Evaluation of the biological potencies of newly synthesized berberine derivatives bearing benzothiazole moieties with substituted functionalities
Benzothiazole moieties substituted with various functional groups were utilized to link with the isoquinoline alkaloid berberine through a pentyl side chain. Entitled analogs were screened for antioxidant potency using the DPPH and ABTS bioassays and for their in vitro anticancer activities against...
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| Format: | Article |
| Language: | English |
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Elsevier
2017-02-01
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| Series: | Journal of Saudi Chemical Society |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1319610315001374 |
| _version_ | 1828727898699202560 |
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| author | Bhupendra Mistry Rahul V. Patel Young-Soo Keum Doo Hwan Kim |
| author_facet | Bhupendra Mistry Rahul V. Patel Young-Soo Keum Doo Hwan Kim |
| author_sort | Bhupendra Mistry |
| collection | DOAJ |
| description | Benzothiazole moieties substituted with various functional groups were utilized to link with the isoquinoline alkaloid berberine through a pentyl side chain. Entitled analogs were screened for antioxidant potency using the DPPH and ABTS bioassays and for their in vitro anticancer activities against HeLa, CaSki (cervical cancer), and SK-OV-3 (ovarian cancer) cell lines using the SRB bioassay. The compounds were evaluated for their toxicity to the Madin–Darby canine kidney (MDCK) cell line. The final compounds demonstrated significant antioxidant potency with IC50 levels of 13.03–24.50 μg/mL and 4.958–7.570 μg/mL in the DPPH and ABTS radical scavenging bioassays, respectively. The 5e analog with a methoxy functional group and the 5m analog with a cyano functional group had the most significant DPPH and ABTS radical scavenging activities, respectively. Moreover, the 5m cyano-based analog had the highest potency against all cancer cell lines, with IC50 levels of 5.474, 5.311, and 32.61 μg/mL against the HeLa, CaSki, and SK-OV-3 cell lines, respectively. All the synthesized compounds were characterized by IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. |
| first_indexed | 2024-04-12T14:05:45Z |
| format | Article |
| id | doaj.art-a7721ea4eef54a2c931613fcb2f3b38f |
| institution | Directory Open Access Journal |
| issn | 1319-6103 |
| language | English |
| last_indexed | 2024-04-12T14:05:45Z |
| publishDate | 2017-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Saudi Chemical Society |
| spelling | doaj.art-a7721ea4eef54a2c931613fcb2f3b38f2022-12-22T03:30:05ZengElsevierJournal of Saudi Chemical Society1319-61032017-02-0121221021910.1016/j.jscs.2015.11.002Evaluation of the biological potencies of newly synthesized berberine derivatives bearing benzothiazole moieties with substituted functionalitiesBhupendra Mistry0Rahul V. Patel1Young-Soo Keum2Doo Hwan Kim3Organic Research Laboratory, Department of Bioresources and Food Science, College of Life and Environmental Sciences, Konkuk University, Seoul, Republic of KoreaDepartment of Food Science and Biotechnology, Dongguk University, Biomedical Campus, 32 Dongguk-ro, Ilsandong-gu, Goyang-si, Gyenggi-do, Republic of KoreaOrganic Research Laboratory, Department of Bioresources and Food Science, College of Life and Environmental Sciences, Konkuk University, Seoul, Republic of KoreaOrganic Research Laboratory, Department of Bioresources and Food Science, College of Life and Environmental Sciences, Konkuk University, Seoul, Republic of KoreaBenzothiazole moieties substituted with various functional groups were utilized to link with the isoquinoline alkaloid berberine through a pentyl side chain. Entitled analogs were screened for antioxidant potency using the DPPH and ABTS bioassays and for their in vitro anticancer activities against HeLa, CaSki (cervical cancer), and SK-OV-3 (ovarian cancer) cell lines using the SRB bioassay. The compounds were evaluated for their toxicity to the Madin–Darby canine kidney (MDCK) cell line. The final compounds demonstrated significant antioxidant potency with IC50 levels of 13.03–24.50 μg/mL and 4.958–7.570 μg/mL in the DPPH and ABTS radical scavenging bioassays, respectively. The 5e analog with a methoxy functional group and the 5m analog with a cyano functional group had the most significant DPPH and ABTS radical scavenging activities, respectively. Moreover, the 5m cyano-based analog had the highest potency against all cancer cell lines, with IC50 levels of 5.474, 5.311, and 32.61 μg/mL against the HeLa, CaSki, and SK-OV-3 cell lines, respectively. All the synthesized compounds were characterized by IR, 1H NMR, 13C NMR spectroscopy and elemental analysis.http://www.sciencedirect.com/science/article/pii/S1319610315001374BerberineBenzothiazoleAntioxidantCervical cancerOvarian cancer |
| spellingShingle | Bhupendra Mistry Rahul V. Patel Young-Soo Keum Doo Hwan Kim Evaluation of the biological potencies of newly synthesized berberine derivatives bearing benzothiazole moieties with substituted functionalities Journal of Saudi Chemical Society Berberine Benzothiazole Antioxidant Cervical cancer Ovarian cancer |
| title | Evaluation of the biological potencies of newly synthesized berberine derivatives bearing benzothiazole moieties with substituted functionalities |
| title_full | Evaluation of the biological potencies of newly synthesized berberine derivatives bearing benzothiazole moieties with substituted functionalities |
| title_fullStr | Evaluation of the biological potencies of newly synthesized berberine derivatives bearing benzothiazole moieties with substituted functionalities |
| title_full_unstemmed | Evaluation of the biological potencies of newly synthesized berberine derivatives bearing benzothiazole moieties with substituted functionalities |
| title_short | Evaluation of the biological potencies of newly synthesized berberine derivatives bearing benzothiazole moieties with substituted functionalities |
| title_sort | evaluation of the biological potencies of newly synthesized berberine derivatives bearing benzothiazole moieties with substituted functionalities |
| topic | Berberine Benzothiazole Antioxidant Cervical cancer Ovarian cancer |
| url | http://www.sciencedirect.com/science/article/pii/S1319610315001374 |
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