An easy and simple method for the immobilization of dyes through click reactions: activated alkyne, copper not needed

Sánchez-Bodón, Julia; García-García, Ane; Diaz-Galbarriatu, Maria; Vilas-Vilela, José Luis; Moreno-Benítez, Isabel

doi:10.1039/d4ra01776e

RSC Adv.

2024

DOI: 10.1039/d4ra01776e

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An easy and simple method for the immobilization of dyes through click reactions: activated alkyne, copper not needed

Julia Sánchez-Bodón,

Ane García-García,

Maria Diaz-Galbarriatu

et al.

Abstract: The copper-free azide–alkyne click reaction has shown to be a successful alternative to immobilize covalently a fluorescente compound onto poly(-l-lactic) acid (PLLA) surfaces.

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Expanding (Bio)Conjugation Strategies: Metal-Free Thiol-Yne Photo-Click Reaction for Immobilization onto PLLA Surfaces

Sánchez-Bodón,

Diaz-Galbarriatu,

Pérez-Álvarez

et al. 2024

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The study delves into the use of the thiol-yne click reaction to enhance (bio)conjugation methodologies, particularly focusing on immobilizing biomolecules onto PLLA surfaces. The thiol-yne click reaction, known for its efficiency, selectivity, and versatility in forming carbon-sulfur bonds under mild conditions without transition metal catalysts, is explored for conjugating the fluorophore dansyl onto PLLA surfaces. This approach aims to broaden bioconjugation strategies beyond traditional methods like the Michael-type reaction, expanding their applicability to diverse biomolecules. Utilizing a photoinitiator and specific light for photo-immobilization, the thiol-yne click reaction offers spatial and temporal control, with the absence of transition metal catalysts mitigating concerns of cytotoxicity and metal contamination, rendering it suitable for biomedical applications. The objectives of this research encompass demonstrating the feasibility of the thiol-yne click reaction for surface functionalization and enriching bioconjugation strategies for tailoring PLLA surfaces, ultimately advancing biomedical technologies through precise control over surface properties and functionality. For this purpose, PLLA surfaces were activated through hydrolysis and amidation to introduce the activated alkyne moiety (PLLA-Alkyne), followed by photo-induced dansyl immobilization (PLLA-Dns) with Irgacure 651. Various surface characterization techniques, including SEM, WCA, XPS, ATR-FTIR, and fluorescence microscopy and spectroscopy, validated the successful conjugation. This metal-free method preserves the material’s bulk properties while enabling thiol-containing molecule immobilization.

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Expanding (Bio)Conjugation Strategies: Metal-Free Thiol-Yne Photo-Click Reaction for Immobilization onto PLLA Surfaces

Sánchez-Bodón,

Diaz-Galbarriatu,

Pérez-Álvarez

et al. 2024

Coatings

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An easy and simple method for the immobilization of dyes through click reactions: activated alkyne, copper not needed

Abstract: The copper-free azide–alkyne click reaction has shown to be a successful alternative to immobilize covalently a fluorescente compound onto poly(-l-lactic) acid (PLLA) surfaces.

Cited by 1 publication

References 49 publications

Expanding (Bio)Conjugation Strategies: Metal-Free Thiol-Yne Photo-Click Reaction for Immobilization onto PLLA Surfaces

Expanding (Bio)Conjugation Strategies: Metal-Free Thiol-Yne Photo-Click Reaction for Immobilization onto PLLA Surfaces

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