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Abstract
Phenolic acids possess many beneficial biological activities, including antioxidant and anti-inflammatory properties. Unfortunately, their low bioavailability restricts their potential medical uses, as it limits the concentration of phenolic acids achievable in the organism. The conjugation with phospholipids constitutes one of the most effective strategies to enhance compounds bioavailability in biological systems. In the present study, the conjugates of anisic (ANISA) and veratric acid (VA) with phosphatidylcholine (PC) were investigated. Since both ANISA and VA are inhibitors of tyrosinase, a melanocyte enzyme, the expression of which increases during tumorigenesis, anticancer potential of the conjugates was tested in several metastatic melanoma cell lines. The conjugates proved to be antiproliferative, apoptosis-inducing and cell-cycle-affecting agents, selective for cancerous cells and not affecting normal fibroblasts. The conjugates substituted by ANISA and VA, respectively, at both the sn-1 and sn-2 positions of PC, appeared the most promising, since they were effective against the vast majority of metastatic melanoma cell lines. Additionally, the conjugation of phenolic acids to PC increased their antioxidant activity. Molecular modeling was employed for the first time to estimate the features of the investigated conjugates relevant to their anticancer properties and membrane permeation. Again, the conjugates substituted by phenolic acid at both the sn-1 and sn-2 positions of PC seemed to be presumably most bioavailable.
Highlights
Phenolic acids constitute an important class of plant secondary metabolites
The conjugates substituted by ANISA and veratric acid (VA), respectively, at both the sn-1 and sn-2 positions of PC, turned to be especially promising since they were effective against the vast majority of the studied metastatic melanoma cell lines
The compounds were tested in the concentration range from 50 to
Summary
Phenolic acids constitute an important class of plant secondary metabolites They are ingested by humans with food, contributing to its nutritional properties, as well as taste and smell qualities. Phospholipid conjugates of doxorubicin have been demonstrated to have improved absorption, better pharmacodynamic properties and increased selectivity between normal and cancerous cells [15,16]. The conjugation of tamoxifen to bile acid phospholipid yielded the derivative characterized by enhanced gut absorption, blood circulation and selective accumulation in tumor site that led to preferential anticancer activity in comparison with the parent drug [17]. The conjugates substituted by ANISA and VA, respectively, at both the sn-1 and sn-2 positions of PC, turned to be especially promising since they were effective against the vast majority of the studied metastatic melanoma cell lines. The conjugates substituted by phenolic acid at both the sn-1 and sn-2 positions of PC seemed to be potentially the most bioavailable
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