In Search of Effective Anticancer Agents—Novel Sugar Esters Based on Polyhydroxyalkanoate Monomers

Abstract

Cancer is one of the deadliest illness globally. Searching for new solutions in cancer treatments is essential because commonly used mixed, targeted and personalized therapies are sometimes not sufficient or are too expensive for common patients. Sugar fatty acid esters (SFAEs) are already well-known as promising candidates for an alternative medical tool. The manuscript brings the reader closer to methods of obtaining various SFAEs using combined biological, chemical and enzymatic methods. It presents how modification of SFAE’s hydrophobic chains can influence their cytotoxicity against human skin melanoma and prostate cancer cell lines. The compound’s cytotoxicity was determined by an MTT assay, which followed an assessment of SFAEs’ potential metastatic properties in concentrations below IC50 values. Despite relatively high IC50 values (63.3–1737.6 μM) of the newly synthesized SFAE, they can compete with other sugar esters already described in the literature. The chosen bioactives caused low polymerization of microtubules and the depolymerization of actin filaments in nontoxic levels, which suggest an apoptotic rather than metastatic process. Altogether, cancer cells showed no propensity for metastasis after treating them with SFAE. They confirmed that lactose-based compounds seem the most promising surfactants among tested sugar esters. This manuscript creates a benchmark for creation of novel anticancer agents based on 3-hydroxylated fatty acids of bacterial origin.

Rhamnopyranoside-Based Fatty Acid Esters as Antimicrobials: Synthesis, Spectral Characterization, PASS, Antimicrobial, and Molecular Docking Studies

“…In compound 5, the C-2 hydroxyl group is free. We have exploited the position for further esterification which confirmed the synthesized structure 3,4-di-O-stearoyl-α-L-rhamnopyranoside (5) and provided some novel biologically potential rhamnopyranoside esters. Firstly, 3,4-di-O-stearate 5 on reaction with hexanoyl chloride (1.1 eq.)…”

“…The structure and position of the signals were also confirmed by the 2D HMBC spectrum (Figures 2B and S13). As a result, the compound with the lower R f was established as methyl 3,4-di-O-stearoyl-α-L-rhamnopyranoside (5).…”

“…SEs have generated a great deal of scientific attention Molecules 2023, 28, 986 2 of 19 and have a wide range of applications in both industry and medicine due primarily to their significant insecticidal and antibacterial capabilities [5][6][7][8]. Notably, SEs' hydrophobic chains can influence cytotoxicity against human skin melanoma and prostate cancer cell lines [5]. In the medical and pharmaceutical fields, SEs and associated medications have also opened a new door for drug delivery.…”

Distinctive carbohydrate profiles of black ginseng revealed by IM-MS combined with PMP labeling and multivariate data analysis

“…To our knowledge, we are the first group to detect the five monosaccharides in ginseng. Carbohydrates containing alkene functional group, esters, or amino group have exhibited diverse biological activities including anti-cancer, anti-microbial, and anti-inflammatory properties ( Campana et al, 2019 ; Chesnokov et al, 2014 ; Nagaoka et al, 2011 ; Snoch et al, 2021 ). So we expect highly potent activities can be found in these black ginseng varieties in the future research.…”

Naturally Occurring Rhamnopyranosides as Anticancer Agents: Molecular Docking and ADMET Study

“…Recently (2022), ethyl acetate and chloroform extracts of Ifloga spicata were found highly active against HepG-2 cell line (MTT assay, IC50 values 5.54 and 6.52 μg/mL, respectively) [35]. According to Snoch et al [36], altering the hydrophobic chains of sugar fatty acid esters (SFAEs) can change how hazardous they are to human skin melanoma and prostate cancer cell lines. The synthesized SFAEs showed potential metastatic properties with IC50 values 63.3-1737.6 µM.…”