Synthesis, Characterization, and Antibacterial and Cytotoxic Study of Metal Complexes with Schiff Base Ligands

2008 ◽  
Vol 61 (4) ◽  
pp. 288 ◽  
Author(s):  
Lei Shi ◽  
Rui-Qin Fang ◽  
Jia-Yu Xue ◽  
Zhu-Ping Xiao ◽  
Shu-Hua Tan ◽  
...  
Keyword(s):  
Schiff Base ◽  
Metal Complexes ◽  
Cytotoxic Activity ◽  
Cell Line ◽  
Primary Amines ◽  
Tumour Cell Line ◽  
Cytotoxic Activities ◽  
Ionization Mass ◽  
Schiff Base Ligands

The synthesis of 16 metal complexes from four Schiff bases prepared from 5-chloro-2-hydroxybenzaldehyde and primary amines has been described. The synthesized Schiff base ligands and their complexes were characterized by elemental analyses, spectroscopic (UV, IR, 1H and 13C NMR, electrospray ionization-mass spectrometry) methods, and magnetic and conductance measurements. Furthermore, complexes 1a, 1b, 3d, 4a, and 4d were characterized by X-ray diffraction analysis. After the structural characterization, all the compounds were tested in vitro for their antibacterial (Bacillus subtilis, Escherichia coli, Pseudomonas fluorescens, and Staphylococcus aureus) activities. The cytotoxic activities of the synthesized compounds were evaluated in vitro against human chronic myeloid leukaemia cells (K562) and a human nasopharyngeal epidermoid tumour cell line. The results indicated that most of the complexes showed good cytotoxic activity against human cancer cell lines but weak cytotoxic activity against a human normal cell line (L02). Among the compounds tested, the cobalt complexes 1a, 2a, 3a, and 4a showed the most favourable antibacterial and cytotoxic activities.

scholarly journals In Vitro Evaluation of the Potential Pharmacological Activity and Molecular Targets of New Benzimidazole-Based Schiff Base Metal Complexes

Antibiotics ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 728
Author(s):  
Alberto Aragón-Muriel ◽  
Yamil Liscano ◽  
Yulieth Upegui ◽  
Sara M. Robledo ◽  
María Teresa Ramírez-Apan ◽  
...  
Keyword(s):  
Schiff Base ◽  
Molecular Docking ◽  
Lanthanide Complexes ◽  
Human Tumor ◽  
Model Membranes ◽  
Leishmania Braziliensis ◽  
Cytotoxic Activities ◽  
Schiff Base Ligands ◽  
Major Interest

Metal-based drugs, including lanthanide complexes, have been extremely effective in clinical treatments against various diseases and have raised major interest in recent decades. Hence, in this work, a series of lanthanum (III) and cerium (III) complexes, including Schiff base ligands derived from (1H-benzimidazol-2-yl)aniline, salicylaldehyde, and 2,4-dihydroxybenzaldehyde were synthesized and characterized using different spectroscopic methods. Besides their cytotoxic activities, they were examined in human U-937 cells, primate kidney non-cancerous COS-7, and six other, different human tumor cell lines: U251, PC-3, K562, HCT-15, MCF-7, and SK-LU-1. In addition, the synthesized compounds were screened for in vitro antiparasitic activity against Leishmania braziliensis, Plasmodium falciparum, and Trypanosoma cruzi. Additionally, antibacterial activities were examined against two Gram-positive strains (S. aureus ATCC® 25923, L. monocytogenes ATCC® 19115) and two Gram-negative strains (E. coli ATCC® 25922, P. aeruginosa ATCC® 27583) using the microdilution method. The lanthanide complexes generally exhibited increased biological activity compared with the free Schiff base ligands. Interactions between the tested compounds and model membranes were examined using differential scanning calorimetry (DSC), and interactions with calf thymus DNA (CT-DNA) were investigated by ultraviolet (UV) absorption. Molecular docking studies were performed using leishmanin (1LML), cruzain (4PI3), P. falciparum alpha-tubulin (GenBank sequence CAA34101 [453 aa]), and S.aureus penicillin-binding protein 2a (PBP2A; 5M18) as the protein receptors. The results lead to the conclusion that the synthesized compounds exhibited a notable effect on model membranes imitating mammalian and bacterial membranes and rolled along DNA strands through groove interactions. Interactions between the compounds and studied receptors depended primarily on ligand structures in the molecular docking study.

SYNTHESIS, SPECTRAL CHARACTERIZATION AND ANTICANCER EVALUATION OF NEW DIAZENYL SCHIFF BASE DERIVATIVES

INDIAN DRUGS ◽  
2017 ◽  
Vol 54 (02) ◽  
pp. 20-28
Author(s):  
P. K. N. Sarangi ◽  
◽  
J. Sahoo ◽  
S. K Paidesetty ◽  
G. P. Mohanta
Keyword(s):  
Schiff Base ◽  
Anticancer Activity ◽  
Cell Line ◽  
Leukemia Cell ◽  
Cancer Cell Line ◽  
Leukemia Cell Line ◽  
Primary Amines ◽  
Schiff Base Derivatives ◽  
Mcf 7

A series of several diazenyl Schiff base derivatives were designed and synthesized through azo coupling of diazotised primary amines with the novel synthesized Schiff base ligand (E)-N-((2-chloroquinolin-3-yl) methylene)-4-phenylthiazol-2-amine. All the synthesized compounds have been analysed by different spectral techniques such as elemental analysis, 1H NMR, FT-IR, UV-Vis and LC-MS for their structural confirmation. The above conjugates have been studied for their solvent effects by treating them with different solvents. The results of in vitro cytotoxic study of the synthesized compounds against MCF 7 (human breast cancer cell line) and K562 (Chronic Myeloid Leukemia cell line) revealed that some of the compounds show cytotoxic effect. However, the compounds (NZ)-N-(((4-bromo-3-methylphenyl) diazenyl) (2-chloroquinolin-3-yl) methylene)-4-phenylthiazol-2-amine: (5d) and 4-(((Z)-(2-chloroquinolin-3- yl)(4-phenylthiazol-2-ylimino)methyl)diazenyl)phenol (5e) showed potent cytotoxic activity in comparison to other compounds against MCF 7. Corroborating the results of anticancer activity, it is found to be observed that the compound 4- (((Z)- (2-chloroquinolin-3-yl) (4-phenylthiazol-2-ylimino)methyl) diazenyl) phenol (5e) showed excellent anticancer activity against MCF 7, which is further justified by the apoptosis study through Annexin V-FITC/PI analysis.

scholarly journals SYNTHESIS, MOLLUSCICIDALAND ANTIMICROBIAL POTENTIALITIES OF IRON TRIAD MONONUCLEAR METAL COMPLEXES INCORPORATING TRIDENTATE ASYMMETRICAL SCHIFF BASE LIGANDS CONTAINING SOFT SULFUR COORDINATING ATOM

2019 ◽  
pp. 103-113
Author(s):  
AMAL M ALOSAIMI ◽  
INES EL MANNOUBI ◽  
SAMI A ZABIN
Keyword(s):  
Schiff Base ◽  
Metal Complexes ◽  
Metal Ion ◽  
Lethal Dose ◽  
Analytical Techniques ◽  
Central Metal ◽  
Schiff Base Ligands ◽  
Molluscicidal Activity

Objective: This work aimed at synthesizing tridentates asymmetrical Schiff base ligands containing sulfur atom and using them for preparing metal complexes with the iron triad metals. The prepared compounds were assayed in vitro for antimicrobial potential and in vivo molluscicidal activity. Methods: The unsymmetrical tridentate Schiff bases (SL1, SL2, and SL3) were prepared using 2-aminothiophenol as primary amine and condensed with 2-carboxybenzaldehyde, 2-hydroxy-1-naphthaldehyde, and 7-formyl-8-hydroxyquinoline. These ligands were used in preparing metal complexes with iron triad metals. The synthesized Schiff base ligands and their corresponding metal complexes were characterized and their proposed structures were confirmed using different physical and spectroscopic analytical techniques. All ligands and their corresponding metal complexes were assayed against different bacterial and fungal strains using the agar disk-diffusion technique. The molluscicidal activity was performed according to the standard reported methods as cited in the literature and by observing the toxicity and lethal dose according to the WHO guidelines. Results: The synthesized ligands behave as tridentate (NOS) ligands and form mononuclear complexes with the general formula [M(SL)2] with an octahedral geometry around the central metal ion. Metal complexes were non-electrolytic in nature. The in vitro antibacterial and antifungal examination results showed weak activity of the ligands, and there was enhanced activity with the complexes. The in vivo molluscicidal activity of the tested compounds showed good activity. Conclusion: The targeted compounds were prepared successfully, characterized, and showed some biological activity but lower than the standard reference drugs.

scholarly journals Synthesis and Structural Studies of Transition Metal Complexes with Bidentate Schiff Base Derived from 3-Acetyl-6-methyl-(2H)-pyran-2,4(3H)-dione

2011 ◽  
Vol 8 (s1) ◽  
pp. S245-S252 ◽  
Author(s):  
Praveen S. Mane ◽  
Sanjiv M. Salunke ◽  
Balagi S. More
Keyword(s):  
Schiff Base ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Octahedral Geometry ◽  
Ligand Field ◽  
Schiff Base Ligands ◽  
H Nmr ◽  
Dehydroacetic Acid ◽  
Ligand Field Parameters

The solid complexes of Cu(II), Ni(II), Co(II), Mn(II) and Fe(III) with Schiff base ligands derived from heterocyclic compounds 3-acetyl-6-methyl-(2H)-pyran-2,4(3H)-dione (Dehydroacetic acid) ando-chloroaniline were synthesized and characterized by elemental analysis, conductance, magnetic, thermal, UV-Vis and1H-NMR spectroscopy. The ligand field parameters have been evaluated for Cu(II), Ni(II), Co(II), Mn(II) and Fe(III) complexes which suggest an octahedral geometry for each of them. The magnetic moment and spectral data suggest the dimeric nature of Mn(II) complexes with octahedral geometry. The fungicidal activities of the ligands and their metal complexes have been screened in vitro againstAspergillus nigerand the percentage inhibition of the metal complexes is found to be increased considerably then that of their corresponding ligands and the order is Cu>Ni>Fe>Mn>Co.

scholarly journals Antibacterial Co(II), Ni(II), Cu(II) and Zn(II) complexes with biacetyl-derived Schiff bases

2010 ◽  
Vol 75 (8) ◽  
pp. 1075-1084 ◽  
Author(s):  
Muhammad Imran ◽  
Mitu Liviu ◽  
Shoomaila Latif ◽  
Zaid Mahmood ◽  
Imtiaz Naimat ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Schiff Base ◽  
Metal Complexes ◽  
Schiff Bases ◽  
Bacterial Species ◽  
Electronic Spectroscopy ◽  
Salmonella Typhi ◽  
Schiff Base Ligands ◽  
No Donor

The condensation reactions of biacetyl with orthohydroxyaniline and 2-aminobenzoic acid to form bidendate NO donor Schiff bases were studied. The prepared Schiff base ligands were further utilized for the formation of metal chelates having the general formula [ML2.2H2O] where M = Co(II), Ni(II), Cu(II) and Zn(II) and L = HL1 and HL2. These new compounds were characterized by conductance measurements, magnetic susceptibility measurements, elemental analysis, and IR, 1H-NMR and electronic spectroscopy. Both Schiff base ligands were found to have a mono-anionic bidentate nature and octahedral geometry was assigned to all metal complexes. All the complexes contained coordinated water which was lost at 141-160 ?C. These compounds were also screened for their in-vitro antibacterial activity against four bacterial species, namely; Escherichia coli, Staphylococcus aureus, Salmonella typhi and Bacillus subtillis. The metal complexes were found to have greater antibacterial activity than the uncomplexed Schiff base ligands.

Synthesis of α-Aminoalkyl Phosphonate Derivatives of Resveratrol as Potential Antitumour Agents

2008 ◽  
Vol 61 (6) ◽  
pp. 472 ◽  
Author(s):  
Lei Shi ◽  
Xian-Feng Huang ◽  
Zhen-Wei Zhu ◽  
Huan-Qiu Li ◽  
Jia-Yu Xue ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Line ◽  
Tumour Cell Line ◽  
Partial Synthesis ◽  
Antitumour Agents ◽  
Inhibition Concentration ◽  
Ic50 Values ◽  
Epidermoid Tumour ◽  
Derivatives Of

Several α-aminoalkyl phosphonate derivatives of resveratrol were first prepared by partial synthesis from resveratrol. Antitumour activities of the synthesized compounds were determined against a human nasopharyngeal epidermoid tumour cell line KB and a human normal cell line L02 in vitro. The results indicated that these compounds showed good cytotoxic activity against KB but weak cytotoxic activity against L02. Compounds 5c and 5d showed significant cytotoxic activity against KB, with median inhibition concentration (IC50) values of 0.4 μM and 0.9 μM, respectively. On the basis of the biological results, the structure–activity relationship is discussed concisely. The potent antitumour activities shown by 5c and 5d make these resveratrol phosphonate derivatives of great interest for further investigations.

scholarly journals New Schiff bases of 2-(quinolin-8-yloxy)acetohydrazide and their Cu(ii), and Zn(ii) metal complexes: their in vitro antimicrobial potentials and in silico physicochemical and pharmacokinetics properties

2020 ◽  
Vol 18 (1) ◽  
pp. 591-607
Author(s):  
Hanan A. Althobiti ◽  
Sami A. Zabin
Keyword(s):  
Schiff Base ◽  
Metal Complexes ◽  
In Silico ◽  
Gram Negative Bacteria ◽  
Bacterial Strains ◽  
Schiff Base Ligands ◽  
Gram Positive ◽  
Gram Negative ◽  
Gi Absorption

AbstractThe purpose of this work was to prepare Schiff base ligands containing quinoline moiety and using them for preparing Cu(ii) and Zn(ii) complexes. Four bidentate Schiff base ligands (SL1–SL4) with quinoline hydrazine scaffold and a series of mononuclear Cu(ii) and Zn(ii) complexes were successfully prepared and characterized. The in vitro antibacterial and antifungal potential experimentation revealed that the ligands exhibited moderate antibacterial activity against the Gram-positive bacterial types and were inactive against the Gram-negative bacteria and the fungus strains. The metal complexes showed some enhancement in the activity against the Gram-positive bacterial strains and were inactive against the Gram-negative bacteria and the fungus strains similar to the parent ligands. The complex [Cu(SL1)2] was the most toxic compound against both Gram-positive S. aureus and E. faecalis bacteria. The in silico physicochemical investigation revealed that the ligand SL4 showed highest in silico absorption (82.61%) and the two complexes [Cu(SL4)2] and [Zn(SL4)2] showed highest in silico absorption with 56.23% for both compounds. The in silico pharmacokinetics predictions showed that the ligands have high gastrointestinal (GI) absorption and the complexes showed low GI absorption. The ligands showed a good bioavailability score of 0.55 where the complexes showed moderate to poor bioavailability.

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