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ITS » Paper and Presentation » Kimia - S2
Posted by at 07/03/2016 11:28:11  •  1116 Views



Author :
RAHMAYANTI, ARDHANA ( 1412201016 )


Kanker hati termasuk lima jenis kanker utama dan merupakan jenis kanker kedua penyebab kematian dengan 600.000 kasus tiap tahun. Terapi kanker yang ada sampai saat ini masih memiliki kelemahan sehingga dibutuhkan obat yang spesifik untuk menghentikan sel kanker tersebut. Isatin dan turunannya diketahui memiliki aktivitas anti kanker. Isatin sitotoksik terhadap sel kanker leukemia U937 dengan IC50 565 61549M. Gugus pensubtitusi pada posisi C-3 dapat mempengaruhi bioaktivitas isatin seperti yang dijumpai alkaloida konvolutamidina A dan konvolutamidina B yang masing-masing aktif menghambat sel kanker leukemia HL-60 dengan IC50 01-25 dan 12-25 61549gmL. Gugus pensubtitusi pada C-5-nya mempengaruhi bioaktivitas isatin sebagai contoh 5-nitroisatin memiliki aktivitas anti kanker leukemia U937 yang lebih baik IC50 132 61549M dari pada isatin IC50 565 956M. Gugus nitro dapat juga menurunkan sitotoksisitas sebagaimana 3-hidroksi-5-nitro-3-1H-indol-3- ilindolin-2-ona mempunyai IC50 195 61549M terhadap sel kanker kolon WiDr sedangkan 3-hidroksi-3-1H-indol-3-ilindolin-2-ona dengan IC50 37 61549M. 11- Nitro-6-demetoksiakronisina memiliki aktivitas terhadap sel kanker leukemia L1210 yang lebih baik dari pada 11-amino-6-demetoksiakronisina sedangkan dimetoksi-1-nitro-5-2-NN-dimetilamino-etil-5H-dibenzoch16naftiridin-6- ona memiliki aktivitas terhadap terhadap sel kanker leukemia RPMI 8402 yang tidak lebih baik dari pada 1-amino-dimetoksi-5-2-NN-dimetilamino-etil-5Hdibenzo ch16naftiridin-6-ona. Gugus metil pada atom nitrogen unit isatin dapat pula mempengaruhi bioaktivitas sebagaimana halnya N-metilisatin IC50 238 956M yang lebih poten dari pada isatin IC50 565 956M tetapi gugus N-metil pada kerangka E-metil-3-N-metil-23-dioxo-23-dihidro-1H-inden-5-ilakrilata memiliki bioaktivitas terhadap sel kanker leukemia K562 yang tidak lebih baik dari pada E-metil-323-dihidro-1H-inden-5ilakrilata dengan IC50 masingmasing 03461617009 dan 02261617009 61549M. Penelitian yang telah dilakukan telah berhasil mensintesis turunan isatin baru 3-hidroksi-3-1H-pirol-2-ilindolin-2- ona 3-hidroksi-5-nitro-3-1H-pirol-2-ilindolin-2-ona 3-hidroksi-N-metil-5-nitro- 3-1H-pirol-2-ilindolin-2-ona dan 5-amino-3-hidroksi-3-1H-pirol-2-ilindolin- 2-ona masing-masing dengan rendemen 47 50 63 dan 47 . Uji sitotoksisitas mendapatkan bahwa 3-hidroksi-5-nitro-3-1H-pirol-2ilindolin-2-ona sitotoksik terhadap sel kanker hati HepG2 dengan IC50 468 956M sedangkan 3-hidroksi-3- 1H-pirol-2ilindolin-2-ona 3-hidroksi-N-metil-5-nitro-3-1H-pirol-2ilindolin-2- ona dan 5-amino-3-hidroksi-3-1H-pirol-2ilindolin-2-ona kurang sitotoksik terhadap sel kanker hati HepG2 dengan IC50 masing-masing 10332 1330 dan 4636 956Mml. Gugus pensubtitusi nitro maupun gugus amino pada C-5 unit isatin dapat meningkatkan sitotoksisitas senyawa sedangkan adanya gugus N-metil dapat menurunkan sitotoksisitas senyawa terhadap sel kanker hati HepG2.


Liver cancer is the fifth most common cancer worldwide and the second cause of cancer death with 600000 cases each year. Cancer therapies that exist until this day still has disadvantage so it needs a specific drug to stop the cancer cells . Isatin and its derivatives are known to have anti-cancer activity. Isatin has cytotoxicity on leukemic cancer cells U937 with IC50 565 61549M. subtituent group at C-3 isatin affect its bioactivity convolutamidine A and convolutamidine B can inhibite leukemic cancer cell HL-60 with IC50 01-25 and 12-25 61549gmL respectively. Subtituent group at C-5 in 5-nitroisatin also affect the bioactivity to leukemic cancer cells U937 such as 5-nitroisatin with IC50 132 61549M. It is known to have anti-cancer activity better than the isatin. Nitro groups can also decrease the cytotoxicity as the 3-hydroxy-5-nitro-3-1H-indole-3-ylindoline-2-one that have IC50 195 61549M to colon cancer cells WiDr while the 3-hydroxy-3-1H-indole-3- ylindoline-2-one have IC50 37 61549M. 11-nitro-6-demetoksiakronisina has activity against leukemia cancer cells L1210 better than the 11-amino-6- demethoxyacronisina whereas compounds with aromatic amine group 1-amino- 89-dimethoxy-5-2-NN-dimethylamino-ethyl-5Hdibenzo ch16napthyridin-6-one has better activity to leukemia cancer cell RPMI 8402 than aromatic nitro group 89-dimethoxy-1-nitro-5-2-NNdimethylamino- ethyl-5H-dibenzoch16napthyridin-6one. N-methyl at isatin also affect bioactivity for example N-methylisatin IC50 238 956M is more potential than isatin IC50565 956M as anti-cancer but E-methyl 3-N-methyl- 23-dioxoindolin-5ylacrylate has worse bioactivity than E-methyl 3-23- dioxoindolin-5ylacrylate with IC50 03461617009 and 02261617009 61549M respectively. Research has been done succefully synthesize novel isatin derivatives 3-hydroxy- 3-1H-pyrrol-2-ylindolin-2-one 3-hydroxy-5-nitro-3-1H-pyrrol-2-ylindolin-2- one 3-hydroxy-N-methyl-5-nitro -3-1H-pyrrol-2-ylindolin-2-one and 5-amino- 3- hydroxy-3-1H-pyrro-2-ylindolin- 2-one obtained with yield 47 50 63 and 47 respectively. Cytotoxicity test found that 3-hydroxy-5-nitro-3-1H-pyrrol-2- ylindolin-2-one citotoxic to liver cancer cell HepG2 with IC50 468 956M whereas 3-hydroxy-3-1H-pyrrol-2-ylindolin-2-one 3-hydroxy-N-methyl-5-nitro -3-1Hpyrrol- 2-ylindolin-2-one and 5-amino-3- hydroxy-3-1H-pyrro-2-ylindolin- 2- one less cytotoxic with IC50 10332 1330 and 4636 956M respectively. Nitro and amino group substituen at C-5 unit isatin can enhance the cytotoxicity whereas the presence of N-methyl group can lower cytotoxicity to liver cancer cells HepG2.

Keywordssintesis, turunan isatin, pirola, sitotoksik, sel kanker hati HepG2
Subject:  Kanker
  1. Prof. Mardi Santoso, Ph.D.
Date Create: 07/03/2016
Type: Text
Format: PDF
Language: Indonesian
Identifier: ITS-paper-14121150008626
Collection ID: 14121150008626
Call Number: RTKi 615.907 Rah s

Paper And Presentation Of Chemistry RTKi 615.907 Rah s, 2016

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