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SIMPLE, BIOCOMPATIBLE and ROBUST MODIFICATION of CELLULOSE MEMBRANES for the ECO2-FRIENDLY PREPARATION of IMMUNOASSAY DEVICES Julie Credou

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SIMPLE, BIOCOMPATIBLE and ROBUST MODIFICATION of CELLULOSE MEMBRANES for the ECO2-FRIENDLY PREPARATION of IMMUNOASSAY DEVICES Julie Credou SIMPLE, BIOCOMPATIBLE AND ROBUST MODIFICATION OF CELLULOSE MEMBRANES FOR THE ECO2-FRIENDLY PREPARATION OF IMMUNOASSAY DEVICES Julie Credou To cite this version: Julie Credou. SIMPLE, BIOCOMPATIBLE AND ROBUST MODIFICATION OF CELLULOSE MEMBRANES FOR THE ECO2-FRIENDLY PREPARATION OF IMMUNOASSAY DEVICES. Chemical Sciences. École Polytechnique, 2014. English. tel-01071399 HAL Id: tel-01071399 https://pastel.archives-ouvertes.fr/tel-01071399 Submitted on 14 Oct 2014 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Thèse de doctorat de l’École Polytechnique Spécialité : Science des matériaux Présentée par Julie CREDOU SIMPLE, BIOCOMPATIBLE AND ROBUST MODIFICATION OF CELLULOSE MEMBRANES FOR THE ECO²-FRIENDLY PREPARATION OF IMMUNOASSAY DEVICES MODIFICATION SIMPLE, BIOCOMPATIBLE ET ROBUSTE DE MEMBRANES DE CELLULOSE POUR LA PREPARATION ECOLOGIQUE ET ECONOMIQUE DE DISPOSITIFS D'IMMUNOANALYSE Soutenance prévue le 18 Septembre 2014 devant le jury composé de : Dr. Vincent HUC Université Paris-Sud Rapporteur Pr. Nicole JAFFREZIC Université Claude Bernard Lyon 1 Rapporteur Pr. Vincent SOL Université de Limoges Examinateur Pr. Laura FIONI Ecole Polytechnique Examinateur Dr. Thomas BERTHELOT CEA Saclay Directeur de Thèse Acknowledgements Ces travaux de thèse ont été réalisés au CEA de Saclay, dans le Laboratoire d'Innovation en Chimie des Surfaces et Nanosciences (CEA / DSM / IRAMIS / NIMBE / LICSEN) et le Laboratoire d'Études et de Recherches en Immunoanalyse (CEA / DSV / iBiTec-S / SPI / LERI). Je ties tout d’aod à eeie Sege Palai et Hev Vollad de ’avoi aueillie das leus laoatoies espetifs LCSI, ate du LICSEN, et LERI. Mei d’avoi u e a apait à ee à ie e pojet. Je souhaite esuite eeie tout patiulieet Thoas Bethelot, d’aod eadat puis dieteu de cette thèse, pou ’avoi guide tout au long de ces trois années. S’il est faile pou u supeviseu de poite du doigt les hoses ui ne conviennent pas, il paraît beaucoup moins naturel de féliciter un travail satisfaisant. Pourtant, Thomas a toujours su hooe et aspet du tavail d’eadat et ’a jaais ah sa satisfatio devat les tavau aoplis, u’il s’agisse de la datio d’atiles ou de sultats d’epietatios. Ce fut u aspet ts appiale de so eadeet. Il est très motivant de savoir que son travail est apprécié et estimé, ue l’o vous fait ofiae. Mei do Thoas pou la ofiae ue tu ’as aode au long de ces trois années. J’aimerais esuite eeie tous eu ui ’ot consacré un peu (voire beaucoup) de leur temps et m’ont aidée au laboratoire. Tout d’aod, ei à Julie Dao pou ’avoi iitie au aipulatios de Biologie et transmis son savoir- faie das l’laoatio de adelettes de diagosti. U gad ei galeet à Else Yag pou ’avoi iitie à la bactériologie, avoir pris le temps de me coacher dans les manipulations et avoir répondu à toutes mes questions du ieu u’elle pouvait. Merci à Xavier Lefevre pour avoir accompagné mes premiers pas dans le laboratoire de Chimie. Merci à Cédric Zobrist et son sbire Thibault Percerou, les magiciens du laboratoire, qui faisaient sortir les produits finis de leur chapeau…ou plutôt du frigo. Merci à Laure Fillaud pour m’avoir, le temps d’une journée, fais rencontrer les petits canards de l’électrochimie. Merci à Pascale Jegou et Jocelyne Leroy, les reines de l’XPS. Je tiens également à remercier mes compagnons de galère, les autres doctorants - Jérôme Laporte, Ingrid Kikkas, Tiphaine Bourgeteau, Romain Brisse, Claire Soum - pour leur écoute et leur soutien tout au long de ces trois ans. Romain, je te laisse les clés du bureau. Tu es le nouveau concierge. J’espère que tu ne te sentiras pas trop seul pour les nocturnes. Claire, bon courage pour la fin. Tu es la prochaine sur la liste. Je remercie également mes compagnons de nocturne au bâtiment de Biologie : Hervé Bernard et Alexandre Charcosset. Merci également aux compagnons de jour, notamment Karine Moreau pour sa bonne humeur communicative. Côté Chimie, merci aux sportifs : Bruno Jousselme, le roi du catch en mousse, et Guy Deniau, le spécialiste Rugby. Merci à la « Team Berthel’ », en particulier à sa doyenne, Cécile Baudin, et à l’Anglais de l’équipe, Alexandre Causier. Merci aux LEMuriens avec qui nous avons fusionné : Vincent Derycke, notre nouveau chef, et Stéphane Campidelli, mon compatriote Ciel & Blanc (Vive le Racing !). Merci à tous les membres du LICSEN, aux stagiaires de passage que j’ai plus ou moins connus. Merci à « la maman » du labo, ou plutôt la marraine la bonne fée, Catherine Julien, pour son écoute, son soutien et son incroyable capacité à rendre les méandres de l’administratif moins tortueux. Ensuite, je voudrais remercier chaleureusement ceux sans qui cette thèse n’aurait jamais commencé, Pascal Viel et Vincent Huc, et celle sans qui elle n’aurait pas fini aussi bien, Rita Faddoul. Docteur Faddoul ! Je ne saurais dire à quel point j’ai apprécié faire équipe avec toi pour cette dernière ligne droite. Merci pour tous ces moments passés ensemble au laboratoire, les discussions devant le MEB ou l’imprimante, les pauses (café ou non), et tes nombreux conseils. Et Vincent, merci d’avoir toujours été là quand j’en ai eu besoin, d’avoir été à l’écoute. Et un grand merci d’avoir accepté d’être rapporteur de cette thèse. Et merci de m’avoir présenté Pascal. Je voudrais particulièrement adresser un énorme merci à Pascal Viel et Ekaterina Shilova pour leur soutien inconditionnel, au labo comme en dehors. Et pour ce qui est d’en dehors, je voudrais également remercier mes consultants en mécanique des matériaux et amis : Aurélien Souto Lebel, Benoît Beaubier, Pierre Gaborit et tous les membres du LMT- Cachan. Merci pour votre soutien moral tout au long de ces trois ans. Pour finir, je voudrais remercier mes amis et ma famille de m’avoir épaulée et d’avoir supporté sans broncher mon mode de vie « aléatoire » pendant les phases de rédaction. Merci Maman pour les croq’ de 6h du matin, et Stall pour les montagnes de vaisselle. Ma dernière pensée ira à Christophe Agius qui, sans le savoir, m’a tenu compagnie pendant de longues nuits de rédaction. 1 / 110 2 / 110 Keywords Point-of-care diagnostics; Bioactive Paper; Immunoassay; Biosensor; Cellulose; Surface Chemistry Abstract Since the papyri, cellulose has played a significant role in human culture, especially as paper. Nowadays, this ancient product has found new applications in the expanding sector of bioactive paper. Simple paper-based detection devices such as lateral flow immunoassays (LFIAs) are inexpensive, rapid, user-friendly and therefore highly promising for providing resource-limited settings with point-of-care diagnostics. Recently, paper-based biosensing technology has trended towards three-dimensional microfluidic devices and multiplexed assay platforms. Yet, many multiplexed paper- based biosensors implement methods incompatible with the conventional LFIA carrier material: nitrocellulose. It thus tends to be replaced by pure cellulose. This major material change implies to undertake a covalent immobilization of biomolecules on cellulose which preserves their biological activity. Furthermore, the current global issues have stimulated the search for both ecologically and economically friendly (eco²- friendly) materials and processes. As a sustainable and affordable biopolymer, cellulose is an ideal material for developing diagnostic devices. However, the frame material is not the only aspect to consider. The whole device design and production, as well as the biosensing material immobilization or the non-sensing membranes treatment, should be as eco²-friendly as possible. Hence, the spatially controlled modification of cellulose surface seems crucial in the development of such devices since it enables to save expensive matter and to pattern surface properties. In any case, modification procedures should abide by the economic and ecological objectives aforementioned. In this perspective, three processes allowing easy, robust and sustainable modification of cellulose sheets were developed. All are environmentally friendly, simple, time and cost-saving, and versatile. The first procedure is a functionalization of cellulose membranes for covalent antibody immobilization. While cellulose chemical modification is usually operated under harsh conditions in organic solvents, the diazonium-based procedure developed was performed in water, at room temperature, in a single step. Paper sheets have thus been modified and bear different chemical functions which enable to graft biomolecules by common bioconjugate techniques and to perform LFIAs. The second is a chemical-free photoimmobilization procedure which allowed antibodies to be immobilized on cellulose without any photocoupling intermediate nor any biomolecule or substrate pretreatment. This immobilization technique was further combined to inkjet printing to localize the antibodies according to any desired pattern. Native antibodies have thus been printed and immobilized on paper sheets which therefore enable to perform LFIAs. Membranes’ performances were evaluated in terms of visual detection limit and challenged nitrocellulose performances. The third is a modification of cellulose membranes by polymer grafting. Unlike the two previous processes, this technique was developed in order to increase the functionality of the non-sensing cellulose parts of paper-based devices. Yet, it may be employed as another functionalization method for covalent antibody immobilization on cellulose. While cellulose graft copolymerization is usually performed through complex and expensive procedures, the diazonium-based approach employed was performed in water, at room temperature, in a short single step. Cellulose sheets have thus been grafted with several acrylic polymers, first globally through a dipping procedure and then locally by inkjet printing.
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