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{{short description|Dye used for molecular genetics}} |
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{{Chembox |
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| ImageFile = SYBR Green I.png |
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| verifiedrevid = 447380975 |
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| ImageFile = SYBR green I.svg |
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| IUPACName = N',N'-dimethyl-N--1-phenylquinolin-1-ium-2-yl]-N-propylpropane-1,3-diamine |
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| IUPACName = ''N',N'''-dimethyl-''N''--1-phenylquinolin-1-ium-2-yl]-''N''-propylpropane-1,3-diamine |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| PubChem = 10436340 |
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| PubChem = 10436340 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1198924 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 163795-75-3 |
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| CASNo = 163795-75-3 |
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| SMILES = CCCN(CCCN(C)C)C1=CC(=Cc2sc3ccccc32C)c2ccccc2N1c1ccccc1 |
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| SMILES = }} |
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| InChI = 1S/C32H37N4S/c1-5-20-35(22-13-21-33(2)3)31-23-25(24-32-34(4)29-18-11-12-19-30(29)37-32)27-16-9-10-17-28(27)36(31)26-14-7-6-8-15-26/h6-12,14-19,23-24H,5,13,20-22H2,1-4H3/q+1 |
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| Section2 = {{Chembox Properties |
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| InChIKey = CGNLCCVKSWNSDG-UHFFFAOYSA-N }} |
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| Formula = C<sub>32</sub>H<sub>37</sub>N<sub>4</sub>S<sup>+<sup> |
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|Section2={{Chembox Properties |
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| MolarMass = 509.73 ]·]<sup>−1</sup> |
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| Formula = C<sub>32</sub>H<sub>37</sub>N<sub>4</sub>S<sup>+</sup> |
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| MolarMass = 509.73{{nbsp}}]/] |
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| SolubleOther = Soluble in ] }} |
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| SolubleOther = Normally supplied solvated in ] }} |
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| Section3 = {{Chembox Hazards |
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'''SYBR Green I''' ('''SG''') is an asymmetrical ]<ref>{{cite journal |author=Zipper H, Brunner H, Bernhagen J, Vitzthum F |title=Investigations on DNA intercalation and surface binding by SYBR Green I, its structure determination and methodological implications |journal=Nucleic acids research |volume=32 |issue=12 |pages=e103 |year=2004 |pmid=15249599 |pmc=484200 |doi=10.1093/nar/gnh101 |url=}}</ref> used as a ] ] in ]. SYBR Green I binds to ]. The resulting DNA-dye-complex absorbs blue light (λ<sub>max</sub> = 488 nm) and emits green light (λ<sub>max</sub> = 522 nm). The stain preferentially binds to double-stranded DNA, but will stain single-stranded DNA with lower performance. |
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'''SYBR Green I''' ('''SG''') is an asymmetrical ]<ref>{{cite journal |author=Zipper H|author2=Brunner H|author3=Bernhagen J|author4=Vitzthum F |title=Investigations on DNA intercalation and surface binding by SYBR Green I, its structure determination and methodological implications |journal=Nucleic Acids Research |volume=32 |issue=12 |pages=e103 |date=2004 |pmid=15249599 |pmc=484200 |doi=10.1093/nar/gnh101 }}</ref> used as a ] ] in ]. The SYBR family of dyes is produced by ], now owned by ]. SYBR Green I binds to ]. The resulting DNA-dye-complex best absorbs 497 nanometer blue light (λ<sub>max</sub> = 497 nm) and emits green light (λ<sub>max</sub> = 520 nm). The stain preferentially binds to double-stranded DNA, but will stain single-stranded (ss) DNA with lower performance. SYBR Green can also stain ] with a lower performance than ssDNA. |
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] illuminated by blue light in an ]. The SYBR green in the sample binds to the sperm DNA and, once bound, fluoresces giving off green light when illuminated by blue light]] |
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==Uses== |
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==Uses== |
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SYBR Green finds usage in several areas of ] and ]. It is used as a dye for the quantification of double stranded DNA in some methods of ].<ref>{{cite journal |author=Mackay IM|author2= Arden KE|author3=Nitsche A |title=Real-time PCR in virology |journal=Nucleic Acids Res. |volume=30 |issue=6 |pages=1292–305 |date=March 2002 |pmid=11884626 |pmc=101343 |doi= 10.1093/nar/30.6.1292|url=}}</ref> It is also used to visualise DNA in ]. Higher concentrations of SYBR Green can be used to stain ]s 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 ] and ]. In these cases ] treatment may be required to reduce background from RNA in the cells. |
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SYBR green is used as a dye for the quantification of double stranded DNA in some methods of ].<ref>{{cite journal |author=Mackay IM, Arden KE, Nitsche A |title=Real-time PCR in virology |journal=Nucleic Acids Res. |volume=30 |issue=6 |pages=1292–305 |year=2002 |month=March |pmid=11884626 |pmc=101343 |doi= 10.1093/nar/30.6.1292|url=http://nar.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11884626}}</ref> It is also used to visualise DNA in ]. |
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A comprehensive Study of Thiazole-Orange-Based DNA Dyes were 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 spectro-scopically 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 facilitate the DNA marker selection for analytical purposes. <ref name=" Comprehensive Study of Thiazole-Orange-Based DNA Dyes ">{{cite journal |last1=Domahidy |first1=Farkas |last2=Kovács |first2=Beatrix |last3=Cseri |first3=Levente |last4=Katona |first4=Gergely |last5=Rózsa |first5=Balázs |last6=Mucsi |first6=Zoltán |last7=Kovács |first7=Ervin |display-authors=5 |title=Comprehensive Study of Thiazole-Orange-Based DNA Dyes |journal=ChemPhotoChem |date=19 June 2024 |doi=10.1002/cptc.202400080 |language=en |issn=2367-0932|doi-access=free }}{{Creative Commons text attribution notice|cc=by4|from this source=yes}}</ref> |
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This study showed that Sybr Green exhibits the highest fluorescence enhancement (AFE) and provided the best characteristic for PCR methods. The second best was TOPhBu, which is close in values to Sybr Green. |
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==Safety== |
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==Safety== |
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SYBR Green I is marketed as a replacement for the ] ], 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 ], including SYBR. |
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SYBR Green I is marketed as a replacement for ], a potential human ], as both safer to work with and free from the complex waste disposal issues of ethidium bromide. However any ] capable of binding DNA with high affinity is a possible ], including SYBR Green. |
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In a study using the ], 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.<ref name=Singer>{{cite journal |author=Singer VL, Lawlor TE, Yue S |title=Comparison of SYBR Green I nucleic acid gel stain mutagenicity and ethidium bromide mutagenicity in the Salmonella/mammalian microsome reverse mutation assay (Ames test) |journal=Mutation research |volume=439 |issue=1 |pages=37–47 |year=1999 |month=February |pmid=10029672 |doi= |url=}}</ref> Ethidium bromide was more mutagenic at higher concentrations, however SYBR green I could not be tested at these concentrations as it was ] at a much lower concentration than ethidium bromide.<ref name=Singer/> SYBR green I readily penetrates living cells, whereas ethidium bromide is efficiently excluded from live cells.<ref name=Singer/> |
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In a study using the ], which measures the ability of chemicals to cause mutations, when assayed at the same concentration SYBR Green I was on the order of 30 times less mutagenic than ethidium bromide.<ref name=Singer>{{cite journal |author=Singer VL|author2=Lawlor TE|author3= Yue S |title=Comparison of SYBR Green I nucleic acid gel stain mutagenicity and ethidium bromide mutagenicity in the Salmonella/mammalian microsome reverse mutation assay (Ames test) |journal=Mutation Research |volume=439 |issue=1 |pages=37–47 |date=February 1999 |pmid=10029672 |doi= 10.1016/s1383-5718(98)00172-7|bibcode=1999MRGTE.439...37S }}</ref> |
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==Related dyes== |
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== Similar cyanine dyes == |
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* ] (PG) |
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Similar cyanine dyes: |
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* SYBR Green II |
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* ] |
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* SYBR Gold |
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* ] |
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* ] (TO) |
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* YO (Oxazole Yellow) |
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* ] (YO) |
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* TO (Thiazole Orange) |
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* Safe-Green |
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* PG (PicoGreen) |
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* Chai Green |
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== See also == |
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* ] |
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== References == |
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== References == |
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{{reflist}} |
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{{Reflist}} |
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{{DEFAULTSORT:Sybr Green I}} |
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