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).
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| Names | |
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| IUPAC name
(Z)-4-((3-Methylbenzo[d]thiazol-2(3H)-ylidene)methyl)-1-propylquinolin-1-ium 4-methylbenzenesulfonate
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| Identifiers | |
3D model (JSmol)
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| 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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A comprehensive study of Thiazole-Orange-Based DNA Dyes was published, involving SYBR Safe, SYBR Green, PicoGreen, SYTO-16, SYTO-9 and a new derivative TOPhBu. Here, the synthesis of these compounds are published and characterised spectroscopically to quantify their fluorescence enhancement upon binding to double-stranded DNA. The ability of the dyes to detect DNA at low concentrations was evaluated using two new metrics, absolute fluorescence enhancement (AFE) and relativefluorescence enhancement (RFE). They were tested in qPCR experiments showing some important differences in the sensitivity and qPCR efficiency, which facilitates the DNA marker selection for analytical purposes. [3]
Safety
editSYBR Safe is marketed as a safer alternative to ethidium bromide.[4] 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,[5][6][7] 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.[8] 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
edit- TO (Thiazole Orange)
- SYBR Green I
- SYBR Green II
- SYBR Gold
- YO (Oxazole Yellow)
- PG (PicoGreen)
See also
edit- GelGreen - competing product with a different molecular structure and size
References
edit- ^ 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.
- ^ it is most commonly used as a DNA stain in agarose gel electrophoresis
- ^ Domahidy, Farkas; Kovács, Beatrix; Cseri, Levente; Katona, Gergely; Rózsa, Balázs; et al. (19 June 2024). "Comprehensive Study of Thiazole‐Orange‐Based DNA Dyes". ChemPhotoChem. doi:10.1002/cptc.202400080. ISSN 2367-0932.
This article incorporates text from this source, which is available under the CC BY 4.0 license.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
