SYBR Safe

SYBR Safe
Names
IUPAC name
(Z)-4-((3-Methylbenzo[d]thiazol-2(3H)-ylidene)methyl)-1-propylquinolin-1-ium 4-methylbenzenesulfonate
Identifiers
1030826-36-8 YesY
Properties
C28H28N2O3S2
Molar mass 504.66 g/mol
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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Infobox references

SYBR Safe is a cyanine dye[1] 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).

Uses

SYBR Safe is most commonly used as a DNA stain for identifying DNA in agarose gels.

Safety

SYBR Safe is a safer alternative to the known mutagen ethidium bromide. Although it is still a carcinogen, as it binds DNA just like ethidium bromide. However, as the molecule itself is quite a bit larger than ethidium bromide, it does not bind to the column of a gel extraction as easily, making it less efficient when trying to clone a DNA fragment into a plasmid. Interestingly, SYBR Safe is 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 less mutagenic.[2] 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

Notes and 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. ↑ 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.
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