{{chembox | Verifiedfields = changed | verifiedrevid = 477226461 | Reference=<ref name="ref">[http://www.interchim.fr/ft/1/132303.pdf 7-Aminoactinomycin D] at Interchim</ref> | ImageFile=7-Aminoactinomycin D.png | IUPACName= | OtherNames=7-Amino-actinomycin D |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 21326185 | EINECS = 635-285-6 | Beilstein = 5915844 | InChI = 1/C62H87N13O16/c1-26(2)42-59(85)74-21-17-19-36(74)57(83)70(13)24-38(76)72(15)48(28(5)6)61(87)89-32(11)44(55(81)66-42)68-53(79)34-23-35(63)30(9)51-46(34)65-47-40(41(64)50(78)31(10)52(47)91-51)54(80)69-45-33(12)90-62(88)49(29(7)8)73(16)39(77)25-71(14)58(84)37-20-18-22-75(37)60(86)43(27(3)4)67-56(45)82/h23,26-29,32-33,36-37,42-45,48-49H,17-22,24-25,63-64H2,1-16H3,(H,66,81)(H,67,82)(H,68,79)(H,69,80)/t32-,33-,36+,37+,42-,43-,44+,45+,48+,49+/m1/s1 | InChIKey = YXHLJMWYDTXDHS-IRFLANFNBD | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C62H87N13O16/c1-26(2)42-59(85)74-21-17-19-36(74)57(83)70(13)24-38(76)72(15)48(28(5)6)61(87)89-32(11)44(55(81)66-42)68-53(79)34-23-35(63)30(9)51-46(34)65-47-40(41(64)50(78)31(10)52(47)91-51)54(80)69-45-33(12)90-62(88)49(29(7)8)73(16)39(77)25-71(14)58(84)37-20-18-22-75(37)60(86)43(27(3)4)67-56(45)82/h23,26-29,32-33,36-37,42-45,48-49H,17-22,24-25,63-64H2,1-16H3,(H,66,81)(H,67,82)(H,68,79)(H,69,80)/t32-,33-,36+,37+,42-,43-,44+,45+,48+,49+/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YXHLJMWYDTXDHS-IRFLANFNSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=7240-37-1 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = DXS32PH95R | PubChem=16218991 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 52304 | SMILES=O=C3C(C)=C2OC1=C(C)C(N)=CC(C(N[C@H](C(N[C@@H](C7=O)[C@H](C)C)=O)[C@@H](C)OC([C@H]([C@H](C)C)N(C)C(CN(C)[C@]([C@H]6N7CCC6)=O)=O)=O)=O)=C1N=C2C(C(N[C@H](C(N[C@H]([C@H](C)C)C4=O)=O)[C@@H](C)OC([C@H]([C@@H](C)C)N(C)C(CN(C)[C@@]([C@H]5N4CCC5)=O)=O)=O)=O)=C3N }} |Section2={{Chembox Properties | Formula=C<sub>62</sub>H<sub>87</sub>N<sub>13</sub>O<sub>16</sub> | MolarMass=1270.43 g/mol | Appearance=Red to dark purple powder | Density= | MeltingPt= | BoilingPt= | Solubility= }} |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = | GHSPictograms = {{GHS06}}{{GHS08}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|300|310|315|319|330|335|350|360}} | PPhrases = {{P-phrases|201|202|260|261|262|264|270|271|280|281|284|301+310|302+350|302+352|304+340|305+351+338|308+313|310|312|320|321|322|330|332+313|337+313|361|362|363|403+233|405|501}} }} }}

'''7-Aminoactinomycin D''' ('''7-AAD''') is a fluorescent chemical compound with a strong affinity for DNA. It is used as a fluorescent marker for DNA in fluorescence microscopy and flow cytometry. It intercalates in double-stranded DNA, with a high affinity for GC-rich regions,<ref>{{cite journal |author=Liu X |author2=Chen H |author3=Patel D |title=Solution structure of actinomycin-DNA complexes: drug intercalation at isolated G-C sites |journal=J Biomol NMR |volume=1 |issue=4 |pages=323–47 |date=1991 |pmid=1841703 |doi=10.1007/BF02192858|s2cid=40569430 }}</ref> making it useful for chromosome banding studies.<ref>{{cite journal |author=Latt S |title=Fluorescent probes of chromosome structure and replication |journal=Can J Genet Cytol |volume=19 |issue=4 |pages=603–23 |date=1977 |doi=10.1139/g77-065 |pmid=76502}}</ref>

== Applications== With an absorption maximum at 546&nbsp;nm, 7-AAD is efficiently excited using a 543&nbsp;nm helium–neon laser; it can also be excited with somewhat lower efficiency using a 488&nbsp;nm or 514&nbsp;nm argon laser lines. Its emission has a very large Stokes shift with a maximum in the deep red: 647&nbsp;nm. 7-AAD is therefore compatible with most blue and green fluorophores &ndash; and even many red fluorophores &ndash; in multicolour applications.

7-AAD does not readily pass through intact cell membranes; if it is to be used as a stain for imaging DNA fluorescence, the cell membrane must be permeabilized or disrupted. This method can be used in combination with formaldehyde fixation of samples.

7-AAD is also used as a cell viability stain. Cells with compromised membranes will stain with 7-AAD, while live cells with intact cell membranes will remain dark. Viability of the cells in flow cytometry should be around 95% but not less than 90%.<ref>{{cite web|url=https://medicine.yale.edu/immuno/flowcore/protocols/analysis/|title=Flow cytometry (FACS) staining protocol (Cell surface staining)|website=Yale School of Medicine - Yale Flow Cytometry|accessdate=2023-10-17}}</ref> [[File:Flow cytometric viability by 7-AAD.png|thumb|center|Flow cytometry using 7-AAD, wherein a lower signal indicates viable cells. Therefore, this case shows good viability.]]

== Actinomycin D == {{main|Actinomycin}} The related compound actinomycin D is nonfluorescent, but binds DNA in the same way as 7-AAD. Its absorbance changes when bound to DNA, and it can be used as a stain in conventional transmission microscopy.

==References== {{reflist}}

==Gallery== <gallery> File:7-AADSpektrum.png|Absorptions </gallery>

== External links == * [https://web.archive.org/web/20070517233816/http://probes.invitrogen.com/servlets/structure?item=1310 Structure from Invitrogen] * [http://www.fermentek.co.il/MSDS/7AAD-MSDS.htm MSDS] {{Webarchive|url=https://web.archive.org/web/20140806234251/http://www.fermentek.co.il/MSDS/7AAD-MSDS.htm |date=2014-08-06 }}

{{DEFAULTSORT:Aminoactinomycin D, 7-}} Category:Fluorescent dyes Category:Cell imaging Category:Staining dyes Category:Cell biology Category:DNA intercalaters