Synthesis and biological evaluation of Foscan® bile acid conjugates to target esophageal cancer cells
Item Type:Journal Article
Citation: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.
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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.
Science Foundation Ireland (SFI)
SFI P.I. 09/IN.1/B2650
Type of material:Journal Article
Series/Report no:Bioorganic & Medicinal Chemistry Letters
Availability:Full text available