Porphyrin and Galactosyl Conjugated Micelles
199
16. Oseroff AR, Ohuoha D, Ara G, McAuliffe D, Foley J, Cincotta
L. Intramitochondrial dyes allow selective in vitro photolysis of
carcinoma cells. Proc Natl Acad Sci USA. 1986;83:9729–33.
17. Park EK, Lee SB, Lee YM. Preparation and characterization of
methoxy poly(ethylene glycol)/poly(epsilon-caprolactone) amphi-
philic block copolymeric nanospheres for tumor-specific folate-
mediated targeting of anticancer drugs. Biomaterials. 2005;26:1053–
61.
icity to both HEp2 cells and HepG2 cells. Importantly,
Gal-APP-PAEMA-PCL micelles could be selectively rec-
ognized by HepG2 cells and subsequently preferentially
accumulate in HepG2 cells, resulting in the higher photo-
toxicity effect.
18. Bae Y, Fukushima S, Harada A, Kataoka K. Design of environ-
ment-sensitive supramolecular assemblies for intracellular drug
delivery: polymeric micelles that are responsive to intracellular
pH change. Angew Chem Int Ed. 2003;42:4640–3.
19. Nasongkla N, Shuai X, Ai H, Weinberg BD, Pink J, Boothman
DA. cRGD-functionalized polymer micelles for targeted doxor-
ubicin delivery. Angew Chem Int Ed. 2004;43:6323–7.
20. Fallon RJ, Schwartz AL. Receptor-mediated delivery of drugs to
hepatocytes. Adv Drug Deliv Rev. 1989;4:49–63.
21. Donati I, Gamini A, Vetere A, Campa C, Paoletti S. Synthesis,
characterization, and preliminary biological study of glycoconju-
gates of poly(styrene-co-maleic acid). Biomacromolecules.
2002;3:805–12.
22. Eisenberg C, Seta N, Appel M, Feldmann G, Durand G, Feger J.
Asialoglycoprotein receptor in human isolated hepatocytes from
normal liver and its apparent increase in liver with histological
alterations. J Hepatol. 1991;13:305–9.
23. Ashwell G, Harford J. Carbohydrate-specific receptors of the
liver. Annu Rev Biochem. 1982;51:531–54.
24. Adler AD, Longo FR, Shergalis W. Mechanistic investigations of
porphyrin syntheses. I. preliminary studies on ms-tetraphenyl-
porphin. J Am Chem Soc. 1964;86:3145–9.
25. Kruper WJ, Chamberlin TA, Kochanny M. Regiospecific aryl
nitration of meso-substituted tetraarylporphyrins: a simple route
to bifunctional porphyrins. J Org Chem. 1989;54:2753–6.
26. Wu DQ, Sun YX, Xu XD, Cheng SX, Zhang XZ, Zhuo RX.
Biodegradable and pH-sensitive hydrogels for cell encapsulation
and controlled drug release. Biomacromolecules. 2008;9:1155–62.
27. Wei H, Zhang XZ, Zhou Y, Cheng SX, Zhuo RX. Self-
assembled thermoresponsive micelles of poly(N-isopropylacryla-
mide-b-methyl methacrylate). Biomaterials. 2006;27: 2028–34.
28. Zhu JL, Zhang XZ, Cheng H, Li YY, Cheng SX, Zhuo RX.
Synthesis and characterization of well-defined, amphiphilic Poly
(N-isopropylacrylamide)-b-[2-hydroxyethyl methacrylate- poly(ε-
caprolactone)]n graft Copolymers by RAFT polymerization and
macromonomer method. J Polym Sci Pol Chem. 2007;45:5354–64.
29. Velapoldi RA, Tønnesen HH. Corrected emission spectra and
quantum yields for a series of fluorescent compounds in the
visible spectral region. J Fluoresc. 2004;14:465–72.
ACKNOWLEDGEMENT
The financial supports from National Natural Science
Foundation of China (50633020), Ministry of Science and
Technology of China (2005CB623903) and Ministry of
Education of China (Cultivation Fund of Key Scientific
and Technical Innovation, Project 707043) are gratefully
acknowledged.
REFERENCES
1. Detty MR, Gibson SL, Wanger SJ. Current clinical and
preclinical photosensitizers for use in photodynamic therapy. J
Med Chem. 2004;47:3897–915.
2. Kessel D. Relocalization of cationic porphyrins during photo-
dynamic therapy. Photochem Photobiol Sci. 2002;11:837–40.
3. Banfi S, Caruso E, Caprioli S, Mazzagatti L, Canti G, Ravizza R,
et al. Photodynamic effects of porphyrin and chlorin photo-
sensitizers in human colon adenocarcinoma cells. Bioorg Med
Chem. 2004;12:4853–60.
4. Castano AP, Liu Q, Hamblin MR. A green fluorescent protein-
expressing murine tumour but not its wild-type counterpart is
cured by photodynamic therapy. Br J Cancer. 2006;13:391–7.
5. Nishiyama N, Stapert HR, Zhang GD, Takasu D, Jiang DL,
Nagano T, et al. Light-harvesting ionic dendrimer porphyrins as
new photosensitizers for photodynamic therapy. Bioconjugate
Chem. 2003;14:58–66.
6. Sharman WM, Allen CM, van Lier JE. Photodynamic therapeu-
tics: basic principles and clinical applications. Drug Discov
Today. 1999;11:507–17.
7. Desjardins A, Flemming J, Sternberg ED, Dolphin D. Nitrogen
extrusion from pyrazoline-substituted porphyrins and chlorins using
long wavelength visible light. Chem Commun. 2002;22:2622–3.
8. Li H, Fedorova OS, Trumble WR, Fletcher TR, Czuchajowski L.
Site-specific photomodification of DNA by porphyrinoligonu-
cleotide conjugates synthesized via a solid-phase H-phosphonate
approach. Bioconjugate Chem. 1997;8:49–56.
30. Seybold PG, Gouterman M. Porphyrins: XIII: fluorescence
spectra and quantum yields. J Mol Spectrosc. 1969;31:1–13.
9. Hamblin MR, Newman EL. Photosensitizer targeting in photo- 31. Inoue T, Chen G, Nakamae K, Hoffman AS. An AB block
dynamic therapy. II. Conjugates of haematoporphyrin with serum
lipoproteins. J Photochem Photobiol B: Bio. 1994;26:147–57.
10. Gijsens A, Missiaen L, Merlevede W, de Witte P. Epidermal
copolymer of oligo(methyl methacrylate) and poly(acrylic acid)
for micellar delivery of hydrophobic drugs. J Control Release.
1998;51:221–9.
growth factor-mediated targeting of chlorin e6 selectively poten- 32. Morita T, Horikiri Y, Suzuki T, Yoshino H. Preparation of gelatin
tiates its photodynamic activity. Cancer Res. 2000;60:2197–202.
11. Hudson R, Carcenac M, Smith K, Madden L, Clarke OJ,
Pelegrin A, et al. The development and characterization of
porphyrin isothiocyanate-monoclonal antibody conjugates for
photoimmunotherapy. Br J Cancer. 2005;92:1442–9.
microparticles by co-lyophilization with poly(ethylene glycol):
characterization and application to entrapment into biodegrad-
able microspheres. Int J Pharm. 2001;219:127–37.
33. Giacomelli C, Schmidt V, Borsali R. Nanocontainers formed by
self-assembly of poly(ethylene oxide)-b-poly(glycerol monome-
thacrylate)-drug conjugates. Macromolecules. 2007; 40:2148–57.
12. Li G, Pandey SK, Graham A, Dobhal MP, Mehta R, Chen Y, et al.
Functionalization of OEP-based benzochlorins to develop carbo- 34. Ye YQ, Yang FL, Hu FQ, Du YZ, Yuan H, Yu HY. Core-
hydrateconjugated photosensitizers. Attempt to target beta-
galactosiderecognized proteins. J Org Chem. 2004;69:158–72.
13. Chen X, Gentry C, Kopeckova P, Kopecek J. HPMA copolymer-
anticancer drug-OV-TL16 antibody conjugates. II. Processing in
modified chitosan-based polymeric micelles for controlled
release of doxorubicin. Int J Pharm. 2008;352:294–301.
35. Kanofsky JR. Quenching of singlet oxygen by human plasma.
Photochem Photobiol. 1990;51:299–303.
epithelial ovarian carcinoma cells in vitro. Int J Cancer. 1998; 36. Kornguth SE, Kalinke T, Robins HI, Cohen JD, Turski P.
75:600–8.
Preferential binding of radiolabeled Poly-L-lysines to C6 and
U87 MG glioblastomas compared with endothelial cells in vitro.
Cancer Res. 1989;49:6390–5.
14. Soukos NS, Hamblin MR, Hasan T. The effect of charge on
cellular uptake and phototoxicity of polylysine chlorin(e6)
conjugates. Photochem Photobiol. 1997;65:723–9.
15. Pandey RK, Smith NW, Shiau FY, Dougherty TJ, Smith KM.
Syntheses of cationic porphyrins and chlorines. J Chem Soc
Chem Commun. 1991;22:1637–8.
37. Sibrian-Vazquez M, Jensen TJ, Fronczek FR, Hammer RP,
Vicente MGH. Synthesis and characterization of positively
charged porphyrin-peptide conjugates. Bioconjugate Chem.
2005;16:852–63.