Conjugation of the photosensitizer Chlorin e6 to pluronic F127 for enhanced cellular internalization for photodynamic therapy

Biomaterials

Volumn 34, Issue 28, 2013, Pages 6992-7000

  Park, Hyung ^a   Na, Kun ^a  

^a The Catholic University of Korea   (South Korea)

Author keywords

Chlorin e6; Internalization rate; Photosensitizer; Pluronic F127 ; Site specific distribution

Indexed keywords

CELLULAR INTERNALIZATION; CHLORIN E6; FLUORESCENCE ACTIVATED CELL SORTING; HYDROPHOBIC INTERACTION CHROMATOGRAPHY; INTERNALIZATION RATE; PLURONIC F-127; SINGLET OXYGEN GENERATION; SITE-SPECIFIC;

EFFICIENCY; FLUORESCENCE; LIQUID CHROMATOGRAPHY; MAMMALS; PHOTODYNAMIC THERAPY; PHOTOSENSITIZERS;

TUMORS;

CHLORINE DERIVATIVE; PHOTOSENSITIZING AGENT; SINGLET OXYGEN;

ANIMAL MODEL; ANIMAL TISSUE; AQUEOUS SOLUTION; ARTICLE; CANCER INHIBITION; COLON TUMOR; CONJUGATION; CONTROLLED STUDY; FLUORESCENCE; FLUORESCENCE ACTIVATED CELL SORTING; HYDROPHOBIC INTERACTION CHROMATOGRAPHY; IN VITRO STUDY; IN VIVO STUDY; INTERNALIZATION; IRRADIATION; MOUSE; NONHUMAN; PHOTODYNAMIC THERAPY; PHOTOTOXICITY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SOLUBILITY; TUMOR CELL;

ANIMALS; CELL LINE, TUMOR; FLOW CYTOMETRY; MICE; PHOTOCHEMOTHERAPY; POLOXAMER; PORPHYRINS; RADIATION-SENSITIZING AGENTS; SINGLET OXYGEN;

MUS;

EID: 84879459808     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2013.05.070     Document Type: Article

References (46)

1. Dougherty T.J., Henderson B.W., Gomer C.J., Jori G., Kessel D., Korbelik M., et al. Photodynamic therapy. JNatl Cancer Inst 1998, 90:889-905.
2. Dolmans D.E., Fukumura D., Jain R.K. Photodynamic therapy for cancer. Nat Rev Cancer 2003, 3:380-387.
3. Henderson B.W., Dougherty T.J. How does photodynamic therapy work?. Photochem Photobiol 2008, 55:145-157.
4. Usuda J., Kato H., Okunaka T., Furukawa K., Tsutsui H., Yamada K., et al. Photodynamic therapy (PDT) for lung cancers. JThorac Oncol 2006, 1:489-493.
5. Baek S., Na K. Anano complex of hydrophilic phthalocyanine and polyethylenimine for improved cellular internalization efficiency and phototoxicity. Colloids Surf B Biointerfaces 2013, 101:492-500.
6. Chen K., Preuss A., Hackbarth S., Wacker M., Langer K., Röder B. Novel photosensitizer-protein nanoparticles for photodynamic therapy: photophysical characterization and invitro investigations. JPhotochem Photobiol B 2009, 96:66-74.
7. Bechet D., Couleaud P., Frochot C., Viriot M.L., Guillemin F., Barberi-Heyob M. Nanoparticles as vehicles for delivery of photodynamic therapy agents. Trends Biotechnol 2008, 26:612-621.
8. Lee S.J., Koo H., Lee D.E., Min S., Lee S., Chen X., et al. Tumor-homing photosensitizer-conjugated glycol chitosan nanoparticles for synchronous photodynamic imaging and therapy based on cellular on/off system. Biomaterials 2011, 32:4021-4029.
9. Bonnett R. Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy. Chem Soc Rev 1995, 24:19-33.
10. Lukyanov A.N., Torchilin V.P. Micelles from lipid derivatives of water-soluble polymers as delivery systems for poorly soluble drugs. Adv Drug Deliv Rev 2004, 56:1273-1289.
11. Miao W., Shim G., Lee S., Lee S., Choe Y.S., Oh Y.-K. Safety and tumor tissue accumulation of pegylated graphene oxide nanosheets for co-delivery of anticancer drug and photosensitizer. Biomaterials 2013, 34:3402-3410.
12. Ling D., Bae B.-C., Park W., Na K. Photodynamic efficacy of photosensitizers under an attenuated light dose via lipid nano-carrier-mediated nuclear targeting. Biomaterials 2012, 33:5478-5486.
13. Derycke A.S., de Witte P.A. Liposomes for photodynamic therapy. Adv Drug Deliv Rev 2004, 56:17-30.
14. Hamblin M.R., Miller J.L., Rizvi I., Ortel B., Maytin E.V., Hasan T. Pegylation of a chlorine6 polymer conjugate increases tumor targeting of photosensitizer. Cancer Res 2001, 61:7155-7162.
15. Park H.J., Kwon S., Lee M., Chung H., Kim J.-H., Kim Y.S., et al. Self-assembled nanoparticles based on glycol chitosan bearing hydrophobic moieties as carriers for doxorubicin: invivo biodistribution and anti-tumor activity. Biomaterials 2006, 27:119-126.
16. Park J.S., Han T.H., Lee K.Y., Han S.S., Hwang J.J., Moon D.H., et al. N-acetyl histidine-conjugated glycol chitosan self-assembled nanoparticles for intracytoplasmic delivery of drugs: endocytosis, exocytosis and drug release. JControl Release 2006, 115:37-45.
17. Na K., Bae Y.H. Self-assembled hydrogel nanoparticles responsive to tumor extracellular pH from pullulan derivative/sulfonamide conjugate: characterization, aggregation, and adriamycin release invitro. Pharm Res 2002, 19:681-688.
18. Meerum Terwogt J.M., ten Bokkel Huinink W.W., Schellens J.H., Schot M., Mandjes I.A., Zurlo M.G., et al. Phase I clinical and pharmacokinetic study of PNU166945, a novel water-soluble polymer-conjugated prodrug of paclitaxel. Anticancer Drugs 2001, 12:315-323.
19. Park W., Park S.-J., Na K. The controlled photoactivity of nanoparticles derived from ionic interactions between a water soluble polymeric photosensitizer and polysaccharide quencher. Biomaterials 2011, 32:8261-8270.
20. Thanou M., Verhoef J.C., Junginger H.E. Oral drug absorption enhancement by chitosan and its derivatives. Adv Drug Deliv Rev 2001, 52:117-126.
21. Kostenich G.A., Zhuravkin I.N., Zhavrid E.A. Experimental grounds for using chlorin e6 in the photodynamic therapy of malignant tumors. JPhotochem Photobiol B 1994, 22:211-217.
22. Wang M., Lu P., Wu B., Tucker J.D., Cloer C., Lu Q. High efficiency and low toxicity of polyethyleneimine modified pluronics (PEI-Pluronic) as gene delivery carriers in cell culture and dystrophic mdx mice. JMater Chem 2012, 22:6038-6046.
23. Alakhov V.Y., Kabanov A.V. Block copolymeric biotransport carriers as versatile vehicles for drug delivery. Expert Opin Investig Drugs 1998, 7:1453-1473.
24. Batrakova E.V., Li S., Elmquist W.F., Miller D.W., Alakhov V.Y., Kabanov A.V. Mechanism of sensitization of MDR cancer cells by pluronic block copolymers: selective energy depletion. Br J Cancer 2001, 85:1987-1997.
25. Batrakova E.V., Li S., Brynskikh A.M., Sharma A.K., Li Y., Boska M., et al. Effects of pluronic and doxorubicin on drug uptake, cellular metabolism, apoptosis and tumor inhibition in animal models of MDR cancers. JControl Release 2010, 143:290-301.
26. Batrakova E.V., Han H.-Y., Alakhov V.Y., Miller D.W., Kabanov A.V. Effects of pluronic block copolymers on drug absorption in Caco-2 cell monolayers. Pharm Res 1998, 15:850-855.
27. Gebhart C.L., Sriadibhatla S., Vinogradov S., Lemieux P., Alakhov V., Kabanov A.V. Design and formulation of polyplexes based on pluronic-polyethyleneimine conjugates for gene transfer. Bioconjug Chem 2002, 13:937-944.
28. ® block copolymers: novel functional molecules for gene therapy. Adv Drug Deliv Rev 2002, 54:223-233.
29. ® block copolymers as novel polymer therapeutics for drug and gene delivery. JControl Release 2002, 82:189-212.
30. ® block copolymers for overcoming drug resistance in cancer. Adv Drug Deliv Rev 2002, 54:759-779.
31. Batrakova E.V., Kabanov A.V. Pluronic block copolymers: evolution of drug delivery concept from inert nanocarriers to biological response modifiers. JControl Release 2008, 130:98-106.
32. ® and pheophorbide a, a bacteriochlorin, in photodynamic therapy of colonic cancer cells. Photochem Photobiol 2002, 75:140-148.
33. Maeda H. Tumor-selective delivery of macromolecular drugs via the EPR effect: background and future prospects. Bioconjug Chem 2010, 21:797-802.
34. Cheng Y., Samia A.C., Meyers J.D., Panagopoulos I., Fei B., Burda C. Highly efficient drug delivery with gold nanoparticle vectors for invivo photodynamic therapy of cancer. JAm Chem Soc 2008, 130:10643-10647.
35. Bae B., Na K. Self-quenching polysaccharide-based nanogels of pullulan/folate-photosensitizer conjugates for photodynamic therapy. Biomaterials 2010, 31:6325-6335.
36. Hoebeke M., Damoiseau X. Determination of the singlet oxygen quantum yield of bacteriochlorin a: a comparative study in phosphate buffer and aqueous dispersion of dimiristoyl-L-α-phosphatidylcholine liposomes. Photochem Photobiol Sci 2002, 1:283-287.
37. Fernandez J.M., Bilgin M.D., Grossweiner L.I. Singlet oxygen generation by photodynamic agents. JPhotochem Photobiol B 1997, 37:131-140.
38. Lee S.J., Park K., Oh Y.K., Kwon S.H., Her S., Kim I.S., et al. Tumor specificity and therapeutic efficacy of photosensitizer-encapsulated glycol chitosan-based nanoparticles in tumor-bearing mice. Biomaterials 2009, 30:2929-2939.
39. Kurtoglu Y.E., Mishra M.K., Kannan S., Kannan R.M. Drug release characteristics of PAMAM dendrimer-drug conjugates with different linkers. Int J Pharm 2010, 384:189-194.
40. Khandare J., Kolhe P., Pillai O., Kannan S., Lieh-Lai M., Kannan R.M. Synthesis, cellular transport, and activity of polyamidoamine dendrimer-methylprednisolone conjugates. Bioconjug Chem 2005, 16:330-337.
41. Pham Trong L.C., Djabourov M., Ponton A. Mechanisms of micellization and rheology of PEO-PPO-PEO triblock copolymers with various architectures. JColloid Interface Sci 2008, 328:278-287.
42. Lin J.-J., Chen J.-S., Huang S.-J., Ko J.-H., Wang Y.-M., Chen T.-L., et al. Folic acid-Pluronic F127 magnetic nanoparticle clusters for combined targeting, diagnosis, and therapy applications. Biomaterials 2009, 30:5114.
43. Gaur U., Sahoo S.K., De T.K., Ghosh P.C., Maitra A., Ghosh P. Biodistribution of fluoresceinated dextran using novel nanoparticles evading reticuloendothelial system. Int J Pharm 2000, 202:1-10.
44. Takemura T., Ohta N., Nakajima S., Sakata I. Critical importance of the triplet lifetime of photosensitizer in photodynamic therapy of tumor. Photochem Photobiol 1989, 50:339-344.
45. Webber J., Luo Y., Crilly R., Fromm D., Kessel D. An apoptotic response to photodynamic therapy with endogenous protoporphyrin invivo. JPhotochem Photobiol B 1996, 35:209-211.
46. Phillips M.A., Gran M.L., Peppas N.A. Targeted nanodelivery of drugs and diagnostics. Nano Today 2010, 5:143-159.