Synthesis and biological evaluation of Foscan® bile acid conjugates to target esophageal cancer cells
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2013Access:
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Rogers, L.; Majer, F.; Sergeeva, N. N.; Paszko, E.; Gilmer, J. F.; Senge, M. O., Synthesis and biological evaluation of Foscan® bile acid conjugates to target esophageal cancer cells, Bioorganic & Medicinal Chemistry Letters, 23, 9, 2013, 2495 2499.Download Item:
Abstract:
Porphyrins and chlorins such as Foscan? have a natural proclivity to accumulate in cancer cells.
This trait has made them good candidates for photosensitizers and as imaging agents in
phototherapy. In order to improve on cellular selectivity to lower post-treatment photosensitivity
bile acid porphyrin bioconjugates have been prepared and investigated in esophageal cancer
cells. Bile acids which are known to selectively bind to, or be readily taken up by cancer cells
were chosen as targeting moieties. Synthesis of the conjugates was achieved via selective
nucleophilic monofunctionalization of 5,10,15,20-tetrahydroxyphenylporphyrins with propargyl
bromide followed by Cu(I) mediated cycloaddition with bile acid azides in good yields. The
compounds were readily taken up by esophageal cancer cells but showed no PDT activity. 2013
Elsevier Ltd. All rights reserved.
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Science Foundation Ireland (SFI)
SFI P.I. 09/IN.1/B2650
Author's Homepage:
http://people.tcd.ie/sengemhttp://people.tcd.ie/gilmerjf
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Bioorganic & Medicinal Chemistry Letters23
9
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porphyrinsDOI:
http://dx.doi.org/10.1016/j.bmcl.2013.03.040Metadata
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