Porphyrin and galactosyl conjugated micelles for targeting photodynamic therapy

Pharmaceutical Research

Volumn 27, Issue 1, 2010, Pages 187-199

  Wu, De Qun ^a   Li, Ze Yong ^a   Li, Cao ^a   Fan, Jian Jun ^a   Lu, Bo ^a   Chang, Cong ^a   Cheng, Si Xue ^a   Zhang, Xian Zheng ^a   Zhuo, Ren Xi ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

Drug delivery; Galactosyl micelle; Phototoxicity; Porphyrin

Indexed keywords

5 (4 AMINOPHENYL) 10,15,20 TRIPHENNYLPORPHYRIN; GALACTOSE; LACTONE; MONO AMINOPHORPHYRIN; POLY(2 AMINOETHYL METHACRYLATE) POLYCAPROLACTONE; PORPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG RELEASE; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LARYNX CARCINOMA; LIVER CELL CARCINOMA; MICELLE; PHOTODYNAMIC THERAPY; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ASIALOGLYCOPROTEIN RECEPTOR; CELL LINE, TUMOR; CELL SURVIVAL; DRUG CARRIERS; DRUG COMPOUNDING; DRUG DELIVERY SYSTEMS; DRUG SCREENING ASSAYS, ANTITUMOR; GALACTOSE; HEP G2 CELLS; HUMANS; MICELLES; MODELS, BIOLOGICAL; PARTICLE SIZE; PHOTOCHEMOTHERAPY; POLYESTERS; POLYMERS; PORPHYRINS;

EID: 72949110174     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-009-9998-8     Document Type: Article

References (37)

1. MR Detty SL Gibson SJ Wanger 2004 Current clinical and preclinical photosensitizers for use in photodynamic therapy J Med Chem. 47 3897 915 10.1021/jm040074b 15267226 (Pubitemid 38970949)
2. D Kessel 2002 Relocalization of cationic porphyrins during photodynamic therapy Photochem Photobiol Sci. 11 837 40 10.1039/b206046a (Pubitemid 37069807)
3. S Banfi E Caruso S Caprioli L Mazzagatti G Canti R Ravizza M Gariboldi E Monti 2004 Photodynamic effects of porphyrin and chlorin photosensitizers in human colon adenocarcinoma cells Bioorg Med Chem. 12 4853 60 10.1016/j.bmc.2004.07.011 15336264 (Pubitemid 39164393)
4. AP Castano Q Liu MR Hamblin 2006 A green fluorescent protein-expressing murine tumour but not its wild-type counterpart is cured by photodynamic therapy Br J Cancer. 13 391 7 10.1038/sj.bjc.6602953 (Pubitemid 43237563)
5. N Nishiyama HR Stapert GD Zhang D Takasu DL Jiang T Nagano T Aida K Kataoka 2003 Light-harvesting ionic dendrimer porphyrins as new photosensitizers for photodynamic therapy Bioconjugate Chem. 14 58 66 10.1021/bc025597h (Pubitemid 36169017)
6. WM Sharman CM Allen JE van Lier 1999 Photodynamic therapeutics: basic principles and clinical applications Drug Discov Today. 11 507 17 10.1016/S1359-6446(99)01412-9 (Pubitemid 29497854)
7. A Desjardins J Flemming ED Sternberg D Dolphin 2002 Nitrogen extrusion from pyrazoline-substituted porphyrins and chlorins using long wavelength visible light Chem Commun. 22 2622 3 10.1039/b208368j
8. H Li OS Fedorova WR Trumble TR Fletcher L Czuchajowski 1997 Site-specific photomodification of DNA by porphyrinoligonucleotide conjugates synthesized via a solid-phase H-phosphonate approach Bioconjugate Chem. 8 49 56 10.1021/bc960074t (Pubitemid 27064222)
9. MR Hamblin EL Newman 1994 Photosensitizer targeting in photodynamic therapy. II. Conjugates of haematoporphyrin with serum lipoproteins J Photochem Photobiol B: Bio 26 147 57 10.1016/1011-1344(94)07036-9 (Pubitemid 24345424)
10. 6 selectively potentiates its photodynamic activity Cancer Res. 60 2197 202 10786684
11. R Hudson M Carcenac K Smith L Madden OJ Clarke A Pelegrin J Greenman RW Boyle 2005 The development and characterization of porphyrin isothiocyanate-monoclonal antibody conjugates for photoimmunotherapy Br J Cancer. 92 1442 9 10.1038/sj.bjc.6602517 15812551 (Pubitemid 40705011)
12. G Li SK Pandey A Graham MP Dobhal R Mehta Y Chen A Gryshuk K Rittenhouse-Olson A Oseroff RK Pandey 2004 Functionalization of OEP-based benzochlorins to develop carbohydrateconjugated photosensitizers. Attempt to target beta-galactosiderecognized proteins J Org Chem. 69 158 72 10.1021/jo030280b 14703392 (Pubitemid 38040821)
13. X Chen C Gentry P Kopeckova J Kopecek 1998 HPMA copolymer-anticancer drug-OV-TL16 antibody conjugates. II. Processing in epithelial ovarian carcinoma cells in vitro Int J Cancer. 75 600 8 10.1002/(SICI)1097-0215(19980209)75: 4<600::AID-IJC18>3.0.CO;2-C (Pubitemid 28094108)
14. 6) conjugates Photochem Photobiol. 65 723 9 10.1111/j.1751-1097.1997.tb01916.x 9114750
15. RK Pandey NW Smith FY Shiau TJ Dougherty KM Smith 1991 Syntheses of cationic porphyrins and chlorines J Chem Soc Chem Commun. 22 1637 8 10.1039/c39910001637
16. AR Oseroff D Ohuoha G Ara D McAuliffe J Foley L Cincotta 1986 Intramitochondrial dyes allow selective in vitro photolysis of carcinoma cells Proc Natl Acad Sci USA. 83 9729 33 10.1073/pnas.83.24.9729 3467335
17. EK Park SB Lee YM Lee 2005 Preparation and characterization of methoxy poly(ethylene glycol)/poly(epsilon-caprolactone) amphiphilic block copolymeric nanospheres for tumor-specific folate-mediated targeting of anticancer drugs Biomaterials. 26 1053 61 10.1016/j.biomaterials.2004.04.008 15369694 (Pubitemid 39208991)
18. Y Bae S Fukushima A Harada K Kataoka 2003 Design of environment-sensitive supramolecular assemblies for intracellular drug delivery: polymeric micelles that are responsive to intracellular pH change Angew Chem Int Ed. 42 4640 3 10.1002/anie.200250653 (Pubitemid 37271305)
19. N Nasongkla X Shuai H Ai BD Weinberg J Pink DA Boothman 2004 cRGD-functionalized polymer micelles for targeted doxorubicin delivery Angew Chem Int Ed. 43 6323 7 10.1002/anie.200460800 (Pubitemid 40029462)
20. RJ Fallon AL Schwartz 1989 Receptor-mediated delivery of drugs to hepatocytes Adv Drug Deliv Rev. 4 49 63 10.1016/0169-409X(89)90037-9 (Pubitemid 19264320)
21. I Donati A Gamini A Vetere C Campa S Paoletti 2002 Synthesis, characterization, and preliminary biological study of glycoconjugates of poly(styrene-co-maleic acid) Biomacromolecules. 3 805 12 10.1021/bm020018x 12099826 (Pubitemid 34905222)
22. C Eisenberg N Seta M Appel G Feldmann G Durand J Feger 1991 Asialoglycoprotein receptor in human isolated hepatocytes from normal liver and its apparent increase in liver with histological alterations J Hepatol. 13 305 9 10.1016/0168-8278(91)90073-K 1808223
23. G Ashwell J Harford 1982 Carbohydrate-specific receptors of the liver Annu Rev Biochem. 51 531 54 10.1146/annurev.bi.51.070182.002531 6287920
24. AD Adler FR Longo W Shergalis 1964 Mechanistic investigations of porphyrin syntheses. I. preliminary studies on ms-tetraphenylporphin J Am Chem Soc. 86 3145 9 10.1021/ja01069a035
25. WJ Kruper TA Chamberlin M Kochanny 1989 Regiospecific aryl nitration of meso-substituted tetraarylporphyrins: a simple route to bifunctional porphyrins J Org Chem. 54 2753 6 10.1021/jo00272a057
26. DQ Wu YX Sun XD Xu SX Cheng XZ Zhang RX Zhuo 2008 Biodegradable and pH-sensitive hydrogels for cell encapsulation and controlled drug release Biomacromolecules. 9 1155 62 10.1021/bm7010328 18307310 (Pubitemid 351639567)
27. H Wei XZ Zhang Y Zhou SX Cheng RX Zhuo 2006 Self-assembled thermoresponsive micelles of poly(N-isopropylacrylamide-b-methyl methacrylate) Biomaterials. 27 2028 34 10.1016/j.biomaterials.2005.09.028 16225918 (Pubitemid 41759496)
28. n graft Copolymers by RAFT polymerization and macromonomer method J Polym Sci Pol Chem. 45 5354 64 10.1002/pola.22280 (Pubitemid 350044174)
29. RA Velapoldi HH Tønnesen 2004 Corrected emission spectra and quantum yields for a series of fluorescent compounds in the visible spectral region J Fluoresc. 14 465 72 10.1023/B:JOFL.0000031828.96368.c1 15617389
30. PG Seybold M Gouterman 1969 Porphyrins: XIII: fluorescence spectra and quantum yields J Mol Spectrosc. 31 1 13 10.1016/0022-2852(69)90335-X
31. T Inoue G Chen K Nakamae AS Hoffman 1998 An AB block copolymer of oligo(methyl methacrylate) and poly(acrylic acid) for micellar delivery of hydrophobic drugs J Control Release. 51 221 9 10.1016/S0168-3659(97)00172-7 9685920 (Pubitemid 28252874)
32. T Morita Y Horikiri T Suzuki H Yoshino 2001 Preparation of gelatin microparticles by co-lyophilization with poly(ethylene glycol): characterization and application to entrapment into biodegradable microspheres Int J Pharm. 219 127 37 10.1016/S0378-5173(01)00642-1 11337173 (Pubitemid 32391372)
33. C Giacomelli V Schmidt R Borsali 2007 Nanocontainers formed by self-assembly of poly(ethylene oxide)-b-poly(glycerol monomethacrylate)-drug conjugates Macromolecules. 40 2148 57 10.1021/ma062562u (Pubitemid 46502632)
34. YQ Ye FL Yang FQ Hu YZ Du H Yuan HY Yu 2008 Core-modified chitosan-based polymeric micelles for controlled release of doxorubicin Int J Pharm. 352 294 301 10.1016/j.ijpharm.2007.10.035 18096336
35. JR Kanofsky 1990 Quenching of singlet oxygen by human plasma Photochem Photobiol. 51 299 303 10.1111/j.1751-1097.1990.tb01714.x 2356225
36. SE Kornguth T Kalinke HI Robins JD Cohen P Turski 1989 Preferential binding of radiolabeled Poly-L-lysines to C6 and U87 MG glioblastomas compared with endothelial cells in vitro Cancer Res. 49 6390 5 2804985
37. M Sibrian-Vazquez TJ Jensen FR Fronczek RP Hammer MGH Vicente 2005 Synthesis and characterization of positively charged porphyrin-peptide conjugates Bioconjugate Chem. 16 852 63 10.1021/bc050057g (Pubitemid 41026172)