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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.
318:-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.
314:. 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, which has a methyl group attached to the charged nitrogen, whereas SYBR Safe has an
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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
594:
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".
120:
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
97:
559:
Evenson, William E.; Boden, Lauren M.; Muzikar, Katy A.; OāLeary, Daniel J. (27 November 2012). "1H and 13C NMR Assignments for the
Cyanine Dyes SYBR Safe and Thiazole Orange".
249:
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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".
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Haines, Alicia M.; Tobe, Shanan S.; Kobus, Hilton J.; Linacre, Adrian (March 2015). "Properties of nucleic acid staining dyes used in gel electrophoresis".
638:
Evenson WE; Boden LM; Muzikar KA; O'Leary DJ (2012). "1H and 13C NMR Assignments for the
Cyanine Dyes SYBR Safe and Thiazole Orange".
377:
Evenson WE; Boden LM; Muzikar KA; O'Leary DJ (2012). "1H and 13C NMR Assignments for the
Cyanine Dyes SYBR Safe and Thiazole Orange".
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Domahidy, Farkas; KovĆ”cs, Beatrix; Cseri, Levente; Katona, Gergely; RĆ³zsa, BalĆ”zs; et al. (19 June 2024).
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286:. SYBR Safe is one of a number of SYBR dyes made by the Life Technologies Corporation. SYBR Safe binds to
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Except where otherwise noted, data are given for materials in their
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359:- competing product with a different molecular structure and size
51:)-ylidene)methyl)-1-propylquinolin-1-ium 4-methylbenzenesulfonate
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426:"Comprehensive Study of ThiazoleāOrangeāBased DNA Dyes"
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CCC1ccc(C=C2Sc3ccccc3N2C)c2ccccc21.Cc1ccc(S(=O)(=O))cc1
290:. The resulting DNA-dye-complex absorbs blue light (Ī»
310:SYBR Safe is marketed as a safer alternative to
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411:it is most commonly used as a DNA stain in
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294:= 509 nm) and emits green light (Ī»
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123:Key: YTHKVAWQFBVEJQ-UHFFFAOYSA-M
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16:DNA gel stain for molecular genetics
597:Physical Chemistry Chemical Physics
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561:The Journal of Organic Chemistry
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230:(at 25 Ā°C , 100 kPa).
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47:)-4-((3-Methylbenzothiazol-2(3
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640:Journal of Organic Chemistry
379:Journal of Organic Chemistry
413:agarose gel electrophoresis
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530:10.1002/elps.201700489
487:10.1002/elps.201400496
439:10.1002/cptc.202400080
327:TO (Thiazole Orange)
322:Similar cyanine dyes
646:(23): 10967ā10971.
609:2011PCCP...1312595B
603:(27): 12595ā12602.
567:(23): 10967ā10971.
385:(23): 10967ā10971.
343:YO (Oxazole Yellow)
207: gĀ·mol
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617:10.1039/C1CP20812H
257:Infobox references
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652:10.1021/jo3021659
573:10.1021/jo3021659
524:(12): 1474ā1477.
391:10.1021/jo3021659
284:molecular biology
265:Chemical compound
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298:= 524 nm).
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277:nucleic acid
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74:1030826-36-8
57:Identifiers
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273:cyanine dye
217:Soluble in
153:Properties
695:Quinolines
674:Categories
364:References
275:used as a
213:Solubility
200:Molar mass
85:3D model (
64:CAS Number
40:IUPAC name
20:SYBR Safe
460:CC BY 4.0
448:2367-0932
339:SYBR Gold
269:SYBR Safe
660:23137048
625:21660321
581:23137048
538:29645293
503:27324826
495:25546455
462:license.
399:23137048
357:GelGreen
351:See also
605:Bibcode
546:4790798
250:what is
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306:Safety
245:verify
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205:504.66
137:SMILES
34:Names
542:S2CID
499:S2CID
280:stain
271:is a
112:InChI
87:JSmol
656:PMID
621:PMID
577:PMID
534:PMID
491:PMID
444:ISSN
395:PMID
648:doi
613:doi
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483:doi
434:doi
387:doi
296:max
292:max
288:DNA
282:in
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316:N
240:Y
193:2
190:S
187:3
184:O
181:2
178:N
172:H
166:C
89:)
49:H
45:Z
43:(
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
