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Cy3 Picolyl Azide

Introduction

Click chemistry describes a class of chemical reactions that use bio-orthogonal or biologically unique moieties to label and detect a molecule of interest in mild, aqueous conditions. The click reaction involves a copper-catalyzed triazole formation from an azide and an alkyne. The azide and alkyne moieties can be used interchangeably; either one can be used to tag the molecule of interest, while the other is used for subsequent detection.

Picolyl azide is a functionalized organic azide derivative that incorporates a picolyl group (a pyridine ring attached to a methylene group) which can chelate copper ions, enhancing the rate and efficiency of copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions.

The Cy3 picolyl azide is reactive with terminal alkyne via a copper-catalyzed click reaction at a much lower copper (I) concentration without sacrificing reaction efficiency, which protects against undesired copper side reactions with proteins (e.g., GFP, RPE), nucleic acids (e.g., RNA, oligos), and even small molecules (e.g., phalloidin).

Features

  • Faster reaction rate — The copper-chelating ability significantly accelerates the CuAAC reaction;
  • Reduced catalyst loading — Allows for a substantial reduction in the amount of copper catalyst needed;
  • Improved biocompatibility — Lower copper catalyst levels lead to less toxicity, making it suitable for use in living systems and imaging.


 
Figure 1. Click chemistry labeling


Specifications

Label: Cy3
Ex/Em: 555/565 nm
Detection Method: Fluorescent
Solubility: DMSO, DMF
Product Size: 0.5 µmol
Storage Conditions: -20 ℃, protect from light
Shipping Condition: Room Temperature

Applications
Bioconjugation, biomolecular labeling, live-cell imaging, and flow cytometry.

 

To order

Buy Cat.No. Product Name Ex/Em(nm) Unit Price
C344 Cy3 Picolyl Azide 555/565 0.5 µmol $200
 

Documents

Datasheet (PDF): C344
MSDS (PDF): C344

Reference

Click-mediated labeling of bacterial membranes through metabolic modification of the lipopolysaccharide inner core.
Dumont A, Malleron A, Awwad M, Dukan S, Vauzeilles B,
Angew Chem Int Ed Engl (2012) 51:3143-3146

Winz ML, Samanta A, Benzinger D, Jäschke A,
Nucleic Acids Res (2012) 40:e78-e78

Ngo JT, Schuman EM, Tirrell DA,
Proc Natl Acad Sci U S A (2013) 110:4992-4997
Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells.
Hsu TL, Hanson SR, Kishikawa K, Wang SK, Sawa M, Wong CH
Proc Natl Acad Sci U S A (2007) 104:2614-2619

Metabolic labeling of sialic acids in living animals with alkynyl sugars.
Chang PV, Chen X, Smyrniotis C, Xenakis A, Hu T, Bertozzi CR, Wu P
Angew Chem Int Ed Engl (2009) 48:4030-4033