Study on a host–guest interaction of hydroxypropyl-β-cyclodextrin with ofloxacin

Misiuk, Wieslawa; Jozefowicz, Magdalena

doi:10.1016/j.molliq.2014.12.029

Cited by 39 publications

(14 citation statements)

References 25 publications

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“…Moreover, the improved solubility of the hesperidin and hesperetin increased their antioxidant potential as well as the ability to inhibit cholinesterases. References [ 85 , 86 , 87 ] are cited in the Supplementary Materials .…”

Section: Discussionmentioning

confidence: 99%

Amorphous Inclusion Complexes: Molecular Interactions of Hesperidin and Hesperetin with HP-Β-CD and Their Biological Effects

Wdowiak

Rosiak

Tykarska

et al. 2022

IJMS

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This study aimed at obtaining hesperidin (Hed) and hesperetin (Het) systems with HP-β-CD by means of the solvent evaporation method. The produced systems were identified using infrared spectroscopy (FT-IR), X-ray powder diffraction (XRPD), and differential scanning calorimetry (DSC). Moreover, in silico docking and molecular dynamics studies were performed to assess the most preferable site of interactions between tested compounds and HP-β-CD. The changes of physicochemical properties (solubility, dissolution rate, and permeability) were determined chromatographically. The impact of modification on biological activity was tested in an antioxidant study as well as with regards to inhibition of enzymes important in pathogenesis of neurodegenerative diseases. The results indicated improvement in solubility over 1000 and 2000 times for Hed and Het, respectively. Permeability studies revealed that Hed has difficulties in crossing biological membranes, in contrast with Het, which can be considered to be well absorbed. The improved physicochemical properties influenced the biological activity in a positive manner by the increase in inhibitory activity on the DPPH radical and cholinoesterases. To conclude the use of HP-β-CD as a carrier in the formation of an amorphous inclusion complex seems to be a promising approach to improve the biological activity and bioavailability of Hed and Het.

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Section: Discussionmentioning

confidence: 99%

Amorphous Inclusion Complexes: Molecular Interactions of Hesperidin and Hesperetin with HP-Β-CD and Their Biological Effects

Wdowiak

Rosiak

Tykarska

et al. 2022

IJMS

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“…Furthermore, characterization of 17-AAG:HPβCD by infrared analysis (Szente, 1996 ) revealed that 17-AAG indeed established molecular interactions with HPβCD. The displacement or absence of typical bands in the spectra of pure 17-AAG compared to those of the 17-AAG:HPβCD could be interpreted as a shift in the hydrogen bonds between 17-AAG and cyclodextrin (Misiuk and Jozefowicz, 2015 ). Of note, hydroxyl groups for HPβCD might interact with the carbonyl group of 17-AAG, and shortening of 17-AAG bands confirms the formation of such interactions by hydrogen bondings (Misiuk and Jozefowicz, 2015 ).…”

Section: Discussionmentioning

confidence: 99%

“…The displacement or absence of typical bands in the spectra of pure 17-AAG compared to those of the 17-AAG:HPβCD could be interpreted as a shift in the hydrogen bonds between 17-AAG and cyclodextrin (Misiuk and Jozefowicz, 2015 ). Of note, hydroxyl groups for HPβCD might interact with the carbonyl group of 17-AAG, and shortening of 17-AAG bands confirms the formation of such interactions by hydrogen bondings (Misiuk and Jozefowicz, 2015 ). Therefore, these findings collectively indicate that changes on characteristic peaks of 17-AAG might be attributed to the inclusion of this drug within the HPβCD cavity.…”

Section: Discussionmentioning

confidence: 99%

Encapsulation of the HSP-90 Chaperone Inhibitor 17-AAG in Stable Liposome Allow Increasing the Therapeutic Index as Assessed, in vitro, on Leishmania (L) amazonensis Amastigotes-Hosted in Mouse CBA Macrophages

Petersen

Campos

Dantas

et al. 2018

Front. Cell. Infect. Microbiol.

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The current long-term treatment for leishmaniasis causes severe side effects and resistance in some cases. An evaluation of the anti-leishmanial potential of an HSP90-inhibitor, 17-allylamino-17-demethoxygeldanamycin (17-AAG), demonstrated its potent effect against Leishmania spp. in vitro and in vivo. We have previously shown that 17-AAG can kill L. (L) amazonensis promastigotes with an IC50 of 65 nM and intracellular amastigote at concentrations as low as 125 nM. As this compound presents low solubility and high toxicity in human clinical trials, we prepared an inclusion complex containing hydroxypropyl-β-cyclodextrin and 17-AAG (17-AAG:HPβCD) to improve its solubility. This complex was characterized by scanning electron microscopy, and X-ray diffraction. Liposomes-containing 17-AAG:HPβCD was prepared and evaluated for encapsulation efficiency (EE%), particle size, polydispersity index (PDI), pH, and zeta potential, before and after accelerated and long-term stability testing. An evaluation of leishmanicidal activity against promastigotes and intracellular amastigotes of L. (L) amazonensis was also performed. The characterization techniques utilized confirmed the formation of the inclusion complex, HPβCD:17-AAG, with a resulting 33-fold-enhancement in compound water solubility. Stability studies revealed that 17-AAG:HPβCD-loaded liposomes were smaller than 200 nm, with 99% EE. Stability testing detected no alterations in PDI that was 0.295, pH 7.63, and zeta potential +22.6, suggesting liposome stability, and suitability for evaluating leishmanicidal activity. Treatment of infected macrophages with 0.006 nM of 17-AAG:HPβCD or 17-AAG:HPβCD-loaded liposomes resulted in almost complete amastigote clearance inside macrophages after 48 h. This reduction is similar to the one observed in infected macrophages treated with 2 μM amphotericin B. Our results showed that nanotechnology and drug delivery systems could be used to increase the antileishmanial efficacy and potency of 17-AAG in vitro, while also resulting in reduced toxicity that indicates these formulations may represent a potential therapeutic strategy against leishmaniasis.

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“…The formulations proposed to enhance ofloxacin solubility are cocrystal and cyclodextrin complex. 39,40 Initially, such formulations were developed for ophthalmic topical preparations. Minocycline does not present aqueous solubility issues, 22 instead, newer strategies such as release modifications are aiming to improve its permeability.…”

Section: Drug Water Solubility Enhancementmentioning

confidence: 99%

Innovative drug delivery systems for leprosy treatment

Rocha¹,

Barbosa²,

Araujo³

et al. 2022

IJDVL

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Most drugs used for leprosy treatment have low water solubility, which limits their bioavailability. [14][15][16] Accordingly, administration of high doses required for reaching therapeutic blood levels aggravate adverse effects. Poor water solubility of these drugs may also result in their variable serum concentration, thus increasing the likelihood of bacterial resistance. [17][18][19] Additionally, rifampicin and clofazimine bioavailability may be limited, respectively, by stomach degradation and recrystallization depending on pH. 11,20,21 Unlike other drugs, minocycline is highly water soluble, its major limitation being intestinal permeability. 22 New formulations have been proposed for leprosy therapy to address these problems. This article aims to highlight the recent advances in drug delivery systems, which may be utilized to overcome these hurdles. Innovative pharmaceutical strategies towards enhancement of therapeutic efficacyRecent advances in drug delivery systems may overcome solubility impairment, common in pharmaceutical development. 23 The oral formulations proposed for multidrug therapy drugs are focused on two main strategies: increasing the apparent drug water solubility or modifying the drug release.Figure 1 summarizes the improvements and the expected results of multidrug therapy innovative formulations. In vitro evaluation, in vivo, and in silico performances of these preparations are provided in Table 1, if available, showing their potential therapeutic efficacy. As the following steps,

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Study on a host–guest interaction of hydroxypropyl-β-cyclodextrin with ofloxacin

Cited by 39 publications

References 25 publications

Amorphous Inclusion Complexes: Molecular Interactions of Hesperidin and Hesperetin with HP-Β-CD and Their Biological Effects

Amorphous Inclusion Complexes: Molecular Interactions of Hesperidin and Hesperetin with HP-Β-CD and Their Biological Effects

Encapsulation of the HSP-90 Chaperone Inhibitor 17-AAG in Stable Liposome Allow Increasing the Therapeutic Index as Assessed, in vitro, on Leishmania (L) amazonensis Amastigotes-Hosted in Mouse CBA Macrophages

Innovative drug delivery systems for leprosy treatment

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