GelRed

GelRed
Names
Preferred IUPAC name
5,5′-(6,22-Dioxo-11,14,17-trioxa-7,21-diazaheptacosane-1,27-diyl)bis(3,8-diamino-6-phenylphenanthridin-5-ium) diiodide
Other names
Dye No. 35, ET-27
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C60H70N8O5.2HI/c61-45-21-25-49-51-27-23-47(63)41-55(51)67(59(53(49)39-45)43-15-5-1-6-16-43)31-11-3-9-19-57(69)65-29-13-33-71-35-37-73-38-36-72-34-14-30-66-58(70)20-10-4-12-32-68-56-42-48(64)24-28-52(56)50-26-22-46(62)40-54(50)60(68)44-17-7-2-8-18-44;;/h1-2,5-8,15-18,21-28,39-42,63-64H,3-4,9-14,19-20,29-38,61-62H2,(H2,65,66,69,70);2*1H
    Key: JGBUYEVOKHLFID-UHFFFAOYSA-N
  • c1ccccc1-c2c3cc(N)ccc3c4ccc(N)cc4[n+]2CCCCCC(=O)NCCCOCCOCCOCCCNC(=O)CCCCC[n+]5c6cc(N)ccc6c7ccc(N)cc7c5-c8ccccc8.[I-].[I-]
Properties
C60H72I2N8O5
Molar mass 1239.07 g/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).

GelRed is an intercalating nucleic acid stain used in molecular genetics for agarose gel DNA electrophoresis. GelRed structurally consists of two ethidium subunits that are bridged by a linear oxygenated spacer.

GelRed is a fluorophore, and its optical properties are essentially identical to those of ethidium bromide. When exposed to ultraviolet light, it fluoresces with an orange color that strongly intensifies after binding to DNA. The substance is marketed as a less toxic and more sensitive alternative to ethidium bromide. GelRed is sold as a solution in anhydrous DMSO or ultrapurified water. One benefit of using GelRed instead of EtBr, is that GelRed is unable to cross cell membranes. This is caused by the chemical structure of GelRed, being a large, charged molecule, which doesn't permit it to penetrate the cell membrane, which greatly reduces the risks of mutations . This makes it not toxic to living cells, and a better choice as a fluorescent dye.

See also

References

  1. 1 2 3 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. 1 2 3 GelRed and GelGreen: Environmentally safe and ultra-sensitive nucleic acid gel stains for replacing EtBr, Biotium Inc., retrieved December 4, 2012
  4. ↑ Carson, Susan; Miller, Heather B.; Witherow, D. Scott (2012-01-01). "Lab Session 3 - PCR Amplification of egfp and Completion of Vector Preparation". Molecular Biology Techniques (3rd ed.). Academic Press. pp. 21–29. doi:10.1016/B978-0-12-385544-2.00003-X. ISBN 978-0-12-385544-2.
  5. ↑ "Top 10 GelRed Questions and Answers". GoldBio. Retrieved 2026-09-16.