Overview
BCN-succinimidyl ester is a specialized bicyclo[6.1.0]nonyne (BCN) derivative designed for bioorthogonal chemistry applications. As an NHS ester, it reacts selectively with primary amines (e.g., lysine residues or N-termini of proteins) to form stable amide bonds. The BCN group subsequently undergoes rapid, copper-free click chemistry with azide-containing molecules. This reagent is particularly valuable in biological research where traditional copper-catalyzed azide-alkyne cycloaddition (CuAAC) is impractical due to cytotoxicity. Its ring strain provides exceptional reactivity with azides, enabling efficient labeling even at low concentrations.
Physical and Chemical Properties
BCN-succinimidyl ester typically presents as a moisture-sensitive crystalline solid with moderate solubility in polar aprotic solvents like DMSO or DMF. The NHS ester moiety hydrolyzes in aqueous solutions (half-life ~30 min at pH 7.4), necessitating immediate use after dissolution. The BCN core exhibits remarkable kinetic stability against nucleophiles while maintaining high azide reactivity (second-order rate constant ~0.1-1 M⁻¹s⁻¹). This selectivity arises from its strained cycloalkyne structure, which lowers the activation energy for [3+2] cycloaddition without metal catalysts.
Main Applications
In proteomics, BCN-NHS ester enables site-specific labeling of antibodies for fluorescence microscopy or mass spectrometry. Pharmaceutical researchers employ it to construct antibody-drug conjugates (ADCs) with precise drug-to-antibody ratios (DAR). The reagent also facilitates live-cell imaging through metabolic labeling strategies. When conjugated to biomolecules like peptides or oligonucleotides, it allows real-time tracking of cellular processes without copper toxicity concerns. Emerging applications include hydrogel modification and surface functionalization for biosensors.
Safety and Storage
As an active ester compound, BCN-succinimidyl ester may cause skin/eye irritation and respiratory sensitization. Always handle in a fume hood using nitrile gloves and protective eyewear. Avoid inhalation of powder and contact with moisture. For long-term storage, aliquot the reagent under argon in sealed amber vials with desiccant. Repeated freeze-thaw cycles degrade performance. Discard hydrolyzed solutions (indicated by precipitation or pH change) as they lose conjugation efficiency.
B2B Procurement Guide
When sourcing BCN-succinimidyl ester, prioritize suppliers providing comprehensive analytical data (HPLC, NMR, MS). Batch-to-batch consistency is critical for reproducible bioconjugation yields. Technical specifications should include: - Purity ≥95% (essential for minimizing side reactions) - Moisture content <0.5% (verified by Karl Fischer titration) - Validated reactivity with standard azide probes Consider ordering small test quantities before bulk purchases. For GMP applications, request additional documentation including residual solvent analysis and endotoxin testing.
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