Cancer is one of the leading causes of death in the United States. Chemotherapeutics and other anticancer drugs have come a long way since their discovery, however the vast majority of them cause unintended side effects. Often, these side effects can be attributed to the high rate at which healthy, noncancerous cells are damaged along alongside the cancer cells. Highly desirable new treatments for cancer are ones that can selectively target cancerous cells while excluding healthy cells. One way that we can selectively target cancerous cells is using photoisomerizable compounds such as azo-stilbenes.<br/>Photoisomerizable compounds are molecules that are isomerized by light. In other words, their structure changes when exposed to specific light wavelengths. The azo-stilbenes, in particular, undergo a trans to cis isomerization when irradiated with blue or UV light. This isomerization is easily reversible and can be accomplished quickly by irradiating the molecule with a longer wavelength of light (typically &gt;500 nm) or more slowly by thermal reversion in the absence of light.<br/>Given their reversible photoisomerization, compounds like the azo-stilbene group have found wide utility in many fields, such as functional materials, yet these azo-compounds have only recently begun to be explored as photopharmaceuticals. Given that shape and electrostatic complementarity is critical for many drug-target interactions, photoisomerization results in a change in the bioactivity of these molecules. Judicious application of the appropriate wavelengths of light can be used as a switch that will allow for local targeting in cytotoxic treatments. With the use of azo-stilbenes, off-target side effects could be greatly reduced and potentially eradicated.<br/>One potential target for photo-switchable therapeutics is c-Raf. This kinase plays a key role in a pathway that regulates the cellular cycle including cell proliferation and apoptosis, which is dysregulated in some cancers. This work will describe the design, completed synthesis, photokinetic analysis, and preliminary bioactivity measurements for three lead molecules with potential as photoswitchable drugs based upon a previously reported c-Raf inhibitor.

Synthesis and biological evaluation of photoisomerizable c-Raf inhibitor

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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