Anti-Amoebic Properties of Carbonyl Thiourea Derivatives

Abstract

Thiourea derivatives display a broad spectrum of applications in chemistry, various industries, medicines and various other fields. Recently, different thiourea derivatives have been synthesized and explored for their anti-microbial properties. In this study, four carbonyl thiourea derivatives were synthesized and characterized, and then further tested for their anti-amoebic properties on two potential pathogenic species of Acanthamoeba, namely A. castellanii (CCAP 1501/2A) and A. polyphaga (CCAP 1501/3A). The results indicate that these newly-synthesized thiourea derivatives are active against both Acanthamoeba species. The IC 50 values obtained were in the range of 2.39-8.77 µg·mL -1 (9.47-30.46 µM) for A. castellanii and 3.74-9.30 µg·mL -1 (14.84-31.91 µM) for A. polyphaga. Observations on the amoeba morphology indicated that the compounds caused the reduction of the amoeba size, shortening of their acanthopodia structures, and gave no distinct vacuolar and nuclear structures in the amoeba cells. Meanwhile, fluorescence microscopic observation using acridine orange and propidium iodide (AOPI) staining revealed that the synthesized compounds induced compromised-membrane in the amoeba cells. The results of this study proved that these new carbonyl thiourea derivatives, especially compounds M1 and M2 provide potent cytotoxic properties toward pathogenic Acanthamoeba to suggest that they can be developed as new anti-amoebic agents for the treatment of Acanthamoeba keratitis.

Synthesis and structural characterization of new bioactive ligands and their Bi(III) derivatives

“…The 13 C NMR analysis further supports the structure of the precursors and their bismuth(III) complexes by displaying the characteristic signals for the thioamide (C═S) and the amide (C═O) carbons in range 180–184 and 167–170 ppm for all precursors and complexes. As suggested from previously published data, the methyl groups show signals at anticipated values . Carbonyl carbons resonate in the range 165–170 ppm and C═S signals appear around 175–185 ppm.…”

Characterization of some amino acid derivatives of benzoyl isothiocyanate: Crystal structures and theoretical prediction of their reactivity

“…5. The experimental bond distance of S(1)eC(2) ¼ 1.670(2) Å in compound I is consistent with the C]S of the thione [22], whilst the C(1)eO(1) and C(4)eO (3) 16.5713 (7) 13.3896 (8) 12.7108 (5) 13.4905 (6) a ( ) 1295.96 (9) 1398.01 (14) 744.39 (5) the same molecule and the hydroxyl O(3) of the adjoining molecule (Fig. S20).…”

“…The cobalt(II), copper(II) and nickel(II) complexes of the aspartic acid, glutamic acid, methionine, leucine and tryptophan derivatives of benzoyl isothiocyanates have been synthesized and tested for their antibacterial activity [15]. Some thiourea derivatives of various amines have also been synthesized in acetone and tested for their anti-amoebic properties [16]. Cyclohexanecarbonyl isothiocyanate has been reacted with various amines in acetone, with a slightly different work-up procedure which involved the addition of 0.1 N hydrochloric acid to the mother liquor before filtration, and this was reported to give higher yields of between 86 and 93% [17].…”

Ultrastructural Study of Acanthamoeba polyphaga Trophozoites and Cysts Treated In Vitro with Cationic Carbosilane Dendrimers

“…Many of the current drugs used to treat AK have been found to act on cellular membranes. For example, chlorhexidine, a positively charged molecule, targets the plasma membrane and affects its permeability [ 8 ], while polyhexamethylene biguanide (PHMB) interacts nonspecifically with membranes on prokaryotic cells and causes the loss of lipopolysaccharides (LPS) and loss of function in membrane proteins [ 6 ]. Furthermore, some diamidines with positive charges interact with amphipathic lipids and produce changes in membrane permeability [ 9 ].…”