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Comparative Positron-Emission Tomography (PET) Imaging and Phototherapeutic Potential of 124I- Labeled Methyl- 3-(1′-iodobenzyloxyethyl)pyropheophorbide-a vs the Corresponding Glucose and Galactose Conjugates

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PDT Center and Department of Dermatology, Roswell Park Cancer Institute, Buffalo, New York 14263, and Department of Nuclear Medicine, State University of New York, Buffalo, New York 14214
* To whom correspondence should be addressed. For R.K.P.: phone, 716-845-3203; fax, 716-845-8920; e-mail, [email protected]. For M.S.: phone, 716-838-5889, extension 118; fax, 716-838-4918; e-mail, [email protected]
†PDT Center, Roswell Park Cancer Institute.
‡State University of New York.
§Department of Dermatology, Roswell Park Cancer Institute.
Cite this: J. Med. Chem. 2009, 52, 2, 445–455
Publication Date (Web):December 17, 2008
https://doi.org/10.1021/jm8012213
Copyright © 2008 American Chemical Society

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    Abstract

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    In our present study, 3-(1-m-iodobenzyloxyethyl)pyropheophorbide-a methyl ester 1, 3-(1′-m-iodobenzyloxyethyl)-172-{(2-deoxy)glucose}pyropheophorbide-a 2, and 3-(1′-m-iodobenzyloxyethyl)-172-{(1-deoxy)galactose}pyropheophorbide-a 3 were synthesized and converted into the corresponding 124I-labeled analogues by reacting the intermediate trimethyltin analogues with Na124I. Photosensitizers 13 were evaluated for the PDT efficacy in C3H mice bearing RIF tumors at variable doses and showed a significant long-term tumor cure. Among the compounds investigated, the non-carbohydrate analogue 1 was most effective. These results were in contrast to the in vitro data, where compared to the parent analogue the corresponding galactose and glucose derivatives showed enhanced cell kill. Among the corresponding 124I-labeled analogues, excellent tumor images were obtained from compound 1 in both tumor models (RIF and Colon-26) and the best tumor contrast was observed at 72 h after injection. Conjugating a glucose moiety to photosensitizer 1 initially diminished its tumor uptake, whereas with time the corresponding galactose analogue showed improved tumor contrast.

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    1H NMR spectra for compounds 13, 6, 9, 10, and 12 and the analytical details of compounds 112. This material is available free of charge via the Internet at http://pubs.acs.org.

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