FLUORINATED ANALOGUES OF RIBOFLAVIN: POTENTIAL ANTIMETABOLITES
Abstract
A history of riboflavin and a review of the "analogues" of riboflavin that have shown biological activity is presented. The most common methods of making o-phenylenediamines and condensing them to get the isoalloxazine structure are presented along with a brief review of riboflavin and its "analogues" in relation to cancer. Based on the few studies of the analogues of riboflavin that have shown some antitumor activity, a series of fluorinated riboflavins was proposed and their syntheses undertaken. Of the three proposed fluorinated riboflavins only one was successfully synthesized. The hexafluororiboflavin was synthesized by a modification of the published method for its synthesis. After its synthesis was completed two other new hexafluoroflavins were synthesized by similar methods. All three hexafluoroflavins were tested for biological activity in PS, KB, and L-1210 tumor cells but were found to be inactive with ED(,50)'s greater than 100 (mu)g/mL. They were also found not to inhibit the growth of Staphylococcus aureus. (,) The hexafluororiboflavin was tested in Lactobacillus casei. Preliminary results show that alone it does not promote the growth of L. casei; in the presence of a low basal level of riboflavin, the hexafluororiboflavin has some growth stimulating activity at high concentrations; at very high concentrations of the hexafluororiboflavin inhibition is observed.
Degree
Ph.D.
Subject Area
Organic chemistry
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