Enhancement in anti-tubercular activity of indole based thiosemicarbazones on complexation with copper(I) and silver(I) halides: Structure elucidation, evaluation and molecular modelling

Khan, Ashiq; Jasinski, Jerry P.; Smolenski, Victoria A.; Hotchkiss, Ethan P.; Kelley, Patrick T.; Shalit, Zachary A.; Kaur, Manpreet; Paul, Kamaldeep; Sharma, R. C.

doi:10.1016/j.bioorg.2018.06.027

Cited by 27 publications

(10 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Cu(1)−S(2)−C(17)−N(5), Cu(1)−P(1)−C(33)−C(34) and Cu(1)−P(1)−C(39)−C(40) torsional angles were 170.83(14), 56.97(15), and 26.54(16)°, respectively. As mentioned earlier, the reports on copper(I) TSC complexes are quite rare [60–65,73] . Even in the presence of excess triphenylphosphine (as can be seen in Scheme 2), the copper(I) ion preferred to bind to two TSC ligands as observed by Dorairaj et al [73] …”

Section: Resultsmentioning

confidence: 92%

See 1 more Smart Citation

Cytotoxicity of copper(I) complexes containing indole‐based thiosemicarbazones and triphenylphosphine

Arockia Doss,

Haribabu,

Balakrishnan

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

The research and development department continues searching for effective and definite anticancer medications that would help eradicate cancer. The thiosemicarbazone ligands with indole fragment were utilized to create four new copper(I) complexes. Several spectral examinations and elemental analyses validated the formation of the complexes (1–4). Single crystal X‐ray diffraction (XRD) also proved that complex 4 had the expected tetrahedral structure. Complexes 1–4 were assessed for their cytotoxic property on different cell lines such as immortalized human vascular endothelial (EAhy.926), hepatocellular carcinoma (HepG‐2), and bladder cancer (T24), and kidney epithelial normal cells extracted from an African green monkey (Vero). The complexes showed reduced toxicity towards healthy Vero cells while being active in cancer cell lines. While the standard cisplatin revealed IC50 values of 26.60 and 49.90 μM, the N‐phenyl substituted complex 3 displayed a superior cytotoxic effect with IC50 values of 13.82 and 24.93 μM towards EAhy.926 and HepG‐2 cells, respectively.

show abstract

Section: Resultsmentioning

confidence: 92%

“…As mentioned earlier, the reports on copper(I) TSC complexes are quite rare. [60][61][62][63][64][65]73] Even in the presence of excess triphenylphosphine (as can be seen in Scheme 2), the copper(I) ion preferred to bind to two TSC ligands as observed by Dorairaj et al [73]…”

Section: Crystal Structurementioning

confidence: 99%

Cytotoxicity of copper(I) complexes containing indole‐based thiosemicarbazones and triphenylphosphine

Arockia Doss,

Haribabu,

Balakrishnan

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…[ 11–13,23–25 ] Biological applications of thiosemicarbazones become more important when they form complexes with metal ions, as thiosemicarbazones provides chelate N, S‐binding pocket for the coordination to metals thus affects the biological activities. [ 26–48 ]…”

Section: Introductionmentioning

confidence: 99%

Structure and bonding trends of bisthiosemicarbazones: An overview

Ain

Sharma

2023

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

This review gives a comprehensive account in terms of the synthesis, characterization and biological application of bisthiosemicarbazone ligands and their metal complexes that have been reported until 2022. Their coordination chemistry with p and d block elements, where the structure is solved by single crystal X‐ray crystallography is explored. Complexes are placed group‐wise and their structure as well as bonding aspects are discussed separately. Various spectroscopic techniques for the characterization of ligands and their complexes like infrared (IR), ultraviolet‐visible (UV–Vis), electron spin resonance (ESR), and nuclear magnetic resonance (NMR) (1H, 13C, 31P, 59Co, 119Hg) are discussed. Complexes formed by bisthiosemicarbazones are generally mononuclear; however, in some cases, binuclear or polynuclear complexes have also been found. Square planar, square pyramidal, octahedral, and pentagonal pyramidal are some of the common geometries exhibited by these complexes. Structure–activity relationship was established for substituted and unsubstituted diimine bisthiosemicarbazone complexes of different metal ions. The effect of co‐ligands on biological activity is also discussed.

show abstract

“…Most notable here is 3-aminopyridine-2-carboxaldehyde (3-AP or Triap-ine®), which is currently tested in a randomized phase III trial as an addition to the usual chemotherapy treatment (Cisplatin) during radiation therapy for advanced-stage cervical and vaginal cancers [12,13]. Several copper(I) and silver(I) complexes of thiosemicarbazide derivatives have been prepared and characterized, and an unusual enhancement in antitubercular activity has been observed for some of these complexes [14]. We recently reported a series of metal thiourea complexes prepared by reacting copper(I) or silver(I) halide with triphenylphosphane and 1-(4-nitrophenyl)thiourea, NPTU [15][16][17]; we report herein the synthesis and crystal structures of copper(I) and silver(I) chloride complexes containing triphenylphosphine (PPh 3 ) and 4-phenylthiosemicarbazide (4-PTSC) ligands (Fig.…”

Section: Introductionmentioning

confidence: 99%

Crystal structures of copper(I) and silver(I) chloride complexes containing 4-phenylthiosemicarbazide and triphenylphosphine ligands

Wattanakanjana¹,

Janwatthana²,

Romyen³

et al. 2021

ScienceAsia

View full text Add to dashboard Cite

Copper(I) and silver(I) chloride complexes containing triphenylphosphine (PPh 3 ) and 4-phenylthiosemicarbazide (4-PTSC) ligands were prepared and structurally analyzed, namely [CuCl(4-PTSC)(PPh 3 ) 2 ] (1) and [AgCl(4-PTSC)(PPh 3 ) 2 ]CH 3 CN (2). Both compounds (1) and (2) exhibit a distorted tetrahedral metal coordination environment with two P atoms from two PPh 3 ligands, one terminal S atom from the 4-PTSC ligand and a chloride ion. Intramolecular N−H • • • Cl and N−H • • • N hydrogen bonds are observed (graph set motifs S(6) and S(5), respectively). In the crystals of both complexes, molecules are linked to form dimers via bifurcated N−H • • • Cl hydrogen bonds involving the amine and chloride units. For compound (2), a solvate acetonitrile molecule acts as a hydrogen bond donor and acceptor via C−H(CH 3 CN) • • • Cl and C−H • • • N(CH 3 CN) interactions, leading to the formation of 1D chains along [010].

show abstract

Enhancement in anti-tubercular activity of indole based thiosemicarbazones on complexation with copper(I) and silver(I) halides: Structure elucidation, evaluation and molecular modelling

Cited by 27 publications

References 33 publications

Cytotoxicity of copper(I) complexes containing indole‐based thiosemicarbazones and triphenylphosphine

Cytotoxicity of copper(I) complexes containing indole‐based thiosemicarbazones and triphenylphosphine

Structure and bonding trends of bisthiosemicarbazones: An overview

Crystal structures of copper(I) and silver(I) chloride complexes containing 4-phenylthiosemicarbazide and triphenylphosphine ligands

Contact Info

Product

Resources

About