Toward novel antiparasitic formulations: Complexes of Albendazole desmotropes and β-cyclodextrin

Chattah, Ana K.; Pfund, Laura Y.; Zoppi, Ariana; Longhi, Marcela Raquel; Garnero, Claudia

doi:10.1016/j.carbpol.2017.01.098

Cited by 21 publications

(12 citation statements)

References 22 publications

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“…The photomicrograph of pure ABZ (A) revealed the presence of crystalline particles with Figure 6. Albendazole as raw material was previously characterized by our team [19] and the obtained spectra was in good agreement with the existent literature data [2,20,21] ar shape, rough surface and a strong tendency to aggregate. The pure PU (B) appeared material with plain surfaces.…”

Section: Morphological Characterizationsupporting

confidence: 88%

“…Figure 6. Albendazole as al was previously characterized by our team [19] and the obtained spectra was in g ent with the existent literature data [2,20,21]. The main characteristic peaks observed in ectrum were assigned as follows: 3323.35 cm −1 , N-H stretching in carbamate; 2956.87 cm −1 cm −1 , C-H aliphatic stretching vibration; 2663.69 cm −1 -NH intramolecular in imidaz 9 cm −1 , bending vibration of C=O bond in carbamate; 1635 cm −1 , C=C aromatic and -N-H ou ne bending in benzimidazole; 1523.76 cm −1 stretching vibration of C=N group.…”

Section: Morphological Characterizationsupporting

confidence: 66%

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Solid Polymeric Nanoparticles of Albendazole: Synthesis, Physico-Chemical Characterization and Biological Activity

et al. 2020

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Albendazole is a benzimidazole derivative with documented antitumor activity and low toxicity to healthy cells. The major disadvantage in terms of clinical use is its low aqueous solubility which limits its bioavailability. Albendazole was incorporated into stable and homogeneous polyurethane structures with the aim of obtaining an improved drug delivery system model. Spectral and thermal analysis was used to investigate the encapsulation process and confirmed the presence of albendazole inside the nanoparticles. The in vitro anticancer properties of albendazole encapsulated in polyurethane structures versus the un-encapsulated compound were tested on two breast cancer cell lines, MCF-7 and MDA-MB-231, in terms of cellular viability and apoptosis induction. The study showed that the encapsulation process enhanced the antitumor activity of albendazole on the MCF-7 and MDA-MB-23 breast cancer lines. The cytotoxic activity manifested in a concentration-dependent manner and was accompanied by changes in cell morphology and nuclear fragmentation.

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Section: Morphological Characterizationsupporting

confidence: 88%

Section: Morphological Characterizationsupporting

confidence: 66%

Solid Polymeric Nanoparticles of Albendazole: Synthesis, Physico-Chemical Characterization and Biological Activity

et al. 2020

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“…In particular, inclusion of drugs into cyclodextrin (CD) cavities is well-known to not only alleviate problems related to their low solubility [22], but also to increase their chemical stability [23] and, often, enhance their pharmacological properties [24]. To cite some recent examples, CDs favor the intestinal absorption of curcumin [25], decrease the degradation rate of benzylpenicillin [26], allow the intraoral release of fluconazole [27] and albendazol [28] and increase the solubility and stability of the multitarget neuroprotective agent ITH-12674 [29]. The pharmacokinetic profile of the potential anticancer agent phenoxodiol was notably improved through β-cyclodextrin complex formation, thereby leading to reduced side effects [30].…”

Section: Introductionmentioning

confidence: 99%

Enhanced Stability and Bioactivity of Natural Anticancer Topoisomerase I Inhibitors through Cyclodextrin Complexation

et al. 2021

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The use of cyclodextrins as drug nano-carrier systems for drug delivery is gaining importance in the pharmaceutical industry due to the interesting pharmacokinetic properties of the resulting inclusion complexes. In the present work, complexes of the anti-cancer alkaloids camptothecin and luotonin A have been prepared with β-cyclodextrin and hydroxypropyl-β-cyclodextrin. These cyclodextrin complexes were characterized by nuclear magnetic resonance spectroscopy (NMR). The variations in the 1H-NMR and 13C-NMR chemical shifts allowed to establish the inclusion modes of the compounds into the cyclodextrin cavities, which were supported by docking and molecular dynamics studies. The efficiency of the complexation was quantified by UV-Vis spectrophotometry and spectrofluorimetry, which showed that the protonation equilibria of camptothecin and luotonin A were drastically hampered upon formation of the inclusion complexes. The stabilization of camptothecin towards hydrolysis inside the cyclodextrin cavity was verified by the quantitation of the active lactone form by reverse phase liquid chromatography fluorimetric detection, both in basic conditions and in the presence of serum albumin. The antitumor activity of luotonin A and camptothecin complexes were studied in several cancer cell lines (breast, lung, hepatic carcinoma, ovarian carcinoma and human neuroblastoma) and an enhanced activity was found compared to the free alkaloids, particularly in the case of hydroxypropyl-β-cyclodextrin derivatives. This result shows that the cyclodextrin inclusion strategy has much potential towards reaching the goal of employing luotonin A or its analogues as stable analogues of camptothecin.

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“…Therefore, the increment of the aqueous solubility and dissolution rate of ABZ implies a great challenge to achieve a more efficient treatment of hydatidosis. In this sense, different technologies were used to increase the solubility/dissolution rate of ABZ, such as: (i) solid dispersions (Castro et al, 2010, Jiménez de los Santos et al, 2017, Kohri et al, 1999, Martinez-Marcos et al, 2016), (ii) complexation with β-cyclodextrins (Chattah et al, 2017, Evrard et al, 2002, García et al, 2014, Palomares-Alonso et al, 2010) and acyclic cucurbit[n]uril molecular containers (Ma et al, 2012), (iii) co-griding with various excipients by jet-mill (Vogt et al, 2008), (iv) extrusion/spheronization (Ibrahim and Al-Anazi, 2013), (v) emulsification/solvent evaporation methods (Abulaihaiti et al, 2015, Souza and Marchetti, 2012), (vi) spray-drying (García et al, 2013b, García et al, 2013a, Ibrahim et al, 2014, Priotti et al, 2017), vii) high pressure homogenization combined with spray-drying (Paredes et al, 2016), (viii) solvent recrystallization and spherical agglomeration (Thakur et al, 2015), (ix) encapsulation in liposomes (Haitao et al, 2016, Li et al, 2015, Panwar et al, 2010) and (x) nanoformulations (Movahedi et al, 2017). In general, these techniques require numerous production stages, several materials and organics solvents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of mesoporous SBA-15 and SBA-16 as carriers to improve albendazole dissolution rate

Adrover

Pedernera

Bonne

et al. 2020

Saudi Pharmaceutical Journal

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Albendazole (ABZ, anti-parasitic active pharmaceutical ingredient) is a crystalline low water-soluble drug, thus the dissolution rate in gastrointestinal fluids is limited. Consequently, the improvement of the water solubility and dissolution rate of ABZ implies a great challenge for a more efficient treatment of hydatidosis. In this context, SBA-15 and SBA-16 ordered mesoporous silica materials were synthetized and loaded with ABZ. X-ray diffraction, FT-IR spectroscopy, nitrogen physisorption manometry, particle size distribution and scanning electronic microscopy were used to characterize unloaded and loaded materials (ABZ/SBA-15 and ABZ/SBA-16). The loaded ABZ amount in the carriers was estimated by elemental analysis. For the loaded materials, the drug solubility and release profile were evaluated. In addition, mathematical models were compared to explain the dissolution kinetics of ABZ from mesoporous solids. ABZ was successfully loaded into the mesopores. The amorphous state of the adsorbed ABZ was confirmed by differential scanning calorimetry that resulted in a notable increment in the dissolution rate compared to crystalline ABZ. Drug release behaviors were well simulated by the Weibull model for ABZ/SBA-15 and by the Gompertz function for pure ABZ and ABZ/SBA-16. The SBA-15 carrier exhibited the highest drug loading and dissolution rate becoming a promising material to improve ABZ bioavailability.

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Toward novel antiparasitic formulations: Complexes of Albendazole desmotropes and β-cyclodextrin

Cited by 21 publications

References 22 publications

Solid Polymeric Nanoparticles of Albendazole: Synthesis, Physico-Chemical Characterization and Biological Activity

Solid Polymeric Nanoparticles of Albendazole: Synthesis, Physico-Chemical Characterization and Biological Activity

Enhanced Stability and Bioactivity of Natural Anticancer Topoisomerase I Inhibitors through Cyclodextrin Complexation

Synthesis and characterization of mesoporous SBA-15 and SBA-16 as carriers to improve albendazole dissolution rate

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