GelGreen

GelGreen is an intercalating nucleic acid stain used in molecular genetics for agarose gel DNA electrophoresis. GelGreen consists of two acridine orange subunits that are bridged by a linear oxygenated spacer.[1][2]

GelGreen
Names
Preferred IUPAC name
10,10′-(6,22-Dioxo-11,14,17-trioxa-7,21-diazaheptacosane-1,27-diyl)bis[3,6-bis(dimethylamino)acridin-10-ium] diiodide
Other names
Dye No. 20,[1] AOAO-13[1]
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C56H78N8O5.2HI/c1-59(2)47-23-19-43-37-44-20-24-48(60(3)4)40-52(44)63(51(43)39-47)29-13-9-11-17-55(65)57-27-15-31-67-33-35-69-36-34-68-32-16-28-58-56(66)18-12-10-14-30-64-53-41-49(61(5)6)25-21-45(53)38-46-22-26-50(62(7)8)42-54(46)64;;/h19-26,37-42H,9-18,27-36H2,1-8H3;2*1H
    Key: TWYVVGMYFLAQMU-UHFFFAOYSA-N
  • InChI=1/C56H78N8O5.2HI/c1-59(2)47-23-19-43-37-44-20-24-48(60(3)4)40-52(44)63(51(43)39-47)29-13-9-11-17-55(65)57-27-15-31-67-33-35-69-36-34-68-32-16-28-58-56(66)18-12-10-14-30-64-53-41-49(61(5)6)25-21-45(53)38-46-22-26-50(62(7)8)42-54(46)64;;/h19-26,37-42H,9-18,27-36H2,1-8H3;2*1H
    Key: TWYVVGMYFLAQMU-UHFFFAOYAG
  • O=C(NCCCOCCOCCOCCCNC(CCCCC[N+]1=C2C(C=CC(N(C)C)=C2)=CC3=C1C=C(N(C)C)C=C3)=O)CCCCC[N+]4=C5C(C=CC(N(C)C)=C5)=CC6=C4C=C(N(C)C)C=C6.[I-].[I-]
Properties
C56H80I2N8O5
Molar mass 1198.43 g/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
0
0
0
Flash point > 100 °C (212 °F; 373 K)
Safety data sheet (SDS) 10,000X in water, Biotium Inc.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Its fluorophore, and therefore its optical properties, are essentially identical to those of other N-alkylacridinium orange dyes. When exposed to ultraviolet light, it will fluoresce with a greenish color that strongly intensifies after binding to DNA.[3] The substance is marketed as a less toxic and more sensitive alternative to ethidium bromide.[3] GelGreen is sold as a solution in either DMSO or water.[3]

See also

References
  1. US application 2010323453, Mao, Fei & Leung, Wai-Yee, "Methods of Using Dyes in Association with Nucleic Acid Staining or Detection and Associated Technology"
  2. GelRed & GelGreen (PDF), Biotium Inc., August 21, 2012, retrieved December 4, 2012
  3. GelRed and GelGreen: Environmentally safe and ultra-sensitive nucleic acid gel stains for replacing EtBr, Biotium Inc., retrieved December 4, 2012
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