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"Pendahuluan: Asam galat adalah salah satu senyawa aktif yang dapat menyebabkan apoptosis pada sel kanker paru manusia. Aktivitas antikanker paru yang mengesankan dari asam galat mendorong dilakukannya penelitian untuk menguji aktivitas sitotoksik senyawa turunan asam galat (alkil amida galat) terhadap sel kanker paru A549. Metode: Enam senyawa alkil amida galat hasil sintesis, yaitu Senyawa metil amida galat, etil amida galat, butil amida galat, sek-butil amida galat, ters-butil amida galat, dan heksil amida galat diuji aktivitas sitotoksiknya terhadap sel kanker paru A549 dengan metode MTT Proliferation assay. Data yang dihasilkan dianalisa menggunakan analisis regresi linear untuk mendapatkan nilai IC50. Hasil uji aktivitas sitotoksik senyawa alkil amida galat hasil sintesis dibandingkan dengan hasil uji aktivitas sitotoksik asam galat sebagai senyawa asli dan doxorubicin selaku kontrol positif. Hasil: Jika dibandingkan dengan asam galat (IC50: 23.2 μM) dan doxorubicin (IC50: 31.1 μM), keenam senyawa alkil amida galat, yaitu metil amida galat, etil amida galat, butil amida galat, sek-butil amida galat, ters-butil amida galat, dan heksil amida galat memperlihatkan sitotoksisitas yang lebih kuat terhadap sel kanker paru A549 dengan nilai IC50 berkisar dari 5.4 μM hingga 30.0 μM. Kesimpulan: Enam senyawa alkil amida galat berpotensi dikembangkan lebih lanjut sebagai agen antikanker paru.

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Objective: Gallic acid has shown its potential to induce apoptosis in lung cancer cells. Its impressive anti-lung cancer agent prompted us to conduct research that is aimed to evaluate six alkyl amide derivatives of gallic acid against lung cancer A549 cells.

Methods: six synthesized compounds of alkyl amide gallate, which are methyl amide gallate, ethyl amide gallate, butyl amide gallate, sec-butyl gallate, ters-butyl gallate and hexyl amide gallate, will be evaluated their cytotoxicities agains lung A549 cells by MTT Proliferation assay. Linear regression analysis is used to analyzed the data to generate IC50 value. Cytotoxicity results of alkyl amide gallates will be compared with cytotoxicity result of gallic acid as an original compound and with doxorubicin as positive control.

Results: Compared with gallic acid (IC50 23.2 μM) and doxorubicin (IC50 31.1 μM), six derivatives of aklyl amide gallates (methyl-, butyl-, sec-butyl-, ters- butyl, and hexyl amide gallate) shows better cytotoxic activity against lung A549 cells, with IC50 value range from 5.4 μM to 30.0 μM.

Conclusion: Six compounds of Alkyl amide gallate could be further developed as anti-lung cancer agent."

"Asam galat adalah senyawa yang memiliki efek anti kanker termasuk pada kanker paru. Diduga, efektivitas asam galat sebagai agen sitotoksik dapat ditingkatkan dengan perubahan gugus samping. Penelitian ini bertujuan untuk menguji aktivitas sitotoksik asam galat dan turunan asam galat (alkil ester galat dan asam metoksi galat). Pada penelitian ini, sel A549 diberikan asam galat dan turunannya lalu diinkubasi selama 48 jam lalu akan diukur persentase viabilitas sel terhadap kontrol menggunakan MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) assay. Data kemudian dianalisis menggunakan GraphPad Prism untuk mendapatkan inhibitory concentration (IC50).Hasil penelitian menunjukkan bahwa asam galat, metil galat, etil galat, propil galat, butil galat, isobutil galat, t-butil galat, dan amil galat tidak memiliki aktivitas sitotoksik. Sedangkan isoamil galat menunjukkan aktivitas sitotoksik namun IC50 dari isoamil galat kemungkinan >51,2 μg/ml. Heptil galat dan oktil galat adalah dua senyawa yang memiliki efek sitotoksik pada sel A549 dengan nilai IC50 <51,2 μg/ml yaitu 19,11 μg/ml dan 41,23 μg/ml secara berurutan. Disimpulkan bahwa heptil galat dan oktil galat memiliki aktivitas sitotoksik yang lebih baik dari asam galat pada sel A549, sedangkan asam metoksi galat tidak memiliki aktivitas sitotoksik pada sel A549.

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Gallic acid is a substance with anti-cancer activity including lung cancer. The potency of gallic acid as a cytotoxic agent can be improved by modifying its side chains. This study was aimed to examine the cytotoxic activity of gallic acid and its derivates in lung cancer cells, A549. In this study, cells were treated with gallic acid and its derivates and were incubated for 48 hour. After incubation period, percentage of cell viability over control were tested using MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulophenyl)-2Htetrazolium) assay. Afterwards, data were analysed using GraphPad Prism to obtain inhibitory concentration (IC50).The result showed gallic acid, methyl gallate, ethyl gallate, propyl gallate, butyl gallate, isobutyl gallate, t-butyl gallate, and amyl gallate did not have cytotoxic activity. Isoamyl gallate showed cytotoxic activity, but the IC50 value was probably >51,2 μg/ml. That gallic acid derivatives with cytotoxic activities and IC50 <51,2 μg/ml were heptyl gallate and octyl gallate with IC50 values of 19,11 μg/ml and 41,23 μg/ml, respectively. However, methoxy gallate (monometohoxy gallate, dimethoxy gallate, and trimethoxy gallate) did not show any cytotoxic activity. We conclude that heptyl gallate and octyl gallate have better cytotoxic activity in A549 cells compared to gallic acid, while methoxy gallates do not have cytotoxic activity in cell A549."

"Latar Belakang: Kanker kolorektal merupakan salah satu kanker dengan prevalensi yang cukup tinggi dan penanganan yang tersedia dapat menyebabkan efek samping buruk. Oleh karena itu, pengobatan alternatif untuk kanker kolorektal perlu dikembangkan. Asam galat telah menunjukkan aksi menghambatan proliferasi sel di berbagai tipe sel kanker termasuk HCT 15 colon cancer cells. Penambahan grup hidrofobik ke asam galat diduga dapat meningkatkan efek anti kanker asam galat. Riset ini dilakukan untuk mengobservasi efek antikanker derivat asam galat, (enam senyawa alkil amida galat hasil sintesis) terhadap sel kolon karsinoma HCT 116. Metode: Menggunakan MTT, enam (6) senyawa alkil amida galat, yaitu: -metil, -etil, -butil, -sek-butil, -ters-butil dan heksil amida galat diuji efek antikankernya terhadap sel HCT 116. Penentuan nilai IC50 dilakukan dengan menggunakan metoda regresi linear untuk analisis data. Hasil uji efek antikanker senyawa turunan alkil amida galat dibandingkan dengan hasil uji efek antikanker asam galat sebagai senyawa awal dan doxorubicin sebagai kontrol positif. Jika dibandingkan dengan asam galat (IC50: 0.05 μg/mL) dan doxorubicin (IC50: 0.001 μg/mL), keenam senyawa turunan alkil amida galat memiliki aktivitas antikanker yang lebih rendah terhadap sel kanker kolon HCT 116. Diantara ke-enam senyawa alkil amida galat hasil sintesis, heksil amida galat dengan IC50 0,07 μg/mL memiliki aktivitas antikanker terbaik. Kesimpulan: Dari hasil studi yang telah dilakukan ini, dapat disimpulkan bahwa heksil amida galat memiliki potensi untuk dikembangkan menjadi agen antikanker kolon.

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Background: Colorectal cancer is one of the most prevalent cancers and its common managements still evoke undesirable side effects. Therefore, there needs to be a development of a safer alternative. Gallic acid has exhibited significant cell proliferation inhibition in a variety of cancer cell lines including HCT 15 colon cancer cells. Addition of hydrophobic groups to gallic acid has been postulated to increase the anti-cancer effects of gallic acid and henceforth this research is conducted to observe the derivatives of gallic acid (six derivative compounds of alkyl amide gallate) on HCT 116 cells. Methods: With the utilization of MTT assay, six synthesized compounds of alkyl amide gallate, namely methyl-, ethyl-, butyl-, sec-butyl-, tert-butyl-, and hexyl amide gallate were measured for their anticancer effect on HCT 116 cells. Determination of IC50 values was carried out by the linear regression method for data analysis. Lastly, results were compared with gallic acid as an original compound and doxorubicin as a positive control. Results: In comparison to gallic acid (IC50: 0.05 μg/mL) and doxorubicin (IC50: 0.001 μg/mL), a lower anticancer effect on colon HCT 116 cells was displayed by all the six- synthesized alkyl amide gallates. Hexyl amide gallate with IC50 value of 0.07 μg/mL shows the strongest anticancer and inhibitory effect on HCT 116 cells. Conclusion: Result of the study indicates that hexyl amide gallate has the potential to undergo further development as a promising anti- colon cancer agent."

"[Asam galat merupakan zat polifenol dengan kemampuan sitotoksik. Studisebelumnya menunjukkan turunan asam galat mampu menghambat pertumbuhansel kanker. Sampai saat ini, belum banyak studi yang mempelajari turunan alkilester galat dan turunan metoksi galat terhadap pertumbuhan kanker kolon. Tujuandari penelitian ini adalah untuk mengetahui aktivitas sitotoksik turunan alkil estergalat dan metoksi galat pada sel kanker kolon. Penelitian ini dilakukan dengandesain eksperimental secara in vitro. Kemampuan sitotoksik asam galat danturunannya diuji pada sel HCT116 (sel kanker kolon) dengan menggunakan MTS(3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2Htetrazolium)assay. Data yang diperoleh dianalisis untuk mendapatkan IC50 setiapsenyawa. Hasil penelitian menunjukkan modifikasi asam galat menjadi senyawametil galat, propil galat, butil galat, t-butil galat, amil galat, oktil galat dan ketigaturunan metoksi galat tidak menunjukkan peningkatan aktivitas sitotoksik denganpeningkatan konsentrasi yang diuji. Dari semua senyawa yang memilikikecenderungan menghambat, heptil galat memiliki aktivitas yang paling baik.Disimpulkan, metil galat, propil galat, butil galat, t-butil galat, amil galat, dan oktilgalat merupakan turunan alkil galat yang tidak aktif. Etil galat, isobutil galat,isoamil galat, dan heptil galat merupakan turunan alkil galat yang memiliki aktivitassitotoksik pada sel kanker kolon. Ketiga tur;Gallic acid is a polyphenol with anticancer activity. Previous studies had shown thatthe derivatives of gallic acid had cytotoxic activity in cancer cell. To date, fewstudies evaluated the activity of alkyl ester derivatives of gallic acid and methoxyderivatives of gallic acid in colon cancer cell. The objective of this study was toexamine the cytotoxic activity of alkyl ester derivatives and methoxy derivatives ofgallic acid in colon cancer cell. This study was conducted in in-vitro study inHCT116 colon cancer cell. Cytotoxic activity of gallic acid and its derivatives wereevaluated in HCT116 colon cancer cell using MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) assay. Data fromthis experiment was analyzed to obtain IC50 of each compound. The result showedthat modification of gallic acid to methyl gallate, propyl gallate, butyl gallat, t-butylgallate, pentyl gallate, octyl gallate and three methoxy derivatives of gallic acid didnot increase cytotoxic activity in all concentrations tested. Among all derivatives ofgallic acid, heptyl gallate has the best cytotoxic activity. In conclusion, methylgallate, propyl gallate, butyl gallate, t-butyl gallate, pentyl gallate, and octyl gallateare alkyl ester derivatives of gallic acid with no cytotoxic activity. Ethyl gallate,isobutyl gallate, isopentyl gallate, and heptyl gallate are active derivatives of gallicacid. All methoxy derivatives of gallic acid do not show any cytotoxic activity incolon cancer cell.;Gallic acid is a polyphenol with anticancer activity. Previous studies had shown thatthe derivatives of gallic acid had cytotoxic activity in cancer cell. To date, fewstudies evaluated the activity of alkyl ester derivatives of gallic acid and methoxyderivatives of gallic acid in colon cancer cell. The objective of this study was toexamine the cytotoxic activity of alkyl ester derivatives and methoxy derivatives ofgallic acid in colon cancer cell. This study was conducted in in-vitro study inHCT116 colon cancer cell. Cytotoxic activity of gallic acid and its derivatives wereevaluated in HCT116 colon cancer cell using MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) assay. Data fromthis experiment was analyzed to obtain IC50 of each compound. The result showedthat modification of gallic acid to methyl gallate, propyl gallate, butyl gallat, t-butylgallate, pentyl gallate, octyl gallate and three methoxy derivatives of gallic acid didnot increase cytotoxic activity in all concentrations tested. Among all derivatives ofgallic acid, heptyl gallate has the best cytotoxic activity. In conclusion, methylgallate, propyl gallate, butyl gallate, t-butyl gallate, pentyl gallate, and octyl gallateare alkyl ester derivatives of gallic acid with no cytotoxic activity. Ethyl gallate,isobutyl gallate, isopentyl gallate, and heptyl gallate are active derivatives of gallicacid. All methoxy derivatives of gallic acid do not show any cytotoxic activity incolon cancer cell., Gallic acid is a polyphenol with anticancer activity. Previous studies had shown thatthe derivatives of gallic acid had cytotoxic activity in cancer cell. To date, fewstudies evaluated the activity of alkyl ester derivatives of gallic acid and methoxyderivatives of gallic acid in colon cancer cell. The objective of this study was toexamine the cytotoxic activity of alkyl ester derivatives and methoxy derivatives ofgallic acid in colon cancer cell. This study was conducted in in-vitro study inHCT116 colon cancer cell. Cytotoxic activity of gallic acid and its derivatives wereevaluated in HCT116 colon cancer cell using MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) assay. Data fromthis experiment was analyzed to obtain IC50 of each compound. The result showedthat modification of gallic acid to methyl gallate, propyl gallate, butyl gallat, t-butylgallate, pentyl gallate, octyl gallate and three methoxy derivatives of gallic acid didnot increase cytotoxic activity in all concentrations tested. Among all derivatives ofgallic acid, heptyl gallate has the best cytotoxic activity. In conclusion, methylgallate, propyl gallate, butyl gallate, t-butyl gallate, pentyl gallate, and octyl gallateare alkyl ester derivatives of gallic acid with no cytotoxic activity. Ethyl gallate,isobutyl gallate, isopentyl gallate, and heptyl gallate are active derivatives of gallicacid. All methoxy derivatives of gallic acid do not show any cytotoxic activity incolon cancer cell.]"

"Asam galat adalah salah satu senyawa yang berpotensi menjadi obat baru bagi kanker. Banyak penelitian yang telah menguji aktivitas asam galat sebagai antikanker, tetapi asam galat bersifat sangat hidrofilik sehingga sulit untuk menembus membran sel. Untuk meningkatkan aktivitas sitotoksisitas dan hidrofobisitas, dibuat senyawa turunan asam galat yaitu alkil galat dan metoksi galat. Aktivitas diuji pada sel MCF-7 menggunakan MTS (3-(4,5-dimethylthiazol- 2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) assay dengan inkubasi selama 48 jam. Aktivitas setiap senyawa ditentukan dengan menggunakan nilai IC50. Dari seluruh senyawa yang diuji, isoamil galat, heptil galat dan oktil galat, merupakan senyawa yang aktif sebagai antikanker MCF-7 dengan nilai IC50 58,11; 25,94 dan 42,34. Berdasarkan ekstrapolasi garis, isobutil galat dan juga dapat menurunkan persentase viabilitas sel, meskipun nilai IC50-nya belum dapat ditentukan dari penelitian ini. Metoksi galat tidak memiliki efek penghambatan pada sel kanker payudara MCF-7. Oleh karena itu, dapat disimpulkan bahwa isobutil, isoamil, heptil dan oktil galat merupakan senyawa turunan asam galat yang memiliki aktivitas sitotoksik sedangkan metoksi galat tidak memiliki aktivitas sitotoksik terhadap MCF-7.

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Gallic acid is a potential chemotherapeutic agent. Many studies have proven the anti cancer activity of gallic acid, including in breast cancer. However, gallic acid is a hydrophilic molecule, which restrict the substance from passing the cell membrane. To increase the potential cytotoxicity and its hydrophobicity, two groups of gallic acid derivatives, alkyl gallates and methoxy gallates, were developed. The activity of these derivatives were tested in MCF-7 cell lines, using MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4- sulfophenyl)-2H-tetrazolium) assay, and then incubated for 48 hours. Percentage of cell viability over control were assessed. Cytotoxic activities of gallic acid and its derivatives were determined using IC50 values. Among all of the gallic acid derivatives, isoamyl gallate, heptyl gallate and octyl gallate were the most potential drugs to treat MCF-7 breast cancer with IC50 values of 58,11; 25,94 and 42,34 μg/ml, respectively. Based on the trendline prediction, isobutyl gallate also showed cytotoxic activity towards MCF-7, although the IC50 values cannot be determined in this research. Methoxy gallates do not have any inhibitory activity towards breast cancer MCF-7. In conclusion, isobutyl, isoamyl, heptyl and octyl gallate are gallic acid derivatives with cytotoxic activity, while methoxy gallates do not have any cytotoxic activity towards MCF-7."

"Kanker serviks merupakan jenis kanker yang paling banyak dialami oleh wanita di Indonesia. Gangguan pada proses apoptosis merupakan tahapan yang penting dalam perkembangan tumor dan menyebabkan sel tumor lebih resisten terhadap terapi sitotoksik konvensional. Protein antiapoptosis Bcl-2 merupakan protein yang berperan penting dalam proses apoptosis yang bisa dijadikan molekul target obat antikanker. Asam galat merupakan senyawa penuntun yang telah terbukti secara in vitro memiliki aktivitas sebagai anti kanker. Penelitian ini bertujuan untuk mendesain, mensintesis dan menguji aktivitas sitotoksik turunan asam galat terhadap sel HeLa. Desain turunan asam galat dilakukan dengan metode structure based drug design untuk mendapatkan senyawa turunan yang menghambat protein anti apoptosis Bcl-2 dengan lebih baik. Lima senyawa turunan asam galat yang memberikan nilai ΔG terkecil dipilih untuk disintesis. Tiga senyawa turunan asam galat disintesis dengan reaksi kondensai dengan alkil halida, sedangkan dua turunan yang lain disintesis dengan reaksi esterifikasi menggunakan katalis DIC dan DMAP. Senyawa hasil sintesis diidentifikasi dengan menggunakan spektrofotometer FT-IR, Spektrometer massa, 1H-NMR dan 13C-NMR. Senyawa hasil sintesis dilakukan uji sitotoksisitas dengan metode MTT. Hasil pengujian sitotoksisitas menunjukkan bahwa tiga turunan ester asam galat memiliki aktivitas penghambatan yang lebih besar pada sel HeLa dibandingkan dengan asam galat dengan IC50 berkisar antara 30,20-34,43 μM.

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Cervical cancer is the most common cancer among women in Indonesia. Impaired apoptosis is a central step in tumor development and renders the tumor cell more resistant to conventional cytotoxic therapy. Proteins Bcl-2, a protein that plays an important role in the process of apoptosis, could be used as an anticancer drugs target molecule. Gallic acid is a lead compound that has been proven have anticancer activity in vitro. The aims of this research are to design, synthesize, and evaluate the cytotoxic activity of gallic acid derivatives in HeLa cells. Gallic acid derivatives is designed by structure-based drug design as anti-apoptotic protein Bcl- 2. Five gallic acid derivatives with the smallest ΔG value are selected for synthesized. Three gallic acid derivatives synthesized by condensation reaction with an alkyl halide, while the other two derivatives were synthesized by esterification reaction using DIC and DMAP catalysts.The synthesized product identified by FT-IR, MS Spectrometer, 1H-NMR and 13C-NMR. Cytotoxicity evaluation are then done by MTT methode. It shows that three derivatives exhibited as a greater anticancer activity against HeLa Cell cells than the lead compound gallic acid with IC50 ranging of 30,20-34,43 μM."

"ABSTRAKKanker payudara adalah kanker kedua terbanyak diderita di dunia, sedangkan di Indonesia kanker payudara menempati peringkat kedua jenis kanker yang paling sering terdiagnosis setelah kanker serviks di Indonesia. Terdapat beberapa pilihan terapi untuk kanker payudara seperti operasi, kemoterapi, dan radiasi yang memiliki efektivitas rendah pada stadium lanjut dan kerap menimbulkan efek samping. Oleh karena itu dibutuhkan pilihan terapi lain dengan efek terapetik yang optimal dan efek samping yang minimal. Salah satu senyawa alami yang berpotensi dikembangkan sebagai antikanker adalah asam galat. Penelitian ini dilakukan untuk mengetahui aktivitas sitotoksik senyawa asam galat dan derivatnya dengan menggunakan 8 variasi konsentrasi, yaitu 0,07; 0,13; 0,27; 0,53; 1,07; 2,13; 4,27 dan 8,53 g/ml pada lini sel kanker payudara T47-D. Dengan metode MTT assay, didapatkan nilai absorbansi dan viabilitas sel yang kemudian diolah dengan menggunakan GraphPad Prism untuk mendapatkan nilai IC50 dari tiap senyawa uji. Hasil menunjukkan alil galat, amil galat, trans-heksinil galat, benzil galat, sekunder amil galat, propil galat, dan isoamil galat memiliki IC50 yang rendah, yaitu 1,25 g/mL, 2,78 g/mL, 3,17 g/mL, 4,82 g/mL, 5,32 g/mL, 7,84 g/mL, dan 8,02 g/mL. Hasil penelitian menunjukkan bahwa modifikasi asam galat melalui penambahan rantai samping alkil ester, penambahan gugus aromatis, dan konfigurasi cis-trans dapat meningkatkan aktivitas sitotoksik senyawa asam galat.

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ABSTRAKBreast cancer is the second most suffered cancer in the world, whereas in Indonesia is the second most suffered after cervix cancer. There are several treatments for breast cancer such as surgery, chemotherapy, and radiation, however these treatments have low effectiveness at advanced stage and often cause side effects. Therefore, there are significant need of treatment with the optimal therapeutic effect and minimal side effects. Gallic acid is a natural compound which could be developed as anticancer agent. This study was conducted to determine the cytotoxic activity of gallic acid and its derivatives by using 8 variety of concentrations, namely 0,07 0,13 0,27 0,53 1,07 2,13 4,27 and 8,53 g ml against breast cancer cell line T47 D. Anticancer activity of the tested samples were evaluated by MTT assay, the absorbance and cell viability values are obtained and processed using GraphPad Prism application to get the IC50 value of each compound. The result showed that allyl gallate, amyl gallate, trans hexynyl gallate, benzyl gallate, sec amyl gallate, propyl gallate, and isoamyl gallate have anticancer activity higher than gallic acid with IC50 value 1,25 g mL, 2,78 g mL, 3,17 g mL, 4,82 g mL, 5,32 g mL, 7,84 g mL, and 8,02 g mL, respectively. It could be concluded that the structure modification of gallic acid through the addition of a side chain alkyl ester, the addition of aromatic groups, and cis trans configuration in gallic acid derivatives could increase its cytotoxic activity."

" ABSTRAKAdenokarsinoma paru merupakan keganasan epitel paru yang paling seringdijumpai baik pada perokok aktif maupun pasif. Seiring bertambah majunyateknologi, sudah ditemukan beberapa terapi untuk adenokarsinoma paru, sepertikemoterapi dan farmakogenetik terhadap gen tertentu. Akan tetapi , efek sampingterapi tersebut cukup besar dan hanya ampuh untuk gen tertentu. Oleh karena itu,diperlukan penelitian baru untuk menemukan alternatif terapi adenokarsinoma paru.Asam galat telah lama dikenal memiliki aktivitas antikanker yang baik. Namun,kadar asam galat yang diperlukan untuk menghambat pertumbuhan sel A549 adenokarsinoma paru masih terhitung besar. Untuk memperbaiki farmakokinetikdan farmakodinamik asam galat, dibuatlah derivat-derivatnya melalui modifikasistruktur, dengan menambahkan gugus alkil ester dan alkil eter pada asam galat.Penelitian ini bertujuan untuk membandingkan dan menemukan IC50 asam galatbeserta derivatnya terhadap sel A549 berbasis konsentrasi. Peneliti menggunakandelapan variasi konsentrasi, berkisar antara 0,26 g/ml hingga 33,33 g/ml. Tiapsumur yang berisi sel A549 diinkubasi bersama asam galat dan derivatnya selama24 jam. Pembacaan absorbansi dilakukan menggunakan MTT assay. Hasilpengolahan data menunjukkan etil galat, isoamil galat, sekunder amil galat, heksilgalat, cis-2-heksenil galat, cis-2-oksi-heksenil galat, dan trans-heksenil galatmemiliki nilai IC50 yang lebih baik dari asam galat. Hasil tersebut menunjukkanbahwa modifikasi gugus karboksil pada asam galat dengan gugus alkil ester rantailurus, rantai bercabang, maupun alkil ester yang memiliki ikatan rangkap berisomergeomeri cis dan trans, dapat memperbaiki sitotoksisitas derivat asam galat terhadapsel adenokarsinoma paru A549.Kata kunci: Derivat asam galat, alkil galat, sel paru A549, sitotoksisitas.

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ABSTRAKLung adenocarcinoma is the most common lung epithelial malignancy found inboth active and passive smoker. Recently, chemotherapy and genetic therapy havebeen widely used to treat the lung cancer. Unfortunately, thechemotherapy has theside effects, and the gene therapy can be used only for certain gene involved in thepathogenesis. These facts indicated that the search for new anti lung cancer agentsis needed. Gallic acid has been known to have anticancer activities. However, ittakes a high concentration of gallic acid to inhibit lung adenocarcinoma A549 cells.Therefore, research and development of the new gallic acid derivatives that showhigher cytotoxicity in lower concentration is required. The purpose of this researchis to compare and to find the IC50 value of gallic acid and its derivatives againstlung A549 cells in eight variety of concentrations, ranging of 0,26 g ml to 33,33 g ml. Each lung A549 cells in well is incubated with gallic acid and its derivativesfor 24 hours. The absorbance was read by using MTT assay. The results showedthat ethyl gallate, isoamyl gallate, secondary amyl gallate, hexyl gallate, cis 2 hexenyl gallate, cis 2 oxy hexenyl gallate, and trans hexenyl gallate show lowerIC50 value than gallic acid. These results suggested Thar structure modification oncarboxyl group of gallic acid withalkyl ester group having linear chain andbranched chain, as well as having the double bond with cis or trans configuration,could improve the cytotoxicities of gallic acid derivatives against lung A549 cells.Keyword alkyl gallate, cytotoxicity, gallic acid derivatives, lung A549 cell."

"Kanker paru merupakan salah satu penyebab terbanyak kematian akibat kanker di Indonesia. Namun, terapi kanker konvensional memiliki kelemahan seperti efek samping terhadap tubuh dan tingginya biaya yang dibutuhkan. Oleh karena itu, studi mengenai pengobatan alternatif kanker menggunakan tumbuhan herbal mulai banyak dilakukan. Bunga rosela merah (Hibiscus sabdariffa) sebagai salah satu tanaman herbal di Indonesia diketahui memiliki aktivitas biologis, namun penelitiannya masih terbatas. Penelitian ini dilakukan untuk mengetahui kandungan fitokimia, aktivitas antioksidan, dan aktivitas sitotoksik bunga rosela merah secara in vitro terhadap sel kanker paru A549. Penelitian eksperimental ini diawali dengan maserasi sampel dalam pelarut etanol, etil asetat, dan n-heksana. Kemudian, dilakukan uji kromatografi lapis tipis dan uji fitokimia untuk mengetahui kandungan metabolit sekundernya. Aktivitas antioksidan dari ekstrak ditentukan dengan metode DPPH, sedangkan aktivitas sitotoksik dari ekstrak terhadap sel kanker paru A549 ditentukan dengan uji MTT assay secara invitro. Hasil uji kromatografi lapis tipis menunjukkan terdapat lima komponen senyawa, sedangkan hasil uji fitokimia memberikan hasil positif untuk flavonoid, tanin, glikosida, alkaloid, triterpenoid, dan steroid. Uji aktivitas antioksidan untuk ekstrak etanol dan etil asetat Hibiscus sabdariffa memberikan nilai IC50 lebih dari 50 g/mL. Sementara itu, uji sitotoksik in vitro ekstrak etanol, etil asetat dan n-heksana Hibiscus sabdariffa terhadap sel kanker paru A549 memberikan nilai IC50 lebih dari 200 g/mL. Kesimpulan dari penelitian ini adalah ekstrak Hibiscus sabdariffa memiliki aktivitas antioksidan yang tergolong lemah hingga moderat, dan menunjukkan aktivitas sitotoksik yang tergolong lemah terhadap sel kanker paru A549, sehingga ekstrak Hibiscus sabdariffa berpotensi untuk dikembangkan sebagai antioksidan dan agen antikanker paru.

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Lung cancer is one of the leading causes of cancer death in Indonesia. Treatment for lung cancer has side effects and requires high cost. Therefore, the study concerning natural anticancer from plants has intensified, in this study focused on Hibiscus sabdariffa. The purpose of this research is to evaluate the phytochemistry composition, antioxidant activity, and cytotoxic activity of Hibiscus sabdariffa extracts against the A549 lung cancer cell line. The research was carried out by macerated the sample with ethanol, ethyl acetate, and n-hexane solvents. The extracts were analyzed using TLC and phytochemistry tests to determine secondary metabolites. The antioxidant activity of the extract was determined using the DPPH method, while the cytotoxic activity of the extract against the A549 lung cancer cells was determined in vitro using the MTT assay. As a result, the TLC analysis revealed that Hibiscus sabdariffa extracts contained five organic compounds, while the phytochemistry tests revealed positive for flavonoids, tannins, glycosides, alkaloids, triterpenes, and steroids. The antioxidant activity test of the ethanol and ethyl acetate extracts showed the IC50 value of more than 50 g/mL. Furthermore, the cytotoxic activity of the ethanol, ethyl acetate, and n-hexane extract against the A549 lung cancer cell line showed the IC50 value of more than 200 g/mL. In conclusion, Hibiscus sabdariffa extracts had the low to moderate antioxidant activity and the weak anticytotoxic activity against the A549 lung cancer cell line, so Hibiscus sabdariffa extracts are potential to be developed as antioxidant and anticancer."

"Asam galat merupakan senyawa polihidroksilfenolik yang mempunyai peran penting dalam berbagai aktivitas selektif terhadap banyak sel line. Desain senyawa dengan modifikasi struktur dan mekanisme aksi dari lead compound asam galat diharapkan dapat meningkatkan aktivitas baik lipofilisitas maupun aksi sitotoksiknya. Penelitian ini bertujuan untuk mendesain dan memodifikasi struktur asam galat, melakukan simulasi docking, mensintesis, serta melakukan uji aktivitas sitotoksik senyawa derivat asam galat terhadap sel line kanker kolon HCT-116. Simulasi docking dilakukan dengan beberapa software adalah is MarvinSketch 15.5.11, Chimera 1.10.2, Autodock 4.2, Pymol 1.7.4.5 dan LigPlot v.1.4.5.; sintesis senyawa derivat asam galat melibatkan beberapa reaksi yaitu esterifikasi, metilasi dan hidrolisis; serta melakukan uji sitotoksik terhadap sel kanker kolon HCT-116. Hasil simulasi docking menghasilkan empat senyawa derivat asam galat dengan nilai binding energy terkecil yaitu benzil galat -7,36 kkal/mol , 2-hidroksi benzil galat -7,63 kkal/mol , 4-metoksi- 2-hidroksi benzil galat -7,18 kkal/mol dan feniletil galat -7,47 kkal/mol . Selanjutnya senyawa derivat asam galat disintesis dan dikarakterisasi menggunakan FT-IR, spektrometer Massa, 1H NMR dan 13C NMR. Sintesis senyawa derivat asam galat menghasilkan rendemen masing-masing adalah 62,11 ; 53,25 ; 51,05 dan 58,87 . Uji sitotoksik keempat senyawa derivat asam galat memiliki aktivitas penghambatan yang baik terhadap sel line kanker kolon HCT-116 dengan nilai IC50 masing-masing adalah 24,79 g/mL; 21,82 g/mL; 26,98 g/mL; dan 19,93 g/mL. Senyawa terbaik yang memberikan aktivitas penghambatan terhadap sel kanker kolon HCT-116 adalah feniletil galat dengan IC50 sebesar 19,93 g/mL.

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Gallic acid is a polyhydroxyphenolic compound that has an important role in a variety of selective activity against many cell line. Design modifications of compounds with structures and mechanisms of action of lead compound gallic acid is expected to increase the activity of both lipophilicity and cytotoxic action. This research aims to design and modify the structure of gallic acid, docking simulation, synthesis, and test the cytotoxic activity of gallic acid derivative compounds against colon cancer cell line HCT 116. Docking simulation perfomed with some software is MarvinSketch 15.5.11, Chimera 1.10.2, Autodock 4.2, Pymol 1.7.4.5 and LigPlot v.1.4.5. Synthesis of compound gallic acid derivatives which involves several reaction that is esterification, methylation and hydrolysis. As well as to test the cytotoxic against colon cancer cell HCT 116. Docking simulation results produced four compounds gallic acid derivatives with a value of binding energy smallest that is benzyl gallate 7.36 kcal mol , 2 hydroxy benzyl gallate 7.63 kcal mol , 4 metoksi 2 hydroxy , benzyl gallate 7.18 kcal mol and phenylethyl gallate 7.47 kcal mol . Further synthesized compound gallic acid derivatives with yield respectively is 62.11 53.25 51.05 and 58.87 . Analysis of compound characterization using FT IR, mass spectrometry, 1H NMR and 13C NMR. Test fourth cytotoxic compound gallic acid derivatives have good inhibitory activity against colon cancer cell line HCT 116 with a value IC50 respectively is 24.79 g mL 21.82 g mL 26.98 g mL and 19.93 g L. Compounds that give the best inhibitory activity against colon cancer cells HCT 116 is phenylethyl gallate with IC50 of 19.93 g mL."