Porphyrin - Cyclodextrin conjugates as a nanosystem for versatile drug delivery and multimodal cancer therapy

Journal of Medicinal Chemistry

Volumn 53, Issue 1, 2010, Pages 128-138

  Králová, Jarmila ^a   Kejík, Zdeněk ^b,d   Bříza, Tomáš ^b,d   Poučková, Pavla ^d   Král, Aleš ^d   Martásek, Pavel ^d   Král, Vladimír ^b,c  

^a INSTITUTE OF MOLECULAR GENETICS   (Czech Republic)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^c Zentiva Prague   (Czech Republic)

^d CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOPTERIN; CISPLATIN; CYCLODEXTRIN PORPHYRIN CONJUGATE; DOCETAXEL; DOXORUBICIN; FLUOROURACIL; IMATINIB; LAPATINIB; LOMUSTINE; METHOTREXATE; NANOPARTICLE; PACLITAXEL; PORPHYRIN DERIVATIVE; SUNITINIB; TIOGUANINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; CANCER CELL CULTURE; CELL STRAIN K 562; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG POTENTIATION; DRUG STABILITY; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PH; PHOTODYNAMIC THERAPY; PHOTOSENSITIZATION; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC COMBINED CHEMOTHERAPY PROTOCOLS; CELL DEATH; CELL LINE, TUMOR; COMBINED MODALITY THERAPY; CYCLODEXTRINS; DRUG DELIVERY SYSTEMS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICE; NANOTECHNOLOGY; NEOPLASMS; PORPHYRINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 74849103978     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9007278     Document Type: Article

References (42)

1. Kopecek, J.; Kopeckova, P.; Minko, T.; Lu, Z. R.; Peterson, C. M. Water soluble polymers in tumor targeted delivery. J. Controlled Release 2001, 74, 147-158.
2. Ladewig, M. S.; Karl, S. E.; Hamelmann, V.; Helb, H. M.; Scholl, H. P. N.; Holz, F. G.; Eter, N. Combined intravitreal bevacizumab and photodynamic therapy for neovascular age-related macular degeneration. Graefe's Arch. Clin. Exp.Ophthalmol. 2008, 246, 17-25.
3. Lunardi, C. N.; Tedesco, A. C. Synergic photosensitizers: a new trend in photodynamic therapy. Curr. Org. Chem. 2005, 9, 813-821.
4. He, H.; Zhou, Y.; Liang, F.; Li, D.; Wu, J.; Yang, L.; Zhou, X.; Zhang, X.; Cao, X. Combination of porphyrins and DNA-alkylation agents: synthesis and tumor cell apoptosis induction. Bioorg. Med. Chem. 2006, 14, 1068-1077.
5. Uekama, K.; Hirayama, F.; Arima, H. Recent aspect of cyclodextrin-based drug delivery system. J. Inclusion Phenom. Macrocyclic Chem. 2006, 56, 3-8.
6. Rihova, B.; Strohalm, J.; Prausova, J.; Kubackova, K.; Jelinkova, M.; Rozprimova, L.; Sirova, M.; Plocova, D.; Etrych, T.; Subr, V.; Mrkvan, T.; Kovar, M.; Ulbrich, K. Cytostatic and immunomobilizing activities of polymer-bound drugs: experimental and first clinical data. J. Controlled Release 2003, 91, 1-16.
7. Vicent, M. J.; Greco, F.; Nicholson, R. I.; Paul, A.; Griffiths, P. C.; Duncan, R. Polymer therapeutics designed for a combination therapy of hormone-dependent cancer. Angew. Chem., Int. 2005, 44, 4061-4066.
8. Loftsson, T.; Masson, M. Cyclodextrins in topical drug formulations: theory and practice. Int. J. Pharm. 2001, 225, 15-30.
9. Hipler, U. C.; Schoenfelder, U.; Hipler, C.; Elsner, P. Influence of cyclodextrins on the proliferation of HaCaT keratinocytes in vitro. J. Biomed. Mater. Res., Part A 2007, 83, 70-79.
10. Uekama, K. Design and evaluation of cyclodextrin-based drug formulation. Chem. Pharm. Bull. 2004, 52, 900-915.
11. Cserhati, T.; Hollo, J. Interaction of taxol and other anticancer drugs with hydroxypropyl-beta-cyclodextrin. Int. J. Pharm. 1994, 108, 69-75.
12. Ceschel, G. C.; Mora, P. C.; Borgia, S. L.; Maffei, P.; Ronchi, C. Skin permeation study of dehydroepiandrosterone (DHEA) compared with its alpha-cyclodextrin complex form. J. Pharm. Sci. 2002, 91, 2399-2407.
13. Alcaro, S.; Ventura, C. A.; Paolino, D.; Battaglia, D.; Ortuso, F.; Cattel, L.; Puglisi, G.; Fresta, M. Preparation, characterization, molecular modeling and in vitro activity of paclitaxel-cyclodextrin complexes. Bioorg. Med. Chem. Lett. 2002, 12, 1637-1641.
14. Hagiwara, Y.; Arima, H.; Hirayama, F.; Uekama, K. Prolonged retention of doxorubicin in tumor cells by encapsulation of gamma-cyclodextrin complex in pegylated liposomes. J. Inclusion Phenom. Macrocyclic Chem. 2006, 56, 65-68.
15. Liu, Y.; Chen, Y. Cooperative binding and multiple recognition by bridged bis(beta-cyclodextrin)s with functional linkers. Acc. Chem. Res. 2006, 39, 681-691.
16. Liu, Y.; Chen, G. S.; Li, L.; Zhang, H. Y.; Cao, D. X.; Yuan, Y. J. Inclusion complexation and solubilization of paclitaxel by bridged bis(beta-cyclodextrin)s containing a tetraethylenepentaamino spacer. J. Med. Chem. 2003, 46, 4634-4637.
17. Liu, Y.; Yang, Y. W.; Yang, E. C.; Guan, X. D. Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s. J. Org. Chem. 2004, 69, 6590-6602.
18. Liu, Y.; Li, L.; Chen, Y.; Yu, L.; Fan, Z.; Ding, F. Molecular recognition thermodynamics of bile salts by beta-cyclodextrin dimers: factors governing the cooperative binding of cyclodextrin dimers. J. Phys. Chem. B 2005, 109, 4129-4134.
19. Allison, R. R.; Bagnato, V. S.; Cuenca, R.; Downie, G. H.; Sibata, C. H. The future of photodynamic therapy in oncology. Future Oncol. 2006, 2, 53-71.
20. Castano, A. P.; Mroz, P.; Hamblin, M. R. Photodynamic therapy and anti-tumour immunity. Nat. Rev. Cancer 2006, 6, 535-545.
21. Kral, V.; Kralova, J.; Kaplanek, R.; Briza, T.; Martasek, P. Quo vadis porphyrin chemistry? Physiol. Res. 2006, 55, S3-S26.
22. Kralova, J.; Koivukorpi, J.; Kejik, Z.; Pouckova, P.; Sievaenen, E.; Kolehmainen, E.; Kral, V. Porphyrin-bile acid conjugates: from saccharide recognition in the solution to the selective cancer cell fluorescence detection. Org. Biomol. Chem. 2008, 6, 1548-1552.
23. Wu, J. J.; Ma, H. L.; Mao, H. S.; Wang, Y.; Jin, W. J. Investigation on disassociation of porphyrin J-aggregates induced by β-cyclodextrins using absorption and fluorescence spectroscopy. J. Photochem. Photobiol., A 2005, 173, 296-300.
24. Luca, G.; Romeo, A.; Scolaro, L. M. Aggregation properties of hyperporphyrins with hydroxyphenyl substituents. J. Phys. Chem. B 2006, 110, 14135-14141.
25. Banfi, S.; Caruso, E.; Caprioli, S.; Mazzagatti, L.; Canti, G.; Ravizza, R.; Gariboldi, M.; Monti, E. Photodynamic effects of porphyrin and chlorin photosensitizers in human colon adenocarcinoma cells. Bioorg. Med. Chem. 2004, 12, 4853-4860.
26. Samaroo, D.; Vinodu, M.; Chen, X.; Drain, C. M. meso-Tetra- (pentafluorophenyl)porphyrin as an efficient platform for combinatorial synthesis and the selection of new photodynamic therapeutics using a cancer cell line. J. Comb. Chem. 2007, 9, 998-1011.
27. Synytsya, A.; Kral, V.; Synytsya, A.; Volka, K.; Sessler, J. L. In vitro interaction of macrocyclic photosensitizers with intact mitochondria: a spectroscopic study. Biochim. Biophys. Acta, Gen. Subj. 2003, 1620, 85-96.
28. Kral, V.; Rusin, O.; Charvatova, J.; Anzenbacher, P.; Fogl, J. Porphyrin phosphonates: novel anionic receptors for saccharide recognition. Tetrahedron Lett. 2000, 41, 10147-10151.
29. Kralova, J.; Synytsya, A.; Pouckova, P.; Koc, M.; Dvorak, M.; Kral, V. Novel porphyrin conjugates with a potent photodynamic antitumor effect: differential efficacy of mono- and bis-beta-cyclodextrin derivatives in vitro and in vivo. Photochem. Photobiol. 2006, 82, 432-438.
30. Zaruba, K.; Vasek, P.; Kral, V. Study of molecular recognition of 5,10,15,20-tetrakis-(pentafluorophenyl)porphyrin-β-cyclodextrin conjugate covalently immobilized on a silica surface. Supramol. Chem. 2004, 16, 529-536.
31. Rusin, O.; Hub, M.; Kral, V. Novel water-soluble porphyrin-based receptors for saccharide recognition. Mater. Sci. Eng. 2001, C18, 135-140.
32. Kralova, J.; Briza, T.; Moserova, I.; Dolensky, B.; Vasek, P.; Pouckova, P.; Kejik, Z.; Kaplanek, R.; Martasek, P.; Dvorak, M.; Kral, V. Glycol porphyrin derivatives as potent photodynamic inducers of apoptosis in tumor cells. J. Med. Chem. 2008, 51, 5964-5973.
33. Hosseini, A.; Hodgson, M. C.; Tham, F. S.; Reed, C. A.; Boyd, P. D. V. Tapes, sheets, and prisms. Identification of the weak C - F interactions that steer fullerene - porphyrin cocrystallization. Cryst. Growth Des. 2006, 6, 397-403.
34. Toth, G.; Bowers, S. G.; Truong, A. P.; Probst, G. The role and significance of unconventional hydrogen bonds in small molekule recognition by biological receptors of pharmaceutical relevance. Curr. Pharm. Des. 2007, 13, 3476-3493.
35. Puglisi, A.; Purrello, R.; Rizzarelli, E.; Sortino, S.; Vecchio, G. Spectroscopic and self-association behavior of a porphyrin-β-cyclodextrin conjugate. New J. Chem. 2007, 31, 1499-1506.
36. Leng, X.; Choi, Ch.-F.; Lo, P.-Ch.; Dennis, K. P. Assembling a mixed phthalocyanine - porphyrin array in aqueous media through host - guest interactions. Org. Lett. 2007, 9, 231-234.
37. Lang, K.; Kral, V.; Kapusta, P.; Kubat, P.; Vasek, P. Photoinduced electron transfer within porphyrin-cyclodextrin conjugates. Tetrahedron Lett. 2002, 43, 4919-4922.
38. Vinodu, M.; Goldberg, I. Synthesis and versatile supra-molecular self-assembly of the 5,15-bis(4-hydroxyphenyl)-10, 20-bis(4-carboxyphenyl) porphyrin scaffold. CrystEngComm 2004, 6, 215-220.
39. Lazzeri, D.; Durantini,E.N. Synthesis of meso-substituted cationic porphyrins as potential photodynamic agents. ARKIVOC2003, 10, 227-239.
40. Lang, L.; Kral, V.; Kapusta, P; Kubat, P.; Vasek, P. Photoinduced electron transfer within porphyrin - cyclodextrin conjugates. Tetrahedron Lett. 2002, 43, 4919-4922.
41. Kralova, J.; Dvorak, M.; Koc, M.; Kral, V. p38 MAPK plays an essential role in apoptosis induced by photoactivation of a novel ethylene glycol porphyrin derivative. Oncogene 2008, 27, 3010-3020.
42. Zimmermann, A.; Walt, H.; Haller, U.; Baas, P.; Klein, S. D. Effects of chlorin-mediated photodynamic therapy combined with fluoropyrimidines in vitro and in a patient. Cancer Chemother. Pharmacol. 2003, 51, 147-154.