Probing the potency of triazole tethered Schiff base complexes and the effect of substituents on their biological attributes

Utthra, Ponnukalai Ponya; Raman, Natarajan

doi:10.1016/j.ijbiomac.2018.05.009

Cited by 13 publications

(3 citation statements)

References 63 publications

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“…In this regard, the Schiff bases and their metal complexes play an important role in the bioinorganic chemistry due to their structural diversity and wide spectrum of their biological activities. A number of copper and silver complexes with Schiff bases have been already studied for antibacterial activity [4][5][6][7][8][9][10][11][12][13][14]. Actually, there is not a drug that incorporates a copper in their structure, but is available only one product with silver, silver sulfadiazine (SSD).…”

Section: Introductionmentioning

confidence: 99%

Silver(I) and copper(I) complexes with a Schiff base derived from 2-aminofluorene with promising antibacterial activity

Cifuentes-Vaca

Andrades-Lagos

Campanini-Salinas

et al. 2019

Inorganica Chimica Acta

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By reaction of 2-aminofluorene with 2-pyridinecarboxaldehyde a new Schiff base (L) is obtained. The reaction of this ligand with Ag(I) and Cu(I) salts in different stoichiometry leads to the complexes [Ag(CF 3 SO 3)(L)PPh 3 ] (1) or [ML 2 ]A (M = Ag, Cu; A = CF 3 SO 3 , ClO 4 or BF 4). Structural characterization by X-ray crystallography has been carried out for complexes [AgL 2 ]ClO 4 (4) and [Ag(L)(PPh 3) 2 ](CF 3 SO 3) (6), which confirms the chelate nature of L and the presence of Ag•••H interactions between two molecules. The biological studies show that Schiff base L presents antibacterial activity in Gram-positive bacteria and E. coli. The coordination to silver increases this activity, but the formation of the copper complex does not generate significant changes. Highlights 1. The synthesis of a new Schiff base with fluorene is described. 2. Coordination to silver and copper complexes has been carried out

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Section: Introductionmentioning

confidence: 99%

Silver(I) and copper(I) complexes with a Schiff base derived from 2-aminofluorene with promising antibacterial activity

Cifuentes-Vaca

Andrades-Lagos

Campanini-Salinas

et al. 2019

Inorganica Chimica Acta

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“…www.nature.com/scientificreports www.nature.com/scientificreports/ Molecular docking studies. With a view to confirm and rationalize the experimental results, interaction of compound 31 with DNA (PDB ID: 1BNA) 24 has been investigated by molecular docking studies using Autodock 4.0 25 . Derivative 31 gave −11.1 Kcal/mol minimum binding energy on docking with DNA (Table S2).…”

Section: Physicochemical Properties Evaluation Significant Pharmacokmentioning

confidence: 99%

Synthesis, cytotoxicity, pharmacokinetic profile, binding with DNA and BSA of new imidazo[1,2-a]pyrazine-benzo[d]imidazol-5-yl hybrids

Singh

Luxami

Paul

2020

Sci Rep

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Novel derivatives possessing imidazo[1,2-a]pyrazine and 1H-benzo[d]imidazole scaffolds were synthesized using Suzuki-Miyaura cross-coupling reactions. In vitro anticancer activities against NCI-60 cancer cell panels were tested at 10 µM concentration. The best results were obtained from substitution of two 1-cyclohexyl-1H-benzo[d]imidazole groups present at C-6 and C-8 positions of imidazo[1,2-a] pyrazine (31). Compound 31 was found to be cytotoxic against 51 cell lines and cytostatic against 8 cell lines with broad range of growth inhibitions (−98.48 to 98.86%). GI 50 value of compound 31 was found in the range of 0.80-2.87 µM for 59 human cancer cell lines at five-dose concentration levels. DNA binding study of potent compound 31 was suggested that this compound was intercalated into DNA base pairs with binding constant of 1.25 × 10 4 M −1. Compound 31 showed effective binding with bovine serum albumin (BSA) and presented binding constant value of 3.79 ×10 4 M-1. Pharmacokinetic studies revealed that all compounds are following Lipinski's rule of five and expected to be orally active. Cancer is one of the major reasons for death globally. Millions of people suffer or die from cancer each year, and there is no particular good medication available at present 1. Cancer has significant economic impact, which is increasing gradually. In the field of cancer treatment, chemists have great challenges to discover new and efficient compounds with strong and broad-spectrum anticancer activity. Heterocyclic ring systems play significant role in the discovery of novel bioactive substances due to their minimal side effects and effective at small doses. Heterocyclic moieties are widely present in various natural bioactive compounds 2. Undesirable side effects, toxicity, drug resistance, and low bioavailability are some of the major known problems for currently available anticancer agents 3. Therefore, there is an urgent need for the discovery of more efficient and selective anticancer agent. The biological potential of these heterocycles towards cancer cells has been stated with diverse mechanism of action. Most of the anticancer candidates bind with DNA double-strand and interfere with replication and transcription, thus, interrupt DNA function and alter the cell division. These candidates show interaction between adjacent base pairs or bind with grooves of DNA. These candidates share similar structural features, for example, the presence of planarity in structure, which can help the molecule to bind with DNA through insertion between base-pairs. The basic chain connected with these heterocyclic moieties plays a significant role in the selectivity and affinity 4. Due to their high affinity, the discovery of novel DNA intercalator for cancer therapy is a crucial goal in the medicinal chemistry. These intercalators comprise anthracyclines 5,6 (e.g. doxorubicin and mitoxantrone), ellipticine 7 and acridine derivatives (e.g. amsacrine) 8 , used in the cancer therapy of acute leukemia, breast, and ovarian cancers. On account of r...

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“…Today, cancer has achieved the second highest death rate in the world, behind heart disease, making it one of the deadliest diseases due to the uncontrolled proliferation of cell growth and the capability to spread to essential organs. Current treatment protocols are not always effective, are hurting, and generate chronic disorder for the victims, thus generating the imperative demand for putative medications that are health-friendly and reduce adverse negative impacts [ 1 ]. Every year, about 13.2 million people worldwide die of cancer, and an estimated 21.4 million additional cases will occur by 2030, which is also expected to overtake those of communicable diseases in the next decade [ 2 , 3 ].…”

Section: Introductionmentioning

confidence: 99%

Comprehensive Assessment of Biomolecular Interactions of Morpholine‐Based Mixed Ligand Cu(II) and Zn(II) Complexes of 2,2′‐Bipyridine as Potential Anticancer and SARS‐CoV‐2 Agents: A Synergistic Experimental and Structure‐Based Virtual Screening

Sakthikumar

Krause

Isamura

2022

Bioinorganic Chemistry and Applications

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A new class of pharmacologically active mixed-ligand complexes (1a-2a) [MII(L)2 (bpy)], where L = 2-(4-morpholinobenzylideneamino)phenol), bpy = 2,2′-bipyridine, MII = Cu (1a), and Zn (2a), were assigned an octahedral geometry by analytical and spectral measurements. Gel electrophoresis showed that complex (1a) demonstrated the complete DNA cleavage mediated by H2O2. The overall DNA-binding constants observed from UV-vis, fluorometric, hydrodynamic, and electrochemical titrations were in the following sequence: (1a) > (2a) > (HL), which suggests that the complexes might intercalate DNA, a possibility that is further supported by the biothermodynamic characteristics. The binding constant results of BSA by electronic absorption and fluorometric titration demonstrate that complex (1a) exhibits the highest binding effectiveness among others, which means that all compounds could interact with BSA through a static approach, additionally supported by FRET measurements. Density FunctionalTheory (DFT) and molecular docking calculations were relied on to unveil the electronic structure, reactivity, and interacting capability of all substances with DNA, BSA, and SARS-CoV-2 main protease (Mpro). These observed binding energies fell within the following ranges: −7.7 to −8.6, −7.2 to −10.2, and −6.7 to −8.2 kcal/mol, respectively. The higher reactivity of the complexes compared to free ligand is supported by the Frontier MolecularOrbital (FMO) theory. The in vitro antibacterial, cytotoxic, and radical scavenging characteristics revealed that complex (1a) has the best biological efficacy compared to others. This is encouraged because all experimental findings are closely correlated with the theoretical measurements.

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Probing the potency of triazole tethered Schiff base complexes and the effect of substituents on their biological attributes

Cited by 13 publications

References 63 publications

Silver(I) and copper(I) complexes with a Schiff base derived from 2-aminofluorene with promising antibacterial activity

Silver(I) and copper(I) complexes with a Schiff base derived from 2-aminofluorene with promising antibacterial activity

Synthesis, cytotoxicity, pharmacokinetic profile, binding with DNA and BSA of new imidazo[1,2-a]pyrazine-benzo[d]imidazol-5-yl hybrids

Comprehensive Assessment of Biomolecular Interactions of Morpholine‐Based Mixed Ligand Cu(II) and Zn(II) Complexes of 2,2′‐Bipyridine as Potential Anticancer and SARS‐CoV‐2 Agents: A Synergistic Experimental and Structure‐Based Virtual Screening

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