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Synthesis, DNA-binding and antiproliferative activity of N-(Nitrogen heterocyclic) norcantharidin acylamide acid

100%

Zhu W.-Z., Hu R.-D., Lin Q.-Y., Wang X.-X., Zheng X.-L.

Open Chemistry

2009

vol. 7

issue 3

569-575

Two novel norcantharidin acylamide acids (HL1=N-pyrimidine norcantharidin acylamide acid, C12H13N3O4; HL2=N-pyridine norcantharidin acylamide acid, C13H14N2O4) were synthesized by a reaction of norcantharidin(NCTD) with 2-aminopyrimidine and 2-aminopyridine, respectively. Their structures were characterized by elemental analysis, IR, UV and 1 H NMR. Fluorescence titration and viscosity measurements indicated that HL1, HL2 and HL3 (HL3=N-phenyl norcantharidin acylamide acid, C14H15NO4) can bind calf thymus DNA via partial intercalation. The liner Stern-Volmer quenching constant Ksv values for HL1, HL2 and HL3 were 2.05 × 104 L mol−1, 1.15 × 104 L mol−1 and 8.30×103 L mol−1, respectively. Two compounds containing heterocycle of HL1 and HL2 have been found to cleave pBR322 plasmid DNA at physiological pH and temperature. The test of antiproliferation activity showed that the compounds had moderate to strong antiproliferative ability against the tested cell lines except of HL3 against the SMMC7721 cell line. The results indicated that the heterocycle attached to the norcantharidin was favorable to antiproliferative activity. This result was consistent with the DNA binding experiment. [...]

Effect of extraction conditions of paprika oleoresins on their free radical scavenging and anticancer activity

100%

Šaponjac V., Četojević-Simin D., Ćetković G., Čanadanović-Brunet J., Djilas S., Mandić A., Tepić A.

Open Chemistry

2014

vol. 12

issue 3

377-385

Ground spice paprika was extracted with hexane, by conventional Soxhlet procedure (SX oleoresin), and with supercritical carbon dioxide at three different pressures - 20, 30 and 40 MPa (SF20, SF30 and SF40 oleoresins). The effect of extraction method and conditions on the colour intesity of paprika oleoresins, content of α-tocopherol, as well as antioxidant and antiproliferative activity was examined. Hexane showed highest selectivity for paprika pigments (886.02 ASTA), while α-tocopherol showed highest solubility (3846.9 mg kg−1) in supercritical carbon dioxide at 20 MPa. All paprika oleoresins exhibited good superoxide anion radical scavenging activity SF30 being the best superoxide anion radical scavenger. Cell growth activity was evaluated in vitro in human cell lines:cervix epitheloid carcinoma (HeLa), breast adenocarcinoma (MCF7) and colon adenocarcinoma (HT-29). The highest antiproliferative activity was exhibited by SX in MCF7 cell line (IC50=14.28 mg mL−1). Extract SF40 produced significant and selective antiproliferative action towards HeLa cell line. These results suggest that paprika oleoresins, due to high antiradical and tumor cell-inhibiting activity, can be regarded as functional food ingredients.

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2 Open Chemistry

1 2014

1 2009

1 Djilas S.

1 Hu R.-D.

1 Lin Q.-Y.

1 Mandić A.

1 Tepić A.

1 Wang X.-X.

1 Zheng X.-L.

1 Zhu W.-Z.

1 Ćetković G.

1 Čanadanović-Brunet J.

1 Četojević-Simin D.

1 Šaponjac V.

Search results

Synthesis, DNA-binding and antiproliferative activity of N-(Nitrogen heterocyclic) norcantharidin acylamide acid

Effect of extraction conditions of paprika oleoresins on their free radical scavenging and anticancer activity