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1223357-57-0

1223357-57-0 Structure

1223357-57-0 Structure
IdentificationBack Directory
[Name]

Cy5-alkyne
[CAS]

1223357-57-0
[Synonyms]

Cy5-alkyne
[Molecular Formula]

C35H42ClN3O
[MOL File]

1223357-57-0.mol
[Molecular Weight]

556.19
Chemical PropertiesBack Directory
[storage temp. ]

-20°C
[solubility ]

Soluble in DMSO, DMF, DCM
[form ]

powder
[color ]

Brown to black
[Appearance]

Dark blue solid
[ex/em]

640/664 nm (PBS buffer)
[ε(extinction coefficient)]

250000 L⋅mol−1⋅cm−1
[Φ(quantum yield)]

0.2
[InChIKey]

VOWXUNAERRNFLE-UHFFFAOYSA-N
[SMILES]

C([N+]1=C(C(C)(C)C2=CC=CC=C12)C=CC=CC=C1C(C2=CC=CC=C2N1C)(C)C)CCCCC(=O)NCC#C.[Cl-]
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26
[WGK Germany ]

WGK 3
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Hazard InformationBack Directory
[Description]

Cy5 alkyne is a cynaine linker containing an alkyne group, which enables Click Chemistry to attach deeply colored and photostable Cyanine5 fluorophore to various azide-bearing molecules. Cyanine5 is a popular fluorophore that has been widely used for various applications including intact organism imaging.
[Chemical Properties]

Appearance: Dark blue solid
ex/em: 640/664 nm (PBS buffer)
Extinction coefficient (ε): 250000 L??mol??1??cm??1
Quantum yield (Φ): 0.2
[Uses]

Cyanine5 alkyne (Alkyne-Cy5) is a fluorescent dye used to label azide proteins and can be used to analyse post-translational modifications of proteins, glycosylation etc. Cyanine5 alkyne can also be used as a mitochondrial OXPHOS inhibitor to inhibit the growth of cancer stem cells (CSC)[1][2]. Cyanine5 alkyne is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
[References]

[1] Amanda R Burnham-Marusich, et al. Size-matched alkyne-conjugated cyanine fluorophores to identify differences in protein glycosylation. Electrophoresis. 2014 Sep;35(18):2621-5. DOI:10.1002/elps.201400241
[2] Camillo Sargiacomo, et al. MitoTracker Deep Red (MTDR) Is a Metabolic Inhibitor for Targeting Mitochondria and Eradicating Cancer Stem Cells (CSCs), With Anti-Tumor and Anti-Metastatic Activity In Vivo. Front Oncol. 2021 Jul 30;11:678343. DOI:10.3389/fonc.2021.678343
[Abs/Em Maxima]

646/662 nm
[Fluoresene quantum yield]

0.2
[Extinction Coefficient]

250000
[CF260]

0.03
[CF280]

0.04
[Microscopy Laser Line]

633 or 635 nm
[Flow Cytometry Laser Line]

633 or 635 nm
[Spectrally Similar Dyes]

Alexa Fluor® 647, CF™ 647 Dye, DyLight™649
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