Sintesis dan Penambatan Molekul Senyawa Analog Kurkumin Monoketon Berbahan Dasar Sinamaldehida dan 1-Metil-4-piperidon serta Uji Sitotoksisitas terhadap Sel Kanker Payudara MCF-7

WULAN AZIZAH MIFTAHUL JANAH, Dr. Endang Astuti, M.Si.; Sugeng Triono,S.Si., M.Si.

2025 | Skripsi | KIMIA

Penelitian sintesis dan penambatan molekul senyawa analog kurkumin monoketon berbahan dasar sinamaldehida dan 1-metil-4-piperidon serta uji sitotoksisitas terhadap sel kanker payudara MCF-7 telah berhasil dilakukan. Tahapan pertama penelitian ini adalah sintesis senyawa analog kurkumin monoketon secara eksperimental. Elusidasi struktur senyawa hasil sintesis dilakukan menggunakan ATR-IR, 1H-NMR, dan 13C-NMR. Pada penelitian ini dilakukan penambatan molekul menggunakan AutodockVina terhadap senyawa analog kurkumin monoketon dan kurkumin untuk memprediksi peran regulasinya terhadap 3 protein target yaitu Era, PI3K, dan Bcl-2. Uji aktivitas antikanker senyawa analog kurkumin dilakukan secara in vitro terhadap sel kanker payudara MCF-7 melalui metode MTT.

Sintesis senyawa analog dilakukan dengan mereaksikan sinamaldehida dengan 1-metil-4-piperidon melalui reaksi kondensasi Claisen-Schmidt. Produk yang dihasilkan berupa padatan berwarna kuning dengan persen hasil sebesar 60,14%. Hasil penambatan molekul menunjukkan nilai afinitas ikatan senyawa analog kurkumin dengan protein Era, Bcl-2, dan PI3K secara berturut-turut adalah -8,2; -9,4; dan -7,7 kkal/mol, sedangkan nilai afinitas ikatan senyawa kurkumin dengan protein Era, PI3K, dan Bcl-2 yaitu -7,8 kkal/mol. Pengujian aktivitas antikanker senyawa analog kurkumin monoketon terhadap sel kanker payudara MCF-7 menghasilkan nilai IC50 sebesar 906,93  mg/mL, yang dikategorikan tidak toksik atau kurang potensial untuk dijadikan senyawa antikanker.

The experiment of synthesis and molecular docking of monoketone curcumin analog compound from cinnamaldehyde and 1-methyl-4-piperidone and cytotoxicity assay against MCF-7 breast cancer cell had been carried out. The first step of this study involved the experimental synthesis of monoketone curcumin analog. The product was elucidated using ATR-IR, 1H-NMR, and 13C-NMR. In this study, molecular docking of curcumin analog compound and curcumin was carried out to predict their regulatory role against three target proteins, namely Era, PI3K, and Bcl-2. The in vitro cytotoxicity test of curcumin analog was performed against MCF-7 breast cancer cell using MTT method.

The curcumin analog was obtained by reacting cinnamaldehyde and 1-methyl-4-piperidone via Claisen-Schmidt condensation reaction and was produced in 60,14% yields. The results of molecular docking showed that the binding affinity of curcumin analog compound to Era, Bcl-2, and PI3K were -8,2; -9,4; dan -7,7 kcal/mol, respectively. Meanwhile, the binding affinity values of curcumin with the proteins Era, PI3K, and Bcl-2 were -7.8 kcal/mol. Testing the anticancer activity of curcumin analog compound against MCF-7 showed inactive activity or less potents to be considered as an anticancer compound with an IC50 of 906,93 mg/mL.

Kata Kunci : Analog kurkumin, antikanker, MCF-7, penambatan molekul, sinamaldehida