Functionalization of the PEG corona of nanoparticles by clip photochemistry in water: application to the grafting of RGD ligands on PEGylated USPIO imaging agent
Pourcelle, Vincent; Laurent, Sophie; Welle, Aet al.
2015 • In Bioconjugate Chemistry, 26(5), p. 822-829
CMMI - Centre de Recherche en Microscopie et Imagerie Médicale
Disciplines :
Chemistry
Author, co-author :
Pourcelle, Vincent
Laurent, Sophie ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale
Welle, A
Vriamont, N
Stanicki, Dimitri ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale
Vander Elst, Luce ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale
Muller, Robert ; Université de Mons > Faculté de Médecine et de Pharmacie > FMP - Service du Doyen
Marchand-Brynaert, J.
Language :
English
Title :
Functionalization of the PEG corona of nanoparticles by clip photochemistry in water: application to the grafting of RGD ligands on PEGylated USPIO imaging agent
Publication date :
30 April 2015
Journal title :
Bioconjugate Chemistry
ISSN :
1043-1802
Publisher :
American Chemical Society, United States - District of Columbia
Volume :
26(5)
Pages :
822-829
Peer reviewed :
Peer Reviewed verified by ORBi
Research unit :
M108 - Chimie générale, organique et biomédicale
Research institute :
R550 - Institut des Sciences et Technologies de la Santé R100 - Institut des Biosciences
Cheng, Z., Al Zaki, A., Hui, J. Z., Muzykantov, V. R., and Tsourkas, A. (2012) Multifunctional nanoparticles: cost versus benefit of adding targeting and imaging capabilities Science 338, 903-910
Crommelin, D. J. A. and Florence, A. T. (2013) Towards more effective advanced drug delivery systems Int. J. Pharm. 454, 496-511
Muro, S. (2012) Challenges in design and characterization of ligand-targeted drug delivery systems J. Controlled Release 164, 125-137
Turcheniuk, K., Tarasevych, A. V., Kukhar, V. P., Boukherroub, R., and Szunerits, S. (2013) Recent advances in surface chemistry strategies for the fabrication of functional iron oxide based magnetic nanoparticles Nanoscale 5, 10729-10752
Venditto, V. J. and Szoka, F. C., Jr. (2013) Cancer nanomedicines: So many papers and so few drugs! Adv. Drug Delivery Rev. 65, 80-88
Pourcelle, V., Le Duff, C. S., Freichels, H., Jérôme, C., and Marchand-Brynaert, J. (2012) Clickable PEG conjugate obtained by 'clip' photochemistry: Synthesis and characterization by quantitative 19F NMR J. Fluorine Chem. 140, 62-69
Freichels, H., Pourcelle, V., Le Duff, C. S., Marchand-Brynaert, J., and Jérôme, C. (2011) 'Clip' and 'Click' chemistries combination: toward easy PEGylation of degradable aliphatic polyesters Macromol. Rapid Commun. 32, 616-621
Brunner, J., Senn, H., and Richards, F. M. (1980) 3-Trifluoromethyl-3-phenyldiazirine. A new carbene generating group for photolabeling reagents J. Biol. Chem. 255, 3313-18
Keana, J. F. W. and Cai, S. X. (1990) New reagents for photoaffinity labeling: synthesis and photolysis of functionalized perfluorophenyl azides J. Org. Chem. 55, 3640-3647
Blencowe, A. and Hayes, W. (2005) Development and application of diazirines in biological and synthetic macromolecular systems Soft Matter 1, 178-205
Coco, R., Plapied, L., Pourcelle, V., Jérôme, C., Brayden, D. J., Schneider, Y.-J., and Préat, V. (2013) Drug delivery to inflamed colon by nanoparticles: Comparison of different strategies Int. J. Pharm. 440, 3-12
Danhier, F., Pourcelle, V., Marchand-Brynaert, J., Jérôme, C., Feron, O., and Préat, V. (2012) Chapter eight-targeting of tumor endothelium by RGD-grafted PLGA-nanoparticles Methods Enzymol. 508, 157-175
Freichels, H., Pourcelle, V., Auzély-Velty, R., Marchand-Brynaert, J., and Jérôme, C. (2012) Synthesis of poly(lactide-co-glycolide-co-caprolactone)-graft-mannosylated poly(ethylene oxide) copolymers by combination of 'clip' and 'click' chemistries Biomacromolecules 13, 760-768
Zhang, Z., Lai, Y., Yu, L., and Ding, J. (2010) Effects of immobilizing sites of RGD peptides in amphiphilic block copolymers on efficacy of cell adhesion Biomaterials 31, 7873-7882
Hashimoto, M. and Hatanaka, Y. (2008) Recent progress in diazirine-based photoaffinity labeling Eur. J. Org. Chem. 2008, 2513-2523
Platz, M., Admasu, A. S., Kwiatkowski, S., Crocker, P. J., Imai, N., and Watt, D. S. (1991) Photolysis of 3-aryl-3-(trifluoromethyl)diazirines: a caveat regarding their use in photoaffinity probes Bioconjugate Chem. 2, 337-341
Blencowe, A., Blencowe, C., Cosstick, K., and Hayes, W. (2008) A carbene insertion approach to functionalised poly(ethylene oxide)-based gels React. Funct. Polym. 68, 868-875
Mehenni, H., Pourcelle, V., Gohy, J.-F., and Marchand-Brynaert, J. (2012) Synthesis and application of new photocrosslinkers for poly(ethylene glycol) Aust. J. Chem. 65, 193-201
Pauloehrl, T., Delaittre, G., Winkler, V., Welle, A., Bruns, M., Börner, H. G., Greiner, A. M., Bastmeyer, M., and Barner-Kowollik, C. (2012) Adding spatial control to click chemistry: phototriggered Diels-Alder surface (bio)functionalization at ambient temperature Angew. Chem., Int. Ed. 51, 1071-1074
Tischer, T., Rodriguez-Emmenegger, C., Trouillet, V., Welle, A., Schueler, V., Mueller, J. O., Goldmann, A. S., Brynda, E., and Barner-Kowollik, C. (2014) Photo-patterning of non-fouling polymers and biomolecules on paper Adv. Mater. 26, 4087-4092
Arumugam, S., Orski Sara, V., Mbua Ngalle, E., McNitt, C., Boons, G.-J., Locklin, J., and Popik Vladimir, V. (2013) Pure Appl. Chem. 1499
Arumugam, S. and Popik, V. V. (2014) Sequential 'Click'-'Photo-Click' cross-linker for catalyst-free ligation of azide-tagged substrates J. Org. Chem. 79, 2702-2708
Danhier, F., Vroman, B., Lecouturier, N., Crokart, N., Pourcelle, V., Freichels, H., Jérôme, C., Marchand-Brynaert, J., Feron, O., and Préat, V. (2009) Targeting of tumor endothelium by RGD-grafted PLGA-nanoparticles loaded with Paclitaxel J. Controlled Release 140, 166-173
Fievez, V., Plapied, L., des Rieux, A., Pourcelle, V., Freichels, H., Wascotte, V., Vanderhaeghen, M.-L., Jerôme, C., Vanderplasschen, A., and Marchand-Brynaert, J. 2009, Targeting nanoparticles to M cells with non-peptidic ligands for oral vaccination Eur. J. Pharm. Biopharm. 73, 16-24
Elias, D. R., Poloukhtine, A., Popik, V., and Tsourkas, A. (2013) Effect of ligand density, receptor density, and nanoparticle size on cell targeting Nanomedicine 9, 194-201
Valencia, P. M., Hanewich-Hollatz, M. H., Gao, W., Karim, F., Langer, R., Karnik, R., and Farokhzad, O. C. (2010) Effects of ligands with different water solubilities on self-assembly and properties of targeted nanoparticles Biomaterials 32, 6226-6233
Rerat, V., Laurent, S., Burtéa, C., Driesschaert, B., Pourcelle, V., Vander Elst, L., Muller, R. N., and Marchand-Brynaert, J. (2010) Ultrasmall particle of iron oxide-RGD peptidomimetic conjugate: synthesis and characterisation Bioorg. Med. Chem. Lett. 20, 1861-1865
Bridot, J.-L., Stanicki, D., Laurent, S., Boutry, S., Gossuin, Y., Leclère, P., Lazzaroni, R., Vander Elst, L., and Muller, R. N. (2013) New carboxysilane-coated iron oxide nanoparticles for nonspecific cell labelling Contrast Media Mol. Imaging 8, 466-474
Danhier, F., Le Breton, A., and Préat, V. (2012) RGD-based strategies to target alpha(v) beta(3) integrin in cancer therapy and diagnosis Mol. Pharmaceutics 9, 2961-2973
Tsourkas, A., Shinde-Patil, V. R., Kelly, K. A., Patel, P., Wolley, A., Allport, J. R., and Weissleder, R. (2005) In vivo imaging of activated endothelium using an anti-VCAM-1 magnetooptical probe Bioconjugate Chem. 16, 576-581
Stanicki, D., Boutry, S., Laurent, S., Wacheul, L., Nicolas, E., Crombez, D., Vander Elst, L., Lafontaine, D. L. J., and Muller, R. N. (2014) Carboxy-silane coated iron oxide nanoparticles: a convenient platform for cellular and small animal imaging J. Mater. Chem. B 2, 387-397
McAllister, G. D., Perry, A., and Taylor, R. J. K. (2008) Diaziridines and Diazirines, in Comprehensive Heterocyclic Chemistry III (Alan, R. K., Christopher, A. R., Eric, F. V. S., and Richard, J. K. T., Eds.) pp 539-557, Elsevier, Oxford.
Raimer, B. and Lindel, T. (2013) Photoactivation of (p-methoxyphenyl)(trifluoromethyl)diazirine in the presence of phenolic reaction partners Chem. - Eur. J. 19, 6551-6555
Song, M.-G. and Sheridan, R. S. (2011) Effects of CF3 groups and charged substituents on singlet carbene stabilities-a density functional theory study J. Phys. Org. Chem. 24, 889-893
Hashimoto, M. and Hatanaka, Y. (2006) Practical conditions for photoaffinity labeling with 3-trifluoromethyl-3-phenyldiazirine photophore Anal. Biochem. 348, 154-156
Mayer, T. and Maier, M. E. (2007) Design and synthesis of a tag-free chemical probe for photoaffinity labeling Eur. J. Org. Chem. 2007, 4711-4720
Wang, J., Kubicki, J., Gustafson, T. L., and Platz, M. S. (2008) The dynamics of carbene solvation: an ultrafast study of p-biphenylyltrifluoromethylcarbene J. Am. Chem. Soc. 130, 2304-2313
Hosoya, T., Hiramatsu, T., Ikemoto, T., Nakanishi, M., Aoyama, H., Hosoya, A., Iwata, T., Maruyama, K., Endo, M., and Suzuki, M. (2004) Novel bifunctional probe for radioisotope-free photoaffinity labeling: compact structure comprised of photospecific ligand ligation and detectable tag anchoring units Org. Biomol. Chem. 2, 637-641
Burtea, C., Laurent, S., Port, M., Lancelot, E., Ballet, S., Rousseaux, O., Toubeau, G., Vander Elst, L., Corot, C., and Muller, R. N. (2009) Magnetic resonance molecular imaging of vascular cell adhesion molecule-1 expression in inflammatory lesions using a peptide-vectorized paramagnetic imaging probe J. Med. Chem. 52, 4725-4742
Chen, Z., Ahonen, M., Hämäläinen, H., Bergelson, J. M., Kähäri, V.-M., and Lahesmaa, R. (2002) High-efficiency gene transfer to primary T lymphocytes by recombinant adenovirus vectors J. Immunol. Methods 260, 79-89
Huang, S., Endo, R. I., and Nemerow, G. R. (1995) Upregulation of integrins alpha v beta 3 and alpha v beta 5 on human monocytes and T lymphocytes facilitates adenovirus-mediated gene delivery J. Virol. 69, 2257-63
Laurent, S., Forge, D., Port, M., Roch, A., Robic, C., Vander Elst, L., and Muller, R. N. (2008) Magnetic iron oxide nanoparticles: synthesis, stabilization, vectorization, physicochemical characterizations, and biological applications Chem. Rev. 108, 2064-2110
Roch, A., Muller, R. N., and Gillis, P. (1999) Theory of proton relaxation induced by superparamagnetic particles J. Chem. Phys. 110, 5403-5411
Boutry, S., Brunin, S., Mahieu, I., Laurent, S., Elst, L. V., and Muller, R. N. (2008) Magnetic labeling of non-phagocytic adherent cells with iron oxide nanoparticles: a comprehensive study Contrast Media Mol. Imaging 3, 223-232