7-Aminoactinomycin D

7-Aminoactinomycin D[1]
Names
	Other names 7-Amino-actinomycin D
Identifiers
CAS Number	7240-37-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	5915844
ChEBI	CHEBI:52304 ;
ChemSpider	21326185 ;
ECHA InfoCard	100.163.188
EC Number	635-285-6;
PubChem CID	16218991;
UNII	DXS32PH95R ;
CompTox Dashboard (EPA)	DTXSID30903974 ;
	InChI InChI=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 Key: YXHLJMWYDTXDHS-IRFLANFNSA-N ; 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 Key: YXHLJMWYDTXDHS-IRFLANFNBD;
	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;
Properties
Chemical formula	C62H87N13O16
Molar mass	1270.43 g/mol
Appearance	Red to dark purple powder
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H300, H310, H315, H319, H330, H335, H350, H360
GHS precautionary statements	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).
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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.

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. S2CID 40569430.
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.

Gallery

Absorptions

External links

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[ref-1] 7-Aminoactinomycin D at Interchim

[2] 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. S2CID 40569430.

[3] 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.