Physicochemical characterization and in vitro biological evaluation of solid compounds from furazolidone-based cyclodextrins for use as leishmanicidal agents

Carvalho, Suzana Gonçalves; Cipriano, Daniel F.; Freitas, Jair C. C.; Schettino, Miguel A.; Yapuchura, Enrique R.; Teles, Carolina Bioni Garcia; Gouveia, Aurileya de Jesus; Rodrigues, Rossana Lott; Zanini, Marcos Santos; Villanova, Janaína Cecília Oliveira

doi:10.1007/s13346-020-00841-1

Cited by 14 publications

(6 citation statements)

References 91 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The melting point of FZL is

= 527.9 ± 0.2 K (

= 529.4 ± 0.2 K). Analysis of the FZL melting temperature according to the literature showed a good agreement with the results of the present work [ 23 , 24 ]. According to the TG curves, the melting and degradation processes for both compounds are accompanied by the one-stage mass loss: ~52% for NFT and ~55% for FZL.…”

Section: Resultssupporting

confidence: 90%

A Combined Experimental and Theoretical Study of Nitrofuran Antibiotics: Crystal Structures, DFT Computations, Sublimation and Solution Thermodynamics

et al. 2021

View full text Add to dashboard Cite

Single crystal of furazolidone (FZL) has been successfully obtained, and its crystal structure has been determined. Common and distinctive features of furazolidone and nitrofurantoin (NFT) crystal packing have been discussed. Combined use of QTAIMC and Hirshfeld surface analysis allowed characterizing the non-covalent interactions in both crystals. Thermophysical characteristics and decomposition of NFT and FZL have been studied by differential scanning calorimetry (DSC), thermogravimetric analysis (TG) and mass-spectrometry. The saturated vapor pressures of the compounds have been measured using the transpiration method, and the standard thermodynamic functions of sublimation were calculated. It was revealed that the sublimation enthalpy and Gibbs energy of NFT are both higher than those for FZL, but a gain in the crystal lattice energy of NFT is leveled by an entropy increase. The solubility processes of the studied compounds in buffer solutions with pH 2.0, 7.4 and in 1-octanol was investigated at four temperatures from 298.15 to 313.15 K by the saturation shake-flask method. The thermodynamic functions of the dissolution and solvation processes of the studied compounds have been calculated based on the experimental data. Due to the fact that NFT is unstable in buffer solutions and undergoes a solution-mediated transformation from an anhydrate form to monohydrate in the solid state, the thermophysical characteristics and dissolution thermodynamics of the monohydrate were also investigated. It was demonstrated that a combination of experimental and theoretical methods allows performing an in-depth study of the relationships between the molecular and crystal structure and pharmaceutically relevant properties of nitrofuran antibiotics.

show abstract

“…The melting point of FZL is

= 527.9 ± 0.2 K (

Section: Resultssupporting

confidence: 90%

A Combined Experimental and Theoretical Study of Nitrofuran Antibiotics: Crystal Structures, DFT Computations, Sublimation and Solution Thermodynamics

et al. 2021

View full text Add to dashboard Cite

show abstract

“…However, in the reviewed literature, singular cases of 2D WISE (two-dimensional WIde-line SEparation), 2D HETCOR (two-dimensional HETeronuclear chemical shift CORrelation experiments), GCOSY (Gradient Correlation SpectroscopY), and GHSQC (Gradient Heteronuclear Single Quantum Coherence Spectroscopy) application are present, the latter two in one article [ 102 ]. WISE has been used in cases when an especially high risk of unseparated signals in a spectrum was predicted [ 56 ]. The 2D WISE NMR approach was applied for analysis of site-specific dynamics of the CD-including polymers: polyrotaxanes [ 19 ].…”

Section: Ssnmr Approaches For the Analysis Of Cyclodextrin Complexesmentioning

confidence: 99%

“…An interesting example is the publication regarding the CD-furazolidone complex [ 56 ], where all the above-mentioned reasons can be found: thanks to ssNMR, complex formation has been proven, lyophilization has been found more effective than knitting, CD-guest molar ratio has been suggested, and the observed signal-broadening effect pointed out the loss of crystallinity upon complexation.…”

Section: Ssnmr Applicability For Analysis Of the Cyclodextrin Complexesmentioning

confidence: 99%

A Review of Applications of Solid-State Nuclear Magnetic Resonance (ssNMR) for the Analysis of Cyclodextrin-Including Systems

Mazurek

Szeleszczuk

2023

IJMS

View full text Add to dashboard Cite

Cyclodextrins, cyclic oligosaccharides composed of five or more α-D-glucopyranoside units linked by α-1,4 glycosidic bonds, are widely used both in their native forms as well as the components of more sophisticated materials. Over the last 30 years, solid-state nuclear magnetic resonance (ssNMR) has been used to characterize cyclodextrins (CDs) and CD-including systems, such as host–guest complexes or even more sophisticated macromolecules. In this review, the examples of such studies have been gathered and discussed. Due to the variety of possible ssNMR experiments, the most common approaches have been presented to provide the overview of the strategies employed to characterize those useful materials.

show abstract

“…Many compound classes have exhibited activity in vitro against promastigotes or amastigotes, including thiophene-indole hybrids [82,83], 2-amino-thiophene derivatives [84], pyrazolothiophene hybrids [85], camphor hydrazone derivatives [86], tetroxanes [87], isoxazole derivatives and tetrahydrofuran neolignans [88], piperine derivatives [89], naphthotriazolyl-4-oxoquinolines [90], furazolidone-based cyclodextrins [91], 2-pyrimidinyl-hydrazone and N-acylhydrazone derivatives [92], piperidine-benzodioxole derivatives [93], and methyl gallate [94]. In vivo studies of these compounds are required to elucidate their activity and safety profiles before clinical development can begin.…”

Section: Drug Discovery Targeting a Single Leishmania Speciesmentioning

confidence: 99%

Drug Discovery for Cutaneous Leishmaniasis: A Review of Developments in the Past 15 Years

Corman,

McNamara,

Bakowski

2023

Microorganisms

View full text Add to dashboard Cite

Leishmaniasis is a group of vector-borne, parasitic diseases caused by over 20 species of the protozoan Leishmania spp. The three major disease classifications, cutaneous, visceral, and mucocutaneous, have a range of clinical manifestations from self-healing skin lesions to hepatosplenomegaly and mucosal membrane damage to fatality. As a neglected tropical disease, leishmaniasis represents a major international health challenge, with nearly 350 million people living at risk of infection a year. The current chemotherapeutics used to treat leishmaniasis have harsh side effects, prolonged and costly treatment regimens, as well as emerging drug resistance, and are predominantly used for the treatment of visceral leishmaniasis. There is an undeniable need for the identification and development of novel chemotherapeutics targeting cutaneous leishmaniasis (CL), largely ignored by concerted drug development efforts. CL is mostly non-lethal and the most common presentation of this disease, with nearly 1 million new cases reported annually. Recognizing this unaddressed need, substantial yet fragmented progress in early drug discovery efforts for CL has occurred in the past 15 years and was outlined in this review. However, further work needs to be carried out to advance early discovery candidates towards the clinic. Importantly, there is a paucity of investment in the translation and development of therapies for CL, limiting the emergence of viable solutions to deal with this serious and complex international health problem.

show abstract

Physicochemical characterization and in vitro biological evaluation of solid compounds from furazolidone-based cyclodextrins for use as leishmanicidal agents

Cited by 14 publications

References 91 publications

A Combined Experimental and Theoretical Study of Nitrofuran Antibiotics: Crystal Structures, DFT Computations, Sublimation and Solution Thermodynamics

A Combined Experimental and Theoretical Study of Nitrofuran Antibiotics: Crystal Structures, DFT Computations, Sublimation and Solution Thermodynamics

A Review of Applications of Solid-State Nuclear Magnetic Resonance (ssNMR) for the Analysis of Cyclodextrin-Including Systems

Drug Discovery for Cutaneous Leishmaniasis: A Review of Developments in the Past 15 Years

Contact Info

Product

Resources

About