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Photophysics and ex vivo biodistribution of β-cyclodextrin-meso-tetra(m-hydroxyphenyl)porphyrin conjugate for biomedical applications

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Abstract

Low aqueous solubility of porphyrin-based photosensitizers hampers their clinical use in photodynamic therapy because of complex delivery. In this study, we explore meso-tetra(m-hydroxyphenyl)-21,23H-porphyrin (mTHPP), a potent photosensitizer, covalently attached to β-cyclodextrin (CD-mTHPP) with a focus on topical delivery and cellular uptake. The photophysical properties of CD-mTHPP were examined using steady-state fluorescence and lifetime measurements verifying increased aqueous solubility. Confocal and fluorescence lifetime imaging microscopy on human squamous carcinoma cells (A431) evidenced a cytoplasmic uptake of CD-mTHPP in predominantly monomeric form. CD-mTHPP was also delivered to human skin ex vivo and the skin penetration was assessed using two-photon fluorescence microscopy. The results indicated that CD-mTHPP exhibits improved skin distribution compared to mTHPP alone using aqueous vehicles. Thus the CD-mTHPP conjugate demonstrates improved biodistribution ex vivo compared to mTHPP and is a promising multimodal system for photodynamic therapy.

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Authors and Affiliations

  1. Biomedical Photonics Group, Department of Chemistry and Molecular Biology, Kemivägen 10, SE-412 96, Gothenburg, Sweden

    V. Kirejev & M. B. Ericson

  2. Institute of Advanced Materials Physicochemical Processes, Nanotechnology and Microsystems, Agia Paraskevi Attikis, 15310, Greece

    A. R. Gonçalves, C. Aggelidou & K. Yannakopoulou

  3. Istituto per la Sintesi Organica e la Fotoreattività (ISOF), National Research Council (CNR), via Gobetti 101, 40129, Bologna, Italy

    I. Manet

  4. Chemical and Biological Engineering, Chalmers University of Technology, Kemivägen 10, SE-412 96, Gothenburg, Sweden

    J. Mårtensson

Authors
  1. V. Kirejev
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  2. A. R. Gonçalves
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  3. C. Aggelidou
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  4. I. Manet
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  5. J. Mårtensson
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  6. K. Yannakopoulou
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  7. M. B. Ericson
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Correspondence to V. Kirejev or M. B. Ericson.

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Kirejev, V., Gonçalves, A.R., Aggelidou, C. et al. Photophysics and ex vivo biodistribution of β-cyclodextrin-meso-tetra(m-hydroxyphenyl)porphyrin conjugate for biomedical applications. Photochem Photobiol Sci 13, 1185–1191 (2014). https://doi.org/10.1039/c4pp00088a

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  • DOI: https://doi.org/10.1039/c4pp00088a

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