Meet Inspiring Speakers and Experts at our 3000+ Global Conference Series Events with over 1000+ Conferences, 1000+ Symposiums
and 1000+ Workshops on Medical, Pharma, Engineering, Science, Technology and Business.

Explore and learn more about Conference Series : World's leading Event Organizer

Back

Vakhtang Barbakadze

Tbilisi State Medical University Institute of Pharmacochemistry, Georgia

Title: Plant Macromolecule from different species of Boraginaceae family, its synthetic monomer and their anticancer efficacy

Biography

Biography: Vakhtang Barbakadze

Abstract

The 13C NMR experiments of water-soluble high-molecular preparations from different species of Boraginaceae family were carried out and simulated 13C NMR spectrum was calculated for 2-hydroxy-3-(3',4'-dihydroxyphenyl)-propionic acid residue (I) of the corresponding polyether using ACD/CNMR Version 1.1  program. Signal positions in the 13C NMR spectrum of this hypothetical structure (I) coincided satisfactory with the experimental values. According to 13C, 1H NMR, APT, 2D heteronuclear 1H/13C HSQC and 2D DOSY experiments the main structural element of these preparations was found to be a regularly substituted by 3,4-dihydroxyphenyl  and  carboxyl  groups polyoxyethylene backbone, namely poly[3-(3,4-dihydroxyphenyl)glyceric acid] (PDPGA) or poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene]. The synthesis of racemic monomer of PDPGA 2,3-dihydroxy-3-(3,4-dihydroxyphenyl)propionic acid (DDPPA) and its enantiomers (+)-(2R,3S)-DDPPA and (–)-(2S,3R)-DDPPA was carried out via Sharpless asymmetric dihydroxylation  of  trans-caffeic acid derivatives using a potassium osmate catalyst and enantiocomplementary catalysts cinchona  alkaloid  derivatives  (DHQ)2-PHAL  and  (DHQD)2-PHAL as chiral auxiliaries. The opposite configuration of both enantiomers was confirmed by measurements of the optical rotation (+)/(–)-values and circular dichroism spectra. The determination of enantiomeric purity was performed by HPLC analysis. PDPGA and DDPPA  exerted  anti-cancer efficacy  in vitro  and  in vivo  against    human  prostate cancer (PCA) cells  via  targeting  androgen  receptor,  cell  cycle  arrest  and  apoptosis  without  any  toxicity, together  with  a strong  decrease  in  prostate  specific antigen  level in plasma. However, our  results  showed  that anticancer efficacy of  PDPGA  is more effective compared to its synthetic  monomer. Overall, this study identifies  PDPGA as a potent agent against PCA  without any toxicity, and  supports  its clinical application.