Synthesis, characterization, ADMET<i>, in vitro</i>and<i>in viv</i>o studies of mixed ligand metal complexes from a curcumin Schiff base and lawsone

Jeyaraman, Porkodi; Michael, Samuel; Johnson, Antonysamy; Raman, Natarajan

doi:10.1080/15257770.2020.1867865

Cited by 30 publications

(11 citation statements)

References 49 publications

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“…It was previously reported that therapeutic compounds are the substrate of five major isoforms, CYP1A2, CYP2C19, CYP2C9, CYP2D6, AND CYP3A4. All synthesized conjugates metabolized CYP3A4 both substrate and inhibitor, which renders the oxidation process and facilitates their excretion [36] . On the other hand, all conjugates failed to inhibit CYP2D6 (both substrate and inhibitor), a determinant in biotransformation processes.…”

Section: Resultsmentioning

confidence: 95%

“…All synthesized conjugates metabolized CYP3A4 both substrate and inhibitor, which renders the oxidation process and facilitates their excretion. [36] On the other hand, all conjugates failed to inhibit CYP2D6 (both substrate and inhibitor), a determinant in biotransformation processes. CYP2C19 is involved in the detoxification of potential carcinogens and was not inhibited by all conjugates.…”

Section: Structure Activity Relationship (Sar)mentioning

confidence: 98%

“…Blood-Brain Barrier (Log BB): is a hybrid parameter with a typical range of À 3.0 to + 1.2 that is determined by permeability, plasma, and brain tissue binding. [36] The log BB value of conjugates was in the range of À 0.924 to À 0.672. Plasma Protein Binding (PPB) and glycoprotein P (P-pg) substrate: The second important parameter, PPB showed the calculated percentage of conjugates bound to a protein.…”

Section: Structure Activity Relationship (Sar)mentioning

confidence: 99%

“…[34][35] Similarly, all conjugates indicated ChemistrySelect skin penetration with log Kp values which below À 2.7 (recommended to be less than À 2.5). [36] The distribution of the conjugates was assessed using the glycoprotein P (P-pg) substrate, blood-brain barrier (BBB), and plasma protein binding (PPB) factors. The parameters, BBB and PPB, are two of the important factors affecting the distribution of the compounds in the human body.…”

Section: Structure Activity Relationship (Sar)mentioning

confidence: 99%

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Steroid‐Hymecromone Conjugates with Improved Antiproliferative and Antimicrobial Potential: Synthesis, Biological Evaluation, and in silico ADME Prediction

Erdagi

2023

ChemistrySelect

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In this study, hymecromone with known therapeutic aspects was conjugated with steroids a class of natural products that widely exhibited broad biological functions. Cholic acid, diosgenin, cholesterol, DHEA, and testosterone were selected as steroid moiety, each of which has a different biological mechanism of action. This study focused on developing novel conjugates that can be used as multi‐targeted drugs for treating various diseases. All conjugates were evaluated in vitro for their antiproliferative and antimicrobial activities and discussed for the structure‐activity relationship. The conjugates 5 and 6 exhibited comparable cytotoxic effects to reference drugs against cancer cell lines (K562, MCF‐7, and HeLa) while showing no toxicity against healthy cells (L929). Conjugates 7 and 5 demonstrated antibacterial activity against Gram‐positive and Gram‐negative bacteria, with lower minimum inhibitory concentration (MIC) values than the standard ciprofloxacin drug. Conjugate 6, On the other hand, had the lowest MIC value against the fungus, comparable to that of the standard drug ketoconazole. The physicochemical and pharmacokinetic properties of conjugates were in silico computed and evaluated. Overall, the outputs of this study suggest that these conjugates have promising potential as therapeutic agents, offering a multi‐targeted approach for the treatment of various diseases.

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Section: Resultsmentioning

confidence: 95%

Section: Structure Activity Relationship (Sar)mentioning

confidence: 98%

Section: Structure Activity Relationship (Sar)mentioning

confidence: 99%

Section: Structure Activity Relationship (Sar)mentioning

confidence: 99%

See 2 more Smart Citations

Steroid‐Hymecromone Conjugates with Improved Antiproliferative and Antimicrobial Potential: Synthesis, Biological Evaluation, and in silico ADME Prediction

Erdagi

2023

ChemistrySelect

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“…Interestingly, the antimicrobial activity of curcumin can be further enhanced by exposure to light. However, to further increase the antimicrobial activity of curcumin, a complex with metal or curcumin nanoparticles was developed, which considerably increased its activity [48,49]. It has been observed that metal-curcumin-conjugated DNA complexes display a prolonged lag phase in bacterial growth curves of Escherichia coli and Bacillus subtilis [9], indicating their bacterial growth suppressing effects.…”

Section: Antimicrobialmentioning

confidence: 99%

Metal–Curcumin Complexes in Therapeutics: An Approach to Enhance Pharmacological Effects of Curcumin

Prasad

DuBourdieu²,

Srivastava³

et al. 2021

IJMS

127

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Curcumin, an active component of the rhizome turmeric, has gained much attention as a plant-based compound with pleiotropic pharmacological properties. It possesses anti-inflammatory, antioxidant, hypoglycemic, antimicrobial, neuroprotective, and immunomodulatory activities. However, the health-promoting utility of curcumin is constrained due to its hydrophobic nature, water insolubility, poor bioavailability, rapid metabolism, and systemic elimination. Therefore, an innovative stride was taken, and complexes of metals with curcumin have been synthesized. Curcumin usually reacts with metals through the β-diketone moiety to generate metal–curcumin complexes. It is well established that curcumin strongly chelates several metal ions, including boron, cobalt, copper, gallium, gadolinium, gold, lanthanum, manganese, nickel, iron, palladium, platinum, ruthenium, silver, vanadium, and zinc. In this review, the pharmacological, chemopreventive, and therapeutic activities of metal–curcumin complexes are discussed. Metal–curcumin complexes increase the solubility, cellular uptake, and bioavailability and improve the antioxidant, anti-inflammatory, antimicrobial, and antiviral effects of curcumin. Metal–curcumin complexes have also demonstrated efficacy against various chronic diseases, including cancer, arthritis, osteoporosis, and neurological disorders such as Alzheimer’s disease. These biological activities of metal–curcumin complexes were associated with the modulation of inflammatory mediators, transcription factors, protein kinases, antiapoptotic proteins, lipid peroxidation, and antioxidant enzymes. In addition, metal–curcumin complexes have shown usefulness in biological imaging and radioimaging. The future use of metal–curcumin complexes may represent a new approach in the prevention and treatment of chronic diseases.

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New homoleptic imine derivative of lawsone and its metal complexes: Preparation, characterization, in vitro and in silico biological investigation

Sheela,

Kumar,

Raman

2023

Applied Organom Chemis

Self Cite

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In this article, a Schiff base derivative has been prepared using 2‐hydroxy‐1,4‐naphthoquinone and 3‐amino‐1,2,4‐triazole, and consecutively, four metal complexes (Co(II), Ni(II), Cu(II) and Zn(II)) have been synthesized using this Schiff base derivative as precursor ligand. Characterization of the synthesized compounds are done by employing spectral techniques such as UV–vis, infrared (IR), nuclear magnetic resonance (NMR), mass and electron paramagnetic resonance (EPR). All these methods establish the existence of imine group and the octahedral geometry of the complexes. The synthesized complexes are evaluated for their DNA binding properties that confirm that the binding mode is intercalation. The bioactive ligand and its complexes also exhibit pronounced pharmacological activities such as antioxidant and antimicrobial activities against bacteria such as Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Salmonella typhi; fungi, namely, Aspergillus niger, Aspergillus flavus, Candida albicans and Rhizoctonia bataticola. Moreover, the compounds are examined for their density functional theory (DFT) studies using Gaussian 09 programme. Various reactivity descriptors are calculated based on the highest occupied molecular orbital–lowest unoccupied molecular orbital (HOMO‐LUMO) energies. Molecular docking is conducted with two different receptors 1BNA and 1HD2 proteins to get a wide knowledge on the in vitro biological examination and also the interaction of the compounds with different proteins.

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Synthesis, characterization, ADMET, in vitroandin vivo studies of mixed ligand metal complexes from a curcumin Schiff base and lawsone

Cited by 30 publications

References 49 publications

Steroid‐Hymecromone Conjugates with Improved Antiproliferative and Antimicrobial Potential: Synthesis, Biological Evaluation, and in silico ADME Prediction

Steroid‐Hymecromone Conjugates with Improved Antiproliferative and Antimicrobial Potential: Synthesis, Biological Evaluation, and in silico ADME Prediction

Metal–Curcumin Complexes in Therapeutics: An Approach to Enhance Pharmacological Effects of Curcumin

New homoleptic imine derivative of lawsone and its metal complexes: Preparation, characterization, in vitro and in silico biological investigation

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