Insights of 8-hydroxyquinolines: A novel target in medicinal chemistry

Gupta, Rohini; Luxami, Vijay; Paul, Kamaldeep

doi:10.1016/j.bioorg.2021.104633

Cited by 83 publications

(45 citation statements)

References 152 publications

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“…It is well known that 8-hydroxyquinoline and its derivatives manifest antibacterial, antifungal, and antiviral activities [ 91 , 92 , 93 ] and are of low toxicity to humans [ 94 ]. They have great potential in the development of new therapeutics for the treatment of bacterial and fungal diseases resistant to traditional chemotherapeutics, as well as for the treatment of some neurodegenerative diseases [ 95 ].…”

Section: Electrospun Fibrous Materials With Antifungal Activity Again...mentioning

confidence: 99%

Electrospun Polymer Materials with Fungicidal Activity: A Review

et al. 2022

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In recent years, there has been special interest in innovative technologies such as polymer melt or solution electrospinning, electrospraying, centrifugal electrospinning, coaxial electrospinning, and others. Applying these electrokinetic methods, micro- or nanofibrous materials with high specific surface area, high porosity, and various designs for diverse applications could be created. By using these techniques it is possible to obtain fibrous materials from both synthetic and natural biocompatible and biodegradable polymers, harmless to the environment. Incorporation of low-molecular substances with biological activity (e.g., antimicrobial, antifungal) is easily feasible. Moreover, biocontrol agents, able to suppress the development and growth of plant pathogens, have been embedded in the fibrous materials as well. The application of such nanotechnologies for the creation of plant protection products is an extremely promising new direction. This review emphasizes the recent progress in the development of electrospun fungicidal dressings and their potential to be applied in modern agriculture.

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Section: Electrospun Fibrous Materials With Antifungal Activity Again...mentioning

confidence: 99%

Electrospun Polymer Materials with Fungicidal Activity: A Review

et al. 2022

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“…8-Hydroxyquinoline (8HQ) presents an excellent ability to bind diverse metal ions and has been used in their gravimetric analysis and separation [ 6 ]. Additionally, it is considered a privileged structure for drug development due to its numerous reported biological activities [ 7 , 8 , 9 , 10 ]. Our hypothesis is that extending the coordination ability of 8HQ by attaching additional donor groups adjacent to the quinoline nitrogen will modify the properties of the metal-based complexes, increasing their stability and activity by the assembly of different bioactive organic moieties.…”

Section: Introductionmentioning

confidence: 99%

Liposomal Formulations of a New Zinc(II) Complex Exhibiting High Therapeutic Potential in a Murine Colon Cancer Model

Ribeiro

Albino

Ferreira

et al. 2022

IJMS

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Colorectal cancer is the second leading cause of cancer-related mortality. Many current therapies rely on chemotherapeutic agents with poor specificity for tumor cells. The clinical success of cisplatin has prompted the research and design of a huge number of metal-based complexes as potential chemotherapeutic agents. In this study, two zinc(II) complexes, [ZnL2] and [ZnL(AcO)], where AcO is acetate and L is an organic compound combining 8-hydroxyquinoline and a benzothiazole moiety, were developed and characterized. Analytical and spectroscopic studies, namely, NMR, FTIR, and UV-Vis allowed us to establish the complexes’ structures, demonstrating the ligand-binding versatility: tetradentate in [ZnL(AcO)] and bidentate in [ZnL2]. Complexes were screened in vitro using murine and human colon cancer cells cultured in 2D and 3D settings. In 2D cells, the IC50 values were <22 µM, while in 3D settings, much higher concentrations were required. [ZnL(AcO)] displayed more suitable antiproliferative properties than [ZnL2] and was chosen for further studies. Moreover, based on the weak selectivity of the zinc-based complex towards cancer cell lines in comparison to the non-tumorigenic cell line, its incorporation in long-blood-circulating liposomes was performed, aiming to improve its targetability. The resultant optimized liposomal nanoformulation presented an I.E. of 76% with a mean size under 130 nm and a neutral surface charge and released the metal complex in a pH-dependent manner. The antiproliferative properties of [ZnL(AcO)] were maintained after liposomal incorporation. Preliminary safety assays were carried out through hemolytic activity that never surpassed 2% for the free and liposomal forms of [ZnL(AcO)]. Finally, in a syngeneic murine colon cancer mouse model, while free [ZnL(AcO)] was not able to impair tumor progression, the respective liposomal nanoformulation was able to reduce the relative tumor volume in the same manner as the positive control 5-fluorouracil but, most importantly, using a dosage that was 3-fold lower. Overall, our results show that liposomes were able to solve the solubility issues of the new metal-based complex and target it to tumor sites.

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“…The 8-hydroxyquinoline derivatives exhibit diverse biological activities: antitumor, antiviral, neuroprotective, antimicrobial, and antifungal [ 18 , 19 , 20 ]. They also have low toxicity to humans.…”

Section: Introductionmentioning

confidence: 99%

Electrospun 5-Chloro-7-iodo-8-hydroxyquinoline (Clioquinol)-Containing Poly(3-hydroxybutyrate)/Polyvinylpyrrolidone Antifungal Materials Prospective as Active Dressings against Esca

et al. 2022

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Esca is a grapevine disease known for centuries which pertains to the group of so-called vine trunk diseases. Phaeomoniella chlamydospora (P. chlamydospora) and Phaeoacremonium aleophilum (P. aleophilum) are the two main fungal pathogens associated with esca. Novel fibrous materials with antifungal properties based on poly(3-hydroxybutyrate) (PHB), polyvinylpyrrolidone (PVP) and 5-chloro-7-iodo-8-hydroxyquinoline (clioquinol, CQ) were developed. One-pot electrospinning (“in” strategy) or electrospinning in conjunction with electrospraying (“on” strategy) were applied to obtain the materials. The materials’ morphology and their surface chemical composition were examined using scanning electron microscopy (SEM), X-ray photoelectron spectroscopy (XPS) and attenuated total reflection Fourier transform infrared spectroscopy (ATR-FTIR). CQ incorporated in the bulk of the fibers or in PVP particles deposited on the fibers was in the amorphous phase, which was confirmed by differential scanning calorimetry (DSC) and X-ray diffraction analysis (XRD). The in vitro release of CQ depended on the composition of the electrospun materials and on their design. The performed microbiological screening revealed that, unlike the non-loaded mats, the fibrous mats loaded with CQ were effective in inhibiting the growth of the pathogenic P. chlamydospora and P. aleophilum fungi. Therefore, the created materials are promising as active dressings for grapevine protection against esca.

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Insights of 8-hydroxyquinolines: A novel target in medicinal chemistry

Cited by 83 publications

References 152 publications

Electrospun Polymer Materials with Fungicidal Activity: A Review

Electrospun Polymer Materials with Fungicidal Activity: A Review

Liposomal Formulations of a New Zinc(II) Complex Exhibiting High Therapeutic Potential in a Murine Colon Cancer Model

Electrospun 5-Chloro-7-iodo-8-hydroxyquinoline (Clioquinol)-Containing Poly(3-hydroxybutyrate)/Polyvinylpyrrolidone Antifungal Materials Prospective as Active Dressings against Esca

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