Utilization of micelles formed from poly(ethylene glycol)-block- poly(ε-caprolactone) block copolymers as nanocarriers to enable hydrophobic red two-photon absorbing emitters for cells imaging

Journal of Biomedical Materials Research - Part A

Volumn 93, Issue 3, 2010, Pages 1068-1079

  Tian, Yanqing ^a,c   Wu, Wen Chung ^a   Chen, Ching Yi ^a   Jang, Sei Hum ^a   Zhang, Meng ^b   Strovas, Tim ^a   Anderson, Judy ^b   Cookson, Brad ^b   Li, Yongzhong ^c   Meldrum, Deirdre ^c   Chen, Wen Chang ^d   Jen, Alex K Y ^a  

^a University of Washington   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

^c ARIZONA STATE UNIVERSITY   (United States)

^d NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Block copolymers; Cytotoxicity; Molecular imaging; Nanoparticles; Two photon absorbing materials

Indexed keywords

ABSORBING MATERIALS; AMINO MOIETY; BENZOTHIADIAZOLES; BIO-IMAGING; CAPROLACTONE; CELL INTERNALIZATION; CYTOPLASMIC REGIONS; DYE CONCENTRATION; MOLECULAR IMAGING; NANOCARRIERS; POLYMER CONCENTRATIONS; RED EMITTER; TOXICITY ASSESSMENT; TWO PHOTON;

BLOCK COPOLYMERS; CHROMOPHORES; COPOLYMERIZATION; CYTOLOGY; ETHYLENE; ETHYLENE GLYCOL; HYDROPHOBICITY; LIGHT ABSORPTION; MICELLES; NANOPARTICLES; PHOTONS; POLYETHYLENE OXIDES; TOXICITY;

POLYETHYLENE GLYCOLS;

COPOLYMER; MACROGOL; NANOCARRIER; POLYCAPROLACTONE; TOLUENE;

ANIMAL CELL; ARTICLE; ATOMIC FORCE MICROSCOPY; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; CYTOPLASM; CYTOTOXICITY; FLUORESCENCE MICROSCOPY; HYDROPHOBICITY; INTERNALIZATION; LIGHT SCATTERING; MACROPHAGE; MICELLE; MOLECULAR IMAGING; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD;

ABSORPTION; ANIMALS; CELL DEATH; CELL LINE; CELL SURVIVAL; CHROMATOGRAPHY, GEL; DRUG CARRIERS; HYDROPHOBICITY; IMAGING, THREE-DIMENSIONAL; LACTONES; MACROPHAGES; MICE; MICELLES; MICROSCOPY, CONFOCAL; NANOSTRUCTURES; PHOTONS; POLYETHYLENE GLYCOLS; SCATTERING, RADIATION; SOLVENTS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 77950683868     PISSN: 15493296     EISSN: 15524965     Source Type: Journal    
DOI: 10.1002/jbm.a.32607     Document Type: Article

References (56)

1. He G, Tan LS, Zheng Q, Prasad PN. Multiphoton absorbing materials: Molecular designs, characterizations, and applications. Chem Rev 2008;108:1245-1330. (Pubitemid 351638815)
2. Denk W, Strickler JH, Web WW. Two-photon laser scanning fluorescence microscopy. Science 1990;248:73-76. (Pubitemid 20139273)
3. Cahalan MD, Parker I, Wei SH, Miller MJ. Two-photon tissue imaging: Seeing the immune system in a fresh light. Nat Rev Immun 2002;2:872-880. (Pubitemid 37328709)
4. Rubart M. Two-photon microscopy of cells and tissue. Circ Res 2004;95:1154-1166.
5. Sánchez SA, Gratton E. Lipid-protein interactions revealed by two-photon microscopy and fluorescence correlation spectroscopy. Acc Chem Res 2005;38:469-477. (Pubitemid 40994869)
6. So PTC, Dong CY, Masters BR, Berland KM. Two-photon excitation fluorescence microscopy. Annu Rev Biomed Eng 2000;2:399-429.
7. Xu C, Webb WW. Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm. J Opt Soc Am B 1996;13:481-491. (Pubitemid 126052726)
8. Zipfel WR, Williams RM, Webb WW. Nonlinear magic: Multiphoton microscopy in the biosciences. Nat Biotechnol 2003;21:1369-1377.
9. Albota M, Beljonne D, Brédas JL, Ehrlich JE, Fu JY, Heikal AA, Hess SE, Kogej T, Levin MD, Marder SR, Mccord-Maughon D, Perry JW, Röckel H, Rumi M, Subramaniam G, Webb WW, Wu XL, Xu C. Design of organic molecules with large two-photon absorption cross sections. Science 1998;281:1653-1656. (Pubitemid 28435576)
10. Rumi M, Ehrlich JE, Heikal AA, Perry JW, Barlow S, Hu ZY, Mccord-Maughton D, Parker TC, Röckel H, Thayumanavan S, Marder SR, Beljonne D, Brédas JL. Structure-property relationships for two-photon absorbing chromophores: Bis-donor diphenylpolyene and bis(styryl)benzene derivatives. J Am Chem Soc 2000;122:9500-9510.
11. Ventelon L, Charier S, Moreaux L, Mertz J, Blanchard-Desce M. Nanoscale push-push dihydrophenanthrene derivatives as novel fluorophores for two-photon-excited fluorescence. Angew Chem Int Ed 2001;40:2098-2101. (Pubitemid 33644327)
12. Yoo J, Yang SK, Jeong MY, Ahn HC, Jeon SJ, Cho BR. Bis-1,4-(p- diarylaminostyryl)-2,5-dicyanobenzene derivatives with large two-photon absorption cross-sections. Org Lett 2003;5:645-648. (Pubitemid 37141069)
13. Woo HY, Liu B, Kohler B, Korystov D, Mikhailovsky A, Bazan GC. Solvent effects on the two-photon absorption of distyrylbenzene chromophores. J Am Chem Soc 2005;127:14721-14729. (Pubitemid 41511010)
14. Woo HY, Hong JW, Liu B, Mikhailovsky A, Korystov D, Bazan GC. Water-soluble [2.2]paracyclophane chromophores with large two-photon action cross sections. J Am Chem Soc 2005;127:820-821.
15. Woo HY, Korystov D, Mikhailovsky A, Nguyen TQ, Bazan GC. Two-photon absorption in aqueous micellar solutions. J Am Chem Soc 2005;127:13794-13795. (Pubitemid 41437021)
16. Weissleder R, Ntziachristos V. Shedding light onto live molecular targets. Nat Med 2003;9:123-128. (Pubitemid 36098273)
17. Kato SI, Matsumoto T, Shigeiwa M, Gorohmaru H, Maeda S, Ishii T, Mataka S. Novel 2,1,3-benzothiadiazole-based red-fluorescent dyes with enhanced two-photon absorption crosssections. Chem Eur J 2006;12:2303-2317.
18. Thomas KRJ, Lin JT, Velusamy M, Tao Y, Chuen C. Color tuning in benzo[1,2,5]thiadiazole-based small molecules by amino conjugation/ deconjugation: Bright red-light-emitting diodes. Adv Funct Mater 2004;14:83-90.
19. Kato S, Matsumoto T, Ishii T, Thiemann T, Shigeiwa M, Gorohmaru H, Maeda S, Yamashita Y, Mataka S. Strongly red-fluorescent novel donor-pi-bridge- acceptor-pi-bridge-donor (D-pi-A-pi-D) type 2,1,3-benzothiadiazoles with enhanced two-photon absorption cross-sections. Chem Commun 2004;2342-2343.
20. Brousmiche DW, Serin JM, Fréchet JMJ, He GS, Lin TC, Chung SJ, Prasad PN, Kannan R, Tan LS. Fluorescence resonance energy transfer in novel multiphoton absorbing dendritic structures. J Phys Chem B 2004;108:8592-8600.
21. Margineanu A, Hofkens J, Cotlet M, Habuchi S, Stefan A, Qu J, Kohl C, Muellen K, Vercammen J, Engelborghs Y, Gensch T, De Schryver FC. Photophysics of a water-soluble rylene dye: Comparison with other fluorescent molecules for biological applications. J Phys Chem B 2004;108:12242-12251.
22. Fu LM, Wen XF, Ai XC, Sun Y, Wu YS, Zhang JP, Wang Y. Efficient two-photon-sensitized luminescence of a europium(III) complex. Angew Chem Int Ed 2005;44:747-750. (Pubitemid 40203987)
23. Adronov A, Fréchet JMJ. Light-harvesting dendrimers. Chem Commun 2000;1701-1710.
24. Barigelletti F, Flamigni L. Photoactive molecular wires based on metal complexes. Chem Soc Rev 2000;29:1-12.
25. Choi MS, Yamazaki T, Yamazaki I, Aida T. Bioinspired molecular design of light-harvesting multiporphyrin arrays. Angew Chem Int Ed 2004;43:150-158. (Pubitemid 38082098)
26. Bertazza L, Celotti L, Fabbrini G, Loi MA, Maggini M, Mancin F, Marcuz S, Menna E, Muccini M, Tonellato U. Cell penetrating silica nanoparticles doped with two-photon absorbing fluorophores. Tetrahedron 2006;62:10434-10440. (Pubitemid 44397113)
27. Lebret V, Raehm L, Durand JO, Smaïhi M, Gérardin C, Nerambourg N, Werts MHV, Blanchard-Desce M. Synthesis and characterization of fluorescently doped mesoporous nanoparticles for two-photon excitation. Chem Mater 2008;20:2174-2183. (Pubitemid 351489865)
28. Lebret V, Raehm L, Durand JO, Smaihi M, Werts MHV, Blanchard-Desce M, Méthy-Gonnod D, Dubernet C. Surface functionalization of two-photon dye-doped mesoporous silica nanoparticles with folic acid: Cytotoxicity studies with HeLa and MCF-7 cancer cells. J Sol-Gel Sci Technol 2008;48:32-39.
29. Law WC, Yong KT, Roy I, Xu G, Ding H, Bergey EJ, Zeng H, Prasad PN. Optically and magnetically doped organically modified silica nanoparticles as efficient magnetically guided biomarkers for two-photon imaging of live cancer cells. J Phys Chem C 2008;112:7972-7977.
30. Kim S, Pudavar HE, Bonoiu A, Prasad PN. Aggregation-enhanced fluorescence in organically modified silica nanoparticles: A novel approach toward high-signal-output nanoprobes for two-photon fluorescence bioimaging. Adv Mater 2007;19:3791-3795. (Pubitemid 350190414)
31. Kim S, Pudavar HE, Prasad PN. Dye-concentrated organically modified silica nanoparticles as a ratiometric fluorescent pH probe by one- and two-photon excitation. Chem Commun 2006;2071-2073. (Pubitemid 43726003)
32. Kim S, Ohulchanskyy TY, Pudavar HE, Pandey RK, Prasad PN. Organically modified silica nanoparticles co-encapsulating photosensitizing drug and aggregation-enhanced two-photon absorbing fluorescent dye aggregates for two-photon photodynamic therapy. J Am Chem Soc 2007;129:2669-2675. (Pubitemid 46364075)
33. Hadjichristidis N, Pispas S, Floudas GA. Block Copolymers-Synthetic Strategies, Physical Properties, and Applications. New Jersey: Wiley-Interscience; 2002.
34. Kataoka K, Harada A, Nagasaki Y. Block copolymer micelles for drug delivery: Design, characterization and biological significance. Adv Drug Delivery Rev 2001;47:113-131. (Pubitemid 32209236)
35. Torchilin VP. Structure and design of polymeric surfactant-based drug delivery systems. J Controlled Release 2001;73:137-172. (Pubitemid 32544594)
36. Van Nostrum CF. Polymeric micelles to deliver photosensitizers for photodynamic therapy. Adv Drug Delivery Rev 2004;56:9-16. (Pubitemid 38045421)
37. Jain TK, Morales MA, Sahoo SK, Leslie-Pelecky DL, Labhasetwar V. Iron oxide nanoparticles for sustained delivery of anticancer agents. Mol Pharm 2005;2:194-205. (Pubitemid 40917416)
38. Kim BS, Qiu JM, Wang JP, Taton TA. Magnetomicelles: composite nanostructures from magnetic nanoparticles and cross-linked amphiphilic block copolymers. Nano Lett 2005;5:1987-1991.
39. Gao XH, Yang L, Petros JA, Marshall FF, Simons JW, Nie S. In vivo molecular and cellular imaging with quantum dots. Curr Opin Biotechnol 2005;16:63-72.
40. Savic R, Luo L, Eisenberg A, Maysinger D. Micellar nanocontainers distribute to defined cytoplasmic organelles. Science 2003;300:615-618. (Pubitemid 36520581)
41. Shin J, Thompson DH. Intracellular Delivery of DNA and Proteins Using Vinyl Ether-Based Drug Delivery Vehicles. In: Svenson S, editor. Carrier-Based Drug Delivery. USA: American Chemical Society; 2004. Chapter 4, p 50-60.
42. Tian YQ, Chen CY, Cheng YJ, Young AC, Tucker NM, Jen AKY. Hydrophobic chromophores in aqueous micellar solution showing large two-photon absorption cross sections. Adv Funct Mater 2007;17:1691-1697.
43. Chen CY, Tian YQ, Cheng YJ, Young AC, Ka JW, Jen AKY. Two-photon absorbing block copolymer as a nanocarrier for porphyrin: Energy transfer and singlet oxygen generation in micellar aqueous solution. J Am Chem Soc 2007;129:7220-7221.
44. Zheng Q, Ohulchanskyy TY, Sahoo Y, Prasad PN. Water-dispersible polymeric structure co-encapsulating a novel hexaperi-hexabenzocoronene core containing chromophore with enhanced two-photon absorption and magnetic nanoparticles for magnetically guided two-photon cellular imaging. J Phys Chem C 2007;111:16846-16851. (Pubitemid 350207443)
45. LiuM, XuW, Xu LJ, Zhong GR, Chen SL, Lu WY. Synthesis and biological evaluation of diethylenetriamine pentaacetic acid-polyethylene glycol-folate: A new folate-derived, (99m)Tc-based radiopharmaceutical. Bioconjug Chem 2005;16:1126-1132.
46. Inoue T, Chen G, Nakamae K, Hoffman AS. An AB block copolymer of oligo(methyl methacrylate) and poly(acrylic acid) for micellar delivery of hydrophobic drugs. J Controlled Release 1998;51:221-229.
47. Lo C, Huang C, Lin K, Hsie GH. Mixed micelles formed from graft and diblock copolymers for application in intracellular drug delivery. Biomaterials 2007;28:1225-1235. (Pubitemid 44809411)
48. Kubin RF, Fletcher AN. Fluorescence quantum yields of some rhodamine dyes. J Lumin 1982;27:455-462.
49. Joshi HS, Jamshidi R, Tor Y. Conjugated 1,10-phenanthrolines as tunable fluorophores. Angew Chem Int Ed 1999;38:2722-2725.
50. Joseph R. Principles of Fluorescence Spectroscopy. New York: Plenum Press; 1983.
51. He XH, Liang L, Xie M, Zhang Y, Lin S, Yan D. Synthesis of novel linear PEO-b-PS-b-PCL triblock copolymers by the combination of ATRP, ROP, and a click reaction. Macromol Chem Phys 2007;208:1797-1802.
52. Meier MAR, Aerts SNH, Staal BBP, Pasa M, Schubert US. PEO-b-PCL block copolymers: Synthesis, detailed characterization, and selected micellar drug encapsulation behavior. Macromol Rapid Commun 2005;26:1918-1924.
53. Song HT, Choi JS, Huh YM, Kim S, Jun YW, Suh JS, Cheon J. Surface modulation of magnetic nanocrystals in the development of highly efficient magnetic resonance probes for intracellular labeling. J Am Chem Soc 2005;127:9992-9993. (Pubitemid 40995431)
54. Lee J, Kim J, Park E, Jo S, Song R. PEG-ylated cationic CdSe/ZnS QDs as an efficient intracellular labeling agent. Phys Chem Chem Phys 2008;10:1739-1742.
55. Jenekhe SA, Lu L, Alam MM. New conjugated polymers with donor-acceptor architectures: Synthesis and photophysics of carbazole-quinoline and phenothiazine-quinoline copolymers and oligomers exhibiting large intramolecular charge transfer. Macromolecules 2001;34:7315-7324. (Pubitemid 33025854)
56. Hong JW, Woo HY, Liu B, Bazan GC. Solvatochromism of distyrylbenzene pairs bound together by [2.2]paracyclophane: Evidence for a polarizable "through-space" delocalized state. J Am Chem Soc 2005;127:7435-7443.