Thiol-ene mediated neoglycosylation of collagen patches: a preliminary study

Laura Russo; Chiara Battocchio; Valeria Secchi; Elena Magnano; Silvia Nappini; Francesca Taraballi; Luca Gabrielli; Francesca Comelli; Antonio Papagni; Barbara Costa; Giovanni Polzonetti; Francesco Nicotra; Antonino Natalello; Silvia M Doglia; Laura Cipolla

doi:10.1021/la404310p

Thiol-ene mediated neoglycosylation of collagen patches: a preliminary study

Laura Russo, Chiara Battocchio, Valeria Secchi, Elena Magnano, Silvia Nappini, Francesca Taraballi, Luca Gabrielli, Francesca Comelli, Antonio Papagni, Barbara Costa, Giovanni Polzonetti, Francesco Nicotra, Antonino Natalello, Silvia M Doglia, Laura Cipolla

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

Abstract

Despite the relevance of carbohydrates as cues in eliciting specific biological responses, the covalent surface modification of collagen-based matrices with small carbohydrate epitopes has been scarcely investigated. We report thereby the development of an efficient procedure for the chemoselective neoglycosylation of collagen matrices (patches) via a thiol-ene approach, between alkene-derived monosaccharides and the thiol-functionalized material surface. Synchrotron radiation-induced X-ray photoelectron spectroscopy (SR-XPS), Fourier transform-infrared (FT-IR), and enzyme-linked lectin assay (ELLA) confirmed the effectiveness of the collagen neoglycosylation. Preliminary biological evaluation in osteoarthritic models is reported. The proposed methodology can be extended to any thiolated surface for the development of smart biomaterials for innovative approaches in regenerative medicine.

Original language	English (US)
Pages (from-to)	1336-42
Number of pages	7
Journal	Langmuir
Volume	30
Issue number	5
DOIs	https://doi.org/10.1021/la404310p
State	Published - Feb 11 2014

Keywords

Animals
Biocompatible Materials
Carbohydrate Sequence
Carbohydrates
Click Chemistry
Collagen
Disease Models, Animal
Enzyme-Linked Immunosorbent Assay
Glycosylation
Male
Molecular Structure
Osteoarthritis
Photoelectron Spectroscopy
Rats
Rats, Wistar
Spectroscopy, Fourier Transform Infrared
Sulfhydryl Compounds
Journal Article
Research Support, Non-U.S. Gov't

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title = "Thiol-ene mediated neoglycosylation of collagen patches: a preliminary study",

abstract = "Despite the relevance of carbohydrates as cues in eliciting specific biological responses, the covalent surface modification of collagen-based matrices with small carbohydrate epitopes has been scarcely investigated. We report thereby the development of an efficient procedure for the chemoselective neoglycosylation of collagen matrices (patches) via a thiol-ene approach, between alkene-derived monosaccharides and the thiol-functionalized material surface. Synchrotron radiation-induced X-ray photoelectron spectroscopy (SR-XPS), Fourier transform-infrared (FT-IR), and enzyme-linked lectin assay (ELLA) confirmed the effectiveness of the collagen neoglycosylation. Preliminary biological evaluation in osteoarthritic models is reported. The proposed methodology can be extended to any thiolated surface for the development of smart biomaterials for innovative approaches in regenerative medicine.",

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author = "Laura Russo and Chiara Battocchio and Valeria Secchi and Elena Magnano and Silvia Nappini and Francesca Taraballi and Luca Gabrielli and Francesca Comelli and Antonio Papagni and Barbara Costa and Giovanni Polzonetti and Francesco Nicotra and Antonino Natalello and Doglia, {Silvia M} and Laura Cipolla",

year = "2014",

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doi = "10.1021/la404310p",

language = "English (US)",

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T1 - Thiol-ene mediated neoglycosylation of collagen patches

T2 - a preliminary study

AU - Russo, Laura

AU - Battocchio, Chiara

AU - Secchi, Valeria

AU - Magnano, Elena

AU - Nappini, Silvia

AU - Taraballi, Francesca

AU - Gabrielli, Luca

AU - Comelli, Francesca

AU - Papagni, Antonio

AU - Costa, Barbara

AU - Polzonetti, Giovanni

AU - Nicotra, Francesco

AU - Natalello, Antonino

AU - Doglia, Silvia M

AU - Cipolla, Laura

PY - 2014/2/11

Y1 - 2014/2/11

N2 - Despite the relevance of carbohydrates as cues in eliciting specific biological responses, the covalent surface modification of collagen-based matrices with small carbohydrate epitopes has been scarcely investigated. We report thereby the development of an efficient procedure for the chemoselective neoglycosylation of collagen matrices (patches) via a thiol-ene approach, between alkene-derived monosaccharides and the thiol-functionalized material surface. Synchrotron radiation-induced X-ray photoelectron spectroscopy (SR-XPS), Fourier transform-infrared (FT-IR), and enzyme-linked lectin assay (ELLA) confirmed the effectiveness of the collagen neoglycosylation. Preliminary biological evaluation in osteoarthritic models is reported. The proposed methodology can be extended to any thiolated surface for the development of smart biomaterials for innovative approaches in regenerative medicine.

AB - Despite the relevance of carbohydrates as cues in eliciting specific biological responses, the covalent surface modification of collagen-based matrices with small carbohydrate epitopes has been scarcely investigated. We report thereby the development of an efficient procedure for the chemoselective neoglycosylation of collagen matrices (patches) via a thiol-ene approach, between alkene-derived monosaccharides and the thiol-functionalized material surface. Synchrotron radiation-induced X-ray photoelectron spectroscopy (SR-XPS), Fourier transform-infrared (FT-IR), and enzyme-linked lectin assay (ELLA) confirmed the effectiveness of the collagen neoglycosylation. Preliminary biological evaluation in osteoarthritic models is reported. The proposed methodology can be extended to any thiolated surface for the development of smart biomaterials for innovative approaches in regenerative medicine.

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KW - Biocompatible Materials

KW - Carbohydrate Sequence

KW - Carbohydrates

KW - Click Chemistry

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KW - Disease Models, Animal

KW - Enzyme-Linked Immunosorbent Assay

KW - Glycosylation

KW - Male

KW - Molecular Structure

KW - Osteoarthritis

KW - Photoelectron Spectroscopy

KW - Rats

KW - Rats, Wistar

KW - Spectroscopy, Fourier Transform Infrared

KW - Sulfhydryl Compounds

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

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DO - 10.1021/la404310p

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JO - Langmuir

JF - Langmuir

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ER -

Thiol-ene mediated neoglycosylation of collagen patches: a preliminary study

Abstract

Keywords

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