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A new strategy for targeted delivery of non-water-soluble porphyrins in chitosan-albumin capsules

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Abstract

This study was focused on obtaining polymer complex of 5-(4′-N-tert-butyloxycarbonylglicinaminophenyl)-10,15,20-triphenylporphine and 5-(4′-amonophenyl)-10,15,20-triphenylporphine with chitosan. The polymer complexes were characterized spectrally and calorimetrically. The existence of a substituent capable of forming hydrogenic complexes with proteins and other biopolymers in porphyrins provides an effective immobilization of a photosensitizer. Binding with porphyrins was found to result in twisting the chitosan globule and encapsulation of porphyrins. Coating of polymer complex with bovine serum albumin promotes neutralization of zeta potential and formation of 180-nm capsules. As the result of the study, a new universal strategy of water insoluble preparation encapsulation in biopolymers for targeted delivery of drugs and their further release was suggested.

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References

  1. Bacellar IO, Tsubone TM, Pavani C, Baptista MS (2015) Photodynamic efficiency: from molecular photochemistry to cell death. Int J Mol Sci 16:20523–20559

    Article  CAS  Google Scholar 

  2. Moan J, Berg K, Bommer JC, Western A (1992) Action spectra of phthalocyanines with respect to photosensitization of cells. Photochem Photobiol 56:171–175

    Article  CAS  Google Scholar 

  3. Weyergang A, Berg K, Kaalhus O, Peng Q, Selbo PK (2008) Photodynamic therapy targets the mTOR signaling network in vitro and in vivo. Mol Pharm 6:255–264

    Article  Google Scholar 

  4. Deda DK, Pavani C, Carita E, Baptista MS, Toma HE, Araki K (2013) Control of cytolocalization and mechanism of cell death by encapsulation of a photosensitizer. J Biomed Nanotechnol 9:1307–1317

    Article  CAS  Google Scholar 

  5. Hwang JY, Lubow DJ, Chu D, Sims J, Alonso-Valenteen F, Gray HB, Gross Z, Farkas DL, Medina-Kauwe LK (2012) Photoexcitation of tumor-targeted corroles induces singlet oxygen-mediated augmentation of cytotoxicity. J Control Release 163:368–373

    Article  CAS  Google Scholar 

  6. Dummin H, Cernay T, Zimmermann H (1997) Selective photosensitization of mitochondria in HeLa cells by cationic Zn (II) phthalocyanines with lipophilic side-chains. J Photochem Photobiol B Biol 37:219–229

    Article  CAS  Google Scholar 

  7. Mohammad RM, Muqbil I, Lowe L, Yedjou C, Hsu H-Y, Lin L-T, Siegelin MD, Fimognari C, Kumar NB, Dou QP, Yang H, Samadi AK, Russo GL, Spagnuolo C, Ray SK, Chakrabarti M, Morre JD, Coley HM, Honoki K, Fujii H, Georgakilas AG, Amedei A, Niccolai E, Amin A, Ashraf SS, Helferich WG, Yang X, Boosani CS, Guha G, Bhakta D, Ciriolo MR, Aquilano K, Chen S, Mohammed SI, Keith WN, Bilsland A, Halicka D, Nowsheen S, Azmi AS (2015) Broad targeting of resistance to apoptosis in cancer. Semin Cancer Biol 35:S78-S103.

  8. Buytaert E, Callewaert G, Hendrickx N, Scorrano L, Hartmann D, Missiaen L, Vandenheede JR, Heirman I, Grooten J, Agostinis P (2006) Role of endoplasmic reticulum depletion and multidomain proapoptotic BAX and BAK proteins in shaping cell death after hypericin-mediated photodynamic therapy. FASEB J 20:756–758

    CAS  Google Scholar 

  9. Buytaert E, Callewaert G, Vandenheede J, Agostinis P (2006) Deficiency in apoptotic effectors Bax and Bak reveals an autophagic cell death pathway initiated by photodamage to the endoplasmic reticulum. Autophagy 2:238–240

    Article  CAS  Google Scholar 

  10. Buytaert E, Dewaele M, Agostinis P (2007) Molecular effectors of multiple cell death pathways initiated by photodynamic therapy. Biochimic Biophys Acta (BBA) Rev Cancer 1776:86–107

    Article  CAS  Google Scholar 

  11. Kessel D, Vicente MGH, Reiners JJ (2006) Initiation of apoptosis and autophagy by photodynamic therapy. Lasers Surg Med 38:482–488

    Article  Google Scholar 

  12. Nassar T, Rom A, Nyska A, Benita S (2009) Novel double coated nanocapsules for intestinal delivery and enhanced oral bioavailability of tacrolimus, a P-gp substrate drug. J Control Release 133:77–84

    Article  CAS  Google Scholar 

  13. Yuasa M, Oyaizu K, Horiuchi A, Ogata A, Hatsugai T, Yamaguchi A, Kawakami H (2004) Liposomal surface-loading of water-soluble cationic iron (III) porphyrins as anticancer drugs. Mol Pharm 1:387–389

    Article  CAS  Google Scholar 

  14. Kamal A, Kashi Reddy M, Viswanath A (2013) The design and development of imidazothiazole–chalcone derivatives as potential anticancer drugs. Expert Opin Drug Discovery 8:289–304

    Article  CAS  Google Scholar 

  15. Kryjewski M, Goslinski T, Mielcarek J (2015) Functionality stored in the structures of cyclodextrin–porphyrinoid systems. Coord Chem Rev 300:101–120

    Article  CAS  Google Scholar 

  16. Lei W, Jiang G, Zhou Q, Zhang B, Wang X (2010) Greatly enhanced binding of a cationic porphyrin towards bovine serum albumin by cucurbit [8] uril. PCCP 12:13255–13260

    Article  CAS  Google Scholar 

  17. Singh S, Aggarwal A, Bhupathiraju NDK, Tiwari K, Drain CM (2015) Glycosylated porphyrins, phthalocyanines, and other porphyrinoids for diagnostics and therapeutics. Chem Rev 115:10261–10306

    Article  CAS  Google Scholar 

  18. Pereira PM, Korsak B, Sarmento B, Schneider RJ, Fernandes R, Tomé JP (2015) Antibodies armed with photosensitizers: from chemical synthesis to photobiological applications. Org Biomol Chem 13:2518–2529

    Article  CAS  Google Scholar 

  19. Blaudszun A-R, Moldenhauer G, Schneider M, Philippi A (2015) A photosensitizer delivered by bispecific antibody redirected T lymphocytes enhances cytotoxicity against EpCAM-expressing carcinoma cells upon light irradiation. J Control Release 197:58–68

    Article  CAS  Google Scholar 

  20. Gravier J, Schneider R, Frochot C, Bastogne T, Schmitt F, Didelon J, Guillemin F, Barberi-Heyob M (2008) Improvement of meta-tetra (hydroxyphenyl) chlorin-like photosensitizer selectivity with folate-based targeted delivery. Synthesis and in vivo delivery studies. J Med Chem 51:3867–3877

    Article  CAS  Google Scholar 

  21. Gonçalves P, Corrêa D, Franzen P, De Boni L, Almeida L, Mendonça CR, Borissevitch I, Zilio SC (2013) Effect of interaction with micelles on the excited-state optical properties of zinc porphyrins and J-aggregates formation. Spectrochim Acta A Mol Biomol Spectrosc 112:309–317

    Article  Google Scholar 

  22. Sheng N, Zong S, Cao W, Jiang J, Wang Z, Cui Y (2015) Water dispersible and biocompatible porphyrin-based nanospheres for biophotonics applications: a novel surfactant and polyelectrolyte-based fabrication strategy for modifying hydrophobic porphyrins. ACS Appl Mater Interfaces 7:19718–19725

    Article  CAS  Google Scholar 

  23. Shieh M-J, Peng C-L, Lou P-J, Chiu C-H, Tsai T-Y, Hsu C-Y, Yeh C-Y, Lai P-S (2008) Non-toxic phototriggered gene transfection by PAMAM-porphyrin conjugates. J Control Release 129:200–206

    Article  CAS  Google Scholar 

  24. Lee SJ, Koo H, Jeong H, Huh MS, Choi Y, Jeong SY, Byun Y, Choi K, Kim K, Kwon IC (2011) Comparative study of photosensitizer loaded and conjugated glycol chitosan nanoparticles for cancer therapy. J Control Release 152:21–29

    Article  CAS  Google Scholar 

  25. Boyle RW, Dolphin D (1996) Structure and biodistribution relationships of photodynamic sensitizers. Photochem Photobiol 64:469–485

    Article  CAS  Google Scholar 

  26. Evstigneeva R, Luzgina V, Kiseleva NY, Konovalova N, Rakitina I (1998) The synthesis and physicochemical properties of mono-and diporphyrin conjugates of tetraphenylporphyrin derivatives and amino acids. Russ J Bioorg Chem 24:204–210

    Google Scholar 

  27. Lebedeva NS, Mikhailovsky K, Vyugin A (2001) Differential calorimeter of titration. Russ J Phys Chem 75:1140–1142

    CAS  Google Scholar 

  28. Ogunsipe A, Nyokong T (2005) Effects of central metal on the photophysical and photochemical properties of non-transition metal sulfophthalocyanine. J Porphyrins Phthalocyanines 9:121–129

    Article  CAS  Google Scholar 

  29. Quimby DJ, Longo FR (1975) Luminescence studies on several tetraarylporphins and their zinc derivatives. J Am Chem Soc 97:5111–5117

    Article  CAS  Google Scholar 

  30. Pavani C, Iamamoto Y, Baptista MS (2012) Mechanism and efficiency of cell death of type II photosensitizers: effect of zinc chelation. Photochem Photobiol 88:774–781

    Article  CAS  Google Scholar 

  31. Ricchelli F, Franchi L, Miotto G, Borsetto L, Gobbo S, Nikolov P, Bommer JC, Reddi E (2005) Meso-substituted tetra-cationic porphyrins photosensitize the death of human fibrosarcoma cells via lysosomal targeting. Int J Biochem Cell Biol 37:306–319

    Article  CAS  Google Scholar 

  32. Ricchelli F (1995) Photophysical properties of porphyrins in biological membranes. J Photochem Photobiol B Biol 29:109–118

    Article  CAS  Google Scholar 

  33. Lim F, Sun AM (1980) Microencapsulated islets as bioartificial endocrine pancreas. Science 210:908–910

    Article  CAS  Google Scholar 

  34. Soon-Shiong P, Feldman E, Nelson R, Heintz R, Yao Q, Yao Z, Zheng T, Merideth N, Skjak-Braek G, Espevik T (1993) Long-term reversal of diabetes by the injection of immunoprotected islets. Proc Natl Acad Sci 90:5843–5847

    Article  CAS  Google Scholar 

  35. Goosen MF, O'Shea GM, Gharapetian HM, Chou S, Sun AM (1985) Optimization of microencapsulation parameters: semipermeable microcapsules as a bioartificial pancreas. Biotechnol Bioeng 27:146–150

    Article  CAS  Google Scholar 

  36. Pommersheim R, Schrezenmeir J, Vogt W (1994) Immobilization of enzymes by multilayer microcapsules. Macromol Chem Phys 195:1557–1567

    Article  CAS  Google Scholar 

  37. Kokufuta E, Shimizu N, Tanaka H, Nakamura I (1988) Use of polyelectrolyte complex-stabilized calcium alginate gel for entrapment of β-amylase. Biotechnol Bioeng 32:756–759

    Article  CAS  Google Scholar 

  38. Bansal V, Sharma PK, Sharma N, Pal OP, Malviya R (2011) Applications of chitosan and chitosan derivatives in drug delivery. Adv Biol Res 5:28–37

    CAS  Google Scholar 

  39. Dutta PK, Dutta J, Tripathi V (2004) Chitin and chitosan: chemistry, properties and applications. J Sci Ind Res 63:20–31

    CAS  Google Scholar 

  40. Ramadas M, Paul W, Dileep K, Anitha MRY, Sharma C (2000) Lipoinsulin encapsulated alginate-chitosan capsules: intestinal delivery in diabetic rats. J Microencapsul 17:405–411

    Article  CAS  Google Scholar 

  41. Chávarri M, Marañón I, Ares R, Ibáñez FC, Marzo F, del Carmen Villarán M (2010) Microencapsulation of a probiotic and prebiotic in alginate-chitosan capsules improves survival in simulated gastro-intestinal conditions. Int J Food Microbiol 142:185–189

    Article  Google Scholar 

  42. Hejazi R, Amiji M (2003) Chitosan-based gastrointestinal delivery systems. J Control Release 89:151–165

    Article  CAS  Google Scholar 

  43. Kumar D, Mishra BA, Shekar KC, Kumar A, Akamatsu K, Kurihara R, Ito T (2013) Novel porphyrin–psoralen conjugates: synthesis, DNA interaction and cytotoxicity studies. Org Biomol Chem 11:6675–6679

    Article  CAS  Google Scholar 

  44. Luz PP, Nobre TM, Serra OA, Zaniquelli ME (2011) Chitosan as a bioadhesive agent between porphyrins and phospholipids in a biomembrane model. J Nanosci Nanotechnol 11:1278–1287

    Article  CAS  Google Scholar 

  45. Berth G, Voigt A, Dautzenberg H, Donath E, Möhwald H (2002) Polyelectrolyte complexes and layer-by-layer capsules from chitosan/chitosan sulfate. Biomacromolecules 3:579–590

    Article  CAS  Google Scholar 

  46. Chen RH, Tsaih ML, Lin W-C (1996) Effects of chain flexibility of chitosan molecules on the preparation, physical, and release characteristics of the prepared capsule. Carbohydr Polym 31:141–148

    Article  CAS  Google Scholar 

  47. Daly MM, Knorr D (1988) Chitosan-alginate complex coacervate capsules: effects of calcium chloride, plasticizers, and polyelectrolytes on mechanical stability. Biotechnol Prog 4:76–81

    Article  CAS  Google Scholar 

  48. Peniche C, Argüelles-Monal W, Peniche H, Acosta N (2003) Chitosan: an attractive biocompatible polymer for microencapsulation. Macromol Biosci 3:511–520

    Article  CAS  Google Scholar 

  49. Shigemasa Y, Minami S (1996) Applications of chitin and chitosan for biomaterials. Biotechnol Genet Eng Rev 13:383–420

    Article  CAS  Google Scholar 

  50. Muzzarelli RA (2013) Chitin. Pergamon Press Ltd., Oxford

    Google Scholar 

  51. Ferreira D, Conceição D, Calhelha R, Sousa T, Socoteanu R, Ferreira I, Ferreira LV (2016) Porphyrin dye into biopolymeric chitosan films for localized photodynamic therapy of cancer. Carbohydr Polym 151:160–171

    Article  CAS  Google Scholar 

  52. Lee R-J, Tamm T, Temmer R, Aabloo A, Kiefer R (2013) Two formation mechanisms and renewable antioxidant properties of suspensible chitosan–PPy and chitosan–PPy–BTDA composites. Synth Met 164:6–11

    Article  CAS  Google Scholar 

  53. Kolhe P, Kannan RM (2003) Improvement in ductility of chitosan through blending and copolymerization with PEG: FTIR investigation of molecular interactions. Biomacromolecules 4:173–180

    Article  CAS  Google Scholar 

  54. Lebedeva NS, Karelin A, Pavlycheva N, Zielenkiewicz W, Swierzewski R (2008) Spectroscopic studies of zinc (II) tetraphenylporphyrin molecular complex with 1, 4-dioxane. Spectrochim Acta A Mol Biomol Spectrosc 70:939–942

    Article  Google Scholar 

  55. Hunter CA, Sanders JK, Stone AJ (1989) Exciton coupling in porphyrin dimers. Chem Phys 133:395–404

    Article  CAS  Google Scholar 

  56. Peters T (1985) Serum albumin. Adv Protein Chem 37:161–245

    Article  CAS  Google Scholar 

  57. Amiri M, Jankeje K, Albani JR (2010) Characterization of human serum albumin forms with pH. Fluorescence lifetime studies. J Pharm Biomed Anal 51:1097–1102

    Article  CAS  Google Scholar 

  58. Yohannes G, Wiedmer SK, Elomaa M, Jussila M, Aseyev V, Riekkola M-L (2010) Thermal aggregation of bovine serum albumin studied by asymmetrical flow field-flow fractionation. Anal Chim Acta 675:191–198

    Article  CAS  Google Scholar 

  59. Cooper CL, Goulding A, Kayitmazer AB, Ulrich S, Stoll S, Turksen S, Yusa S-i, Kumar A, Dubin PL (2006) Effects of polyelectrolyte chain stiffness, charge mobility, and charge sequences on binding to proteins and micelles. Biomacromolecules 7:1025–1035

    Article  CAS  Google Scholar 

  60. Seyrek E, Dubin PL, Tribet C, Gamble EA (2003) Ionic strength dependence of protein-polyelectrolyte interactions. Biomacromolecules 4:273–282

    Article  CAS  Google Scholar 

  61. Liu Y, Huang Y, Boamah PO, Zhang Q, Liu Y, Hua M (2014) Synthesis and in vitro evaluation of manganese (II)-porphyrin modified with chitosan oligosaccharides as potential MRI contrast agents. Chem Res Chin Univ 30:549–555

    Article  CAS  Google Scholar 

  62. Kabanov V, Skobeleva V, Rogacheva V, Zezin A (2004) Sorption of proteins by slightly cross-linked polyelectrolyte hydrogels: kinetics and mechanism. J Phys Chem B 108:1485–1490

    Article  CAS  Google Scholar 

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Funding

The study was supported by the Russian Science Foundation, agreement 16-13-10453.

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Authors and Affiliations

  1. G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, Akademicheskaya, 1, Ivanovo, Russia

    Natalya Sh. Lebedeva, Yury A. Gubarev, Elena S. Yurina & Sergey A. Syrbu

  2. Research Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology, Ivanovo, Russia

    Ekaterina N. Smirnova

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  1. Natalya Sh. Lebedeva
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  2. Yury A. Gubarev
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  3. Elena S. Yurina
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  4. Ekaterina N. Smirnova
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Correspondence to Yury A. Gubarev.

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Lebedeva, N.S., Gubarev, Y.A., Yurina, E.S. et al. A new strategy for targeted delivery of non-water-soluble porphyrins in chitosan-albumin capsules. Colloid Polym Sci 295, 2173–2182 (2017). https://doi.org/10.1007/s00396-017-4191-9

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  • DOI: https://doi.org/10.1007/s00396-017-4191-9

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