Oxazole yellow | CAS#152068-09-2 | Fluorescent cyanine dye

MedKoo Cat#: 341177 | Name: Oxazole yellow

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Oxazole yellow

CAS#152068-09-2

Theoretical Analysis

MedKoo Cat#: 341177

Name: Oxazole yellow

CAS#: 152068-09-2

Chemical Formula: C24H29I2N3O

Exact Mass: 629.0400

Molecular Weight: 629.32

Elemental Analysis: C, 45.81; H, 4.64; I, 40.33; N, 6.68; O, 2.54

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 650.00	2 Weeks

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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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oxazole yellow is a fluorescent cyanine dye that binds to DNA and is used to detect apoptotic cells.

In vitro activity:

This study developed a real-time assay using fluorescent probes for single-virus genome exposure than can report on stages of viral entry including or subsequent to fusion pore formation and prior to viral genome trafficking. This study accomplished this using oxazole yellow nucleic-acid-binding dyes, which can be encapsulated in the lumen of target membranes to permit specific detection of fusion events. Using this assay, this study shows that influenza virus fuses with liposomes of different sizes with indistinguishable kinetics by both testing liposomes extruded through pores of different radii and showing that the fusion kinetics of individual liposomes are uncorrelated with the size of the liposome. Reference: Biophys J. 2022 Dec 6;121(23):4467-4475. https://pubmed.ncbi.nlm.nih.gov/36330566/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 629.32 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

Formulation protocol:

1. Villamil Giraldo AM, Mannsverk S, Kasson PM. Measuring single-virus fusion kinetics using an assay for nucleic acid exposure. Biophys J. 2022 Dec 6;121(23):4467-4475. doi: 10.1016/j.bpj.2022.11.002. Epub 2022 Nov 9. PMID: 36330566; PMCID: PMC9748363. 2. Kucharska K, Pilz M, Bielec K, Kalwarczyk T, Kuźma P, Hołyst R. Two Intercalation Mechanisms of Oxazole Yellow Dimer (YOYO-1) into DNA. Molecules. 2021 Jun 19;26(12):3748. doi: 10.3390/molecules26123748. PMID: 34205435; PMCID: PMC8234192.

In vitro protocol:

In vivo protocol:

TBD

1: Shi H, Li QY, Li H, Wang HY, Fan CX, Dong QY, Pan BC, Ji ZL, Li JY. ROS- induced oxidative stress is a major contributor to sperm cryoinjury. Hum Reprod. 2024 Feb 1;39(2):310-325. doi: 10.1093/humrep/dead250. PMID: 38011909. 2: Villamil Giraldo AM, Mannsverk S, Kasson PM. Measuring single-virus fusion kinetics using an assay for nucleic acid exposure. Biophys J. 2022 Dec 6;121(23):4467-4475. doi: 10.1016/j.bpj.2022.11.002. Epub 2022 Nov 9. PMID: 36330566; PMCID: PMC9748363. 3: Kucharska K, Pilz M, Bielec K, Kalwarczyk T, Kuźma P, Hołyst R. Two Intercalation Mechanisms of Oxazole Yellow Dimer (YOYO-1) into DNA. Molecules. 2021 Jun 19;26(12):3748. doi: 10.3390/molecules26123748. PMID: 34205435; PMCID: PMC8234192. 4: 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. PMID: 29022340. 5: 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. PMID: 26740332. 6: 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. PMID: 26612254. 7: 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. PMID: 24332091. 8: 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. PMID: 23054303. 9: 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. PMID: 21567707. 10: 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. PMID: 19651041; PMCID: PMC2718157. 11: 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. doi: 10.1016/j.bmc.2006.12.044. Epub 2007 Jan 12. PMID: 17981472. 12: Fürstenberg A, Vauthey E. Ultrafast excited-state dynamics of oxazole yellow DNA intercalators. J Phys Chem B. 2007 Nov 1;111(43):12610-20. doi: 10.1021/jp073182t. Epub 2007 Oct 11. PMID: 17929857. 13: 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. doi: 10.1002/chem.200700665. PMID: 17642070. 14: Drouillon V, Houriez F, Buze M, Lagrange P, Herrmann JL. Identification rapide de Mycobacterium tuberculosis complex dans les échantillons respiratoires par amplification d'ARN en temps réel [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. French. doi: 10.1016/j.patbio.2006.07.041. Epub 2006 Oct 5. PMID: 17027192. 15: Thompson M. DNA sequence-directed assembly of two peptide bioconjugates. Bioorg Chem. 2006 Oct;34(5):235-47. doi: 10.1016/j.bioorg.2006.06.001. Epub 2006 Aug 2. PMID: 16887165. 16: Thompson M. Synthesis, photophysical effects, and DNA targeting properties of oxazole yellow-peptide bioconjugates. Bioconjug Chem. 2006 Mar- Apr;17(2):507-13. doi: 10.1021/bc050307t. PMID: 16536484. 17: 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. doi: 10.1002/elps.200410057. PMID: 15690453. 18: Murayama Y, Sano M. Exchange of counterions in DNA condensation. Biopolymers. 2005 Apr 15;77(6):354-60. doi: 10.1002/bip.20243. PMID: 15690415. 19: 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. doi: 10.1002/cyto.a.20059. PMID: 15351985. 20: 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. doi: 10.1021/ac0301550. PMID: 14710806.