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

2021 ◽  
Vol 22 (13) ◽  
pp. 7238
Author(s):  
Wojciech Snoch ◽  
Dawid Wnuk ◽  
Tomasz Witko ◽  
Jakub Staroń ◽  
Andrzej J. Bojarski ◽  
...  

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.

2014 ◽  
Vol 31 (2) ◽  
pp. 95-101
Author(s):  
Xiaobo YAN ◽  
Shaoming WU ◽  
Nan LI ◽  
Huadong LV ◽  
Wusheng FU

2008 ◽  
Vol 59 (9) ◽  
Author(s):  
Daniel I. Hadaruga ◽  
Nicoleta G. Hadaruga ◽  
Anca Hermenean ◽  
Adrian Rivis ◽  
Vasile Paslaru ◽  
...  

This paper presents the thermal stability of the oleic acid encapsulated in a- and b - cyclodextrin. The complexation of the oleic acid was achieved by the ethanol-water solution method and the nanoparticles were analyzed by DSC. The free oleic acid and the encapsulated one were subjected to the thermal degradation in the range of 50-150�C and the degradation products were identified and quantified by GC-MS analysis of the fatty acid esters obtained by deriving with methanol/boron trifluoride, both for free compounds and for the encapsulated ones. The oleic acid complexes were very stable in this range of temperature.


2019 ◽  
Vol 18 (15) ◽  
pp. 2124-2130
Author(s):  
Amany Belal

Background: For further exploration of the promising pyrrolizine scaffold and in continuation of our previous work, that proved the potential anticancer activity of the hit compound I, a new series of pyrrolizines 2-5 and 7-9 were designed and synthesized. Methods: Structures of the new compounds were confirmed by IR, 1H-NMR, 13C-NMR and elemental analysis. Antitumor activity for the prepared compounds against human breast adenocarcinoma (MCF-7), liver (HEPG2) and colon (HCT116) cancer cell lines was evaluated using SRB assay method. Result: Compounds 2, 3 and 5 were the most potent on colon cancer cells, their IC50 values were less than 5 µM. Compounds 2, 3 and 8 were the most potent on liver cancer cells, their IC50 values were less than 10 µM. As for MCF7, compounds 2, 7, 8 and 9 were the most active with IC50 values less than 10 µM. We can conclude that combining pyrrolizine scaffold with urea gave abroad spectrum anticancer agent 2 against the three tested cell lines. Micronucleus assays showed that compounds 2, 3, 8 are mutagenic and can induce apoptosis. In addition, caspase-3 activation was evaluated and compound 2 showed increase in the level of caspase-3 (9 folds) followed by 3 (8.28 folds) then 8 (7.89 folds). Conclusion: The obtained results encourage considering these three compounds as novel anticancer prototypes.


1994 ◽  
Vol 59 (4) ◽  
pp. 833-840
Author(s):  
Slavomír Pirkl

The phase transitions and effective optical rotary power of saturated and monounsaturated aliphatic esters of cholesterol with 18 and 22 carbon atoms in the chain have been described. The effect of cis/trans isomerism on these properties is discussed.


1992 ◽  
Vol 70 (6) ◽  
pp. 448-454 ◽  
Author(s):  
Ewa Świeżewska ◽  
T. Chojnacki ◽  
W. J. Jankowski ◽  
K. Singh ◽  
J. Olsson

The long chain polyprenols composed of 30 and more isoprene units from leaves of plants belonging to the genera Potentilla and Rosa have been described. They occur in the form of fatty acid esters. The composition of polyprenol mixture was species dependent and its content reached ca. 0.5% wet weight. Large scale preparation of individual polyprenols from a natural polyprenol mixture was performed using time-extended liquid chromatography on the hydrophobic gel Lipidex-5000.Key words: long chain polyprenols, Rosaceae.


Author(s):  
R E Pauls ◽  
B Pease

Abstract An ionic liquid (IL) 111 column was compared with other commonly employed stationary phases including polydimethyl siloxane and polyethylene glycol for the separation of fatty acid monomethyl and dimethyl esters. The fatty acid esters employed in this study were derived from metathesis reactions of vegetable oils both with and without olefins. The IL 111 column demonstrated enhanced performance compared with conventional columns for the separation of these esters. These advantages included significantly enhanced retention of dimethyl esters relative to monomethyl esters, excellent cis/trans isomer separation and the ability to analyze higher carbon number dimethyl esters. As a result, these columns are highly suited for the analysis of mixtures of mono- and dimethyl fatty acid esters found in lipid metathesis reaction products or to determine monofunctional impurities in samples of commercial dimethyl esters.


Processes ◽  
2021 ◽  
Vol 9 (2) ◽  
pp. 383
Author(s):  
Milan Jakubek ◽  
Michal Masařík ◽  
Tomáš Bříza ◽  
Robert Kaplánek ◽  
Kateřina Veselá ◽  
...  

The study of human protoporphyrinogen oxidase (hPPO) inhibition can contribute significantly to a better understanding of some pathogeneses (e.g., porphyria, herbicide exposure) and the development of anticancer agents. Therefore, we prepared new potential inhibitors with Schiff base structural motifs (2-hydroxybenzaldehyde-based Schiff bases 9–13 and chromanone derivatives 17–19) as structurally relevant to PPO herbicides. The inhibitory activities (represented by the half maximal inhibitory concentration (IC50) values) and enzymatic interactions (represented by the hPPO melting temperatures) of these synthetic compounds and commercial PPO herbicides used against hPPO were studied by a protoporphyrin IX fluorescence assay. In the case of PPO herbicides, significant hPPO inhibition and changes in melting temperature were observed for oxyfluorten, oxadiazon, lactofen, butafenacil, saflufenacil, oxadiargyl, chlornitrofen, and especially fomesafen. Nevertheless, the prepared compounds did not display significant inhibitory activity or changes in the hPPO melting temperature. However, a designed model of hPPO inhibitors based on the determined IC50 values and a docking study (by using AutoDock) found important parts of the herbicide structural motif for hPPO inhibition. This model could be used to better predict PPO herbicidal toxicity and improve the design of synthetic inhibitors.


ACS Omega ◽  
2021 ◽  
Vol 6 (4) ◽  
pp. 3227-3231
Author(s):  
Chizuru Kogame-Asahara ◽  
Hitomi Iguchi ◽  
Kenichiro Honda ◽  
Hajime Shigemitsu ◽  
Toshiyuki Kida

2009 ◽  
Vol 287 (7) ◽  
pp. 795-799 ◽  
Author(s):  
Hidetaka Noritomi ◽  
Kenji Kagitani ◽  
Yasutaka Muratsubaki ◽  
Satoru Kato

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