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30154

Sigma-Aldrich

Alkyne cyanine dye 718

for copper catalyzed click labeling

Synonym(s):

2-{2-[3-{2-[1,3-Dihydro-3,3-dimethyl-1-(4-sulfobutyl)-2H-indol-2-ylidene]ethylidene]}-2-(2-propyn-1-ylamino)-1-cyclopenten-1-yl]ethenyl}-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium inner salt

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About This Item

Empirical Formula (Hill Notation):
C40H49N3O6S2
CAS Number:
1188292-54-7
Molecular Weight:
731.96
MDL number:
MFCD18452828
UNSPSC Code:
12352200
PubChem Substance ID:
329753444
NACRES:
NA.32

fluorescence

λex 672 nm; λem 718 nm in ethanol

storage temp.

−20°C

SMILES string

CC1(C)\C(=C/C=C2\CCC(\C=C\C3=[N+](CCCCS([O-])(=O)=O)c4ccccc4C3(C)C)=C2NCC#C)N(CCCCS(O)(=O)=O)c5ccccc15

InChI

1S/C40H49N3O6S2/c1-6-25-41-38-30(21-23-36-39(2,3)32-15-7-9-17-34(32)42(36)26-11-13-28-50(44,45)46)19-20-31(38)22-24-37-40(4,5)33-16-8-10-18-35(33)43(37)27-12-14-29-51(47,48)49/h1,7-10,15-18,21-24H,11-14,19-20,25-29H2,2-5H3,(H2,44,45,46,47,48,49)/b30-21+,36-23+

InChI key

YNKZQYLIDKIPBB-GBYGALLISA-N

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 cyanine dye 718 is a reagent for copper catalyzed click labeling.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Charles T Anderson et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(4), 1329-1334 (2012-01-11)
Polysaccharide-rich cell walls are a defining feature of plants that influence cell division and growth, but many details of cell-wall organization and dynamics are unknown because of a lack of suitable chemical probes. Metabolic labeling using sugar analogs compatible with
Frédéric Mercier et al.
Bioconjugate chemistry, 22(1), 108-114 (2010-12-23)
The alkyne-azide Cu(I)-catalyzed Huisgen cycloaddition, a click-type reaction, was used to label a double-stranded oligonucleotide (siRNA) with fluorine-18. An alkyne solid support CPG for the preparation of monostranded oligonucleotides functionalized with alkyne has been developed. Two complementary azide labeling agents
Kido Nwe et al.
Cancer biotherapy & radiopharmaceuticals, 24(3), 289-302 (2009-06-23)
This update summarizes the growing application of "click" chemistry in diverse areas such as bioconjugation, drug discovery, materials science, and radiochemistry. This update also discusses click chemistry reactions that proceed rapidly with high selectivity, specificity, and yield. Two important characteristics
Migle Tomkuviene et al.
Nucleic acids research, 40(14), 6765-6773 (2012-05-09)
Biophysical and mechanistic investigation of RNA function requires site-specific incorporation of spectroscopic and chemical probes, which is difficult to achieve using current technologies. We have in vitro reconstituted a functional box C/D small ribonucleoprotein RNA 2'-O-methyltransferase (C/D RNP) from the

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