SYBR Safe

Source: Wikipedia, the free encyclopedia.
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[1] used as a nucleic acid stain in molecular biology.[2] 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.[3] 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. SYBR Safe has a very similar structure to thiazole orange,[4][5][6] 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.[7] 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

  • GelGreen - competing product with a different molecular structure and size

Notes and references

  1. PMID 23137048
    .
  2. ^ it is most commonly used as a DNA stain in agarose gel electrophoresis
  3. S2CID 27324826
    .
  4. S2CID 4790798
    .
  5. PMID 23137048
    .
  6. PMID 21660321
    .
  7. PMID 23137048
    .
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