SYBR Safe

SYBR Safe
Names
IUPAC name
(Z)-4-((3-Methylbenzo[d]thiazol-2(3H)-ylidene)methyl)-1-propylquinolin-1-ium 4-methylbenzenesulfonate
Identifiers
3D model (JSmol)
  • InChI=1S/C21H21N2S.C7H8O3S/c1-3-13-23-14-12-16(17-8-4-5-9-18(17)23)15-21-22(2)19-10-6-7-11-20(19)24-21;1-6-2-4-7(5-3-6)11(8,9)10/h4-12,14-15H,3,13H2,1-2H3;2-5H,1H3,(H,8,9,10)/q+1;/p-1
    Key: YTHKVAWQFBVEJQ-UHFFFAOYSA-M
  • CCC[n+]1ccc(C=C2Sc3ccccc3N2C)c2ccccc21.Cc1ccc(S(=O)(=O)[O-])cc1
Properties
C28H28N2O3S2
Molar mass 504.66 g·mol−1
Solubility Soluble in dimethylsulfoxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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SYBR Safe is a cyanine dye used as a nucleic acid stain in molecular biology. SYBR Safe is one of a number of SYBR dyes made by the Life Technologies Corporation. SYBR Safe binds to DNA. The resulting DNA-dye-complex absorbs blue light (λmax = 509 nm) and emits green light (λmax = 524 nm).

Safety

SYBR Safe is marketed as a safer alternative to ethidium bromide. SYBR Safe has a very similar structure to thiazole orange, which has a methyl group attached to the charged nitrogen, whereas SYBR Safe has an N-propyl group. Thiazole Orange has been shown to be three to four times less mutagenic than ethidium bromide whereas SYBR Safe is four to five times less mutagenic. Additionally, according to the Life Technologies website, SYBR Safe is not lethal in rats at doses as high as 5 g/kg, and rats don't show symptoms of acute toxicity. Thiazole orange does show toxicity at this dose.

Similar cyanine dyes

See also

References

  1. ↑ Evenson WE; Boden LM; Muzikar KA; O'Leary DJ (2012). "1H and 13C NMR Assignments for the Cyanine Dyes SYBR Safe and Thiazole Orange". Journal of Organic Chemistry. 77 (23): 10967–10971. doi:10.1021/jo3021659. PMID 23137048.
  2. ↑ it is most commonly used as a DNA stain in agarose gel electrophoresis
  3. ↑ Haines, Alicia M.; Tobe, Shanan S.; Kobus, Hilton J.; Linacre, Adrian (March 2015). "Properties of nucleic acid staining dyes used in gel electrophoresis". Electrophoresis. 36 (6): 941–944. doi:10.1002/elps.201400496. PMID 25546455. S2CID 27324826.
  4. ↑ O'Neil, Casey S.; Beach, Jacie L.; Gruber, Todd D. (June 2018). "Thiazole orange as an everyday replacement for ethidium bromide and costly DNA dyes for electrophoresis". Electrophoresis. 39 (12): 1474–1477. doi:10.1002/elps.201700489. PMID 29645293. S2CID 4790798.
  5. ↑ Evenson, William E.; Boden, Lauren M.; Muzikar, Katy A.; O’Leary, Daniel J. (27 November 2012). "1H and 13C NMR Assignments for the Cyanine Dyes SYBR Safe and Thiazole Orange". The Journal of Organic Chemistry. 77 (23): 10967–10971. doi:10.1021/jo3021659. PMID 23137048.
  6. ↑ Biancardi, Alessandro; Tarita, Biver; Alberto, Marini; Benedetta, Mennucci; Fernando, Secco (2011). "Thiazole orange (TO) as a light-switch probe: a combined quantum-mechanical and spectroscopic study". Physical Chemistry Chemical Physics. 13 (27): 12595–12602. Bibcode:2011PCCP...1312595B. doi:10.1039/C1CP20812H. PMID 21660321.
  7. ↑ Evenson WE; Boden LM; Muzikar KA; O'Leary DJ (2012). "1H and 13C NMR Assignments for the Cyanine Dyes SYBR Safe and Thiazole Orange". Journal of Organic Chemistry. 77 (23): 10967–10971. doi:10.1021/jo3021659. PMID 23137048.