Antiproliferative, Antimicrobial and Antiviral Activity of β-Aryl-δ-iodo-γ-lactones, Their Effect on Cellular Oxidative Stress Markers and Biological Membranes

Abstract

The aim of this work was the examination of biological activity of three selected racemic cis-β-aryl-δ-iodo-γ-lactones. Tested iodolactones differed in the structure of the aromatic fragment of molecule, bearing isopropyl (1), methyl (2), or no substituent (3) on the para position of the benzene ring. A broad spectrum of biological activity as antimicrobial, antiviral, antitumor, cytotoxic, antioxidant, and hemolytic activity was examined. All iodolactones showed bactericidal activity against Proteus mirabilis, and lactones 1,2 were active against Bacillus cereus. The highest cytotoxic activity towards HeLa and MCF7 cancer cell lines and NHDF normal cell line was found for lactone 1. All assessed lactones significantly disrupted antioxidative/oxidative balance of the NHDF, and the most harmful effect was determined by lactone 1. Contrary to lactone 1, lactones 2 and 3 did not induce the hemolysis of erythrocytes after 48 h of incubation. The differences in activity of iodolactones 1–3 in biological tests may be explained by their different impact on physicochemical properties of membrane as the packing order in the hydrophilic area and fluidity of hydrocarbon chains. This was dependent on the presence and type of alkyl substituent. The highest effect on the membrane organization was observed for lactone 1 due to the presence of bulky isopropyl group on the benzene ring.

Interaction of 4′-methylflavonoids with biological membranes, liposomes, and human albumin

“…The increase observed in the amount of hemolyzed cells in the presence of compounds ( 5 ) was negligible and did not exceed 3.4% (± 0.61) for 100 μM concentration. This means that the tested compounds are not toxic.The compounds are considered to be slightly toxic when they achieve hemolysis above 10%, toxic when hemolysis is above 50%, and highly toxic with hemolysis exceeding 90% 19 , 20 . These results are compatible with the hemolytic activity studies conducted by Cyboran et al for green tea supplement (GP), epigallocatechin-3-gallate (EGCG), and gallic acid (GA), measured after 1, 2 and 3 h of incubation 21 .…”

“…Amide I is located within the range of 1610–1695 cm –1 and amide II appears within the range of 1480–1575 cm −1 . Amide I and amide II is used for determining the type of protein secondary structure 20 , 36 . An analysis demonstrated that chalcone, flavanone, and flavones are able to shift the maximum of both amide I and amide II bands, e.g.…”

“…Detailed procedures for the preparation of RBCMs and PC are described in ealier. The procedure of sample preparation has been described in our previous papers 3 , 20 , 57 . Briefly, after to remove the water the spectrum of the control (RBCMs or liposomes) and tested samples (RBCMs or PC with tested compounds) at concentration 50 and 25 µM was taken.…”

Organic synthesis and anti-influenza A virus activity of cyclobakuchiols A, B, C, and D

“…Sekine et al reported that the presence and difference of the isopropyl group in a ring of p -menthane monoterpenoids affected termite mortality [ 37 ]. Several studies have reported that the isopropyl group in the compound has biological effects, such as anti-mycobacterial [ 38 , 39 ], anti-amoebic [ 40 ], and anticancer [ 39 ] activities. Therefore, the isopropyl group arrangement is important for the pharmacological activity of the compounds.…”

A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones

“…For example, a synthetic α -amino- γ -lactone ketolide (Entry 19) showed excellent antibacterial activity against erythromycin-susceptible Streptococus pyogenes [ 45 ]. Additionally, hydrazonothiazolyl derivative (Entry 20) [ 46 ], β -cyclocitral derivative (Entry 21) [ 47 ], and α -methylene- γ -butyrolactone (Entry 22) [ 48 ] displayed potent antibacterial activities and a synthetic β -aryl- δ -iodo- γ -butyrolactone (Entry 23) exhibited bactericidal activity against Proteus mirabilis [ 49 , 50 ].…”