageSize=200px
| ImageFile1=DAPI Space Fill.png
| ImageSize1=200px
| IUPACName=2-(4-Amidinophenyl)-1''H''-indole-6-carboxamidine
| OtherNames=4′,6-Diamidino-2-phenylindole
|Section1={{Chembox Identifiers
| InChI = 1/C16H15N5/c17-15(18)10-3-1-9(2-4-10)13-7-11-5-6-12(16(19)20)8-14(11)21-13/h1-8,21H,(H3,17,18)(H3,19,20)
| InChIKey = FWBHETKCLVMNFS-UHFFFAOYAH
| SMILES1 = [H]/N=C(/c1ccc(cc1)c2cc3ccc(cc3[nH]2)/C(=N/[H])/N)\N
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 48217
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H15N5/c17-15(18)10-3-1-9(2-4-10)13-7-11-5-6-12(16(19)20)8-14(11)21-13/h1-8,21H,(H3,17,18)(H3,19,20)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FWBHETKCLVMNFS-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=28718-90-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 76BFW26YJO
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2848
| PubChem=2954
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 51231
| SMILES = [N@H]=C(N)c3ccc(c2cc1ccc(cc1[nH]2)C(=[N@H])N)cc3
}}
|Section2={{Chembox Properties
| C=16 | H=15 | N=5
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
  }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
}}

'''DAPI''' (pronounced 'DAPPY', /ˈdæpiː/), or '''4′,6-diamidino-2-phenylindole''', is a [[fluorescence|fluorescent]] [[staining (biology)|stain]] that binds strongly to [[adenine]]–[[thymine]]-rich regions in [[DNA]].  It is used extensively in [[fluorescence microscopy]]. As DAPI can pass through an intact [[cell membrane]], it can be used to stain both live and [[Fixation (histology)|fixed]] cells, though it passes through the membrane less efficiently in live cells and therefore provides a marker for membrane viability.