Recent developments on the potential biological applications of transition metal complexes of thiosemicarbazone derivatives

Singh, Vipin; Palakkeezhillam, Vishnunarayanan Namboothiri Vadakkedathu; Manakkadan, Vipin; Rasin, Puthiyavalappil; Valsan, Adarsh K.; Kumar, Vaishnu Suresh; Sreekanth, Anandaram

doi:10.1016/j.poly.2023.116658

Cited by 18 publications

(7 citation statements)

References 137 publications

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“…For electrocatalytic hydrogen production using a Pd II complex with the 4-{bis[4-(p-methoxyphenyl)thiosemicarbazone]}-2,3butane derivative, which is relevant for the energy research today, see: Straistari et al (2018). For biological applications of TSCs and their complexes, see: Singh et al (2023). For the antifungal activity and the crystal structure of the nonsubstituted cis-jasmone thiosemicarbazone, see: Orsoni et al, (2020) and for another report concerning the fungistatic effect of this TSC derivative, see: Jamiołkowska et al (2022).…”

Section: Structure Descriptionmentioning

confidence: 99%

2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide

Oliveira,

Bresolin,

Beck

et al. 2023

IUCr Data

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The hydrochloric acid-catalyzed equimolar reaction between cis-jasmone and 4-phenylthiosemicarbazide yielded the title compound, C18H23N3S (common name: cis-jasmone 4-phenylthiosemicarbazone). Concerning the hydrogen bonding, an N—H...N intramolecular interaction is observed, forming a ring with graph-set motif S(5). In the crystal, the molecules are connected into centrosymmetric dimers by pairs of N—H...S and C—H...S interactions, forming rings of graph-set motifs R 2 2(8) and R 2 1(7), with the sulfur atoms acting as double acceptors. The thiosemicarbazone entity is approximately planar, with the maximum deviation from the mean plane through the N/N/C/S/N atoms being 0.0376 (9) Å (the r.m.s.d. amounts to 0.0234 Å). The molecule is substantially twisted as indicated by the dihedral angle between the thiosemicarbazone fragment and the phenyl ring, which amounts to 56.1 (5)°, and because of the jasmone fragment, which bears a chain with sp 3-hybridized carbon atoms in the structure. The Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are: H...H (65.3%), H...C/C...H (16.2%), H...S/S...H (10.9%) and H...N/N...H (5.5%).

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Section: Structure Descriptionmentioning

confidence: 99%

2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide

Oliveira,

Bresolin,

Beck

et al. 2023

IUCr Data

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“…[17] Thiosemicarbazones and their metal complexes possess a wide range of biological features, including the ability to function as antimalarial, anti-inflammatory, antibacterial, antifungal, and anticancer agents. [18][19][20][21][22][23][24][25][26] A review of the literature reveals that Pd(II) and Pt(II) complexes are coordinated by thiosemicarbazones in various ways. [27][28][29][30] When tested on mice with P388 leukaemia, Pd(II) and Pt(II) complexes of pyridine-2-carbaldehyde thiosemicarbazone (Figure 1a) were found to have high in vivo cytotoxicity.…”

Section: Introductionmentioning

confidence: 99%

Palladium(II) Complexes of 4‐Phenyl‐3‐thiosemicarbazone Ligands: Insights Into Cytotoxic Properties and Mode of Cell Death

Mansour,

Khaled,

Radacki

et al. 2024

Chemistry & Biodiversity

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Reactions between sodium tetrachloropalladate and 2‐ (or 4‐) substituted 4‐phenyl‐3‐thiosemicarbazone ligands (HLR), with various electron‐donating and electron‐withdrawing substituents (R = OCH3, NO2, and Cl), afford square‐planar complexes of the general formula [Pd(LR)2]. Ground‐state geometry optimization and the vibrational analysis of cis‐ and trans‐isomers of the complexes were carried out to get an insight into the stereochemistry of the complexes. Natural bond orbital analysis was used to analyze how the nature of the substituent affects the natural charge of the metal center, the type of hybridization, and the strength of the M−N and M−S bonds. Using spectrophotometry, the stability of the complexes, and their DNA binding abilities were assessed. The Pd(II) complexes showed moderate cytotoxicity against HepG‐2 and Caco‐2 cell lines, two of the assessed malignant cell lines, resulting in all known cell death types, including early apoptotic bodies and late apoptotic vacuoles as well as evident necrotic bodies.

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“…[26][27][28][29] Furthermore, there has been much research done on the complexation of thiosemicarbazone chelator with transition metals, particularly with Co 2+ , Ni 2+ , Cu 2+ , and Zn 2+ because these are extremely advantageous sources of therapeutic drugs due to their significant bio-response to controller the pathogen infection as a result of chelation, lipophilicity, and hydrophobicity properties as well as their structural diversify, diffusion power, good therapeutic index, etc., which are crucial requirement for remedial drug. 1,15 These metallic complexes are also used in a variety of biological processes as enzyme catalytic cycles. Thus, the medical applications of Co 2+ , Ni 2+ , Cu 2+ , and Zn 2+ complexes-based TSCs are the center of study due to their important properties as anti-inflammatory, 15 anticancer, 18,19,30 antioxidant, 15 antimalarial, 15 antituberculosis 31 antimicrobial, 4 pro-angiogenic activity, 32 etc.…”

Section: Introductionmentioning

confidence: 99%

“…They are mostly found to be thionic or thiol tautomer, while the thiol tautomer can deprotonate to generate thiolate anions in certain circumstances, particularly when coordinated to a metal center. 1,2 The TSCs can be coordinated with metallic cations in a bidentate behavior via the azomethine nitrogen atom and sulfur atom mainly in a square planar arrangement. 3 Nevertheless, among other possibilities, they can also coordinate in a tetradentate or tridentate behavior.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, structural characterization, density functional theory, anticancer, and antimicrobic studies of Ni²⁺ and Cu²⁺ complexes encompassing tridentate ONS‐donor azo‐thiosemicarbazone

Hassan,

Ebrahium,

Al‐Hakimi

2024

Applied Organom Chemis

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This study focuses on the synthesis of azo‐thiosemicarbazone ligand, which is designed by reacting 2‐hydroxy‐5‐(phenyldiazenyl)benzaldehyde with hydrazine carbothioamide. Hence, this ligand was exploited for chelation with nickel and cupric salts in (1 M:1 L) molar ratio. These synthetics were structurally investigated using a variety of physical, analytical, and spectroscopic (1D/2D‐NMR, UV–Vis, FT‐IR, and E‐mass) tools as well as theoretically. The finding demonstrated that the resulting azo‐thiosemicarbazone (H4Azo‐TSC) bonded with the nickel and cupric ions as mono/di‐basic tridentate chelators, binding them via deprotonated phenolic oxygen, imino nitrogen, and thionic/thiol sulfur atoms adopting square planar geometry. The theoretical investigation was examined by DFT/B3LYP/LanL2dZ, including energetic parameters, HOMO‐LUMO energy gap, dipole moment, and geometrical optimization, which were applied to support the complexes' geometrical structure. The in vitro microbicidal activities of the azo‐thiosemicarbazone, compared with its Ni2+ and Cu2+ complexes, display superior activity over the metal complexes against different bacterial and fungal species. The anticancer efficacy of the synthetics was tested against human lung fibroblast (WI38) and mammary gland breast cancer (MCF‐7) compared with Doxorubicin as a standard drug. The cytotoxic efficiency of metallic complexes exceeded that of un‐chelated azo‐thiosemicarbazone. The most effective complex is Ni2+ complex with IC50 equal to 11.75 and 14.05 μg/ml, respectively. It has been demonstrated that Ni2+ and Cu2+ complexes are more biocompatible than free azo‐thiosemicarbazone; this finding may be related to the chelation process.

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Recent developments on the potential biological applications of transition metal complexes of thiosemicarbazone derivatives

Cited by 18 publications

References 137 publications

2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide

2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide

Palladium(II) Complexes of 4‐Phenyl‐3‐thiosemicarbazone Ligands: Insights Into Cytotoxic Properties and Mode of Cell Death

Synthesis, structural characterization, density functional theory, anticancer, and antimicrobic studies of Ni²⁺ and Cu²⁺ complexes encompassing tridentate ONS‐donor azo‐thiosemicarbazone

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Recent developments on the potential biological applications of transition metal complexes of thiosemicarbazone derivatives

Cited by 18 publications

References 137 publications

2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide

2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide

Palladium(II) Complexes of 4‐Phenyl‐3‐thiosemicarbazone Ligands: Insights Into Cytotoxic Properties and Mode of Cell Death

Synthesis, structural characterization, density functional theory, anticancer, and antimicrobic studies of Ni2+ and Cu2+ complexes encompassing tridentate ONS‐donor azo‐thiosemicarbazone

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Synthesis, structural characterization, density functional theory, anticancer, and antimicrobic studies of Ni²⁺ and Cu²⁺ complexes encompassing tridentate ONS‐donor azo‐thiosemicarbazone