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Revision as of 18:40, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465360826 of page 7-Aminoactinomycin_D for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 12:16, 26 October 2023 edit Mikael Häggström (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers57,759 editsm linked 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 443358125 | verifiedrevid = 477226461
|Reference=<ref> at ]</ref> | Reference=<ref name="ref"> at ]</ref>
|ImageFile=7-Aminoactinomycin D.png | ImageFile=7-Aminoactinomycin D.png
|ImageSize=200px
|IUPACName= | IUPACName=
|OtherNames=7-Amino-actinomycin D | OtherNames=7-Amino-actinomycin D
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21326185 | 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 | 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 | InChIKey = YXHLJMWYDTXDHS-IRFLANFNBD
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YXHLJMWYDTXDHS-IRFLANFNSA-N | StdInChIKey = YXHLJMWYDTXDHS-IRFLANFNSA-N
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 7240-37-1 --> | CASNo=7240-37-1
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem=16218991
| UNII = DXS32PH95R
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | PubChem=16218991
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 52304 | ChEBI = 52304
| SMILES=O=C3C(C)=C2OC1=C(C)C(N)=CC(C(N(C(N(C7=O)(C)C)=O)(C)OC(((C)C)N(C)C(CN(C)(6N7CCC6)=O)=O)=O)=O)=C1N=C2C(C(N(C(N((C)C)C4=O)=O)(C)OC(((C)C)N(C)C(CN(C)(5N4CCC5)=O)=O)=O)=O)=C3N | SMILES=O=C3C(C)=C2OC1=C(C)C(N)=CC(C(N(C(N(C7=O)(C)C)=O)(C)OC(((C)C)N(C)C(CN(C)(6N7CCC6)=O)=O)=O)=O)=C1N=C2C(C(N(C(N((C)C)C4=O)=O)(C)OC(((C)C)N(C)C(CN(C)(5N4CCC5)=O)=O)=O)=O)=C3N
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>62</sub>H<sub>87</sub>N<sub>13</sub>O<sub>16</sub> | Formula=C<sub>62</sub>H<sub>87</sub>N<sub>13</sub>O<sub>16</sub>
| MolarMass=1270.43 g/mol | MolarMass=1270.43 g/mol
| Appearance=Red to dark purple powder | Appearance=Red to dark purple powder
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
| RPhrases = {{R26/27/28}} {{R36/37/38}} | GHSPictograms = {{GHS06}}{{GHS08}}
| GHSSignalWord = Danger
| SPhrases = {{S26}} {{S28}} {{S36/37}} {{S45}}
| 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 ] ] with a strong affinity for ]. It is used as a fluorescent ] for DNA in ] and ]. It ] in double-stranded DNA, with a high affinity for ] 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 ] 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 ]; 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 ] 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 ]s; 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 ]. 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>
] 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 ] 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 ==
*
* {{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-}}
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