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Centre for Stress and Age-Related Disease
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    • A computational protocol to model organophosphonate CWAs and their simulants
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  • Synthesis and evaluation of Resveratrol derivatives

Synthesis and evaluation of Resveratrol derivatives

This research is primarily focused on developing interventions in deleterious processes of human ageing. Our early work demonstrated that the highly-publicised postulated anti-ageing compound, resveratrol, causes premature cellular senescence in primary cells in vitro, but that its more bioavailable metabolite, dihydroresveratrol, does not. The diversity of reported activities of resveratrol and its natural product analogues led us to initiate this project, undertaking the first rational, multidimensional SAR study of stilbenes.

Project timeframe

This work has been ongoing since 2010.

  • Ministry of Education and Science, Republic of Kazakhstan Identification of small molecules capable of removing ageing cells and slowing down the ageing process (£654,000, 2012-14) Collaboration with Universities of Oxford, Cardiff and Nazarbayev.
  • University of Brighton PhD Scholarship Does Sirt1 or cytostasis underlie the anti-ageing activity of stilbenes? (Vishal Birar, 2012-15)

Project aims

Our primary goal is to enable ready access to diverse resveratrol analogues termed 'Resveralogues', such that a programme of bioevaluation spanning multiple collaborators and potential applications can be undertaken. One key outcome of this is to determine the specific structural features required in Resveralogues to reduce selectively the inflammatory effects (Senescence Associated Secretory Phenotype or SASP) of senescent cells in vivo.

STRAND-reseveratrol-diagram

Project findings and impact

We have developed a high yielding one-pot synthesis of the key synthetic step, and used this and specific functional group modifications to synthesise a range (>45 to date) of novel Resveralogues. This panel is now being used to determine the chemical features underlying the (detrimental and beneficial) activities of stilbene molecules, so that future Resveralogues can be designed to maximise desired effects.

This project has the potential to give rise to a lead candidate for intervention in the deleterious processes of human ageing.

Project team

Dr Lizzy Ostler

Professor Richard Faragher

Dr Angela Sheerin

Vishal Birar

Former project and PhD students:

  • Dominick Burton
  • Patricia Majecha
  • Noel Fong
  • Jana Milkovicova

Outputs

Vishal Birar, Angela N Sheerin, Jana Milkovicova, Richard GA Faragher and Elizabeth L Ostler. (2015)  A facile, stereoselective, one-pot synthesis of resveratrol derivatives. Chemistry Central Journal  9:26.

Faragher RGA, Burton DGA, Majecha P, Fong NSY, Davis T, Sheerin A and Ostler EL Resveratrol, but not dihydroresveratrol, induces premature senescence in primary human fibroblasts.  AGE (2010) epub:DOI: 10.1007/s11357-010-9201-5.

Project Partners

Bioevaluation:

  • Lynne Cox (Oxford University)
  • David Kipling and Terry Davis (Cardiff University)
  • James Brown (Aston University)
  • Alexandra Stolzing (Loughborough University)
  • Yingshan Han (McGill University)
  • Charley Chatterjee (University of Brighton)
  • Lorna Harries (Exeter University)

Crystallography/Modelling:

  • Raghu Kothur and Peter Cragg (University of Brighton)
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