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Design, synthesis, and anticancer activity of novel berberine derivatives prepared via CuAAC "click" chemistry as potential anticancer agents.

Jin X, Yan TH, Yan L, Li Q, Wang RL, Hu ZL, Jiang YY, Sun QY, Cao YB - Drug Des Devel Ther (2014)

Bottom Line: The results indicated that most of the compounds displayed notable anticancer activities against the MCF-7 cells compared with berberine.Compound 16 and compound 36 exhibited low cytotoxicity in the HUVEC cell line, with IC50 values of 25.49±3.24 μM and 30.47±3.47 μM.Furthermore, compounds 14, 15, 16, 17, 18, 32, and 36 exhibited much better selectivity than berberine toward the normal cell line HUVEC.

View Article: PubMed Central - PubMed

Affiliation: School of Pharmacy, Second Military Medical University, Shanghai, People's Republic of China ; School of Pharmacy, FuJian University of Traditional Chinese Medicine, Fuzhou, People's Republic of China.

ABSTRACT
A series of novel derivatives of phenyl-substituted berberine triazolyls has been designed and synthesized via copper-catalyzed azide-alkyne cycloaddition click chemistry in an attempt to develop antitumor agents. All of the compounds were evaluated for anticancer activity against a panel of three human cancer cell lines, including MCF-7 (breast), SW-1990 (pancreatic), and SMMC-7721 (liver) and the noncancerous human umbilical vein endothelial cell (HUVEC) cell lines. The results indicated that most of the compounds displayed notable anticancer activities against the MCF-7 cells compared with berberine. Among these derivatives, compound 16 showed the most potent inhibitory activity against the SW-1990 and SMMC-7721 cell lines, with half-maximal inhibitory concentration (IC50) values of 8.54±1.97 μM and 11.87±1.83 μM, respectively. Compound 36 exhibited the most potent inhibitory activity against the MCF-7 cell line, with an IC50 value of 12.57±1.96 μM. Compound 16 and compound 36 exhibited low cytotoxicity in the HUVEC cell line, with IC50 values of 25.49±3.24 μM and 30.47±3.47 μM. Furthermore, compounds 14, 15, 16, 17, 18, 32, and 36 exhibited much better selectivity than berberine toward the normal cell line HUVEC.

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Inhibitory rate (%) of compounds 4–36 against SMMC-7721 cell line at 7.8 μM.Notes: Data are presented as mean ± SD of at last three replicates from three independent experiments. *P<0.05 versus BBR. **P<0.01 versus BBR.Abbreviations: BBR, berberine; Blank, culture medium alone, without compounds; SD, standard deviation; SMMC-7721, human liver carcinoma cell line.
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f4-dddt-8-1047: Inhibitory rate (%) of compounds 4–36 against SMMC-7721 cell line at 7.8 μM.Notes: Data are presented as mean ± SD of at last three replicates from three independent experiments. *P<0.05 versus BBR. **P<0.01 versus BBR.Abbreviations: BBR, berberine; Blank, culture medium alone, without compounds; SD, standard deviation; SMMC-7721, human liver carcinoma cell line.

Mentions: From the IC50 values (Table 1) and percentage inhibition data (Figures 2–4), it is obvious that most of the tested compounds displayed better anticancer activities than that of the reference drug berberine with an IC50 value of 121.91±11.26 μM (MCF-7) and 68.06±7.76 μM (SMMC-7721). However, the activity of berberine against SW-1990 cells was better than that of the derivatives, with an IC50 value of 27.64±3.04 μM. Berberine only exhibited greater than 50% inhibition against SW-1990 cell growth at 62.5 μM. In addition, the tested compounds generally showed a lower effect on noncancer cells (HUVECs) than the reference drug berberine, which had an IC50 value of 18.33±2.31 μM. For example, compounds 4, 14, 15, 17, 18, 26 and 32 against HUVEC cell line had IC50 values of 71.92±9.04, 67.69±8.95, 145.71±19.01, 61.66±6.78, 71.18±9.03, 74.62±9.21 and 65.96±7.26, respectively.


Design, synthesis, and anticancer activity of novel berberine derivatives prepared via CuAAC "click" chemistry as potential anticancer agents.

Jin X, Yan TH, Yan L, Li Q, Wang RL, Hu ZL, Jiang YY, Sun QY, Cao YB - Drug Des Devel Ther (2014)

Inhibitory rate (%) of compounds 4–36 against SMMC-7721 cell line at 7.8 μM.Notes: Data are presented as mean ± SD of at last three replicates from three independent experiments. *P<0.05 versus BBR. **P<0.01 versus BBR.Abbreviations: BBR, berberine; Blank, culture medium alone, without compounds; SD, standard deviation; SMMC-7721, human liver carcinoma cell line.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4128789&req=5

f4-dddt-8-1047: Inhibitory rate (%) of compounds 4–36 against SMMC-7721 cell line at 7.8 μM.Notes: Data are presented as mean ± SD of at last three replicates from three independent experiments. *P<0.05 versus BBR. **P<0.01 versus BBR.Abbreviations: BBR, berberine; Blank, culture medium alone, without compounds; SD, standard deviation; SMMC-7721, human liver carcinoma cell line.
Mentions: From the IC50 values (Table 1) and percentage inhibition data (Figures 2–4), it is obvious that most of the tested compounds displayed better anticancer activities than that of the reference drug berberine with an IC50 value of 121.91±11.26 μM (MCF-7) and 68.06±7.76 μM (SMMC-7721). However, the activity of berberine against SW-1990 cells was better than that of the derivatives, with an IC50 value of 27.64±3.04 μM. Berberine only exhibited greater than 50% inhibition against SW-1990 cell growth at 62.5 μM. In addition, the tested compounds generally showed a lower effect on noncancer cells (HUVECs) than the reference drug berberine, which had an IC50 value of 18.33±2.31 μM. For example, compounds 4, 14, 15, 17, 18, 26 and 32 against HUVEC cell line had IC50 values of 71.92±9.04, 67.69±8.95, 145.71±19.01, 61.66±6.78, 71.18±9.03, 74.62±9.21 and 65.96±7.26, respectively.

Bottom Line: The results indicated that most of the compounds displayed notable anticancer activities against the MCF-7 cells compared with berberine.Compound 16 and compound 36 exhibited low cytotoxicity in the HUVEC cell line, with IC50 values of 25.49±3.24 μM and 30.47±3.47 μM.Furthermore, compounds 14, 15, 16, 17, 18, 32, and 36 exhibited much better selectivity than berberine toward the normal cell line HUVEC.

View Article: PubMed Central - PubMed

Affiliation: School of Pharmacy, Second Military Medical University, Shanghai, People's Republic of China ; School of Pharmacy, FuJian University of Traditional Chinese Medicine, Fuzhou, People's Republic of China.

ABSTRACT
A series of novel derivatives of phenyl-substituted berberine triazolyls has been designed and synthesized via copper-catalyzed azide-alkyne cycloaddition click chemistry in an attempt to develop antitumor agents. All of the compounds were evaluated for anticancer activity against a panel of three human cancer cell lines, including MCF-7 (breast), SW-1990 (pancreatic), and SMMC-7721 (liver) and the noncancerous human umbilical vein endothelial cell (HUVEC) cell lines. The results indicated that most of the compounds displayed notable anticancer activities against the MCF-7 cells compared with berberine. Among these derivatives, compound 16 showed the most potent inhibitory activity against the SW-1990 and SMMC-7721 cell lines, with half-maximal inhibitory concentration (IC50) values of 8.54±1.97 μM and 11.87±1.83 μM, respectively. Compound 36 exhibited the most potent inhibitory activity against the MCF-7 cell line, with an IC50 value of 12.57±1.96 μM. Compound 16 and compound 36 exhibited low cytotoxicity in the HUVEC cell line, with IC50 values of 25.49±3.24 μM and 30.47±3.47 μM. Furthermore, compounds 14, 15, 16, 17, 18, 32, and 36 exhibited much better selectivity than berberine toward the normal cell line HUVEC.

Show MeSH
Related in: MedlinePlus