Fluorophore labeling of core-crosslinked polymeric micelles for multimodal in vivo and ex vivo optical imaging

Nanomedicine

Volumn 10, Issue 7, 2015, Pages 1111-1125

  Shi, Yang ^a   Kunjachan, Sijumon ^b   Wu, Zhuojun ^b,c   Gremse, Felix ^b   Moeckel, Diana ^b   Van Zandvoort, Marc ^b,c   Kiessling, Fabian ^b   Storm, Gert ^a,d   Van Nostrum, Cornelus F ^a   Hennink, Wim E ^a   Lammers, Twan ^a,b,d  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UNIVERSITY HOSPITAL RWTH AACHEN   (Germany)

^c MAASTRICHT UNIVERSITY   (Netherlands)

^d UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

drug targeting; micelles; nanomedicine; optical imaging; PEG; pHPMA; theranostics

Indexed keywords

COPOLYMER; CYSTAMINE; MACROGOL; POLYMER; ACRYLAMIDE DERIVATIVE; CARBOCYANINE; DRUG CARRIER; DY-676; FLUORESCENT DYE; INDOLE DERIVATIVE; MACROGOL DERIVATIVE; MICELLE; MONOMETHOXYPOLYETHYLENE GLYCOL; N-(2-HYDROXYPROPYL)METHACRYLAMIDE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONJUGATION; CROSS LINKING; EX VIVO STUDY; EXTRAVASATION; FLUORESCENCE IMAGING; FLUORESCENCE MICROSCOPY; IN VIVO STUDY; INTERSTITIUM; LASER MICROSCOPY; MICELLE; MOUSE; NONHUMAN; PRIORITY JOURNAL; SYNTHESIS; VASCULAR TUMOR; ANIMAL; CHEMISTRY; COLON; COLONIC NEOPLASMS; DRUG DELIVERY SYSTEM; HUMAN; MULTIMODAL IMAGING; NUDE MOUSE; PATHOLOGY; TISSUE DISTRIBUTION; TUMOR CELL LINE;

ACRYLAMIDES; ANIMALS; CARBOCYANINES; CELL LINE, TUMOR; COLON; COLONIC NEOPLASMS; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; FLUORESCENT DYES; HUMANS; INDOLES; MICE; MICE, NUDE; MICELLES; MULTIMODAL IMAGING; OPTICAL IMAGING; POLYETHYLENE GLYCOLS; TISSUE DISTRIBUTION;

EID: 84929104923     PISSN: 17435889     EISSN: 17486963     Source Type: Journal    
DOI: 10.2217/nnm.14.170     Document Type: Article

References (59)

1. Farokhzad OC, Langer R. Nanomedicine: developing smarter therapeutic and diagnostic modalities. Adv. Drug. Deliv. Rev. 58(14), 1456-1459 (2006).
2. Peer D, Karp JM, Hong S, Farokhzad OC, Margalit R, Langer R. Nanocarriers as an emerging platform for cancer therapy. Nat. Nano 2, 751-760 (2007).
3. Lammers T, Hennink WE, Storm G. Tumour-targeted nanomedicines: principles and practice. Br. J. Cancer. 99(3), 392-397 (2008).
4. Lammers T, Kiessling F, Hennink WE, Storm G. Drug targeting to tumors: principles, pitfalls and (pre-) clinical progress. J. Control. Release 161(2), 175-187 (2012).
5. Jain RK, Stylianopoulos T. Delivering nanomedicine to solid tumors. Nat. Rev. Clin. Oncol. 7(11), 653-664 (2010).
6. Sumer B, Gao J. Theranostic nanomedicine for cancer. Nanomedicine 3(2), 137-140 (2008).
7. Torchilin V. Tumor delivery of macromolecular drugs based on the EPR effect. Adv. Drug Deliv. Rev. 63(3), 131-135 (2011).
8. Deng C, Jiang Y, Cheng R, Meng F, Zhong Z. Biodegradable polymeric micelles for targeted and controlled anticancer drug delivery: promises, progress and prospects. Nano Today 7(5), 467-480 (2012).
9. Jones M-C, Leroux J-C. Polymeric micelles-a new generation of colloidal drug carriers. Eur. J. Pharm. Biopharm. 48(2), 101-111 (1999).
10. Kataoka K, Harada A, Nagasaki Y. Block copolymer micelles for drug delivery: design, characterization and biological significance. Adv. Drug Deliv. Rev. 47(1), 113-131 (2012).
11. Oerlemans C, Bult W, Bos M, Storm G, Nijsen JF, Hennink W. Polymeric micelles in anticancer therapy: targeting, imaging and triggered release. Pharm. Res. 27(12), 2569-2589 (2010).
12. O'Reilly RK, Hawker CJ, Wooley KL. Cross-linked block copolymer micelles: functional nanostructures of great potential and versatility. Chem. Soc. Rev. 35(2), 1068-1083 (2006).
13. Read ES, Armes SP. Recent advances in shell cross-linked micelles. Chem. Commun. 3(12), 3021-3035 (2007).
14. van Nostrum CF. Covalently cross-linked amphiphilic block copolymer micelles. Soft Matter 7(7), 3246-3259 (2011).
15. Shi Y, van den Dungen ETA, Klumperman B, van Nostrum CF, Hennink WE. Reversible addition-fragmentation chain transfer synthesis of a micelle-forming, structure reversible thermosensitive diblock copolymer based on the N-(2-hydroxy propyl) methacrylamide backbone. ACS Macro Lett. 2(5), 403-408 (2013).
16. Shi Y, van Steenbergen MJ, Teunissen EA et al. Π-Π stacking increases the stability and loading capacity of thermosensitive polymeric micelles for chemotherapeutic drugs. Biomacromolecules 14(6), 1826-1837 (2013).
17. Talelli M, Hennink WE. Thermosensitive polymeric micelles for targeted drug delivery. Nanomedicine 6(7), 1245-1255 (2011).
18. Wei H, Cheng SX, Zhang XZ, Zhuo RX. Thermo-sensitive polymeric micelles based on poly(Nisopropylacrylamide) as drug carriers. Prog. Polym. Sci. 34(9), 893-910 (2009).
19. Lammers T, Subr V, Ulbrich K, Hennink WE, Storm G, Kiessling F. Polymeric nanomedicines for image-guided drug delivery and tumor-targeted combination therapy. Nano Today 5(3), 197-212 (2010).
20. Lammers T, Aime S, Hennink WE, Storm G, Kiessling F. Theranostic nanomedicine. Acc. Chem. Res. 44(10), 1029-1038 (2011).
21. Papagiannaros A, Kale A, Levchenko TS, Mongayt D, Hartner WC, Torchilin VP. Near infrared planar tumor imaging and quantification using nanosized Alexa 750-labeled phospholipid micelles. Int. J. Nanomedicine 4, 123-131 (2009).
22. Zhang R, Lu W, Wen X et al. Annexin A5-conjugated polymeric micelles for dual SPECT and optical detection of apoptosis. J. Nucl. Med. 52(6), 958-964 (2011).
23. Gao X, Cui Y, Levenson RM, Chung LWK, Nie S. In vivo cancer targeting and imaging with semiconductor quantum dots. Nat. Biotech. 22(8), 969-976 (2004).
24. Janib SM, Moses AS, MacKay JA. Imaging and drug delivery using theranostic nanoparticles. Adv. Drug Deliv. Rev. 62(11), 1052-1063 (2010).
25. Ding H, Wu F. Image guided biodistribution and pharmacokinetic studies of theranostics. Theranostics 2(11), 1040-1053 (2012).
26. Xing Y, Zhao J, Conti PS, Chen K. Radiolabeled nanoparticles for multimodality tumor imaging. Theranostics 4(3), 290-306 (2014).
27. Yen SK, Padmanabhan P, Selvan ST. Multifunctional iron oxide nanoparticles for diagnostics, therapy and macromolecule delivery. Theranostics 3(12), 986-1003 (2013).
28. Kunjachan S, Gremse F, Theek B et al. Noninvasive optical imaging of nanomedicine biodistribution. ACS Nano 7(1), 252-262 (2012).
29. Gremse F, Theek B, Kunjachan S et al. Absorption reconstruction improves biodistribution assessment of fluorescent nanoprobes using hybrid fluorescence-mediated tomography. Theranostics 4(10), 960-971 (2014).
30. Rijcken CJ, Snel CJ, Schiffelers RM, van Nostrum CF, Hennink WE. Hydrolysable core-crosslinked thermosensitive polymeric micelles: synthesis, characterisation and in vivo studies. Biomaterials 28(36), 5581-5593 (2007).
31. Talelli M, Iman M, Varkouhi AK et al. Core-crosslinked polymeric micelles with controlled release of covalently entrapped doxorubicin. Biomaterials 31(30), 7797-7804 (2010).
32. Crielaard BJ, Rijcken CJ, Quan L et al. Glucocorticoidloaded core-cross-linked polymeric micelles with wailorable release kinetics for targeted therapy of rheumatoid arthritis. Angew. Chem. Int. Ed. 51(29), 7254-7258 (2012).
33. Meng F, Hennink WE, Zhong Z. Reduction-sensitive polymers and bioconjugates for biomedical applications. Biomaterials 30(12), 2180-2198 (2009).
34. Rösler A, Vandermeulen GWM, Klok H-A. Advanced drug delivery devices via self-assembly of amphiphilic block copolymers. Adv. Drug Deliv. Rev. 53(1), 270-279 (2012).
35. Ryu J-H, Chacko RT, Jiwpanich S, Bickerton S, Babu RP, Thayumanavan S. Self-cross-linked polymer nanogels: a versatile nanoscopic drug delivery platform. J. Am. Chem. Soc. 132(48), 17227-17235 (2010).
36. Sun H, Meng F, Cheng R, Deng C, Zhong Z. Reductionsensitive degradable micellar nanoparticles as smart and intuitive delivery systems for cancer chemotherapy. Expert Opin. Drug Deliv. 10(8), 1109-1122 (2013).
37. Yang Y, Pan D, Luo K, Li L, Gu Z. Biodegradable and amphiphilic block copolymer-doxorubicin conjugate as polymeric nanoscale drug delivery vehicle for breast cancer therapy. Biomaterials 34(33), 8430-8443 (2013).
38. Duangjai A, Luo K, Zhou Y, Yang J, Kopeček J. Combination cytotoxicity of backbone degradable HPMA copolymer gemcitabine and platinum conjugates toward human ovarian carcinoma cells. Eur. J. Pharm. Biopharm. 87(1), 187-196 (2014).
39. Zhang R, Luo K, Yang J et al. Synthesis and evaluation of a backbone biodegradable multiblock HPMA copolymer nanocarrier for the systemic delivery of paclitaxel. J. Control. Release 166(1), 66-74 (2013).
40. Luo K, Yang J, Kopečková P, Kopeček J. Biodegradable Multiblock Poly[N-(2-hydroxypropyl)methacrylamide] via reversible addition-fragmentation chain transfer polymerization and click chemistry. Macromolecules 44(8), 2481-2488 (2011).
41. Yang J, Luo K, Pan H, KopečkováP, Kopeček J. Synthesis of biodegradable multiblock copolymers by click coupling of RAFT-generated heterotelechelic polyHPMA conjugates. Reactive Funct. Polym. 71(3), 294-302 (2011).
42. Wong SY, Putnam D. Overcoming limiting side reactions associated with an NHS-activated precursor of polymethacrylamide-based polymers. Bioconjugate Chem. 18(3), 970-982 (2007).
43. Neradovic D, Soga O, Van Nostrum CF, Hennink WE. The effect of the processing and formulation parameters on the size of nanoparticles based on block copolymers of poly(ethylene glycol) and poly(N-isopropylacrylamide) with and without hydrolytically sensitive groups. Biomaterials 25(12), 2409-2418 (2004).
44. Li Y, Lokitz BS, Armes SP, McCormick CL. Synthesis of reversible shell cross-linked micelles for controlled release of bioactive agents. Macromolecules 39(8), 2726-2728 (2006).
45. Xu X, Smith AE, Kirkland SE, McCormick CL. Aqueous RAFT synthesis of pH-responsive triblock copolymer mPEO-PAPMA-PDPAEMA and formation of shell crosslinked micelles. Macromolecules 41(22), 8429-8435 (2008).
46. Zhang J, Jiang X, Zhang Y, Li Y, Liu S. Facile fabrication of reversible core cross-linked micelles possessing thermosensitive swellability. Macromolecules 40(25), 9125-9132 (2007).
47. Neradovic D, van Steenbergen MJ, Vansteelant L, Meijer YJ, van Nostrum CF, Hennink WE. Degradation mechanism and kinetics of thermosensitive polyacrylamides containing lactic acid side chains. Macromolecules 36(20), 7491-7498 (2003).
48. Soga O, van Nostrum CF, Ramzi A et al. Physicochemical characterization of degradable thermosensitive polymeric micelles. Langmuir 20(21), 9388-9395 (2004).
49. Novo L, van Gaal EVB, Mastrobattista E, van Nostrum CF, Hennink WE. Decationized crosslinked polyplexes for redox-triggered gene delivery. J. Control. Release 169(3), 246-256 (2013).
50. Filipe V, Hawe A, Jiskoot W. Critical evaluation of nanoparticle tracking analysis (NTA) by nanosight for the measurement of nanoparticles and protein aggregates. Pharm. Res. 27(5), 796-810 (2010).
51. Jia Z, Wong L, Davis TP, Bulmus V. One-pot conversion of RAFT-generated multifunctional block copolymers of HPMA to doxorubicin conjugated acid- and reductant-sensitive crosslinked micelles. Biomacromolecules 9(11), 3106-3113 (2008).
52. Kakizawa Y, Harada A, Kataoka K. Environment-sensitive stabilization of core-shell structured polyion complex micelle by reversible cross-linking of the core through disulfide bond. J. Am. Chem. Soc. 121(48), 11247-11248 (1999).
53. Allmeroth M, Moderegger D, Biesalski B et al. Modifying the body distribution of hpma-based copolymers by molecular weight and aggregate formation. Biomacromolecules 12(7), 2841-2849 (2011).
54. Allmeroth M, Moderegger D, Gündel D et al. PEGylation of HPMA-based block copolymers enhances tumor accumulation in vivo : A quantitative study using radiolabeling and positron emission tomography. J. Control. Release 172(1), 77-85 (2013).
55. Allmeroth M, Moderegger D, Gündel D et al. HPMA-LMA copolymer drug carriers in oncology: an in vivo PET study to assess the tumor line-specific polymer uptake and body distribution. Biomacromolecules 14(9), 3091-3101 (2013).
56. Borgman MP, Coleman T, Kolhatkar RB, Geyser-Stoops S, Line BR, Ghandehari H. Tumor-targeted HPMA copolymer-(RGDfK)-(CHX-A′-DTPA) conjugates show increased kidney accumulation. J. Control. Release 132(3), 193-199 (2008).
57. Kunjachan S, Pola R, Gremse F et al. Passive versus active tumor targeting using RGD- and NGR-modified polymeric nanomedicines. Nano Lett. 14(2), 972-981 (2014).
58. Kuppusamy P, Li H, Ilangovan G et al. Noninvasive imaging of tumor redox status and its modification by tissue glutathione levels. Cancer Res. 62(1), 307-312 (2002).
59. Lozano N, Al-Jamal WT, Taruttis A et al. Liposome-gold nanorod hybrids for high-resolution visualization deep in tissues. J. Am. Chem. Soc. 134(32), 13256-13258 (2012).