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Synthesis of Avicequinone C and Derivatives Towards the Study of 5α-Reductase Inhibitory Activity

Undergraduate #158
Discipline: Chemistry and Chemical Sciences
Subcategory: Chemistry (not Biochemistry)

Angelica Faith Mack - Howard University


Androgenetic alopecia (AGA) is a class of scalp hair loss. It is caused by the overproduction of androgen 5α- dihydrotestoterone (5α-DHT), a more potent form of testosterone (T) converted by 5α- reductase enzyme (5α-R). Clinical studies have demonstrated that inhibition of 5α-R results in decreased concentrations of 5α-DHT with a concomitant increase in scalp hair. Thus, identifying enzymatic reaction inhibitors is the possible key for AGA treatment. Many synthetic drugs that are currently used to treat AGA have several side effects and lack efficiency. Additionally, although clinical studies have illustrated that particular drugs can improve scalp hair growth in male androgenic alopecia associated with reductions in scalp DHT content, they do not show the same effects for postmenopausal women with female pattern hair loss (FPHL) (2). Therefore, the aim of this research is to synthesize and characterize inhibitors of 5α-R that have a higher efficacy and lower cytotoxicity than those currently in use to treat AGA. Avicequinone C is a drug that has exhibited 5αreductase type 1 inhibitory activity, illustrating reduction of DHT production by 52% (1). Proven effective by human hair dermal papilla cell (HHDPC) based assays, we hypothesize that its derivatives will show comparable results based on scientific ciphering and observations, and further HHDPCs studies. In experimentation, Avicequinone C and its derivatives were examined by molecular docking. Using a human hair dermal papilla cell-based assay, hair cell culture was carried out. The extractions were checked for the presence of T and 5α-DHT by thin layer chromatography (TLC). Simultaneously, three derivatives of Avicequinone C were synthesized and tested for inhibitory activity. Based on TLC results and NMR verification of the compound, the WNK-3, and WNK-4 syntheses were affirmed successful. We concluded from molecular docking studies that Dutasteride, 4-Hydroxycoumarin and Avicequinone C exemplified the best inhibitory activity when reacted with 5α- reductase enzyme type one, while Avicequinone C, WNK-1 and WNK-4 illustrated good inhibitory activity with 5α-reductase enzyme type two. Despite these findings, there is still work to be completed. Currently, there are only ineffective treatments on the market for AGA. Thus, continuous research on more operative treatment for a condition that affects so many is essential. In future work, we intend to repeat column chromatography in order to get complete separation and yield a pure product for WNK-6. Furthermore, other derivatives of Avicequinone C can be docked and tested for 5-α reductase inhibitory activity.

Funder Acknowledgement(s): This research was funded by the National Science Foundation (NSF). I would like to acknowledge Howard University’s Global Education and Awareness Research Undergraduate Program (GEAR-UP) for its help. Funding was provided by the National Science Foundation (NSF)/HBCU-UP grant.

Faculty Advisor: Wiranpat Karnsomwan, and Wanchai DeEknamkul,

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This material is based upon work supported by the National Science Foundation (NSF) under Grant No. DUE-1930047. Any opinions, findings, interpretations, conclusions or recommendations expressed in this material are those of its authors and do not represent the views of the AAAS Board of Directors, the Council of AAAS, AAAS’ membership or the National Science Foundation.

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