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LIPOPHYLIC ANTIOXIDANT GREEN TEA DERIVATIVE WITH HIGH CELLULAR ABSORPTION RATE

AlkylationEpigallocatechin GallateHealthLipophilic ether derivateMedicine

Introduction

Epigallocatechin Gallate (EGCG) is a natural catechin useful in radical species inibition. However, EGCG molecular structure is very much polarized, and this brings to a limited usability in many applications. Some solutions to this problem are already known, but they are very subject to degradation.

The invention relates to an EGCG derivate which is able to efficiently interact with lipidic systems and to maximize the antioxidant effect in cells.

Technical features

EGCG alkylation with a 18 carbon atoms chain leads to a molecule (EGCG-C18) which has same antioxidant behavior and bigger lipophilicity of natural catechin. Thus, the molecule has improved bio-efficiency, improving cellular absorption. EGCG-C18 structure allows the antioxidant to be efficiently embodied into lipidic carriers where EGCG could be embodied only in part. As a consequence, antioxidant can be more efficiently brought into cells. At this regard, the hydrocarbon chain introduced determines for the C18-EGCG an affinity factor for a standard phosphatidylcholine lipid bilayer of 0.76 (R2 = 0.98) which is more than twice that of EGCG (0.35, R2 = 0.93). Studies on retinal cells ARPE19 demonstrates EGCG-C18 has a IC50 value of 222,1 µM (EGCG 312,3 µM). In addition, EGCG-C18 protects ARPE19 cells from H2O2 oxidative stress better than EGCG.

Possible Applications

  • Clinics and Hospitals;
  • Pharmaceutical Companies;
  • Cosmetics and Make-up Companies.

Advantages

  • Increased molecular lipophilicity without antioxidant behaviour reduction, with respect to natural catechin;
  • Increased molecular stability, with respect to ester bond.