WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 341177
CAS#: 152068-09-2
Description: Oxazole yellow is a fluorescent cyanine dye that binds to DNA and is used to detect apoptotic cells. Oxazole yellow does not enter live cells. However, during apoptosis the cytoplasmic membrane becomes slightly permeable, allowing entry of the dye. Oxazole yellow is often used along with propidium iodide, a DNA dead cell stain that does not enter either live or apoptotic cells. The λEx/λEm of Oxazole yellow is 491/509.
MedKoo Cat#: 341177
Name: Oxazole yellow
CAS#: 152068-09-2
Chemical Formula: C24H29I2N3O
Exact Mass: 629.04
Molecular Weight: 629.3249
Elemental Analysis: C, 45.81; H, 4.64; I, 40.33; N, 6.68; O, 2.54
Related CAS #: 152068-09-2 143413-86-9
Synonym: Oxazole yellow; YO-Pro 1; YO Pro 1; YO-Pro-1; YO Pro-1;
IUPAC/Chemical Name: 4-[(3-Methyl-2(3H)-benzoxazolylidene)methyl]-1-[3-(trimethylammonio)propyl]-quinolinium diiodide
InChi Key: ULHRKLSNHXXJLO-UHFFFAOYSA-L
InChi Code: InChI=1S/C24H29N3O.2HI/c1-25-22-12-7-8-13-23(22)28-24(25)18-19-14-16-26(15-9-17-27(2,3)4)21-11-6-5-10-20(19)21;;/h5-8,10-14,16,18H,9,15,17H2,1-4H3;2*1H/q+2;;/p-2
SMILES Code: C[N+](CCC[N+]1=C2C=CC=CC2=C(/C=C3OC4=CC=CC=C4N\3C)C=C1)(C)C.[I-].[I-]
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 629.3249 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Jin C, Cerutti D, Cukier RI. Molecular Dynamics of Oxazole Yellow Dye in its Ground and First Excited Electronic States in Solution and when Intercalated in dsDNA. J Phys Chem B. 2017 Nov 9;121(44):10242-10248. doi: 10.1021/acs.jpcb.7b08187. Epub 2017 Oct 25. PubMed PMID: 29022340.
2: Licari G, Brevet PF, Vauthey E. Fluorescent DNA probes at liquid/liquid interfaces studied by surface second harmonic generation. Phys Chem Chem Phys. 2016 Jan 28;18(4):2981-92. doi: 10.1039/c5cp06151b. PubMed PMID: 26740332.
3: Lindberg DJ, Esbjörner EK. Detection of amyloid-β fibrils using the DNA-intercalating dye YOYO-1: Binding mode and fibril formation kinetics. Biochem Biophys Res Commun. 2016 Jan 8;469(2):313-8. doi: 10.1016/j.bbrc.2015.11.051. Epub 2015 Dec 2. PubMed PMID: 26612254.
4: Mapp CT, Owens EA, Henary M, Grant KB. Oxidative cleavage of DNA by pentamethine carbocyanine dyes irradiated with long-wavelength visible light. Bioorg Med Chem Lett. 2014 Jan 1;24(1):214-9. doi: 10.1016/j.bmcl.2013.11.035. Epub 2013 Nov 25. PubMed PMID: 24332091.
5: Fei X, Gu Y, Li C, Liu Y, Yu L. Synthesis and spectra of a kind of novel longer-wavelength benzoxazole indole styryl cyanine dye with a carbazole-bridged chain. J Fluoresc. 2013 Jan;23(1):221-6. doi: 10.1007/s10895-012-1137-y. Epub 2012 Oct 11. PubMed PMID: 23054303.
6: Friedrich F, Heckel A. Photon cascade with clip-on fluorophores. Chemphyschem. 2011 Aug 1;12(11):2073-5. doi: 10.1002/cphc.201100295. Epub 2011 May 12. PubMed PMID: 21567707.
7: Murade CU, Subramaniam V, Otto C, Bennink ML. Interaction of oxazole yellow dyes with DNA studied with hybrid optical tweezers and fluorescence microscopy. Biophys J. 2009 Aug 5;97(3):835-43. doi: 10.1016/j.bpj.2009.05.024. PubMed PMID: 19651041; PubMed Central PMCID: PMC2718157.
8: Bethge L, Jarikote DV, Seitz O. New cyanine dyes as base surrogates in PNA: forced intercalation probes (FIT-probes) for homogeneous SNP detection. Bioorg Med Chem. 2008 Jan 1;16(1):114-25. Epub 2007 Jan 12. PubMed PMID: 17981472.
9: Fürstenberg A, Vauthey E. Ultrafast excited-state dynamics of oxazole yellow DNA intercalators. J Phys Chem B. 2007 Nov 1;111(43):12610-20. Epub 2007 Oct 11. PubMed PMID: 17929857.
10: Fürstenberg A, Deligeorgiev TG, Gadjev NI, Vasilev AA, Vauthey E. Structure-fluorescence contrast relationship in cyanine DNA intercalators: toward rational dye design. Chemistry. 2007;13(30):8600-9. PubMed PMID: 17642070.
11: Drouillon V, Houriez F, Buze M, Lagrange P, Herrmann JL. [Automated RNA amplification for the rapid identification of Mycobacterium tuberculosis complex in respiratory specimens]. Pathol Biol (Paris). 2006 Oct-Nov;54(8-9):518-22. Epub 2006 Oct 5. French. PubMed PMID: 17027192.
12: Thompson M. DNA sequence-directed assembly of two peptide bioconjugates. Bioorg Chem. 2006 Oct;34(5):235-47. Epub 2006 Aug 2. PubMed PMID: 16887165.
13: Thompson M. Synthesis, photophysical effects, and DNA targeting properties of oxazole yellow-peptide bioconjugates. Bioconjug Chem. 2006 Mar-Apr;17(2):507-13. PubMed PMID: 16536484.
14: Eriksson M, Mehmedovic M, Westman G, Akerman B. Time-resolved electrophoretic analysis of mobility shifts for dissociating DNA ligands. Electrophoresis. 2005 Feb;26(3):524-32. PubMed PMID: 15690453.
15: Murayama Y, Sano M. Exchange of counterions in DNA condensation. Biopolymers. 2005 Apr 15;77(6):354-60. PubMed PMID: 15690415.
16: Uy JL, Asbury CL, Petersen TW, van den Engh G. The polarization of fluorescence of DNA stains depends on the incorporation density of the dye molecules. Cytometry A. 2004 Sep;61(1):18-25. PubMed PMID: 15351985.
17: Kamei T, Paegel BM, Scherer JR, Skelley AM, Street RA, Mathies RA. Integrated hydrogenated amorphous Si photodiode detector for microfluidic bioanalytical devices. Anal Chem. 2003 Oct 15;75(20):5300-5. PubMed PMID: 14710806.
18: Bjorndal MT, Fygenson DK. DNA melting in the presence of fluorescent intercalating oxazole yellow dyes measured with a gel-based assay. Biopolymers. 2002 Oct 5;65(1):40-4. PubMed PMID: 12209471.
19: Fafandel M, Bihari N, Krajcar V, Müller WE, Zahn RK, Batel R. Specific detection of cyclobutane pyrimidine dimers in phytoplankton DNA by a non-radioactive assay based on T4-endonuclease V digestion. Sci Total Environ. 2001 Sep 28;277(1-3):149-59. PubMed PMID: 11589394.
20: Wong M, Kong S, Dragowska WH, Bally MB. Oxazole yellow homodimer YOYO-1-labeled DNA: a fluorescent complex that can be used to assess structural changes in DNA following formation and cellular delivery of cationic lipid DNA complexes. Biochim Biophys Acta. 2001 Jul 2;1527(1-2):61-72. PubMed PMID: 11420144.
