Handbook of Biological Dyes and Stains (Synthesis and Industrial Applications) || Y
7
YO-PRO 1 CAS Registry Number 152068-09-2 Chemical Structure + + 2 I _ N CH (H 2 C) 3 N O N H 3 C H 3 C CH 3 CH 3 CA Index Name Quinolinium, 4-[(3-methyl-2(3H)- benzoxazolylidene)methyl]-1-[3-(trimethylammonio) propyl]-, iodide (1:2) Other Names Quinolinium, 4-[(3-methyl-2(3H)-ben- zoxazolylidene)methyl]-1-[3-(trimethylammonio)pro- pyl]-, diiodide; Oxazole yellow; YO-PRO 1; YO-PRO 1 iodide Merck Index Number Not listed Chemical/Dye Class Cyanine Molecular Formula C 24 H 29 I 2 N 3 O Molecular Weight 629.32 Physical Form Orange-red powder Solubility Soluble in dimethyl sulfoxide, water Melting Point >250 C Absorption (l max ) 491 nm Emission (l max ) 509 nm Synthesis Synthetic method 1 Staining Applications Nucleic acids; 2–7 cells; 8,9 bacte- ria; 18 genes; 10 islets; 11 chromatin; 13 leukocytes; 22 marine prokaryotes; 12 nuclei; 22 micronuclei; 13 megakaryocyte; 14 microorganisms; 20,21 sperms; 15 viruses 23 Biological Applications Nucleic acid hybridiza- tion; 16,17 nucleic acid sequencing; 2–7 detecting nucleic acids, 2–7 cells, 8,9 bacteria, 18 immunodeficiency virus, 19 microorganisms; 20,21 counting embryoblasts, 22 viruses; 23 apoptosis assay; 24 white blood cell functional assay 25 Industrial Applications Not reported Safety/Toxicity Cytotoxicity; 26 neurotoxicity; 27 vaso- toxicity 28 REFERENCES 1. Yue, S. T.; Johnson, I. D.; Huang, Z.; Haugland, R. P. Unsymmetrical cyanine dyes with a cationic side chain for enhanced fluorescence on binding with nucleic acids. U.S. Patent 5321130, 1994; Chem. Abstr. 1994, 121, 129393. 2. Exner, M.; Rogers, A. Methods for identifying nucleic acids and determining melting temperature using multiple fluorophores and FRET. U.S. Pat. Appl. Publ. US 2007172836, 2007; Chem. Abstr. 2007, 147, 182489. 3. Guillo, C.; Ferrance, J. P.; Landers, J. P. Use of a capillary electrophoresis instrument with laser- induced fluorescence detection for DNA quantitation. Comparison of YO-PRO-1 and PicoGreen assays. J. Chromatogr., A 2006, 1113, 239–243. 4. Al-Gubory, K. H. Fibered confocal fluorescence microscopy for imaging apoptotic DNA fragmentation at the single-cell level in vivo. Exp. Cell Res. 2005, 310, 474–481. 5. Deka, C.; Gordon, K. M.; Gupta, R.; Horton, A. Methods and compositions for rapid staining of nucleic acids in whole cells. U.S. Patent 6271035, 2001; Chem. Abstr. 2001, 135, 149591. 6. Suzuki, T.; Fujikura, K.; Higashiyama, T.; Takata, K. DNA staining for fluorescence and laser confocal microscopy. J. Histochem. Cytochem. 1997, 45, 49–53. Handbook of Biological Dyes and Stains By R. W. Sabnis Copyright Ó 2010 John Wiley & Sons, Inc. 495
Transcript of Handbook of Biological Dyes and Stains (Synthesis and Industrial Applications) || Y
YO-PRO 1
CAS Registry Number 152068-09-2
Chemical Structure
+
+
2 I_
N
CH
(H2C)3
N
ON
H3C
H3C
CH3
CH3
CA Index Name Quinolinium, 4-[(3-methyl-2(3H)-benzoxazolylidene)methyl]-1-[3-(trimethylammonio)propyl]-, iodide (1:2)
Other Names Quinolinium, 4-[(3-methyl-2(3H)-ben-zoxazolylidene)methyl]-1-[3-(trimethylammonio)pro-pyl]-, diiodide; Oxazole yellow; YO-PRO 1; YO-PRO 1iodide
Merck Index Number Not listed
Chemical/Dye Class Cyanine
Molecular Formula C24H29I2N3O
Molecular Weight 629.32
Physical Form Orange-red powder
Solubility Soluble in dimethyl sulfoxide, water
Melting Point >250 �CAbsorption (lmax) 491 nm
Emission (lmax) 509 nm
Synthesis Synthetic method1
Staining Applications Nucleic acids;2–7 cells;8,9 bacte-ria;18 genes;10 islets;11 chromatin;13 leukocytes;22 marineprokaryotes;12 nuclei;22 micronuclei;13 megakaryocyte;14
microorganisms;20,21 sperms;15 viruses23
Biological Applications Nucleic acid hybridiza-tion;16,17 nucleic acid sequencing;2–7 detecting nucleicacids,2–7 cells,8,9 bacteria,18 immunodeficiency virus,19
microorganisms;20,21 counting embryoblasts,22 viruses;23
apoptosis assay;24 white blood cell functional assay25
Industrial Applications Not reported
Safety/Toxicity Cytotoxicity;26 neurotoxicity;27 vaso-toxicity28
REFERENCES
1. Yue, S. T.; Johnson, I. D.; Huang, Z.; Haugland, R. P.Unsymmetrical cyanine dyes with a cationic sidechain for enhanced fluorescence on binding withnucleic acids. U.S. Patent 5321130, 1994; Chem.Abstr. 1994, 121, 129393.
2. Exner,M.;Rogers,A.Methods for identifying nucleicacids and determining melting temperature usingmultiple fluorophores and FRET. U.S. Pat. Appl.Publ. US 2007172836, 2007; Chem. Abstr. 2007,147, 182489.
3. Guillo, C.; Ferrance, J. P.; Landers, J. P. Use of acapillary electrophoresis instrument with laser-induced fluorescence detection for DNAquantitation. Comparison of YO-PRO-1 and
PicoGreen assays. J. Chromatogr., A 2006, 1113,239–243.
4. Al-Gubory, K. H. Fibered confocal fluorescencemicroscopy for imaging apoptotic DNAfragmentation at the single-cell level in vivo. Exp.Cell Res. 2005, 310, 474–481.
5. Deka, C.; Gordon, K. M.; Gupta, R.; Horton, A.Methods and compositions for rapid staining ofnucleic acids in whole cells. U.S. Patent 6271035,2001; Chem. Abstr. 2001, 135, 149591.
6. Suzuki, T.; Fujikura, K.; Higashiyama, T.; Takata, K.DNA staining for fluorescence and laser confocalmicroscopy. J. Histochem. Cytochem. 1997, 45,49–53.
Handbook of Biological Dyes and Stains By R. W. Sabnis
Copyright � 2010 John Wiley & Sons, Inc.
495
7. Hoser, M. J. Methods for nucleic acid sequencing.PCT Int. Appl. WO 2004074503, 2004;Chem. Abstr.2004, 141, 237698.
8. Anderson,A. L.;Knutson, C.R.;Mueth,D.; Plewa, J.;Tanner, E.Methods for staining cells for identificationand sorting. U.S. Pat. Appl. Publ. US 2006172315,2006; Chem. Abstr. 2006, 145, 183714.
9. Millard, P. J.; Roth, B. L.; Yue, S. T.; Haugland, R. P.Fluorescent viability assay using cyclic-substitutedunsymmetrical cyanine dyes. U.S. Patent 5534416,1996; Chem. Abstr. 1996, 125, 162751.
10. Stilwell, J. L.; Guan, Y.; Neve, R. M.; Gray, J. W.Systems biology in cancer research: genomics tocellulomics.MethodsMol. Biol. 2007, 356, 353–365.
11. Boffa,D. J.;Waka, J.; Thomas,D.; Suh, S.;Curran,K.;Sharma, V. K.; Besada, M.; Muthukumar, T.; Yang,H.; Suthanthiran, M.; Manova, K. Measurement ofapoptosis of intact human islets by confocal opticalsectioning and stereologic analysis of YO-PRO-1-stained islets. Transplantation 2005, 79, 842–845.
12. Marie, D.; Vaulot, D.; Partensky, F. Application of thenovel nucleic acid dyes YOYO-1, YO-PRO-1, andPicoGreen for flow cytometric analysis of marineprokaryotes. Appl. Environ. Microbiol. 1996, 62,1649–1655.
13. Dertinger, S. D.; Cairns, S. E.; Avlasevich, S. L.;Torous, D. K. Method for enumerating anddifferentiating between mammalian cell micronucleiby differentially staining micronuclei and thechromatin of dead, dying and viable cells. PCT Int.Appl. WO 2006007479, 2006; Chem. Abstr. 2006,144, 124521.
14. Minakami, T.; Mori, Y.; Tsuji, T.; Ikeuchi, Y.Megakaryocyte classification/counting method bydouble fluorescent staining and flow cytometry.Jpn. Kokai Tokkyo Koho JP 2006275985, 2006;Chem. Abstr. 2006, 145, 413679.
15. Matsumoto, T.; Okada, H.; Hamaguchi, Y. Methodand reagent for counting sperm by flow cytometry.Jpn. Kokai Tokkyo Koho JP 2001242168, 2001;Chem. Abstr. 2001, 135, 207869.
16. Erikson, G. H.; Daksis, J. I. Improving the signal/noise ratio of nucleic acid hybridization assays bypreincubation of primer and target with nucleic acidbinding agents. U.S. Pat. Appl. Publ. US2004180345, 2004;Chem. Abstr. 2004, 141, 255469.
17. Hahn, J. H.; Park, N. Electrochemical device andmethods for detection method of nucleic acidhybridization. PCT Int. Appl. WO 2003010338,2003; Chem. Abstr. 2003, 138, 149875.
18. Stopa, P. J.; Mastromanolis, S. A. The use of blue-excitable nucleic-acid dyes for the detection ofbacteria in well water using a simple fieldfluorometer and a flow cytometer. J. Microbiol.Methods 2001, 45, 143–153.
19. Yoshihara, N.; Suzuki, S.; Nakamura, T.; Tanaka, T.Method for detecting immunodeficiency virus. Jpn.Kokai Tokkyo Koho JP 2002085099, 2002; Chem.Abstr. 2002, 136, 259591.
20. Besson, F. I.; Hermet, J. P.; Ribault, S. Reactionmedium and process for universal detection ofmicroorganisms. Fr. Demande FR 2847589, 2004;Chem. Abstr. 2004, 140, 420343.
21. Sunamura, T.; Maruyama, A.; Kurane, R. Method fordetecting and counting microorganism. Jpn. KokaiTokkyo Koho JP 2002291499, 2002; Chem. Abstr.2002, 137, 275332.
22. Heuven, B.; Wong, F. S.; Tsuji, T.; Sakata, T.;Hamaguchi, I. Method for classifying and countingerythroblasts by flow cytometry. Jpn. Kokai TokkyoKoho JP 11326323, 1999; Chem. Abstr. 1999, 132,1804.
23. Bettarel, Y.; Sime-Ngando, T.; Amblard, C.; Laveran,H. A comparison of methods for counting viruses inaquatic systems. Appl. Environ. Microbiol. 2000, 66,2283–2289.
24. Idziorek, T.; Estaquier, J.; De Bels, F.; Ameisen, J. C.YOPRO-1 permits cytofluorometric analysis ofprogrammed cell death (apoptosis) withoutinterfering with cell viability. J. Immunol. Methods1995, 185, 249–258.
25. Denlinger, L. C.; Hogan, K. J.; Bertics, P. J.; Schell,K. White blood cell functional assay. U.S. Pat. Appl.Publ. US 2004253650, 2004; Chem. Abstr. 2004,142, 36899.
26. Reilly, T. P.; MacArthur, R. D.; Farrough, M. J.;Crane, L. R.; Woster, P. M.; Svensson, C. K. Ishydroxylamine-induced cytotoxicity a validmarker for hypersensitivity reactions tosulfamethoxazole in human immunodeficiencyvirus-infected individuals? J. Pharmacol. Exp.Ther. 1999, 291, 1356–1364.
27. Shimazawa, M.; Yamashima, T.; Agarwal, N.; Hara,H. Neuroprotective effects of minocycline against invitro and in vivo retinal ganglion cell damage. BrainRes. 2005, 1053, 185–194.
28. Liao, S. D.; Puro, D. G. NADþ -induced vasotoxicityin the pericyte-containing microvasculature of the ratretina: effect of diabetes. Invest. Ophthalmol. Vis.Sci. 2006, 47, 5032–5038.
496 YO-PRO 1
YO-PRO 3
CAS Registry Number 157199-62-7
Chemical Structure
+
+
2 I_
N
(H2C)3
N
CHCH
HC
ON
H3C
CH3
H3CCH3
CA Index Name Quinolinium, 4-[3-(3-methyl-2(3H)-benzoxazolylidene)-1-propenyl]-1-[3-(trimethylammo-nio)propyl]-, diiodide
Other Names YO-PRO 3; YO-PRO 3 iodide
Merck Index Number Not listed
Chemical/Dye Class Cyanine
Molecular Formula C26H31I2N3O
Molecular Weight 655.36
Physical Form Orange-red powder
Solubility Soluble in dimethyl sulfoxide
Melting Point >250 �CAbsorption (lmax) 612 nm
Emission (lmax) 631 nm
Synthesis Synthetic method1
Staining Applications Nucleic acids;2–4 cells5,6
Biological Applications Nucleic acid hybridization;7,8
detecting nucleic acids,2–4 cells;5,6 monitoring cell cyclekinetics9
Industrial Applications Not reported
Safety/Toxicity No data available
REFERENCES
1. Yue, S. T.; Johnson, I. D.; Huang, Z.; Haugland, R. P.Unsymmetrical cyanine dyeswith a cationic side chainfor enhanced fluorescence on binding with nucleicacids. U.S. Patent 5321130, 1994; Chem. Abstr.1994, 121, 129393.
2. Exner, M.; Rogers, A. Methods for identifying nucleicacids and determining melting temperature usingmultiple fluorophores and FRET. U.S. Pat. Appl.Publ. US 2007172836, 2007; Chem. Abstr. 2007,147, 182489.
3. Miller, B. L.; Krauss, T. D.; Du, H.; Crnkovich, N.;Strohsahl, C. M. Use of sensor arrays containinghairpin probes for detecting nucleic acids ofpathogens. PCT Int. Appl. WO 2004061127, 2004;Chem. Abstr. 2004, 141, 118285.
4. Erikson, G. H.; Daksis, J. I.; Kandic, I.; Picard,P. Conditions for formation of three- and four-stranded nucleic acid complexes and theirdetection and analytical use. PCT Int. Appl.WO 2002103051, 2002; Chem. Abstr. 2002, 138,50812.
5. Anderson, A. L.; Knutson, C. R.; Mueth, D.; Plewa, J.;Tanner, E. Methods for staining cells for identificationand sorting. U.S. Pat. Appl. Publ. US 2006172315,2006; Chem. Abstr. 2006, 145, 183714.
6. Millard, P. J.; Roth, B. L.; Yue, S. T.; Haugland, R. P.Fluorescent viability assay using cyclic-substitutedunsymmetrical cyanine dyes. U.S. Patent 5534416,1996; Chem. Abstr. 1996, 125, 162751.
7. Erikson, G. H.; Daksis, J. I. Improving the signal/noiseratio of nucleic acid hybridization assays bypreincubation of primer and target with nucleic acidbinding agents. U.S. Pat. Appl. Publ. US 2004180345,2004; Chem. Abstr. 2004, 141, 255469.
8. Hahn, J. H.; Park, N. Electrochemical device andmethods for detection method of nucleic acidhybridization. PCT Int. Appl. WO 2003010338,2003; Chem. Abstr. 2003, 138, 149875.
9. Beisker, W.; Weller-Mewe, E. M.; Nusse, M.Fluorescence enhancement of DNA-bound TO-PRO-3 by incorporation of bromodeoxyuridine to monitorcell cycle kinetics. Cytometry 1999, 37, 221–229.
YO-PRO 3 497
YOYO 1
CAS Registry Number 143413-85-8
Chemical Structure
+
++
+
4 I_
N
CH
(H2C)3
N (CH2)3 N
(CH2)3
N
CH
ON NO
H3C
CH3
CH3
H3C
H3C CH3
CA Index Name Quinolinium, 1,10-[1,3-propanediyl-bis[(dimethyliminio)-3,1-propanediyl]]bis[4-[(3-methyl-2(3H)-benzoxazolylidene)methyl]-, iodide (1:4)
Other Names Quinolinium, 1,10-[1,3-propanediylbis[(dimethyliminio)-3,1-propanediyl]]bis[4-[(3-methyl-2(3H)-benzoxazolylidene)methyl]-, tetraiodide; YOYO 1;YOYO 1 iodide
Merck Index Number Not listed
Chemical/Dye Class Cyanine
Molecular Formula C49H58I4N6O2
Molecular Weight 1270.65
Physical Form Orange-red powder
Solubility Soluble in dimethyl sulfoxide, water
Melting Point >250 �CAbsorption (lmax) 491 nm
Emission (lmax) 509 nm
Synthesis Synthetic methods1,2
Staining Applications Nucleic acids;3–8 cells;9,10 anti-bodies;15 genes;11 chromatin;12 micronuclei;12 megakar-yocyte;13 microorganisms;14 peptides;15 proteins;15
sperms16
Biological Applications Nucleic acid hybridiza-tion;17,18 nucleic acid sequencing;7 detecting nucleicacids,3–8 cells,9,10,23 human papilloma virus (HPV),19
pathogens,20 spores,21 cancer cells,21 stress biomarkers,22
viruses23,24
Industrial Applications Not reported
Safety/Toxicity Double-strand breaks in reconstitutedchromatin25
REFERENCES
1. Roth, B. L.; Millard, P. J.; Yue, S. T.; Wells, K. S.;Haugland, R. P. Fluorescent assay for bacterial gramreaction. U.S. Patent 5545535, 1996; Chem. Abstr.1996, 125, 216357.
2. Rye, H. S.; Yue, S.; Wemmer, D. E.; Quesada, M. A.;Haugland, R. P.; Mathies, R. A.; Glazer, A. N. Stablefluorescent complexes of double-stranded DNAwithbis-intercalating asymmetric cyanine dyes: propertiesand applications. Nucleic Acids Res. 1992, 20,2803–2812.
3. Exner,M.;Rogers,A.Methods for identifying nucleicacids and determining melting temperature usingmultiple fluorophores and FRET. U.S. Pat. Appl.Publ. US 2007172836, 2007; Chem. Abstr. 2007,147, 182489.
4. Miller, B. L.; Krauss, T. D.; Du, H.; Crnkovich, N.;Strohsahl, C. M. Use of sensor arrays containinghairpin probes for detecting nucleic acids ofpathogens. PCT Int. Appl. WO 2004061127, 2004;Chem. Abstr. 2004, 141, 118285.
5. Kim, J. M.; Muramatsu, H.; Lee, H. Y.; Kawai, T.Near-field optical imaging of abasic sites on a singleDNA molecule. FEBS Lett. 2003, 555, 611–615.
6. Zheng, J.; Yeung, E. S. Counting single DNAmolecules in a capillary with radial focusing. Aust.J. Chem. 2003, 56, 149–153.
7. Williams, J. G. K.; Anderson, J. P. Field-switch singlemolecule DNA sequencing in a two-electrodechamber. PCT Int. Appl. WO 2005111240, 2005;Chem. Abstr. 2005, 143, 474548.
498 YOYO 1
8. Nomura, Y.; Fuchigami, H.; Kii, H.; Feng, Z.;Nakamura, T.; Kinjo, M. Detection of oxidativestress-induced mitochondrial DNA damage usingfluorescence correlation spectroscopy. Anal.Biochem. 2006, 350, 196–201.
9. Anderson,A. L.;Knutson, C.R.;Mueth,D.; Plewa, J.;Tanner, E.Methods for staining cells for identificationand sorting. U.S. Pat. Appl. Publ. US 2006172315,2006; Chem. Abstr. 2006, 145, 183714.
10. Lacombe, F.; Belloc, F.; Veriac, S.; Lefevre, D.Method of discrimination of at least two cellularpopulations by immunofluorescence flowcytometry and application to oncopathology. Fr.Demande FR 2895087, 2007; Chem. Abstr. 2007,147, 93934.
11. Ferris, M.M.; Yoshida, T. M.; Marrone, B. L.; Keller,R. A. Fingerprinting of single viral genomes. Anal.Biochem. 2005, 337, 278–288.
12. Dertinger, S. D.; Cairns, S. E.; Avlasevich, S. L.;Torous, D. K. Method for enumerating anddifferentiating between mammalian cellmicronuclei by differentially staining micronucleiand the chromatin of dead, dying and viable cells.PCT Int. Appl.WO 2006007479, 2006;Chem. Abstr.2006, 144, 124521.
13. Minakami, T.; Mori, Y.; Tsuji, T.; Ikeuchi, Y.Megakaryocyte classification/counting method bydouble fluorescent staining and flow cytometry.Jpn. Kokai Tokkyo Koho JP 2006275985, 2006;Chem. Abstr. 2006, 145, 413679.
14. Noda, N.; Mizutani, T. Microorganism-measuringmethod using multiple staining. Jpn. Kokai TokkyoKoho JP 2006340684, 2006;Chem. Abstr. 2006, 146,77563.
15. Hahn, K.M.; Toutchkine, A.;Muthyala, R.; Kraynov,V.; Bark, S. J.; Burton, D. R.; Chamberlain, C.Labeled peptides, proteins and antibodies andprocesses and intermediates useful for theirpreparation. U.S. Pat. Appl. Publ. US 2002055133,2002; Chem. Abstr. 2002, 136, 366139.
16. Duty, S. M.; Singh, N. P.; Ryan, L.; Chen, Z.; Lewis,C.; Huang, T.; Hauser, R. Reliability of the cometassay in cryopreserved human sperm. Hum. Reprod.2002, 17, 1274–1280.
17. Erikson, G. H.; Daksis, J. I. Improving the signal/noise ratio of nucleic acid hybridization assays bypreincubation of primer and target with nucleic acidbinding agents. U.S. Pat. Appl. Publ. US2004180345, 2004; Chem. Abstr. 2004, 141,255469.
18. Erikson, G. H. Method for modifying transcriptionand/or translation in an organism byheteropolymeric probes and duplex, triplex orquadruplex hybridization for therapeutic,prophylactic and/or analytic uses. U.S. Pat. Appl.Publ. US 2003181412, 2003; Chem. Abstr. 2003,139, 272000.
19. Poetter, K.; Gould, T. Human papilloma virus (HPV)detection using nucleic acid probes, microbeads, andfluorescence-activated cell sorter (FACS). PCT Int.Appl. WO 2006060872, 2006; Chem. Abstr. 2006,145, 41223.
20. Vannier, E. Methods for detection of pathogens in redblood cells. PCT Int. Appl. WO 2006031544, 2006;Chem. Abstr. 2006, 144, 307966.
21. Levy, M.; Ellington, A. D.; Pai, S. Proximity ligationassays with peptide conjugate �burrs� and aptamersfor the sensitive detection of spores and cancer cells.PCT Int. Appl.WO 2007027796, 2007;Chem. Abstr.2007, 146, 312239.
22. Cullum, M. E.; Duplessis, C. A.; Crepeau, L. J.Method for the detection of stress biomarkersincluding cortisol by fluorescence polarization. U.S. Pat. Appl. Publ US 2006105397, 2006; Chem.Abstr. 2006, 144, 463810.
23. Straus, D. Rapid and sensitive detection of cells andviruses. PCT Int. Appl. WO 2003073817, 2003;Chem. Abstr. 2003, 139, 210425.
24. Transfiguracion, J.; Kamen, A. Detection of intactrecombinant viruses using fluorescent staining andchromatography. PCT Int. Appl. WO 2006053443,2006; Chem. Abstr. 2006, 144, 463861.
25. Yoshikawa, Y.; Hizume, K.; Oda, Y.; Takeyasu, K.;Araki, S.; Yoshikawa, K. Protective effect of vitaminC against double-strand breaks in reconstitutedchromatin visualized by single-moleculeobservation. Biophys. J. 2006, 90, 993–999.
YOYO 1 499
YOYO 3
CAS Registry Number 156312-20-8
Chemical Structure
CA Index Name Quinolinium, 1,10-[1,3-propanediyl-bis[(dimethyliminio)-3,1-propanediyl]]bis[4-[3-(3-meth-yl-2(3H)-benzoxazolylidene)-1-propen-1-yl]-, iodide(1:4)
Other Names Quinolinium, 1,10-[1,3-propanediylbis[(dimethyliminio)-3,1-propanediyl]]bis[4-[3-(3-methyl-2(3H)-benzoxazolylidene)-1-propenyl]-, tetraiodide; YO-YO 3; YOYO 3 iodide
Merck Index Number Not listed
Chemical/Dye Class Cyanine
Molecular Formula C53H62I4N6O2
Molecular Weight 1322.73
Physical Form Orange-red powder
Solubility Soluble in dimethyl sulfoxide
Melting Point >250 �C
Absorption (lmax) 612 nm
Emission (lmax) 631 nm
Synthesis Synthetic method1
Staining Applications Nucleic acids;2–9 cells;10 leuko-cytes;15 nuclei;15 proteins;9 sperms11
Biological Applications Nucleic acid hybridiza-tion;12,13 detecting nucleic acids,2–9 cells,10 pathogens;14
counting embryoblasts;15 monitoring cell cycle kinetics16
Industrial Applications Analyzing polymers17
Safety/Toxicity No data available
REFERENCES
1. Millard, P. J.; Roth, B. L.; Yue, S. T.; Haugland, R. P.Fluorescent viability assay using cyclic-substitutedunsymmetrical cyanine dyes. U.S. Patent 5534416,1996; Chem. Abstr. 1996, 125, 162751.
2. Exner,M.;Rogers,A.Methods for identifying nucleicacids and determining melting temperature usingmultiple fluorophores and FRET. U.S. Pat. Appl.Publ. US 2007172836, 2007; Chem. Abstr. 2007,147, 182489.
3. Wittwer, C. T.; Dujols, V. E.; Reed, G.; Zhou, L.Genotyping by thermal denaturation analysis usingloss of fluorescence of double-stranded DNA-specificdyes as a reporter to monitor denaturation. PCT Int.Appl. WO 2004038038, 2004; Chem. Abstr. 2004,140, 386988.
4. Kim, K. H.; Min, J. H.; Lee, I. H.; Kim, A. G. Methodfor highly sensitive nucleic acid detection usingnanopore and non-specific nucleic acid-binding
++
++
4 I_
N
(H2C)3
N (CH2)3 N
(CH2)3
N
CH
H3C
CH3
CH3
H3C
CHCH
CH
HC CH
ON NO
H3C CH3
500 YOYO 3
agent. U.S. Pat. Appl. Publ. US 2006292605, 2006;Chem. Abstr. 2006, 146, 56513.
5. Miller, B. L.; Krauss, T. D.; Du, H.; Crnkovich, N.;Strohsahl, C. M. Use of sensor arrays containinghairpin probes for detecting nucleic acids ofpathogens. PCT Int. Appl. WO 2004061127, 2004;Chem. Abstr. 2004, 141, 118285.
6. Erikson, G. H.; Daksis, J. I.; Kandic, I.; Picard, P.Conditions for formation of three- and four-strandednucleic acid complexes and their detection andanalytical use. PCT Int. Appl. WO 2002103051,2002; Chem. Abstr. 2002, 138, 50812.
7. Li, J.; Lee, J. Y.; Yeung, E. S. Quantitative screeningof single copies of human papilloma viral DNAwithout amplification. Anal. Chem. 2006, 78,6490–6496.
8. Williams, J. G. K.; Anderson, J. P. Field-switch singlemolecule DNA sequencing in a two-electrodechamber. PCT Int. Appl. WO 2005111240, 2005;Chem. Abstr. 2005, 143, 474548.
9. Alba, F. J.; Bermudez, A.; Daban, J. R. Green-lighttransilluminator for the detection withoutphotodamage of proteins and DNA labeled withdifferent fluorescent dyes. Electrophoresis 2001,22, 399–403.
10. Anderson, A. L.; Knutson, C. R.; Mueth, D.; Plewa,J.; Tanner, E. Methods for staining cells foridentification and sorting. U.S. Pat. Appl. Publ.US 2006172315, 2006; Chem. Abstr. 2006, 145,183714.
11. Matsumoto, T.; Okada, H.; Hamaguchi, Y. Methodand reagent for counting sperm by flow cytometry.Jpn. Kokai Tokkyo Koho JP 2001242168, 2001;Chem. Abstr. 2001, 135, 207869.
12. Erikson, G. H.; Daksis, J. I. Improving the signal/noise ratio of nucleic acid hybridization assays bypreincubation of primer and target with nucleic acidbinding agents. U.S. Pat. Appl. Publ. US2004180345, 2004;Chem. Abstr. 2004, 141, 255469.
13. Hahn, J. H.; Park, N. Electrochemical device andmethods for detection method of nucleic acidhybridization. PCT Int. Appl. WO 2003010338,2003; Chem. Abstr. 2003, 138, 149875.
14. Vannier, E. Methods for detection of pathogens in redblood cells. PCT Int. Appl. WO 2006031544, 2006;Chem. Abstr. 2006, 144, 307966.
15. Heuven, B.; Wong, F. S.; Tsuji, T.; Sakata, T.;Hamaguchi, I. Method for classifying and countingerythroblasts by flow cytometry. Jpn. Kokai TokkyoKoho JP 11326323, 1999; Chem. Abstr. 1999, 132,1804.
16. Beisker, W.; Weller-Mewe, E. M.; Nusse, M.Fluorescence enhancement of DNA-bound TO-PRO-3 by incorporation of bromodeoxyuridine tomonitor cell cycle kinetics. Cytometry 1999, 37,221–229.
17. Gilmanshin, R.; Chan, E. Y. Methods of analyzingpolymers using a spatial network of fluorophores andfluorescence resonance energy transfer. U.S. Patent6263286, 2001; Chem. Abstr. 2001, 135, 104686.
YOYO 3 501
