Norbornene-chitosan spray-dried microspheres for peptide conjugation using thiol-ene “photoclick” chemistry

Pedro M. Alves; Diana R. Fonseca; Rúben F. Pereira; Berta N. Estevinho; Cátia Teixeira; Paula Gomes; M. Cristina L. Martins

doi:10.5821/sibb.30.1.12402

Norbornene-chitosan spray-dried microspheres for peptide conjugation using thiol-ene “photoclick” chemistry

Pedro M. Alves, Diana R. Fonseca, Rúben F. Pereira, Berta N. Estevinho, Cátia Teixeira, Paula Gomes, M. Cristina L. Martins^*

^*Autor correspondente para este trabalho

Resultado de pesquisa › revisão de pares

Resumo

A ação de péptidos bioativos, tais como péptidos antimicrobianos (AMP), no corpo humano é frequentemente comprometida pelo seu limitado tempo de permanência e estabilidade no local alvo. A bioconjugação de péptidos em superfícies de biomateriais é uma das estratégias que pode ajudar a ultrapassar estas limitações. Neste trabalho, microesferas de quitosano-norborneno (NorChit) foram produzidas e modificadas para reagir com péptidos contendo grupos tiol, através da química tiol-eno promovida por exposição a luz UV. As microesferas de NorChit foram produzidas por spray-drying e reticuladas com ditiotreitol (DTT) para evitar a sua solubilização. As microesferas apresentaram um diâmetro de 5 ± 2 μm e uma morfologia redonda e lisa, com poços ao longo da superfície que podem estar relacionados com interações hidrofóbicas internas entre os grupos norborneno. A bioconjugação tiol-eno, efetuada com um péptido modelo fluorescente, teve um rendimento de 45%, enquanto que usando o péptido sem exposição ao UV levou a um máximo de adsorção de 30%. No geral, as microesferas de NorChit têm potencial para transportarem péptidos bioativos podendo vir a ser usadas para proteger e manter os péptidos ativos em ambientes mais adversos no corpo humano.

Idioma original	English
Páginas (de-até)	7-15
Número de páginas	9
Revista	Biomecánica
Volume	30
Número de emissão	1
DOIs	https://doi.org/10.5821/sibb.30.1.12402
Estado da publicação	Publicado - 2022
Publicado externamente	Sim

Keywords

Quitosano-norborneno
Conjugação covalente
Péptido
Spray-drying
Microscopia eletrónica de varrimento
Tiol-eno

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10.5821/sibb.30.1.12402Licença:

Citação

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title = "Norbornene-chitosan spray-dried microspheres for peptide conjugation using thiol-ene “photoclick” chemistry",

abstract = "The action of bioactive peptides, such as antimicrobial peptides (AMP), in the human body is often compromised by limited residence time and stability in the target site. Bioconjugation of peptides to biomaterial surfaces is one of the strategies that may overcome these limitations. Herein, norbornene-chitosan (NorChit) microspheres were engineered to react with thiolated peptides by thiol- ene “photoclick” chemistry. NorChit microspheres were produced by spray drying and crosslinked with dithiothreitol (DTT) to prevent their solubilization. Microspheres with a diameter of 5 ± 2 μm showed round and smooth morphology with pockets over the surface that could be related with hydrophobic interactions between internal norbornene groups. Thiol-ene bioconjugation carried out using a fluorescent model peptide, showed a yield of 45%, whereas using the peptide but without UV exposure indicated a maximum of peptide adsorption of 30%. Altogether, NorChit microspheres show the potential for carrying bioactive peptides, which may open avenues for AMP activity onto harsh environments in the body.",

keywords = "Norbornene-chitosan, Covalent conjugation, Peptide, Spray-drying, Scanning electron microscopy, Thiol-ene, Quitosano-norborneno, Conjuga{\c c}{\~a}o covalente, P{\'e}ptido, Spray-drying, Microscopia eletr{\'o}nica de varrimento, Tiol-eno",

author = "Alves, {Pedro M.} and Fonseca, {Diana R.} and Pereira, {R{\'u}ben F.} and Estevinho, {Berta N.} and C{\'a}tia Teixeira and Paula Gomes and Martins, {M. Cristina L.}",

year = "2022",

doi = "10.5821/sibb.30.1.12402",

language = "English",

volume = "30",

pages = "7--15",

journal = "Biomec{\'a}nica",

issn = "1885-9518",

publisher = "Sociedad Ib{\'e}rica de Biomec{\'a}nica y Biomateriales",

number = "1",

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TY - JOUR

T1 - Norbornene-chitosan spray-dried microspheres for peptide conjugation using thiol-ene “photoclick” chemistry

AU - Alves, Pedro M.

AU - Fonseca, Diana R.

AU - Pereira, Rúben F.

AU - Estevinho, Berta N.

AU - Teixeira, Cátia

AU - Gomes, Paula

AU - Martins, M. Cristina L.

PY - 2022

Y1 - 2022

N2 - The action of bioactive peptides, such as antimicrobial peptides (AMP), in the human body is often compromised by limited residence time and stability in the target site. Bioconjugation of peptides to biomaterial surfaces is one of the strategies that may overcome these limitations. Herein, norbornene-chitosan (NorChit) microspheres were engineered to react with thiolated peptides by thiol- ene “photoclick” chemistry. NorChit microspheres were produced by spray drying and crosslinked with dithiothreitol (DTT) to prevent their solubilization. Microspheres with a diameter of 5 ± 2 μm showed round and smooth morphology with pockets over the surface that could be related with hydrophobic interactions between internal norbornene groups. Thiol-ene bioconjugation carried out using a fluorescent model peptide, showed a yield of 45%, whereas using the peptide but without UV exposure indicated a maximum of peptide adsorption of 30%. Altogether, NorChit microspheres show the potential for carrying bioactive peptides, which may open avenues for AMP activity onto harsh environments in the body.

AB - The action of bioactive peptides, such as antimicrobial peptides (AMP), in the human body is often compromised by limited residence time and stability in the target site. Bioconjugation of peptides to biomaterial surfaces is one of the strategies that may overcome these limitations. Herein, norbornene-chitosan (NorChit) microspheres were engineered to react with thiolated peptides by thiol- ene “photoclick” chemistry. NorChit microspheres were produced by spray drying and crosslinked with dithiothreitol (DTT) to prevent their solubilization. Microspheres with a diameter of 5 ± 2 μm showed round and smooth morphology with pockets over the surface that could be related with hydrophobic interactions between internal norbornene groups. Thiol-ene bioconjugation carried out using a fluorescent model peptide, showed a yield of 45%, whereas using the peptide but without UV exposure indicated a maximum of peptide adsorption of 30%. Altogether, NorChit microspheres show the potential for carrying bioactive peptides, which may open avenues for AMP activity onto harsh environments in the body.

KW - Norbornene-chitosan

KW - Covalent conjugation

KW - Peptide

KW - Spray-drying

KW - Scanning electron microscopy

KW - Thiol-ene

KW - Quitosano-norborneno

KW - Conjugação covalente

KW - Péptido

KW - Spray-drying

KW - Microscopia eletrónica de varrimento

KW - Tiol-eno

U2 - 10.5821/sibb.30.1.12402

DO - 10.5821/sibb.30.1.12402

M3 - Article

SN - 1885-9518

VL - 30

SP - 7

EP - 15

JO - Biomecánica

JF - Biomecánica

IS - 1

ER -

Norbornene-chitosan spray-dried microspheres for peptide conjugation using thiol-ene “photoclick” chemistry

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Keywords

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