Novel vanillin derivatives: synthesis, anti-oxidant, DNA and cellular protection properties.

Scipioni, Matteo; Kay, Graeme; Megson, Ian; Kong Thoo Lin, Paul

Abstract

Antioxidants have been the subject of intense research interest mainly due to their beneficial properties associated with human health and wellbeing. Phenolic molecules, such as naturally occurring Resveratrol and Vanillin, are well known for their anti-oxidant properties, providing a starting point for the development of new antioxidants. Here we report, for the first time, the synthesis of a number of new vanillin through the reductive amination reaction between vanillin and a selection of amines. All the compounds synthesised, exhibited strong antioxidant properties in DPPH, FRAP and ORAC assays, with compounds 1b and 2c being the most active. The latter also demonstrated the ability to protect plasmid DNA from oxidative damage in the presence of the radical initiator AAPH. At cellular level, neuroblastoma SH-SY5Y cells were protected from oxidative damage (H2O2, 400 mM) with both 1b and 2c. The presence of a tertiary amino group, along with the number of vanillin moieties in the molecule contribute for the antioxidant activity. Furthermore, the delocalization of the electron pair of the nitrogen and the presence of an electron donating substituent to enhance the antioxidant properties of this new class of compounds. In our opinion, vanillin derivatives 1b and 2c described in this work can provide a viable platform for the development of antioxidant based therapeutics.

Citation

SCIPIONI, M., KAY, G., MEGSON, I. and KONG THOO LIN, P. 2017. Novel vanillin derivatives: synthesis, anti-oxidant, DNA and cellular protection properties. European journal of medicinal chemistry [online], 143, pages 745-754. Available from: https://doi.org/10.1016/j.ejmech.2017.11.072

• Journal Article Type: Article
• Acceptance Date: Nov 25, 2017
• Online Publication Date: Dec 2, 2017
• Publication Date: Jan 1, 2018
• Deposit Date: Dec 8, 2017
• Publicly Available Date: Dec 3, 2018
• Journal: European journal of medicinal chemistry
• Print ISSN: 0223-5234
• Electronic ISSN: 1768-3254
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 143
• Pages: 745-754
• DOI: https://doi.org/10.1016/j.ejmech.2017.11.072
• Keywords: Vanillin derivatives; Synthetic antioxidants; Antioxidant assays; Oxidative stress; DNA; Cell protection
• Public URL: http://hdl.handle.net/10059/2621
• Contract Date: Dec 8, 2017