Issue 5, 2009
From the journal:

Organic & Biomolecular Chemistry

One- and two-photon activated phototoxicity of conjugated porphyrin dimers with high two-photon absorption cross sections†

Emma Dahlstedt,a   Hazel A. Collins,a   Milan Balaz,a   Marina K. Kuimova,b   Mamta Khurana,c   Brian C. Wilson,*c   David Phillips*b  and  Harry L. Anderson*a  

* Corresponding authors

a Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK
E-mail: harry.anderson@chem.ox.ac.uk
Fax: +44 1865 285002
Tel: +44 1865 275704

b Chemistry Department, Imperial College London, Exhibition Road, London, UK
E-mail: d.phillips@imperial.ac.uk

c Department of Biophysics and BioImaging, Ontario Cancer Institute, University of Toronto, 610 University Ave, Rm 7-417, Toronto, Canada
E-mail: wilson@uhnres.utoronto.ca
Fax: +416 946 6529
Tel: +1 416 946 2952

Abstract

Two-photon excited photodynamic therapy (PDT) has the potential to provide a highly targeted treatment for neoplastic diseases, as excitation can be pin-pointed to small volumes at the laser focus. In addition, two-photon PDT offers deeper penetration into mammalian tissue due to the longer wavelength of irradiation. Here we report the one-photon and two-photon excited PDT results for a collection of conjugated porphyrin dimers with high two-photon absorption cross sections. These dimers demonstrate high one-photon PDT efficacy against a human ovarian adenocarcinoma cell line (SK-OV-3) and exhibit no significant dark-toxicity at concentrations of up to 20 μM. Their one-photon excited PDT efficiencies, following irradiation at 657 nm, approach that of Visudyne®, a drug used clinically for PDT. We investigated and optimised the effect of the photosensitiser concentration, incubation time and the light dose on the PDT efficacy of these dimers. These studies led to the selection of P2C2-NMeI as the most effective porphyrin dimer. We have demonstrated that P2C2-NMeI undergoes a two-photon activated process following excitation at 920 nm (3.6–6.8 mW, 300 fs, 90 MHz) and compared it to Visudyne. We conclude that the in vitro two-photon PDT efficacy of P2C2-NMeI is about twice that of Visudyne. This result highlights the potential of this series of porphyrin dimers for two-photon PDT.

Graphical abstract: One- and two-photon activated phototoxicity of conjugated porphyrin dimers with high two-photon absorption cross sections

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B814792B
Article type
Paper
Submitted
27 Aug 2008
Accepted
10 Nov 2008
First published
09 Jan 2009

Org. Biomol. Chem., 2009,7, 897-904

Permissions

Request permissions

One- and two-photon activated phototoxicity of conjugated porphyrin dimers with high two-photon absorption cross sections

E. Dahlstedt, H. A. Collins, M. Balaz, M. K. Kuimova, M. Khurana, B. C. Wilson, D. Phillips and H. L. Anderson, Org. Biomol. Chem., 2009, 7, 897 DOI: 10.1039/B814792B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements