Modular Synthesis of Semiconducting Graft Copolymers to Achieve "Clickable" Fluorescent Nanoparticles with Long Circulation and Specific Cancer Targeting.
fluorescent nanoparticles
graft copolymers
polymer brushes
polymer dots
semiconducting polymer nanoparticles
Journal
Advanced materials (Deerfield Beach, Fla.)
ISSN: 1521-4095
Titre abrégé: Adv Mater
Pays: Germany
ID NLM: 9885358
Informations de publication
Date de publication:
11 Mar 2023
11 Mar 2023
Historique:
revised:
23
02
2023
received:
13
01
2023
pubmed:
12
3
2023
medline:
12
3
2023
entrez:
11
3
2023
Statut:
aheadofprint
Résumé
Semiconducting polymer nanoparticles (SPNs) are explored for applications in cancer theranostics because of their high absorption coefficients, photostability, and biocompatibility. However, SPNs are susceptible to aggregation and protein fouling in physiological conditions, which can be detrimental for in vivo applications. Here, a method for achieving colloidally stable and low-fouling SPNs is described by grafting poly(ethylene glycol) (PEG) onto the backbone of the fluorescent semiconducting polymer, poly(9,9'-dioctylfluorene-5-fluoro-2,1,3-benzothiadiazole), in a simple one-step substitution reaction, postpolymerization. Further, by utilizing azide-functionalized PEG, anti-human epidermal growth factor receptor 2 (HER2) antibodies, antibody fragments, or affibodies are site-specifically "clicked" onto the SPN surface, which allows the functionalized SPNs to specifically target HER2-positive cancer cells. In vivo, the PEGylated SPNs are found to have excellent circulation efficiencies in zebrafish embryos for up to seven days postinjection. SPNs functionalized with affibodies are then shown to be able to target HER2 expressing cancer cells in a zebrafish xenograft model. The covalent PEGylated SPN system described herein shows great potential for cancer theranostics.
Identifiants
pubmed: 36905683
doi: 10.1002/adma.202300413
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2300413Subventions
Organisme : Medical Research Council
ID : MR/R015651/1
Pays : United Kingdom
Organisme : EPSRC IRC Agile Early Warning Sensing Systems for Infectious Diseases and Antimicrobial Resistance
ID : EP/R00529X/1
Organisme : EPSRC IRC Agile Early Warning Sensing Systems for Infectious Diseases and Antimicrobial Resistance
ID : EP/K031953/1
Organisme : CRUK
ID : 100063
Organisme : CRUK
ID : 27886
Organisme : CRUK
ID : 29385
Organisme : EPSRC Centre for Doctoral Training in Neurotechnology
ID : EP/L016737/1
Organisme : Leverhulme Trust
Organisme : EPSRC
ID : EP/S023518/1
Organisme : EPSRC
ID : EP/K020641/1
Organisme : EPSRC
ID : EP/T517793/1
Organisme : Wellcome Trust
ID : 209121_Z_17_Z
Pays : United Kingdom
Organisme : UK Regenerative Medicine Platform
ID : MR/R015651/1
Organisme : Rosetrees Trust
Organisme : EC
ID : 859458
Organisme : LifeArc
Organisme : NFR
ID : 314684
Organisme : Institute of Cancer Research
Organisme : Royal Society
Organisme : Wolfson Foundation
Organisme : Kreftforeningen
ID : 711091
Organisme : Norges Forskningsrådet
ID : 275873
Organisme : Norges Forskningsrådet
ID : 273319
Organisme : Royal Academy of Engineering Chair in Emerging Technologies
ID : CiET2021/94
Organisme : H2020 Excellent Science
ID : 859458
Organisme : Aker Scholarship
Organisme : EPRSC and SFI Centre for Doctoral Training in Advanced Characterisation of Materials
ID : EP/S023259/1
Organisme : AffibodyAB
Organisme : University College London
Informations de copyright
© 2023 The Authors. Advanced Materials published by Wiley-VCH GmbH.
Références
J. Li, J. Rao, K. Pu, Biomaterials 2018, 155, 217.
J. Li, K. Pu, Acc. Chem. Res. 2020, 53, 752.
Z. Yang, L. Li, A. J. Jin, W. Huang, X. Chen, Mater. Horiz. 2020, 7, 1474.
D. Cui, J. Huang, X. Zhen, J. Li, Y. Jiang, K. Pu, Angew. Chem., Int. Ed. 2019, 58, 5920.
J. Li, J. Huang, Y. Lyu, J. Huang, Y. Jiang, C. Xie, K. Pu, J. Am. Chem. Soc. 2019, 141, 4073.
Z. Yang, W. Fan, W. Tang, Z. Shen, Y. Dai, J. Song, Z. Wang, Y. Liu, L. Lin, L. Shan, Y. Liu, O. Jacobson, P. Rong, W. Wang, X. Chen, Angew. Chem. 2018, 130, 14297.
X. Hu, Y. Tang, Y. Hu, F. Lu, X. Lu, Y. Wang, J. Li, Y. Li, Y. Ji, W. Wang, D. Ye, Q. Fan, W. Huang, Theranostics 2019, 9, 4168.
C. Xie, W. Zhou, Z. Zeng, Q. Fan, K. Pu, Chem. Sci. 2020, 11, 10553.
C. Xie, X. Zhen, Q. Lei, R. Ni, K. Pu, Adv. Funct. Mater. 2017, 27, 1605397.
C. Xie, X. Zhen, Q. Miao, Y. Lyu, K. Pu, Adv. Mater. 2018, 30, 1801331.
R. Islam, H. Maeda, J. Fang, Expert Opin. Drug Delivery 2022, 19, 199.
V. Mittelheisser, P. Coliat, E. Moeglin, L. Goepp, J. G. Goetz, L. J. Charbonnière, X. Pivot, A. Detappe, Adv. Mater. 2022, 34, 2110305.
D. Wang, J. Liu, Z. Liu, Z. Zhang, Z. Sun, C. Wu, G. Wang, ACS Appl. Nano Mater. 2020, 3, 2214.
C. Wu, T. Schneider, M. Zeigler, J. Yu, P. G. Schiro, D. R. Burnham, J. D. McNeill, D. T. Chiu, J. Am. Chem. Soc. 2010, 132, 15410.
Y. Rong, C. Wu, J. Yu, X. Zhang, F. Ye, M. Zeigler, M. E. Gallina, I. C. Wu, Y. Zhang, Y. H. Chan, W. Sun, K. Uvdal, D. T. Chiu, ACS Nano 2013, 7, 376.
C. Sgro, Toxicology 1995, 105, 23.
S. Chen, S. Florinas, A. Teitgen, Z. Q. Xu, C. Gao, H. Wu, K. Kataoka, H. Cabral, R. J. Christie, Sci. Technol. Adv. Mater. 2017, 18, 666.
D. A. Richards, A. Maruani, V. Chudasama, Chem. Sci. 2016, 8, 63.
A. C. Marques, P. J. Costa, S. Velho, M. H. Amaral, J. Controlled Release 2020, 320, 180.
P. Sapra, E. H. Moase, J. Ma, T. M. Allen, Clin. Cancer Res. 2004, 10, 1100.
D. Duan, A. Wang, L. Ni, L. Zhang, X. Yan, Y. Jiang, H. Mu, Z. Wu, K. Sun, Y. Li, Int. J. Nanomed. 2018, 13, 1831.
V. J. B. Ruigrok, M. Levisson, M. H. M. Eppink, H. Smidt, J. van der Oost, Biochem. J. 2011, 436, 1.
C. Grönwall, S. Ståhl, J. Biotechnol. 2009, 140, 254.
D. A. Richards, Drug Discovery Today: Technol. 2018, 30, 35.
G. Kramer-Marek, D. O. Kiesewetter, L. Martiniova, E. Jagoda, S. B. Lee, J. Capala, Eur. J. Nucl. Med. Mol. Imaging 2008, 35, 1008.
J. Mączyńska, C. Da Pieve, T. A. Burley, F. Raes, A. Shah, J. Saczko, K. J. Harrington, G. Kramer-Marek, Cell Death Dis. 2020, 11, 886.
J. Gao, K. Chen, Z. Miao, G. Ren, X. Chen, S. S. Gambhir, Z. Cheng, Biomaterials 2011, 32, 2141.
J. V. Jokerst, Z. Miao, C. Zavaleta, Z. Cheng, S. S. Gambhir, Small 2011, 7, 625.
A. Narsireddy, K. Vijayashree, M. G. Adimoolam, S. V. Manorama, N. M. Rao, Int. J. Nanomed. 2015, 10, 6865.
K. Cheng, H. Chen, C. H. Jenkins, G. Zhang, W. Zhao, Z. Zhang, F. Han, J. Fung, M. Yang, Y. Jiang, L. Xing, Z. Cheng, ACS Nano 2017, 11, 12276.
G. Feng, Y. Fang, J. Liu, J. Geng, D. Ding, B. Liu, Small 2017, 13, 1602807.
J. Liu, G. Feng, D. Ding, B. Liu, Polym. Chem. 2013, 4, 4326.
N. J. K. Dal, A. Kocere, J. Wohlmann, S. Van Herck, T. A. Bauer, J. Resseguier, S. Bagherifam, H. Hyldmo, M. Barz, B. G. De Geest, F. Fenaroli, Small 2020, 16, 1906719.
A. Kocere, J. Resseguier, J. Wohlmann, F. M. Skjeldal, S. Khan, M. Speth, N. J. K. Dal, M. Y. W. Ng, N. Alonso-Rodriguez, E. Scarpa, L. Rizzello, G. Battaglia, G. Griffiths, F. Fenaroli, EBioMedicine 2020, 58, 102902.
S. Bourke, F. Donà, Y. Teijeiro Gonzalez, B. Qazi Chaudhry, M. Panamarova, E. Mackay, P. S. Zammit, L. A. Dailey, U. S. Eggert, K. Suhling, M. A. Green, ACS Appl. Polym. Mater. 2022, 4, 8193.
J. Sun, N. Chen, X. Chen, Q. Zhang, F. Gao, Anal. Chem. 2019, 91, 12414.
C. G. Qian, S. Zhu, P. J. Feng, Y. L. Chen, J. C. Yu, X. Tang, Y. Liu, Q. D. Shen, ACS Appl. Mater. Interfaces 2015, 7, 18581.
D. Yang, S. Zhang, Y. Hu, J. Chen, B. Bao, L. Yuwen, L. Weng, Y. Cheng, L. Wang, RSC Adv. 2016, 6, 114580.
D. Lubanska, S. Alrashed, G. T. Mason, F. Nadeem, A. Awada, M. DiPasquale, A. Sorge, A. Malik, M. Kojic, M. A. R. Soliman, A. C. deCarvalho, A. Shamisa, S. Kulkarni, D. Marquardt, L. A. Porter, S. Rondeau-Gagné, Sci. Rep. 2022, 12, 12078.
S. Cong, A. Creamer, Z. Fei, S. A. J. Hillman, C. Rapley, J. Nelson, M. Heeney, Macromol. Biosci. 2020, 20, 2000087.
A. Creamer, C. S. Wood, P. D. Howes, A. Casey, S. Cong, A. V. Marsh, R. Godin, J. Panidi, T. D. Anthopoulos, C. H. Burgess, T. Wu, Z. Fei, I. Hamilton, M. A. McLachlan, M. M. Stevens, M. Heeney, Nat. Commun. 2018, 9, 3237.
C. Wang, F. Liu, Q. M. Chen, C. Y. Xiao, Y. G. Wu, W. W. Li, Chin. J. Polym. Sci. 2021, 39, 525.
M. Rimmele, F. Glöcklhofer, M. Heeney, Mater. Horiz. 2022, 9, 2678.
Y.-H. Chan, P.-J. Wu, Part. Part. Syst. Charact. 2015, 32, 11.
D. Zhang, M. Wu, Y. Zeng, N. Liao, Z. Cai, G. Liu, X. Liu, J. Liu, J. Mater. Chem. B 2016, 4, 589.
K. Pu, A. J. Shuhendler, M. P. Valta, L. Cui, M. Saar, D. M. Peehl, J. Rao, Adv. Healthcare Mater. 2014, 3, 1292.
K. Pu, J. Mei, J. V. Jokerst, G. Hong, A. L. Antaris, N. Chattopadhyay, A. J. Shuhendler, T. Kurosawa, Y. Zhou, S. S. Gambhir, Z. Bao, J. Rao, Adv. Mater. 2015, 27, 5184.
X. Zhen, K. Pu, X. Jiang, Small 2021, 17, 2004723.
K. Shou, Y. Tang, H. Chen, S. Chen, L. Zhang, A. Zhang, Q. Fan, A. Yu, Z. Cheng, Chem. Sci. 2018, 9, 3105.
K. Pu, A. J. Shuhendler, J. Rao, Angew. Chem. 2013, 125, 10515.
I. Alberg, S. Kramer, M. Schinnerer, Q. Hu, C. Seidl, C. Leps, N. Drude, D. Möckel, C. Rijcken, T. Lammers, M. Diken, M. Maskos, S. Morsbach, K. Landfester, S. Tenzer, M. Barz, R. Zentel, Small 2020, 16, 1907574.
A. Najer, J. Blight, C. B. Ducker, M. Gasbarri, J. C. Brown, J. Che, H. Høgset, C. Saunders, M. Ojansivu, Z. Lu, Y. Lin, J. Yeow, O. Rifaie-Graham, M. Potter, R. Tonkin, J. Penders, J. J. Doutch, A. Georgiadou, H. M. G. Barriga, M. N. Holme, A. J. Cunnington, L. Bugeon, M. J. Dallman, W. S. Barclay, F. Stellacci, J. Baum, M. M. Stevens, ACS Cent. Sci. 2022, 8, 1238.
A. Najer, A. Belessiotis-Richards, H. Kim, C. Saunders, F. Fenaroli, C. Adrianus, J. Che, R. L. Tonkin, H. Høgset, S. Lörcher, M. Penna, S. G. Higgins, W. Meier, I. Yarovsky, M. M. Stevens, Small 2022, 18, 2201993.
J. C. F. Nogueira, K. Paliashvili, A. Bradford, F. Di Maggio, D. A. Richards, R. M. Day, V. Chudasama, Org. Biomol. Chem. 2020, 18, 2215.
C. Bahou, V. Chudasama, Org. Biomol. Chem. 2022, 20, 5879.
F. Campbell, F. L. Bos, S. Sieber, G. Arias-Alpizar, B. E. Koch, J. Huwyler, A. Kros, J. Bussmann, ACS Nano 2018, 12, 2138.
Y. Y. Chen, A. M. Syed, P. MacMillan, J. V. Rocheleau, W. C. W. Chan, Adv. Mater. 2020, 32, 1906274.
Z. Yang, S. Zheng, W. J. Harrison, J. Harder, X. Wen, J. G. Gelovani, A. Qiao, C. Li, Biomacromolecules 2007, 8, 3422.
M. E. Lobatto, C. Calcagno, A. Millon, M. L. Senders, F. Fay, P. M. Robson, S. Ramachandran, T. Binderup, M. P. M. Paridaans, S. Sensarn, S. Rogalla, R. E. Gordon, L. Cardoso, G. Storm, J. M. Metselaar, C. H. Contag, E. S. G. Stroes, Z. A. Fayad, W. J. M. Mulder, ACS Nano 2015, 9, 1837.
P. Müller, P. Schwille, T. Weidemann, Bioinformatics 2014, 30, 2532.
P. Kapusta, Absolute Diffusion Coefficients: Compilation of Reference Data for FCS Calibration, PicoQuant GmbH, Berlin 2010.