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52225 Sigma-Aldrich

Alkyne MegaStokes dye 673

for copper catalyzed click labeling

Synonym: 4-{2-[7-(Diethylamino)-2-oxo-2H-1-benzopyran-3-yl]ethenyl}-1-(4-pentyn-1-yl)-3-sulfo-pyridinium inner salt

  • Empirical Formula (Hill Notation) C25H26N2O5S

  • Molecular Weight 466.55

  •  MDL number MFCD18632540

  •  PubChem Substance ID 329757801

  •  NACRES NA.32

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Properties

Related Categories Biochemicals and Reagents, Chemical Biology, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Copper Click Chemistry,
fluorescence   λex 542 nm; λem 673 nm in ethanol
storage temp.   −20°C
SMILES string   CCN(CC)c1ccc2C=C(\C=C\c3cc[n+](CCC#C)cc3S([O-])(=O)=O)C(=O)Oc2c1
InChI   1S/C24H24N2O5S/c1-4-7-13-25-14-12-18(23(17-25)32(28,29)30)8-9-20-15-19-10-11-21(26(5-2)6-3)16-22(19)31-24(20)27/h1,8-12,14-17H,5-7,13H2,2-3H3
InChI key   ODMGQNUCRFIQIN-UHFFFAOYSA-N

Description

General description

The MegaStokes dyes for „click" biological labeling, licensed by LuminoChem are virtually covering the whole visible spectrum reaching the infra-red regime. Besides dyes that are being capable of participating in classical copper catalyzed 1,3-dipolar cycloaddition reaction with the counterparting function, we also provide dyes containing cyclooctyne moiety an alkyne derivative that enables copper free clicking to azides.
These dyes are noteworthy for their large Stokes-shift (120 or 125 nm). Dyes for this kind are exceptionally useful in fluorescence resonance electron transfer (FRET) applications as they do not interfere with the spectral bands of the second fluorophore a common problem in FRET technology. Azido sugars have been used for click-labeling of surface glycoproteins, recently. We have adapted this system to demonstrate the ability of our dyes to undergo bioorthogonal labeling reaction, efficiently. Prior to labeling, Chinese hamster ovary (CHO) cells were incubated with these MegaStockesdyes to test the possible cytostatic effects of these dyes. Experimental results have shown that neither dye is toxic up to 50 μM concentration.

Application

Alkyne MegaStokes dye 673 is a reagent used for copper catalyzed click labeling.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

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Peer-Reviewed Papers
15

References

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