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79249

Sigma-Aldrich

Alkyne MegaStokes dye 608

for copper-free click labeling

Synonym(s):

1-{3-{[4-(2-Cyclooctyn-1-ylmethyl)benzoyl]amino}propyl}-4-{2-[4-(dimethylamino)phenyl]ethenyl}pyridinium hexafluorophosphate

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About This Item

Empirical Formula (Hill Notation):
C34H40F6N3OP
CAS Number:
Molecular Weight:
651.67
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.32

form

powder

fluorescence

λex 486 nm; λem 608 nm in ethanol

storage temp.

−20°C

SMILES string

F[P-](F)(F)(F)(F)F.CN(C)c1ccc(\C=C\c2cc[n+](CCCNC(=O)c3ccc(CC4CCCCCC#C4)cc3)cc2)cc1

InChI

1S/C34H39N3O.F6P/c1-36(2)33-19-15-28(16-20-33)11-12-29-21-25-37(26-22-29)24-8-23-35-34(38)32-17-13-31(14-18-32)27-30-9-6-4-3-5-7-10-30;1-7(2,3,4,5)6/h11-22,25-26,30H,3-6,8-9,23-24,27H2,1-2H3;/q;-1/p+1

InChI key

NMJWJBDSPFCEOH-UHFFFAOYSA-O

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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