<i>Mycobacterium tuberculosis, </i>the causative agent of tuberculosis, is a disease which impacts nearly two million people globally. An increase in multi-drug resistant (MDR) and extensively drug resistant (XDR) tuberculosis has led to the search for new therapeutics to treat this disease. Our research focuses on the development of new therapeutics which exploit the metabolism of the cell to successfully incorporate photoactive drugs known as photosensitizers directly into the membrane of the cell. These drugs can then be activated by light to kill the bacteria through a process known as photodynamic therapy (PDT). In our previous work we functionalized porphyrin photosensitizers with a sugar known as trehalose that is required for metabolic incorporation. Our results revealed a distance dependent effect between the porphyrin and trehalose on cell killing; shorter distances were most effective in inducing cell death. In this work, we manipulated the number of sugars on the porphyrin to explore valency effects. Here, we present the synthesis of a new series of trehalose-based porphyrins. Our current work focuses on evaluating these structures against a non-pathogenic strain of mycobacterium, <i>Mycobacterium smegmatis</i>, as a model system.

Synthesis of multivalent porphyrins as photosensitizers for treating tuberculosis

ACS Spring 2022

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