Influence of amide versus ester linkages on the anticancer properties of the new flavone–biotin conjugates
-
Monika Stompor
,
Marta Świtalska
Abstract
Novel biotinylated C-6 substituted flavones were synthesised by a one-step method that connects biotin to 6-hydroxyflavone and 6-aminoflavone by esterification and amidation of hydroxyl and amino groups, respectively. The obtained compounds, 6-O-biotinylflavone and 6-biotinylamidoflavone, are the bifunctional molecules composed of a flavone moiety as a fluorescent reporter and biotin as a cancer-targeting unit. Antiproliferative activity was evaluated using SRB assays in MCF-7, MCF-10A, HepG2, MDA-MB-231, 4T1, and Balb/3T3 cell lines. In vitro evaluation revealed that compounds with biotin moiety displayed better cell selectivity between the cancer and normal cells than the parental substrates. These results indicate that anticancer effect is not related to the position of biotin moiety, but it is related to the presence of ester or amide bond. 6-O-Biotinylflavone was more active than 6-hydroxyflavone against human breast (MDA-MB-231) and liver (HepG2) cancer cells with IC50 (concentration of tested agent that inhibits proliferation of the cell population by 50%) values equal to 78.5 ± 18.8 μM and 133.2 ± 14.2 μM, respectively. Non biotinylated 6-aminoflavone was more active than 6-biotinylamidoflavone against all tested cell lines, with IC50 values between 34.3 ± 9.1 μM (4T1) and 173.86 ± 24.3 μM (MCF-7).
Funding source: National Science Centre, Poland
Award Identifier / Grant number: 2017/01/X/NZ9/00161
Funding statement: This study was financed by grant no. 2017/01/X/NZ9/00161 assigned by the National Science Centre, Poland, to M. Stompor.
Author contributions: M. Stompor conceived the research, designed the experiment, performed the synthetic part of the experimental work, analysed the data, and wrote the manuscript. M. Świtalska performed the biological assays. A.B. measured the NMR spectra. J.W. supervised the biological assays.
Conflict of interest: The authors declare that they have no competing interests.
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©2019 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Research Articles
- Ishige sinicola extract stimulates osteoblast proliferation and differentiation via the bone morphogenetic protein 2/runt-related gene 2 signalling pathway
- Rubescins F–H, new vilasinin-type limonoids from the leaves of Trichilia rubescens (Meliaceae)
- Impact of water-soluble zwitterionic Zn(II) phthalocyanines against pathogenic bacteria
- Influence of amide versus ester linkages on the anticancer properties of the new flavone–biotin conjugates
- Metabolomic discrimination of the edible mushrooms Kuehneromyces mutabilis and Hypholoma capnoides (Strophariaceae, Agaricales) by NMR spectroscopy
- Components of rice husk biochar in promoting the growth, sporulation and iturin A production of Bacillus sp. strain IA
Articles in the same Issue
- Frontmatter
- Research Articles
- Ishige sinicola extract stimulates osteoblast proliferation and differentiation via the bone morphogenetic protein 2/runt-related gene 2 signalling pathway
- Rubescins F–H, new vilasinin-type limonoids from the leaves of Trichilia rubescens (Meliaceae)
- Impact of water-soluble zwitterionic Zn(II) phthalocyanines against pathogenic bacteria
- Influence of amide versus ester linkages on the anticancer properties of the new flavone–biotin conjugates
- Metabolomic discrimination of the edible mushrooms Kuehneromyces mutabilis and Hypholoma capnoides (Strophariaceae, Agaricales) by NMR spectroscopy
- Components of rice husk biochar in promoting the growth, sporulation and iturin A production of Bacillus sp. strain IA
