Chemistry:7-Aminoactinomycin D
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| Other names
7-Amino-actinomycin D
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| Identifiers | |
3D model (JSmol)
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| 5915844 | |
| ChEBI | |
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PubChem CID
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| Properties | |
| C62H87N13O16 | |
| Molar mass | 1270.43 g/mol |
| Appearance | Red to dark purple powder |
| Hazards | |
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| GHS Signal word | Danger |
| H300, H310, H315, H319, H330, H335, H350, H360 | |
| P201, P202, P260, P261, P262, P264, P270, P271, P280, P281, P284, P301+310, P302+350, P302+352, P304+340, P305+351+338, P308+313, P310, P312, P320, P321, P322, P330, P332+313, P337+313 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
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,[2] making it useful for chromosome banding studies.[3]
Applications
With an absorption maximum at 546 nm, 7-AAD is efficiently excited using a 543 nm helium–neon laser; it can also be excited with somewhat lower efficiency using a 488 nm or 514 nm argon laser lines. Its emission has a very large Stokes shift with a maximum in the deep red: 647 nm. 7-AAD is therefore compatible with most blue and green fluorophores – and even many red fluorophores – 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%.[4]
Actinomycin D
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
- ↑ 7-Aminoactinomycin D at Interchim
- ↑ Liu X; Chen H; Patel D (1991). "Solution structure of actinomycin-DNA complexes: drug intercalation at isolated G-C sites". J Biomol NMR 1 (4): 323–47. doi:10.1007/BF02192858. PMID 1841703.
- ↑ Latt S (1977). "Fluorescent probes of chromosome structure and replication". Can J Genet Cytol 19 (4): 603–23. doi:10.1139/g77-065. PMID 76502.
- ↑ "Flow cytometry (FACS) staining protocol (Cell surface staining)". https://medicine.yale.edu/immuno/flowcore/protocols/analysis/. Retrieved 2023-10-17.
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Absorptions
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