SYNTHESIS AND CYTOTOXIC ACTIVITY OF CHALCONE DERIVATIVES ON HUMAN BREAST CANCER CELL LINES
Chalcone, an α,β-unsaturated ketone, has been shown have many biological activities such as anticancer and antifungi. This research was conducted to synthesize the chalcone derivatives and to obtain their cytotoxic activity on human cervix cancer cell lines. Synthesis of chalcone and its derivatives...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Department of Chemistry, Universitas Gadjah Mada
2012-12-01
|
| Series: | Indonesian Journal of Chemistry |
| Subjects: | |
| Online Access: | https://jurnal.ugm.ac.id/ijc/article/view/21340 |
| _version_ | 1818924957200023552 |
|---|---|
| author | Nuraini Harmastuti Rina Herowati Dyah Susilowati Harno Dwi Pranowo Sofia Mubarika |
| author_facet | Nuraini Harmastuti Rina Herowati Dyah Susilowati Harno Dwi Pranowo Sofia Mubarika |
| author_sort | Nuraini Harmastuti |
| collection | DOAJ |
| description | Chalcone, an α,β-unsaturated ketone, has been shown have many biological activities such as anticancer and antifungi. This research was conducted to synthesize the chalcone derivatives and to obtain their cytotoxic activity on human cervix cancer cell lines. Synthesis of chalcone and its derivatives, 4II-methylchalcone, 4II-methoxychalcone, and 3II,4II-dichlorochalcone was carried out using starting materials of benzaldehide and acetofenon, p-methylacetophenone, p-methoxyacetophenone, as well as m,p-dichloroacetophenone through Claisen Schmidt condensation catalized by NaOH in ethanol at 15 °C. The purity of synthesized compounds were analyzed by thin layer chromatography, melting range, and gas chromatography. Structure elucidations were conducted by UV spectrophotometer, IR spectrometer, 1H-NMR spectrometer, as well as mass spectrometer. Cytotoxic activities were determined by 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) microculture tetrazolium viability assay. The results showed that chalcone and derivatives compounds have been able to be synthesized and purified and had the same structure as a predicted structure. Chalcone had highest cytotoxic activity compared to that of its derivatives, with the IC50 values of chalcone, 4II-methylchalcone, 4II-methoxychalcone, and 3II,4II-dichlorochalcone were 9.49, 14.79, 11.48, and 24.26 µg/mL respectively. It was concluded that methyl, methoxy as well as chlorine substitution at 3 II and 4II position decrease the cytotoxic activity of chalcone. |
| first_indexed | 2024-12-20T02:33:35Z |
| format | Article |
| id | doaj.art-a104f228c6994803bd119db50f770859 |
| institution | Directory Open Access Journal |
| issn | 1411-9420 2460-1578 |
| language | English |
| last_indexed | 2024-12-20T02:33:35Z |
| publishDate | 2012-12-01 |
| publisher | Department of Chemistry, Universitas Gadjah Mada |
| record_format | Article |
| series | Indonesian Journal of Chemistry |
| spelling | doaj.art-a104f228c6994803bd119db50f7708592022-12-21T19:56:30ZengDepartment of Chemistry, Universitas Gadjah MadaIndonesian Journal of Chemistry1411-94202460-15782012-12-0112326126710.22146/ijc.2134014438SYNTHESIS AND CYTOTOXIC ACTIVITY OF CHALCONE DERIVATIVES ON HUMAN BREAST CANCER CELL LINESNuraini Harmastuti0Rina Herowati1Dyah Susilowati2Harno Dwi Pranowo3Sofia Mubarika4Faculty of Pharmacy, Universitas Setia Budi, Jl. Letjen Sutoyo, Surakarta 57127Faculty of Pharmacy, Universitas Setia Budi, Jl. Letjen Sutoyo, Surakarta 57127Faculty of Pharmacy, Universitas Setia Budi, Jl. Letjen Sutoyo, Surakarta 57127Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Jl. Sekip Utara, Yogyakarta 55281Faculty of Medicine, Universitas Gadjah Mada, Jl. Farmako, Sekip Utara, Yogjakarta 55281Chalcone, an α,β-unsaturated ketone, has been shown have many biological activities such as anticancer and antifungi. This research was conducted to synthesize the chalcone derivatives and to obtain their cytotoxic activity on human cervix cancer cell lines. Synthesis of chalcone and its derivatives, 4II-methylchalcone, 4II-methoxychalcone, and 3II,4II-dichlorochalcone was carried out using starting materials of benzaldehide and acetofenon, p-methylacetophenone, p-methoxyacetophenone, as well as m,p-dichloroacetophenone through Claisen Schmidt condensation catalized by NaOH in ethanol at 15 °C. The purity of synthesized compounds were analyzed by thin layer chromatography, melting range, and gas chromatography. Structure elucidations were conducted by UV spectrophotometer, IR spectrometer, 1H-NMR spectrometer, as well as mass spectrometer. Cytotoxic activities were determined by 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) microculture tetrazolium viability assay. The results showed that chalcone and derivatives compounds have been able to be synthesized and purified and had the same structure as a predicted structure. Chalcone had highest cytotoxic activity compared to that of its derivatives, with the IC50 values of chalcone, 4II-methylchalcone, 4II-methoxychalcone, and 3II,4II-dichlorochalcone were 9.49, 14.79, 11.48, and 24.26 µg/mL respectively. It was concluded that methyl, methoxy as well as chlorine substitution at 3 II and 4II position decrease the cytotoxic activity of chalcone.https://jurnal.ugm.ac.id/ijc/article/view/21340chalcone derivativessynthesisMTTcytotoxicHeLa cell lines |
| spellingShingle | Nuraini Harmastuti Rina Herowati Dyah Susilowati Harno Dwi Pranowo Sofia Mubarika SYNTHESIS AND CYTOTOXIC ACTIVITY OF CHALCONE DERIVATIVES ON HUMAN BREAST CANCER CELL LINES Indonesian Journal of Chemistry chalcone derivatives synthesis MTT cytotoxic HeLa cell lines |
| title | SYNTHESIS AND CYTOTOXIC ACTIVITY OF CHALCONE DERIVATIVES ON HUMAN BREAST CANCER CELL LINES |
| title_full | SYNTHESIS AND CYTOTOXIC ACTIVITY OF CHALCONE DERIVATIVES ON HUMAN BREAST CANCER CELL LINES |
| title_fullStr | SYNTHESIS AND CYTOTOXIC ACTIVITY OF CHALCONE DERIVATIVES ON HUMAN BREAST CANCER CELL LINES |
| title_full_unstemmed | SYNTHESIS AND CYTOTOXIC ACTIVITY OF CHALCONE DERIVATIVES ON HUMAN BREAST CANCER CELL LINES |
| title_short | SYNTHESIS AND CYTOTOXIC ACTIVITY OF CHALCONE DERIVATIVES ON HUMAN BREAST CANCER CELL LINES |
| title_sort | synthesis and cytotoxic activity of chalcone derivatives on human breast cancer cell lines |
| topic | chalcone derivatives synthesis MTT cytotoxic HeLa cell lines |
| url | https://jurnal.ugm.ac.id/ijc/article/view/21340 |
| work_keys_str_mv | AT nurainiharmastuti synthesisandcytotoxicactivityofchalconederivativesonhumanbreastcancercelllines AT rinaherowati synthesisandcytotoxicactivityofchalconederivativesonhumanbreastcancercelllines AT dyahsusilowati synthesisandcytotoxicactivityofchalconederivativesonhumanbreastcancercelllines AT harnodwipranowo synthesisandcytotoxicactivityofchalconederivativesonhumanbreastcancercelllines AT sofiamubarika synthesisandcytotoxicactivityofchalconederivativesonhumanbreastcancercelllines |