Promising applications in drug delivery systems of a novel β-cyclodextrin derivative obtained by green synthesis

Garcı́a, Agustina; Leonardi, Darío; Lamas, María Celina

doi:10.1016/j.bmcl.2015.11.067

Cited by 16 publications

(19 citation statements)

References 36 publications

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“…β-CD spray-dried samples which were studied by multiple techniques [20]. The data support the formation of an equimolar inclusion complex with the aromatic ring partially inserted in the CD cavity and the CH3 group closer to the succinyl methylene groups [20]. However, DS is expected to influence guest-host interactions, as already reported on 2-hydroxyethyl--CD and 2-hydroxypropyl--CD used as hosts of poorly water-soluble drugs [21][22][23].…”

Section: Accepted Manuscriptsupporting

confidence: 55%

Section: Accepted Manuscriptmentioning

confidence: 85%

“…Succinyl-β-CD derivatives with DS 1.3 and 2.9 were obtained by green synthesis as previously reported [20]. For this purpose, succinic acid (8.12 mmol) was dissolved in water (0.8 mL); sodium hypophosphite monohydrate (0.58 mmol) and β-CD (1.16 mmol) were subsequently added.…”

Section: Synthesis Of Succinyl-β-cdmentioning

confidence: 99%

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Succinyl-β-cyclodextrin: Influence of the substitution degree on albendazole inclusion complexes probed by NMR

Priotti

Garcı́a

Leonardi

et al. 2018

Materials Science and Engineering: C

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Succinyl-β-CD derivatives were obtained by green synthesis with degrees of substitution (DS) 1.3 and 2.9. The spray-drying technique was used to obtain albendazole (ABZ):succinyl-β-CD inclusion complexes. Phase solubility diagrams indicated that both succinyl-β-CD derivatives formed 1:1 molar ratio ABZ complexes, but the complex with DS 2.9 has a lower formation constant. The presence of stable inclusion complexes in aqueous solution was confirmed by NMR. For both complexes the aromatic moiety is encapsulated into the host cavity. In the solid-state, C andN NMR spectral differences between ABZ and ABZ included in spray-dried systems showed that strong structural changes occurred in the systems. At least two different ABZ amorphous species were identified based on DS. ABZ species were stable over more than six months based on spectral data. Finally, the influence of DS in the number and type of the inclusion complexes was elucidated.

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Section: Accepted Manuscriptsupporting

confidence: 55%

Section: Accepted Manuscriptmentioning

confidence: 85%

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Succinyl-β-cyclodextrin: Influence of the substitution degree on albendazole inclusion complexes probed by NMR

Priotti

Garcı́a

Leonardi

et al. 2018

Materials Science and Engineering: C

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“…β-CD was donated by Roquette. Sβ-CD and C-β-CD were synthesized in our laboratory as described previously [36,37]. 4T1 cells were kindly provided by Dr. N. Zwirner (IBYME-CONICET), RPMI 1640 was purchased from Gibco (Waltham, Massachusetts, USA), and WST-1 (2-(4-Iodophenyl)-3-(4-nitrophenyl)-5-(2,4disulfophenyl)-2H-tetrazolium) reagent was from Sigma-Aldrich (St. Louis, MO, USA).…”

Section: Methodsmentioning

confidence: 99%

“…Despite their therapeutic efficacy, both ABZ and RBZ present poor aqueous solubility and limited absorption after oral administration. Pharmaceutical technology has developed several strategies to overcome solubility and absorption limitations of insoluble drugs such as solid dispersions [29], micellar formulations [30,31], nano-and microstructured systems [20,32,33], co-crystals [34], and cyclodextrin (CD) inclusion complexes [35][36][37][38][39].…”

Section: Introductionmentioning

confidence: 99%

Repositioning of Anti-parasitic Drugs in Cyclodextrin Inclusion Complexes for Treatment of Triple-Negative Breast Cancer

Priotti

Baglioni²,

Garcı́a

et al. 2018

AAPS PharmSciTech

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This e-offprint is for personal use only and shall not be self-archived in electronic repositories. If you wish to self-archive your article, please use the accepted manuscript version for posting on your own website. You may further deposit the accepted manuscript version in any repository, provided it is only made publicly available 12 months after official publication or later and provided acknowledgement is given to the original source of publication and a link is inserted to the published article on Springer's website. The link must be accompanied by the following text: "The final publication is available at link.springer.com". Abstract.Drug repositioning refers to the identification of new therapeutic indications for drugs already approved. Albendazole and ricobendazole have been used as anti-parasitic drugs for many years; their therapeutic action is based on the inhibition of microtubule formation. Therefore, the study of their properties as antitumor compounds and the design of an appropriate formulation for cancer therapy is an interesting issue to investigate. The selected compounds are poorly soluble in water, and consequently, they have low and erratic bioavailability. In order to improve their biopharmaceutics properties, several formulations employing cyclodextrin inclusion complexes were developed. To carefully evaluate the in vitro and in vivo antitumor activity of these drugs and their complexes, several studies were performed on a breast cancer cell line (4T1) and BALB/c mice. In vitro studies showed that albendazole presented improved antitumor activity compared with ricobendazole. Furthermore, albendazole:citrate-β-cyclodextrin complex decreased significantly 4T1 cell growth both in in vitro and in vivo experiments. Thus, new formulations for anti-parasitic drugs could help to reposition them for new therapeutic indications, offering safer and more effective treatments by using a well-known drug.

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Pharmacological Polarization of Tumor‐Associated Macrophages Toward a CXCL9 Antitumor Phenotype

Enbergs,

Halabi,

Goubet

et al. 2024

Advanced Science

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Tumor‐associated macrophages (TAM) are a diverse population of myeloid cells that are often abundant and immunosuppressive in human cancers. CXCL9Hi TAM has recently been described to have an antitumor phenotype and is linked to immune checkpoint response. Despite the emerging understanding of the unique antitumor TAM phenotype, there is a lack of TAM‐specific therapeutics to exploit this new biological understanding. Here, the discovery and characterization of multiple small‐molecule enhancers of chemokine ligand 9 (CXCL9) and their targeted delivery in a TAM‐avid systemic nanoformulation is reported. With this strategy, it is efficient encapsulation and release of multiple drug loads that can efficiently induce CXCL9 expression in macrophages, both in vitro and in vivo in a mouse tumor model. These observations provide a window into the molecular features that define TAM‐specific states, an insight a novel therapeutic anticancer approach is used to discover.

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Promising applications in drug delivery systems of a novel β-cyclodextrin derivative obtained by green synthesis

Cited by 16 publications

References 36 publications

Succinyl-β-cyclodextrin: Influence of the substitution degree on albendazole inclusion complexes probed by NMR

Succinyl-β-cyclodextrin: Influence of the substitution degree on albendazole inclusion complexes probed by NMR

Repositioning of Anti-parasitic Drugs in Cyclodextrin Inclusion Complexes for Treatment of Triple-Negative Breast Cancer

Pharmacological Polarization of Tumor‐Associated Macrophages Toward a CXCL9 Antitumor Phenotype

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