physical-chemistry-2018-posters-abstracts

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E u r o s c i c o n C o n f e r e n c e o n

Physical Chemistry and

Analytical Separation Techniques

October 08-09 , 2018

Amsterdam, Nether l ands

Journal of Organic & Inorganic Chemistry

ISSN: 2472-1123

Physical Chemistry and Analytical Separation Techniques 2018

ithin the field of pharmacologically active biopolymers the area of stable polyethers seems rather new and attractive. A

new series of linear and regular caffeic acid derived polyether, namely poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene]

or poly[3-(3,4-dihydroxyphenyl)glyceric acid] (PDPGA) was isolated and identified in the water-soluble, high molecular weight

fractions obtained from

Symphytum asperum, S.caucasicum, S.officinale, S.grandiflorum and Anchusa italica

(Boraginaceae).

According to data of

H NMR, 2D

C HSQC experiments, the polyoxyethylene chain is the backbone of the polymer

molecule. 3, 4-Dihydroxyphenyl and carboxyl groups are regular substituents at two carbon atoms in the chain. The repeating unit

of this regular polymer is 3-(3, 4-dihydroxyphenyl) glyceric acid residue. Most of the carboxylic groups of PDPGA from

A. italica

and S.grandiflorum

unlike the

polymer of S.asperum, S.caucasicum and S.officinale

are methylated. The 2D DOSY experiment

gave the similar diffusion coefficient for the methylated and non-methylated signals of

A. italica

PDPGA. Both sets of signals

fell in the same horizontal. This would imply a similar molecular weight for methylated and non-methylated polymers. PDPGA

is endowed with intriguing pharmacological properties as anticomplementary, antioxidant, anti-inflammatory, burn and wound

healing effect. 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 osmiate catalyst and cinchona alkaloid derivatives (DHQ)2-PHAL and (DHQD)2-PHAL

as chiral auxiliaries. 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.

Biopolyether from medicinal plants: as

anticancer agent

Vakhtang Barbakadze

Kutateladze Institute of Pharmacochemistry, Tbilisi State Medical University, Georgia

J Org Inorg Chem 2018 Volume: 4

DOI: 10.21767/2472-1123-C6-018