Over five million people worldwide are diagnosed with non-melanoma skin cancer each year. The endocannabinoid arachidonyl ethanolamine (AEA) has been shown to selectively induce apoptosis in tumorigenic JWF2 keratinocytes with minimal effect on non-tumorigenic HaCaT cells. Conjugation of AEA to a fluorescent group may be helpful in characterizing pharmacokinetic properties needed for effective dosing and clinical development. The synthetic flexibility and bright luminescence of naphthalimides make them attractive probes for this purpose. This study is focused on identifying substituents on naphthalimide that cause minimal interference with intracellular drug localization and metabolism. MTS assays show that a 4-morpholino naphthalimide has a desirable lack of cytotoxicity, but renders AEA inactive when conjugated to it. We hypothesize that extending the linker between the ethanolamide moiety and the reporter group will once again allow for processing by the enzyme COX-2.

Fluorescent derivatives of arachidonic acid: Tools for studying the anti-cancer activity of prostaglandins

253rd National Meeting (2017)

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