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Investigation of the biological and anti-cancer properties of ellagic acid-encapsulated nano-sized metalla-cages.

Dubey A, Park DW, Kwon JE, Jeong YJ, Kim T, Kim I, Kang SC, Chi KW - Int J Nanomedicine (2015)

Bottom Line: Compounds 9 and 10 showed potent antioxidant activity, but 10 had the superior ORACPE value (1.30 ± 0.020).In a tumoricidal assay, ellagic acid (5) and compound 10 induced cytotoxicity in tumor cells, while doxorubicin did not.While free ellagic acid had no effect on the granulocyte-colony stimulating factor and regulated on activation normal T cell expressed and secreted protein, the encapsulated metalla-prism 10 stimulated granulocyte-colony stimulating factor and reduced regulated on activation normal T cell expressed and secreted protein expression in the RAW264.7 macrophage line.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Ulsan, Ulsan, Republic of Korea.

ABSTRACT
Three new large hexanuclear metalla-prisms 9-11 incorporating 1,3, 5-tris(pyridin-4-ylethynyl)benzene (tpeb) 4 and one of the dinuclear arene ruthenium clips [Ru2(p-iPrC6H4Me)2(OO∩OO)][CF3SO3]2 (OO∩OO =2,5-dioxydo-1,4-benzoquinonato [dobq] 1, 5,8-dihydroxy-1,4-naphthaquinonato (donq) 2, and 6,11-dihydroxy-5,12-naphthacenedionato [dotq] 3), which encapsulate the guest molecule ellagic acid (2,3,7,8-tetrahydroxy-chromeno[5,4,3-cde]chromene-5,10-dione, 5) were prepared. All complexes were isolated as triflate salts in good yields and were fully characterized by (1)H NMR spectroscopy and electrospray ionization mass spectrometry. The photophysical properties of these metalla-prisms were also investigated. Compounds 9 and 10 showed potent antioxidant activity, but 10 had the superior ORACPE value (1.30 ± 0.020). Ellagic acid (5) and compound 11 showed weaker activity than that of Trolox. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay showed that the metalla-prism compounds exhibit anticancer properties in vitro. Compound 10 inhibited the growth of all cancer cell lines at micromolar concentrations, with the highest cytotoxicity observed against A549 human lung cancer cells (IC50 =25.9 μM). However, these compounds had a lower anti-cancer activity than that of doxorubicin. In a tumoricidal assay, ellagic acid (5) and compound 10 induced cytotoxicity in tumor cells, while doxorubicin did not. While free ellagic acid had no effect on the granulocyte-colony stimulating factor and regulated on activation normal T cell expressed and secreted protein, the encapsulated metalla-prism 10 stimulated granulocyte-colony stimulating factor and reduced regulated on activation normal T cell expressed and secreted protein expression in the RAW264.7 macrophage line. Our results show that ellagic acid encapsulated in metalla-prisms inhibited cancer cells via the modulation of mRNA induction and protein expression levels of the granulocyte-colony stimulating factor and regulated on activation normal T cell expressed and secreted protein in macrophages.

No MeSH data available.


Related in: MedlinePlus

Calculated (red) and experimental (black) ESI-MS spectra of ellagic acid encapsulated prisms 9–11.Abbreviation: ESI-MS, electrospray ionisation mass spectrometry.
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f3-ijn-10-227: Calculated (red) and experimental (black) ESI-MS spectra of ellagic acid encapsulated prisms 9–11.Abbreviation: ESI-MS, electrospray ionisation mass spectrometry.

Mentions: Electrospray ionization mass spectrometry (ESI-MS) analysis confirmed the formation of [3+2] self-assembled hexanuclear cages 9–11 encapsulating ellagic acid, by the appearance of multiple-charged fragments. The multiple-charged ions were observed: for 9 at m/z =1,112.7 [9−3CF3SO3]3+, for 10 at m/z =1,163.06 [10–3CF3SO3]3+ and for 11 at m/z =1,263.11 [11–3CF3SO3]3+ and these peaks were well resolved isotopically (Figure 3). The appearance of the expected peaks, together with the isotopic patterns, confirmed the formation of the expected ellagic acid-encapsulated self-assembled products 9–11.


Investigation of the biological and anti-cancer properties of ellagic acid-encapsulated nano-sized metalla-cages.

Dubey A, Park DW, Kwon JE, Jeong YJ, Kim T, Kim I, Kang SC, Chi KW - Int J Nanomedicine (2015)

Calculated (red) and experimental (black) ESI-MS spectra of ellagic acid encapsulated prisms 9–11.Abbreviation: ESI-MS, electrospray ionisation mass spectrometry.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4562765&req=5

f3-ijn-10-227: Calculated (red) and experimental (black) ESI-MS spectra of ellagic acid encapsulated prisms 9–11.Abbreviation: ESI-MS, electrospray ionisation mass spectrometry.
Mentions: Electrospray ionization mass spectrometry (ESI-MS) analysis confirmed the formation of [3+2] self-assembled hexanuclear cages 9–11 encapsulating ellagic acid, by the appearance of multiple-charged fragments. The multiple-charged ions were observed: for 9 at m/z =1,112.7 [9−3CF3SO3]3+, for 10 at m/z =1,163.06 [10–3CF3SO3]3+ and for 11 at m/z =1,263.11 [11–3CF3SO3]3+ and these peaks were well resolved isotopically (Figure 3). The appearance of the expected peaks, together with the isotopic patterns, confirmed the formation of the expected ellagic acid-encapsulated self-assembled products 9–11.

Bottom Line: Compounds 9 and 10 showed potent antioxidant activity, but 10 had the superior ORACPE value (1.30 ± 0.020).In a tumoricidal assay, ellagic acid (5) and compound 10 induced cytotoxicity in tumor cells, while doxorubicin did not.While free ellagic acid had no effect on the granulocyte-colony stimulating factor and regulated on activation normal T cell expressed and secreted protein, the encapsulated metalla-prism 10 stimulated granulocyte-colony stimulating factor and reduced regulated on activation normal T cell expressed and secreted protein expression in the RAW264.7 macrophage line.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Ulsan, Ulsan, Republic of Korea.

ABSTRACT
Three new large hexanuclear metalla-prisms 9-11 incorporating 1,3, 5-tris(pyridin-4-ylethynyl)benzene (tpeb) 4 and one of the dinuclear arene ruthenium clips [Ru2(p-iPrC6H4Me)2(OO∩OO)][CF3SO3]2 (OO∩OO =2,5-dioxydo-1,4-benzoquinonato [dobq] 1, 5,8-dihydroxy-1,4-naphthaquinonato (donq) 2, and 6,11-dihydroxy-5,12-naphthacenedionato [dotq] 3), which encapsulate the guest molecule ellagic acid (2,3,7,8-tetrahydroxy-chromeno[5,4,3-cde]chromene-5,10-dione, 5) were prepared. All complexes were isolated as triflate salts in good yields and were fully characterized by (1)H NMR spectroscopy and electrospray ionization mass spectrometry. The photophysical properties of these metalla-prisms were also investigated. Compounds 9 and 10 showed potent antioxidant activity, but 10 had the superior ORACPE value (1.30 ± 0.020). Ellagic acid (5) and compound 11 showed weaker activity than that of Trolox. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay showed that the metalla-prism compounds exhibit anticancer properties in vitro. Compound 10 inhibited the growth of all cancer cell lines at micromolar concentrations, with the highest cytotoxicity observed against A549 human lung cancer cells (IC50 =25.9 μM). However, these compounds had a lower anti-cancer activity than that of doxorubicin. In a tumoricidal assay, ellagic acid (5) and compound 10 induced cytotoxicity in tumor cells, while doxorubicin did not. While free ellagic acid had no effect on the granulocyte-colony stimulating factor and regulated on activation normal T cell expressed and secreted protein, the encapsulated metalla-prism 10 stimulated granulocyte-colony stimulating factor and reduced regulated on activation normal T cell expressed and secreted protein expression in the RAW264.7 macrophage line. Our results show that ellagic acid encapsulated in metalla-prisms inhibited cancer cells via the modulation of mRNA induction and protein expression levels of the granulocyte-colony stimulating factor and regulated on activation normal T cell expressed and secreted protein in macrophages.

No MeSH data available.


Related in: MedlinePlus