Abstract
Bacterial infection remains a worldwide problem that requires urgent addressing. Overuse and poor disposal of antibacterial agents abet the emergence of bacterial resistance mechanisms. There is a clear need for new approaches for the development of antibacterial therapeutics. Herein, the antibacterial potential of molecules based on dithiocarbamate anions, of general formula R(R’)NCS2(−), and metal salts of transition metals and main group elements, is summarized. Preclinical studies show a broad range of antibacterial potential, and these investigations are supported by appraisals of possible biological targets and mechanisms of action to guide chemical syntheses. This bibliographic review of the literature points to the exciting potential of dithiocarbamate-based therapeutics in the crucial battle against bacteria. Additionally, included in this overview, for the sake of completeness, is mention of the far fewer studies on the antifungal potential of dithiocarbamates and even less work conducted on antiparasitic behavior.
Highlights
Dithiocarbamates are mono-anionic 1,1-dithiolate ligands of the general chemical formula of R(R’)CNS2(−) for R, R’ = H, alkyl, and aryl, Figure 1a
In the realm of metal complexes, the zinc complex of the bifunctional dithiocarbamate ligand, ethylenebis, {Zn(S2CN(H)CH2CH2N(H)CS2)}n, known as Zineb®, has been employed as a fungicide since the 1940s [5]; the crystal structure of this material has only recently been reported and revealed a two-dimensional polymer owing to the presence of both chelating and bidentate bridging ligands linked into the three-dimensional crystal via amine-N–H . . . S hydrogen bonding [6]
Sharma et al prepared series of compounds of general formula PhSb(L18,37,65,70)Cl and PhSb(L18,37,65,70)2 [112]. Their antimicrobial properties were screened against two Gram-negative bacteria (E. coli and P. aeruginosa) and two fungal strains (A. flavus and A. niger); the results indicated the incorporation of antimony enhanced the inhibitory effect compared to the free ligand owing to the increased lipophilic character of the metal chelate that aids the permeation of the compounds through the lipid layer of cell membranes [112]
Summary
Dithiocarbamates are mono-anionic 1,1-dithiolate ligands of the general chemical formula of R(R’)CNS2(−) for R, R’ = H, alkyl, and aryl, Figure 1a These molecules are ubiquitous in coordination chemistry being able to coordinate practically every heavy element [1,2] by virtue of having two sulfur atoms available for chelation and a significant contribution of the dithiolate resonance structure, R(R’)C=N(+)S2(2−), Figure 1b. The oxidation of one of the more common dithiocarbamate anions, the diethyl derivative, gives rise to the disulfide, Et2NC(=S)S–SC(=S)NEt2, commonly known as tetraethylthiuram disulphide [3] This molecule is marketed as Antabuse® and Disulfiram®, being a drug employed for the treatment of alcohol abuse [4]. These results are included and discussed to achieve a more comprehensive overview of the field
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