Mononuclear homoleptic organotin(IV) dithiocarbamates: Syntheses, structures and antimicrobial activities

Four new macrocyclic dinuclear dibutyltin(IV) dithiocarbamate complexes of the type [Bu2Sn(dtc)]2, where dtc = hexane‐1,6‐diylbis(4‐fluorobenzyldithiocarbamate) anion (1), hexane‐1,6‐diylbis(4‐chlorobenzyldithiocarbamate) anion (2), hexane‐1,6‐diylbis(furfuryldithiocarbamate) anion (3) and hexane‐1,6‐diylbis(pyrrole‐2‐ylmethyldithiocarbamate) anion (4), have been prepared. The dithiocarbamate ligands efficiently self‐assemble with Bu2Sn(IV) to form bimetallic 26‐membered macrocycles. All the complexes have been characterized using elemental analysis, infrared and NMR (1H and 13C) spectroscopies and X‐ray crystallography. Single‐crystal X‐ray diffraction analysis of all the complexes confirms the formation of the dinuclear metallomacrocycles in which dithiocarbamate ligands are asymmetrically bound to the tin atoms. The coordination sphere around the tin atom in 1–4 can be described as a skew trapezoidal bipyramid. The dimensions of the cavity of the macrocycles of 1–4 are ca 8.0 × 9.0 Å2. Complexes 1–4 were evaluated for their in vitro anticancer activity against MCF‐7 and HL‐60 cells. Complexes 1 and 2 are more active against MCF‐7 and HL‐60. Thermal decomposition of 1 and 4 yielded tin sulfides. They were characterized using powder X‐ray diffraction (PXRD), high‐resolution transmission electron microscopy and UV diffuse reflectance and energy‐dispersive X‐ray spectroscopies. PXRD studies reveal that the as‐prepared tin sulfides are composed of orthorhombic phase of SnS.

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“…TGA studies of similar [Bu 2 Sn(dtc) 2 ] were carried out under air and nitrogen atmosphere. In these cases also, the final residue is SnS …”

Section: Resultsmentioning

confidence: 99%

Synthesis, spectra, crystal structures and anticancer studies of 26‐membered macrocyclic dibutyltin(IV) dithiocarbamate complexes: Single‐source precursors for tin sulfide nanoparticles

Selvaganapathi

Thirumaran

Ciattini³

2019

Applied Organom Chemis

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“…The triorganotin(IV) congeners displayed better antimicrobial potency towards the eight microbials tested (S. aureus, E. coli, B. subtilis, P. multocida, A. niger, A. flavus, R. solani, and A. alternata). Antimicrobial studies on Ph 3 Sn(L 71,77 ), Ph 2 Sn(L 71 )Cl, R 2 Sn(L 71 ) 2 with R = n-Bu and Ph, and Ph 2 Sn(L 77 ) 2 [105] indicated all compounds were effective against E. coli with Ph 3 Sn(L 71 ) being the most effective and Ph 3 Sn(L 77 ) being the least. This shows that in determining antibacterial activity both the tin and dithiocarbamate bound substituents must be taken into consideration.…”

Section: Main Group Element Dithiocarbamatesmentioning

confidence: 99%

Insights into the Antimicrobial Potential of Dithiocarbamate Anions and Metal-Based Species

2021

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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.

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“…Among the few that have been reported, organotin(IV) dithiocarbamate complexes have shown to have useful biological potential [8][9][10][11]. The dithiocarbamate group, the organotin moiety, and the coordination number of the central metal in these complexes play important roles in determining their usefulness as biological agents [12]. Furthermore, the chelation effect due to the polarity of the metal ion also plays a crucial role in their biological property.…”

mentioning

confidence: 99%

“…Some derivatives of coordination compounds containing different organotin(IV) and dithiocarbamate moieties have been synthesized, and their anti-cancer [14][15][16], antimicrobial [12,[17][18][19][20], and antiradical properties [15] have been reported. Significant antitumoral and antimicrobial potential have been reported in the following order: R 3 Sn + >R 2 Sn 2+ >RSn 3+ [15], which shows that the length and number of the alkyl groups attached to the tin center could influence the biological activities of these compounds.…”

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confidence: 99%

Antimicrobial and Cytotoxicity Studies of Some Organotin(IV) N-ethyl-N-phenyl Dithiocarbamate Complexes

Adeyemi

Onwudiwe

2020

Pol. J. Environ. Stud.

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Different approaches to drug discovery have arisen due to the evolution of new diseases, loss in activity of known drugs, and the resistance of pathogens to already used drugs. Some of these methods are carried out by organic chemists and involve a synthetic approach, the development of structural analogues of existing drugs, fortuitous identification, and metal complex therapy, etc. [1]. Metal complex formation has provided a therapeutic platform [2] for making innovative and novel drugs

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Mononuclear homoleptic organotin(IV) dithiocarbamates: Syntheses, structures and antimicrobial activities

Cited by 12 publications

References 40 publications

Synthesis, spectra, crystal structures and anticancer studies of 26‐membered macrocyclic dibutyltin(IV) dithiocarbamate complexes: Single‐source precursors for tin sulfide nanoparticles

Synthesis, spectra, crystal structures and anticancer studies of 26‐membered macrocyclic dibutyltin(IV) dithiocarbamate complexes: Single‐source precursors for tin sulfide nanoparticles

Insights into the Antimicrobial Potential of Dithiocarbamate Anions and Metal-Based Species

Antimicrobial and Cytotoxicity Studies of Some Organotin(IV) N-ethyl-N-phenyl Dithiocarbamate Complexes

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