Viscosity reduction of isotonic solutions of the photosensitizer TPCS_2a by cyclodextrin complexation

References

• PCI Biotech; 2017. [Internet]; [cited 2017 Aug 7]. http://pcibiotech.no/pipeline-2/
   Google Scholar
• Sultan AA, Jerjes W, Berg K, et al. Disulfonated tetraphenyl chlorin (TPCS2a)-induced photochemical internalization of bleomycin in patients with solid malignancies: a phase 1, dose-escalation, first-in-man trial. Lancet Oncol. 2016;17:1217–1229.
   PubMed Web of Science ®Google Scholar
• Lilletvedt M, Tønnesen HH, Høgset A, et al. Physicochemical characterization of the photosensitizers TPCS2a and TPPS2a 1. Spectroscopic evaluation of drug-solvent interactions. Pharmazie. 2010;65:588–595.
   PubMed Web of Science ®Google Scholar
• Lilletvedt M, Kristensen S, Tønnesen HH, et al. Time-domain evaluation of drug-solvent interactions of the photosensitizers TPCS2a and TPPS2a as part of physicochemical characterization. J Photochem Photobiol A: Chem. 2010;214:40–47.
   Web of Science ®Google Scholar
• Lilletvedt M, Tønnesen HH, Høgset A, et al. Evaluation of physicochemical properties and aggregation of the photosensitizers TPCS2a and TPPS2a in aqueous media. Pharmazie. 2011;66:325–333.
   PubMed Web of Science ®Google Scholar
• Lilletvedt M, Smistad G, Tønnesen HH, et al. Solubilization of the novel anionic amphiphilic photosensitizer TPCS2a by nonionic Pluronic block copolymers. Eur J Pharm Sci. 2011;43:180–187.
   PubMed Web of Science ®Google Scholar
• Wang JTW, Berg K, Høgset A, et al. Photophysical and photobiological properties of a sulfonated chlorin photosensitiser TPCS2a for photochemical internalisation (PCI). Photochem Photobiol Sci. 2013;12:519–526.
   PubMed Web of Science ®Google Scholar
• Rubires R, Crusats J, El-Hachemi Z, et al. Self-assembly in water of the sodium salts of meso-sulfonatophenyl substituted porphyrins. New J Chem. 1999;29:189–198.
   Google Scholar
• Loftsson T, Brewster ME. (2013) Drug solubilization and stabilization by cyclodextrin drug carriers. In: D. Douroumis, A. Fahr, editors. Drug delivery strategies for poorly water-soluble drugs. 1st ed. New York: John Wiley & Sons, Ltd.; p. 67–101 [Chapter 3].
   Google Scholar
• Arima H, Hayashi Y, Higashi T, et al. Recent advances in cyclodextrin delivery techniques. Expert Opin Drug Deliv. 2015;12:1425–1441.
   PubMed Web of Science ®Google Scholar
• Desroches M-C, Kasselouri A, Bourdon O, et al. A direct sensitized fluorimetric determination of 5,10,15,20-tetra(m-hydroxyphenyl)chlorin [m-THPC(Foscan)®] in human plasma using a cyclodextrin inclusion complex. Analyst. 2001;126:923–927.
   PubMed Web of Science ®Google Scholar
• Guo X, An W, Shuang S, et al. Study on spectroscopic characterization of meso-tetrakis(4-hydroxyphenyl) porphyrin (THPP) in β-cyclodextrin and its derivates. J Photochem Photobiol A: Chem. 2005;173:258–263.
   Web of Science ®Google Scholar
• Mosinger J, Deumie M, Lang K, et al. Supramolecular sensitizer: complexation of meso-tetrakis(4-sulfonatophenyl)porphyrin with 2-hydroxypropyl-cyclodextrins. J Photochem Photobiol A: Chem. 2000;130:13–20.
   Web of Science ®Google Scholar
• Paul S, Heng PWS, Chan LW. (pH-dependent complexation of hydroxypropyl-beta-cyclodextrin with chlorin e6: effect on solubility and aggregation in relation to photodynamic efficacy. J Pharm Pharmacol. 2016;68:439–449.
   PubMed Web of Science ®Google Scholar
• Ribo JM, Farrera J-A, Valero ML, et al. Self-assembly of cyclodextrins with meso-Tetrakis(4-sulfonatophenyl)porphyrin in aqueous solution. Tetrahedron. 1995;51:3705–3712.
   Web of Science ®Google Scholar
• Hamai S, Ohshida T. Inclusion complexes of cyclodextrins with tetrakis(4-carboxyphenyl)porphyrin and Tetrakis(4-sulfonatophenyl)porphyrin in aqueous solutions. J Incl Phenom Macrocycl Chem. 2004;50:209–217.
   Web of Science ®Google Scholar
• EMA European medicines agency. Background review for cyclodextrins used as excipients; 2014. [Internet]; [cited 2017 Aug 7]. Available from: http://www.ema.europa.eu/docs/en_GB/document_library/Report/2014/12/WC500177936.pdf
   Google Scholar
• FDA. Inactive ingredient search for approved drug products,” cyclodextrin”, US Food and Drug Administration; 2017. [Internet]; [cited 2017 Aug 7]. Available from: https://www.accessdata.fda.gov/scripts/cder/iig/getiigWEB.cfm
   Google Scholar
• Mosinger J, Kliment V Jr, Sejbal J, et al. Host-guest complexes of anionic porphyrin sensitizers with cyclodextrins. J Porphyrins Phthalocyanines. 2002;6:514–526.
   Web of Science ®Google Scholar
• Agostinis P, Berg K, Cengel KA, et al. Photodynamic therapy of cancer: an update. CA Cancer J Clin. 2011;61:250–281.
   PubMed Web of Science ®Google Scholar
• Rawat S, Jain SK. Solubility enhancement of celecoxib using β-cyclodextrin inclusion complexes. Eur J Pharm Biopharm. 2004;57:263–267.
   PubMed Web of Science ®Google Scholar
• Wang X-P, Pan J-H, Shuang S-M. Study on the supramolecular system of meso-tetrakis(4-sulfonatophenyl) porphyrin and cyclodextrins by spectroscopy. Spectrochim Acta Part A. 2001;57:2755–2762.
   PubMed Web of Science ®Google Scholar
• Wang X-P, Pan J-H, Shuang S-M, et al. Determination of the inclusion constants for the inclusion complexes between meso-Tetrakis(4-sulfonatophenyl) porphyrin and cyclodextrins by three methods. Supramol Chem. 2002;14:419–426.
   Web of Science ®Google Scholar
• Guo Y-J, Zhang P, Chao J-B, et al. Study on the supramolecular system of 5-(p-hydroxyphenyl)-10,15,20-tris-(4-chlorophenyl)porphyrin with cyclodextrins and its analytical characteristics. Spectrochim Acta Part A. 2008;71:946–950.
   PubMed Web of Science ®Google Scholar
• Hamai S. Complex formation of tetrakis(4-sulfonatophenyl)porphyrin with γ-cyclodextrin, phenylalanine, and tryptophan in aqueous solution. J Incl Phenom Macrocycl Chem. 2010;67:471–481.
   Web of Science ®Google Scholar
• Yankovsky I, Bastien E, Yakavets I, et al. Inclusion complexation with β-cyclodextrin derivatives alters photodynamic activity and biodistribution of meta-tetra(hydroxyphenyl)chlorin. Eur J Pharm Sci. 2016;91:172–182.
   PubMed Web of Science ®Google Scholar
• Cuccato N, Nardo L, Kristensen S, et al. Solubilization of the chlorin TPCS2a in the presence of Pluronic F127/Tween 80 mixtures. Pharm Dev Technol., submitted.
   Google Scholar