Study of inclusion complex of β-cyclodextrin and levofloxacin and its effect on the solution equilibria between gadolinium(III) ion and levofloxacin

Jelić, Ratomir; Tomović, Marina; Stojanović, Stefan; Joksović, Ljubinka; Jakovljević, Ivan; Đjurdjević, Predrag

doi:10.1007/s00706-015-1482-z

Cited by 22 publications

(19 citation statements)

References 29 publications

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“…We chose the model fluoroquinolone [ 37 , 40 , 43 , 44 , 45 ], levofloxacin and the promising adjuvant eugenol (clove oil) [ 46 , 47 , 48 ], as expected, which showed the effect of synergism, which would reduce the dosage of the main “poisonous” drug [ 49 , 50 , 51 ]. For these “cargos” to function, it is necessary to dissolve them by loading cyclodextrin into the tori and deliver them to the alveolar macrophages of the lungs (for example, intranasal or inhalation forms).…”

Section: Introductionmentioning

confidence: 99%

Spectroscopy Approach for Highly-Efficient Screening of Lectin-Ligand Interactions in Application for Mannose Receptor and Molecular Containers for Antibacterial Drugs

Zlotnikov

Kudryashova

2022

Pharmaceuticals

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Rational search of a ligand for a specific receptor is a cornerstone of a typical drug discovery process. However, to make it more “rational” one would appreciate having detailed information on the functional groups involved in ligand-receptor interaction. Typically, the 3D structure of a ligand-receptor complex can be built on the basis of time-consuming X-ray crystallography data. Here, a combination of FTIR and fluorescence methods, together with appropriate processing, yields valuable information about the functional groups of both the ligand and receptor involved in the interaction, with the simplicity of conventional spectrophotometry. We have synthesized the “molecular containers” based on cyclodextrins, polyethyleneimines (PEI) or spermine with mannose-rich side-chains of different molecular architecture (reticulated, star-shaped and branched) with variable parameters to facilitate delivery to alveolar macrophages. We have shown that synthetic mannose-rich conjugates are highly affine to the model mannose receptor ConA: Kd ≈ 10−5–10−7 M vs. natural ligand trimannoside (10−5 M). Further, it was shown that molecular containers effectively load levofloxacin (dissociation constants are 5·10−4–5·10−6 M) and the eugenol adjuvant (up to 15–80 drug molecules for each conjugate molecule) by including them in the cyclodextrins cavities, as well as by interacting with polymer chains. Promising formulations of levofloxacin and its enhancer (eugenol) in star-shaped and polymer conjugates of high capacity were obtained. UV spectroscopy demonstrated a doubling of the release time of levofloxacin into the external solution from the complexes with conjugates, and the effective action time (time of 80% release) was increased from 0.5 to 20–70 h. The synergy effect of antibacterial activity of levofloxacin and its adjuvants eugenol and apiol on Escherichia coli was demonstrated: the minimum effective concentration of the antibiotic was approximately halved.

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Section: Introductionmentioning

confidence: 99%

Spectroscopy Approach for Highly-Efficient Screening of Lectin-Ligand Interactions in Application for Mannose Receptor and Molecular Containers for Antibacterial Drugs

Zlotnikov

Kudryashova

2022

Pharmaceuticals

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“…Together, these two properties allow a host-guest interaction to form between the cyclodextrin and the hydrophobic drug that can be solubilized in aqueous media. 16 Cyclodextrins are generally regarded as safe (GRAS) by the Food and Drug Administration (FDA) for use as food additives and as a part of several major drug formulations. 17 …”

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confidence: 99%

Synthesis, characterization, in vitro SAR and in vivo evaluation of N,N′bisnaphthylmethyl 2-alkyl substituted imidazolium salts against NSCLC

DeBord

Southerland

Wagers

et al. 2017

Bioorganic & Medicinal Chemistry Letters

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Alkyl- and N,N′-bisnaphthyl-substituted imidazolium salts were tested in vitro for their anti-cancer activity against four non-small cell lung cancer cell lines (NCI–H460, NCI–H1975, HCC827, A549). All compounds had potent anticancer activity with 2 having IC50 values in the nanomolar range for three of the four cell lines, a 17-fold increase in activity against NCI-H1975 cells when compared to cisplatin. Compounds 1–4 also showed high anti-cancer activity against nine NSCLC cell lines in the NCI-60 human tumor cell line screen. In vitro studies performed using the Annexin V and JC-1 assays suggested that NCI-H460 cells treated with 2 undergo an apoptotic cell death pathway and that mitochondria could be the cellular target of 2 with the mechanism of action possibly related to a disruption of the mitochondrial membrane potential. The water solubilities of 1–4 was over 4.4 mg/mL using 2-hydroxypropyl-β-cyclodextrin as a chemical excipient, thereby providing sufficient solubility for systemic administration.

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“…The effect of β-CD on dissociation constants, Ka of levofloxacin, and stability constants of levofloxacin-gadolinium (III) complexes were checked. Also, gadolinium (III) distribution in human blood was showed with computer simulation [39].…”

Section: Cyclodextrins-antibacterial Drug Complexesmentioning

confidence: 99%

An update on cyclodextrins as drug vehicles for antimicrobial applications

Bülbül¹,

Eleftherıadou²,

Okur³

et al. 2020

jpt

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Cyclodextrins belong to cyclic oligosaccharides comprised of α-(1,4) linked glucopyranose groups. Their interesting supramolecular cavity-like structure can host active molecules providing a breeding ground for drug delivery systems. Cyclodextrins, due to their unique functional structure, can produce host-guest complexes with active ingredients, such as drugs, peptides, proteins, etc.; the complexes resulted from intramolecular interactions leading to stable molecules vehicles. Moreover, cyclodextrins are already applied in pharmaceutical industry applications since they can induce the solubility of lipophilic compounds and provide bioavailability and excellent safety profile and stability. In this review, the basic background for cyclodextrins and their current applications in the antimicrobial field are discussed. Besides, the antibacterial and antifungal-applications in the pharmaceutical field attract most researchers because of microbes' resistance. Regarding this, the most recent cyclodextrin inclusion complexes with antimicrobial and antifungal drugs are summarized in this article.

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Study of inclusion complex of β-cyclodextrin and levofloxacin and its effect on the solution equilibria between gadolinium(III) ion and levofloxacin

Cited by 22 publications

References 29 publications

Spectroscopy Approach for Highly-Efficient Screening of Lectin-Ligand Interactions in Application for Mannose Receptor and Molecular Containers for Antibacterial Drugs

Spectroscopy Approach for Highly-Efficient Screening of Lectin-Ligand Interactions in Application for Mannose Receptor and Molecular Containers for Antibacterial Drugs

Synthesis, characterization, in vitro SAR and in vivo evaluation of N,N′bisnaphthylmethyl 2-alkyl substituted imidazolium salts against NSCLC

An update on cyclodextrins as drug vehicles for antimicrobial applications

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