SYBR Green I

SYBR Green I
IUPAC name

N',N'-dimethyl-N-[4-[(E)-(3-methyl-1,3-benzothiazol-2-ylidene)methyl]-1-phenylquinolin-1-ium-2-yl]-N-propylpropane-1,3-diamine
Identifiers
CAS number 163795-75-3
PubChem 10436340
Properties
Molecular formula C32H37N4S+
Molar mass 509.73 g·mol−1
Solubility Soluble in Dimethylsulfoxide
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

SYBR Green I (SG) is an asymmetrical cyanine dye[1] used as a nucleic acid stain in molecular biology. SYBR Green I binds to DNA. The resulting DNA-dye-complex absorbs blue light (λmax = 497 nm) and emits green light (λmax = 520 nm). The stain preferentially binds to double-stranded DNA, but will stain single-stranded DNA with lower performance. SYBR green can also stain RNA with a lower performance than DNA.

Contents

Uses

SYBR green finds usage in several areas of biochemistry and molecular biology. It is used as a dye for the quantification of double stranded DNA in some methods of real time PCR.[2] It is also used to visualise DNA in gel electrophoresis. Higher concentrations of SYBR green can be used to stain agarose gels in order to visualise the DNA present. In addition to labelling pure nucleic acids SYBR green can also be used for labelling of DNA within cells for flow cytometry and fluorescence microscopy. In these cases RNase treatment may be required to reduce background from RNA in the cells.

Safety

SYBR Green I is marketed as a replacement for the mutagen ethidium bromide, as both safer to work with and free from the complex waste disposal issues of ethidium. However anything capable of binding DNA with high affinity is a possible carcinogen, including SYBR.

In a study using the Ames test, which measures the ability of chemicals to cause mutations, when assayed at the same concentration there was no clear pattern in the relative mutagenicities of ethidium bromide and SYBR green I.[3] Ethidium bromide was more mutagenic at higher concentrations, however SYBR green I could not be tested at these concentrations as it was cytotoxic at a much lower concentration than ethidium bromide.[3] SYBR green I readily penetrates living cells, whereas ethidium bromide is efficiently excluded from live cells.[3]

Related dyes

Similar cyanine dyes:

References

  1. ^ Zipper H, Brunner H, Bernhagen J, Vitzthum F (2004). "Investigations on DNA intercalation and surface binding by SYBR Green I, its structure determination and methodological implications". Nucleic Acids Research 32 (12): e103. doi:10.1093/nar/gnh101. PMC 484200. PMID 15249599. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=484200. 
  2. ^ Mackay IM, Arden KE, Nitsche A (March 2002). "Real-time PCR in virology". Nucleic Acids Res. 30 (6): 1292–305. doi:10.1093/nar/30.6.1292. PMC 101343. PMID 11884626. http://nar.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11884626. 
  3. ^ a b c Singer VL, Lawlor TE, Yue S (February 1999). "Comparison of SYBR Green I nucleic acid gel stain mutagenicity and ethidium bromide mutagenicity in the Salmonella/mammalian microsome reverse mutation assay (Ames test)". Mutation research 439 (1): 37–47. PMID 10029672.