Dendrimer porphyrin-based self-assembled nano-devices for biomedical applications

Polymer Journal

Volumn 44, Issue 6, 2012, Pages 512-521

  Jeong, Young Hwan ^a   Yoon, Hee Jae ^a   Jang, Woo Dong ^a  

^a Yonsei University   (South Korea)

Author keywords

biomedical; dendrimer; nano device; photodynamic therapy; phthalocyanine; polymeric micelle; porphyrin

Indexed keywords

BIOMEDICAL; BIOMEDICAL APPLICATIONS; CANCER THERAPY; DENDRITIC WEDGES; DIAGNOSTIC TOOLS; GENE DELIVERY; NANO DEVICE; NANO-DEVICES; PHTHALOCYANINE; POLY(BENZYL ETHER); POLYION COMPLEX MICELLES; POLYMER-METAL COMPLEXES; POLYMERIC MICELLE; SELF-ASSEMBLED; TERNARY COMPLEX;

DENDRIMERS; FUNCTIONAL MATERIALS; GENE TRANSFER; MEDICAL APPLICATIONS; METAL COMPLEXES; MICELLES; PHOTODYNAMIC THERAPY; PORPHYRINS;

FUNCTIONAL POLYMERS;

EID: 84861929622     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2012.20     Document Type: Review

References (67)

1. Newkome, G. R., Moorefield, C. N. & Voegtle, F. Dendrimers and Dendrons: Concepts, Syntheses, Applications (Wiley-VCH, Weinheim, 2001).
2. Fréchet, J. M. J. & Tomalia, D. A. Dendrimers and other Dendritic Polymers (Wiley-VCH, New York, 2001).
3. Bosman, A. W., Janssen, H. M. & Meijer, E. W. About dendrimers: structure, physical properties, and applications. Chem. Rev. 99, 1665-1688 (1999). (Pubitemid 129585157)
4. Lee, I., Athey, B. D., Wetzel, A. W., Meixner, W. & Baker, Jr. J. R. Structural molecular dynamics studies on polyamidoamine dendrimers for a therapeutic application: effects of pH and generation. Macromolecules 35, 4510-4520 (2002). (Pubitemid 34566353)
5. Roy, R., Zanini, D., Meunier, S. J. & Romanowska, A. Solid-phase synthesis of dendritic sialoside inhibitors of influenza A virus haemagglutinin. J. Chem. Soc. Chem. Commun. 1869-1872 (1993). (Pubitemid 24026734)
6. Jang, W.-D. & Kataoka, K. Bioinspired applications of functional dendrimers. J. Drug Del. Sci. Tech 15, 19-30 (2005). (Pubitemid 40208976)
7. Wiener, E. C., Brechbiel, M. W., Brothers, H., Magin, R. L., Gansow, O. A., Tomalia, D. A. & Lauterbur, P. C. Dendrimer-based metal chelates: a new class of magnetic resonance imaging contrast agents. Magn. Reson. Med. 31, 1-8 (1994). (Pubitemid 24016935)
8. Aulenta, F., Hayes, W. & Rannard, S. Dendrimers: a new class of nanoscopic containers and delivery devices. Eur. Polym. J. 39, 1741-1771 (2003).
9. Stiriba, S.-E., Frey, H. & Haag, R. Dendritic polymers in biomedical applications: from potential to clinical use in diagnostics and therapy. Angew. Chem. Int. Ed. 41, 1329-1334 (2002). (Pubitemid 34437413)
10. Patri, A. K., Majoros, I. J. & Baker, J. R. Dendritic polymer macromolecular carriers for drug delivery. Curr. Opin. Chem. Biol. 6, 466-471 (2002). (Pubitemid 34804769)
11. Boas, U. & Heegaard, P. M. H. Dendrimers in drug research. Chem. Soc. Rev. 33, 43-63 (2004). (Pubitemid 38376610)
12. Gorman, C. Metallodendrimers: Structural diversity and functional behavior. Adv. Mater. 10, 295-309 (1998). (Pubitemid 128542847)
13. Zeng, F. & Zimmerman, S. C. Dendrimers in supramolecular chemistry: From molecular recognition to self-assembly. Chem. Rev. 97, 1681-1712 (1997). (Pubitemid 127659610)
14. Fischer, M. & Vögtle, F. Dendrimers: From design to application-A progress report. Angew. Chem., Int. Ed. 38, 884-905 (1999). (Pubitemid 29180954)
15. Tekade, R. K., Kumar, P. V. & Jain, N. K. Dendrimers in oncology: an expanding horizon. Chem. Rev. 109, 49-87 (2009).
16. Mintzer, M. A. & Grinstaff, M. W. Biomedical applications of dendrimers: a tutorial. Chem. Soc. Rev. 40, 173-190 (2011).
17. Liu, M., Kono, K. & Fréchet, J. M. J. Water-soluble dendritic unimolecular micelles: Their potential as drug delivery agents. J. Control. Release 65, 121-131 (2000). (Pubitemid 30122921)
18. Stevelmans, S., van Hest, J. C. M., Jansen, J. F. G. A., van Boxtel, D. A. F. J., de Brabander-van den Berg, E. M. M. & Meijer, E. W. Synthesis, characterization, and guest-host properties of inverted unimolecular dendritic micelles. J. Am. Chem. Soc. 118, 7398-7399 (1996). (Pubitemid 26270628)
19. Gupta, U., Agashe, H. B., Asthana, A. & Jain, N. K. Dendrimers: novel polymeric nanoarchitectures for solubility enhancement. Biomacromolecules 7, 649-658 (2006).
20. Grayson, S. M. & Fréchet, J. M. J. Convergent dendrons and dendrimers: From synthesis to applications. Chem. Rev. 101, 3819-3867 (2001). (Pubitemid 35375219)
21. Sadamoto, R., Tomioka, N. & Aida, T. Photoinduced electron transfer reactions through dendrimer architecture. J. Am. Chem. Soc. 118, 3978-3979 (1996). (Pubitemid 26164895)
22. Pushpan, S. K., Venkatraman, S., Anand, V. G., Sankar, J., Parmeswaran, D., Ganesan, S. & Chandrashekar, T. K. Porphyrins in photodynamic therapy-A search for ideal photosensitizer. Curr. Med. Chem.: Anti-Cancer Agents 2, 187-207 (2002). (Pubitemid 34657137)
23. Sessler, J. L. & Weghorn, S. J. Expanded, Contracted and Isomeric Porphyrins (Elsevier, Oxford, 1997) and references therein.
24. Sessler, J. L., Gebauer, A. & Weghorn, S. J. in Expanded Porphyrins in the Porphyrin Handbook eds. Kadish, K. M., Smith, K. M. & Guilard, R. Vol. 2, 157-230 (Academic Press, New York, 2000).
25. Martinez-Diaz, M. V., de la Torre, G. & Torres, T. Lighting porphyrins and phthalocyanines for molecular photovoltaics. Chem. Commun. 46, 7090-7108 (2010).
26. O'Connor, A. E., Byrne, A. T. & Gallagher, W. M. Porphyrin and non-porphyrin photosensitizers in oncology: pre-clinical and clinical advances in photodynamic therapy. Photochem. Photobiol. 85, 1053-1074 (2009).
27. Macdonald, I. J. & Dougherty, T. J. Basic principles of photodynamic therapy. J. Porphyr. Phthalocya. 5, 105-129 (2001). (Pubitemid 32125231)
28. Lukyanets, E. A. Phthalocyanines as photosensitizers in the photodynamic therapy of cancer. J. Porphyr. Phthalocya. 3, 424-432 (1999).
29. Ethirajan, M., Chen, Y., Joshi, P. & Pandey, R. K. The role of porphyrin chemistry in tumor imaging and photodynamic therapy. Chem. Soc. Rev. 40, 340-362 (2011).
30. Gerhardt, S. A., Lewis, J. W., Kliger, D. S., Zhang, J. Z. & Simonis, U. Effect of micelles on oxygen-quenching processes of triplet-state para-substituted tetraphenylporphyrin photosensitizers. J. Phys. Chem. A 107, 2763-2767 (2003).
31. Sato, T., Jiang, D. L. & Aida, T. A. Blue-luminescent dendritic rod: Poly(phenyleneethynylene) within a light-harvesting dendritic envelope. J. Am. Chem. Soc. 121, 10658-10659 (1999).
32. Nishiyama, N., Stapert, H. R., Zhang, G.-D., Takasu, D., Jiang, D.-L., Nagano, T., Aida, T. & Kataoka, K. Light-harvesting ionic dendrimer porphyrins as new photosensitizers for photodynamic therapy. Bioconjugate Chem. 14, 58-66 (2003). (Pubitemid 36169017)
33. Zhang, G.-D., Harada, A., Nishiyama, N., Jiang, D.-L., Koyama, H., Aida, T. & Kataoka, K. Polyion complex micelles entrapping cationic dendrimer porphyrin: effective photosensitizer for photodynamic therapy of cancer. J. Controlled Release 93, 141-150 (2003). (Pubitemid 37421356)
34. Jang, W.-D., Nishiyama, N., Zhang, G.-D., Harada, A., Jiang, D.-L., Kawauchi, S., Morimoto, Y., Kikuchi, M., Koyama, H., Aida, T. & Kataoka, K. Supramolecular nanocarrier of anionic dendrimer porphyrins with pegylated cationic block copolymer to enhance intracellular photodynamic efficacy. Angew. Chem., Int. Ed. 44, 419-423 (2005). (Pubitemid 40142642)
35. Stapert, H. R., Nishiyama, N., Jiang, D.-L., Aida, T. & Kataoka, K. Polyion complex micelles encapsulating light-harvesting ionic dendrimer zinc porphyrins. Langmuir 16, 8182-8188 (2000).
36. Li, Y., Jang, W.-D., Nishiyama, N., Kishimura, A., Kawauchi, S., Morimoto, Y., Miake, S., Yamashita, T., Kikuchi, M., Aida, T. & Kataoka, K. Dendrimer generation effects on photodynamic efficacy of dendrimer porphyrins and dendrimer-loaded supramolecular nanocarriers. Chem. Mater. 19, 5557-5562 (2007). (Pubitemid 350150581)
37. Renno, R. Z. & Miller, J. W. Photosensitizer delivery for photodynamic therapy of choroidal neovascularization. Adv. Drug. Deliv. Rev. 52, 63-78 (2001). (Pubitemid 32973639)
38. TAP and VIP Study Group. Guidelines for using Verteporfin in photodynamic therapy to treat choroidal neovascularization due to age related macular degeneration and other causes. Retina 22, 6-18 (2002).
39. Ideta, R., Tasaka, F., Jang, W.-D., Nishiyama, N., Zhang, G.-D., Harada, A., Yanagi, Y., Tamaki, Y., Aida, T. & Kataoka, K. Nanotechnology-based photodynamic therapy for neovascular disease using a supramolecular nanocarrier loaded with a dendritic photosensitizer. Nano Lett. 5, 2426-2431 (2005). (Pubitemid 43088890)
40. Nishiyama, N., Okazaki, S., Cabral, H., Miyamoto, M., Kato, Y., Sugiyama, Y., Nishio, K., Matsumura, Y. & Kataoka, K. Novel cisplatin-incorporated polymeric micelles can eradicate solid tumors in mice. Cancer Res. 63, 8977-8983 (2003). (Pubitemid 38064079)
41. Kwon, G., Suwa, S., Yokoyama, M., Okano, T., Sakurai, Y. & Kataoka, K. Enhanced tumor accumulation and prolonged circulation times of micelle-forming poly(ethylene oxide-aspartate) block copolymer-adriamycin conjugates. J. Control. Release 29, 17-23 (1994).
42. Yokoyama, M., Okano, T., Sakurai, Y., Fukushima, S., Okamoto, K. & Kataoka, K. Selective delivery of adiramycin to a solid tumor using a polymeric micelle carrier system. J. Drug Target 7, 171-186 (1999). (Pubitemid 30028961)
43. Ideta, R., Yanagi, Y., Tamaki, Y., Tasaka, F., Harada, A. & Kataoka, K. Effective accumulation of polyion complex micelle to experimental choroidal neovascularization in rats. FEBS Letters 557, 21-25 (2004). (Pubitemid 38115863)
44. Lo, P.-C., Huang, J.-D., Cheng, D. Y. Y., Chan, E. Y. M., Fong, W.-P., Ko, W.-H. & Ng, D. K. P. New amphiphilic silicon(IV) phthalocyanines as efficient photosensitizers for photodynamic therapy: Synthesis, photophysical properties, and in vitro photodynamic activities. Chem. Eur. J. 10, 4831-4838 (2004).
45. Ng, A. C. H., Li, X. & Ng, D. K. P. Synthesis and photophysical properties of nonaggregated phthalocyanines bearing dendritic substituents. Macromolecules 32, 5292-5298 (1999).
46. Sheng, Z., Ye, X., Zheng, Z., Yu, S., Ng, D. K. P., Ngai, T. & Wu, C. Transient absorption and fluorescence studies of disstacking phthalocyanine by poly(ethylene oxide). Macromolecules 35, 3681-3685 (2002). (Pubitemid 34590344)
47. Jang, W.-D., Nakagishi, Y., Nishiyama, N., Kawauchi, S., Morimoto, Y., Kikuchi, M. & Kataoka, K. Polyion complex micelles for photodynamic therapy: incorporation of dendritic photosensitizer excitable at long wavelength relevant to improved tissuepenetrating property. J. Control. Release 113, 73-79 (2006). (Pubitemid 43818161)
48. Nishiyama, N., Nakagishi, Y., Morimoto, Y., Lai, P.-S., Miyazaki, K., Urano, K., Horie, S., Kumagai, M., Fukushima, S., Cheng, Y., Jang, W.-D., Kikuchi, M. & Kataoka, K. Enhanced photodynamic cancer treatment by supramolecular nanocarriers charged with dendrimer phthalocyanine. J. Control. Release 133, 245-251 (2009).
49. Majno, G. & Joris, I. Apoptosis, oncosis, and necrosis. An overview of cell death. Am. J. Phathol 146, 3-15 (1995).
50. Nishiyama, N. Photochemical enhancement of transgene expression by polymeric micelles incorporating plasmid DNA and dendrimer-based photosensitizer. J. Drug Targeting 14, 413-424 (2006). (Pubitemid 44207826)
51. Cabral, H., Nakanishi, M., Kumagai, M., Jang, W.-D., Nishiyama, N. & Kataoka, K. Aphoto-activated targeting chemotherapy using glutathione sensitive camptothecinloaded polymeric micelles. Pharm. Res. 26, 82-92 (2009).
52. Nishiyama, N., Iriyama, A., Jang, W.-D., Miyata, K., Itaka, K., Inoue, Y., Takahashi, H., Yanagi, Y., Koyama, H. & Kataoka, K. Light-induced gene transfer from packaged DNA enveloped in a dendrimeric photosensitizer. Nat. Mater. 4, 934-941 (2005).
53. Koide, A., Kishimura, A., Osada, K., Jang, W.-D., Yamasaki, Y. & Kataoka, K. Semipermeable polymer vesicle (PICsome) self-assembled in aqueous medium from a pair of oppositely charged block copolymers: physiologically stable Micro-/Nano-Containers of water-soluble macromolecules. J. Am. Chem. Soc. 128, 5988-5989 (2006).
54. Kim, J., Yoon, H.-J., Kim, S., Wang, K., Ishii, T., Kim, Y.-R. & Jang, W.-D. Polymermetal complex micelles for the combination of sustained drug releasing and photodynamic therapy. J. Mater. Chem. 19, 4627-4632 (2009).
55. Liu, X. Y., Gao, C. Y., Shen, J. C. & Mohwald, H. Multilayer microcapsules as anticancer drug delivery vehicle: deposition, sustained release, and in vitro bioactivity. Macromol. Biosci. 5, 1209-1219 (2005). (Pubitemid 43015295)
56. De Cock, L. J., De Koker, S., De Geest, B. G., Grooten, J., Vervaet, C., Remon, J. P., Sukhorukov, G. B. & Antipina, M. N. Polymeric multilayer capsules in drug delivery. Angew. Chem., Int. Ed. 49, 6954-6973 (2010).
57. Delcea, M., Yashchenok, A., Videnova, K., Kreft, O., Mohwald, H. & Skirtach, A. G. Multicompartmental micro-and nanocapsules: Hierarchy and applications in biosciences. Macromol. Biosci. 10, 465-474 (2010).
58. Son, K. J., Yoon, H.-J., Kim, J.-H., Jang, W.-D., Lee, Y. & Koh, W.-G. Photosensitizing hollow nanocapsules for combination cancer therapy. Angew. Chem., Int. Ed. 50, 11968-11971 (2011).
59. Hartmann, M., Roeraade, J., Stoll, D., Templin, M. & Joos, T. Protein microarrays for diagnostic assays. Anal. Bioanal. Chem. 393, 1407-1416 (2009).
60. Hu, Y., Uttamchandani, M. & Yao, S. Q. Microarray: a versatile platform for highthroughput functional proteomics. Comb. Chem. High Throughput Screening 9, 203-212 (2006).
61. MacBeath, G. & Schreiber, S. L. Printing proteins as microarrays for high-throughput function determination. Science 289, 1760-1763 (2000).
62. Mitchell, P. A perspective on protein microarrays. Nat. Biotechnol. 20, 225-229 (2002). (Pubitemid 34205415)
63. Arenkov, P., Kukhtin, A., Gemmell, A., Voloshchuk, S., Chupeeva, V. & Mirzabekov, A. Protein microchips: use for immunoassay and enzymatic reactions. Anal. Biochem. 278, 123-131, 2000). (Pubitemid 30090733)
64. Ajikumar, P. K., Kiat, J., Tang, Y. C., Lee, J. Y., Stephanopoulos, G. & Too, H. P. Carboxyl-terminated dendrimer-coated bioactive interface for protein microarray: Highsensitivity detection of antigen in complex biological samples. Langmuir 23, 5670-5677 (2007). (Pubitemid 46826521)
65. Pathak, S., Singh, A. K., McElhanon, J. R. & Dentinger, P. M. Dendrimer-activated surfaces for high density and high activity protein chip applications. Langmuir 20, 6075-6079 (2004).
66. Lee, Y., Kim, J., Kim, S., Jang, W.-D., Park, S. & Koh, W.-G. Protein-conjugated, glucose-sensitive surface using fluorescent dendrimer porphyrin. J. Mater. Chem. 19, 5643-5647 (2009).
67. Son, K. J., Kim, S., Kim, J.-H., Jang, W.-D., Lee, Y. & Koh, W.-G. Dendrimer porphyrinterminated polyelectrolyte multilayer micropatterns for a protein microarray with enhanced sensitivity. J. Mater. Chem. 20, 6531-6538 (2010).