Encapsulation of Drug Molecules into Calix[n]arene Nanobaskets. Role of Aminocalix[n]arenes in Biopharmaceutical Field

Ukhatskaya, Elena V.; Kurkov, Sergey V.; Matthews, Susan E.; Loftsson, Þorsteinn

doi:10.1002/jps.23681

Cited by 58 publications

(64 citation statements)

References 145 publications

(295 reference statements)

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“…[1] [2] [3] [4] During recent years a new family of macrocyclic host molecules, the cucurbit[n]urils (CB[n], n = 5-8, 10,14) have received increasingly intensive attention and have been the subject of a number of reviews due to their potential application in drug formulation and delivery. [5] [6] CB[n] consists of n glycoluril units that are bridged by 2n methylene groups, forming a hydrophobic cavity and two identical carbonyl-lined portals with negative dipole potentials.…”

Section: Introductionmentioning

confidence: 99%

Developmental and organ-specific toxicity of cucurbit[7]uril: in vivo study on zebrafish models

et al. 2015

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The macrocyclic molecular container cucurbit [7]uril (CB[7]), the most water-soluble homologue in the cucurbit[n]uril family (n = 5-8, 10, 14), has been evaluated for its in vivo toxicity profile, including its developmental toxicity such as its effect on hatching, growth and survival, as well as its potential organ-specific toxicities such as cardiotoxicity, hepatotoxicity, and locomotion and behavioral toxicity, using zebrafish models. The results revealed that CB[7] has measureable cardiotoxicity and locomotion and behavioral toxicity at concentrations of ~500 µM or higher, and negligible developmental and hepatotoxicity at concentrations up to 750 µM, although extended exposure to CB[7] at the 500-750 µM concentration range induced the mortality of tested fish. These results demonstrate for the first time with live in vivo animal models that

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Section: Introductionmentioning

confidence: 99%

Developmental and organ-specific toxicity of cucurbit[7]uril: in vivo study on zebrafish models

et al. 2015

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“…The cucurbit[ n ]urils (CB[ n ], where n represents the number of glycoluril units),2, 3 cyclodextrins,4, 5 and calixarenes6, 7 are the three main types of macrocycles that have been examined as drug delivery vehicles.…”

Section: Introductionmentioning

confidence: 99%

The ex vivo neurotoxic, myotoxic and cardiotoxic activity of cucurbituril-based macrocyclic drug delivery vehicles

et al. 2014

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The cucurbituril family of drug delivery vehicles have been examined for their tissue specific toxicity using ex vivo models. Cucurbit[6]uril (CB[6]), cucurbit[7]uril (CB[7]) and the linear cucurbituril-derivative Motor2 were examined for their neuro-, myo- and cardiotoxic activity and compared with β-cyclodextrin. The protective effect of drug encapsulation by CB[7] was also examined on the platinum-based anticancer drug cisplatin. The results show that none of the cucurbiturils have statistically measurable neurotoxicity as measured using mouse sciatic nerve compound action potential. Cucurbituril myotoxicity was measured by nerve-muscle force of contraction through chemical and electrical stimulation. Motor2 was found to display no myotoxicity, whereas both CB[6] and CB[7] showed myotoxic activity via a presynaptic effect. Finally, cardiotoxicity, which was measured by changes in the rate and force of right and left atria contraction, was observed for all three cucurbiturils. Free cisplatin displays neuro-, myo- and cardiotoxic activity, consistent with the side-effects seen in the clinic. Whilst CB[7] had no effect on the level of cisplatin’s neurotoxic activity, drug encapsulation within the macrocycle had a marked reduction in both the drug’s myo- and cardiotoxic activity. Overall the results are consistent with the relative lack of toxicity displayed by these macrocycles in whole animal acute systemic toxicity studies and indicate continued potential of cucurbiturils as drug delivery vehicles for the reduction of the side effects associated with platinum-based chemotherapy.

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“…CAs possess several features that are desirable in functional DDSs: variable conformation, cavity dimensions suitable for small molecule encapsulation (3.0, 7.6, and 11.7 Å for calix[4]arene, calix[6]arene, and calix[8]arene, respectively), the ability to form complexes with larger molecules, the ability to combine ligands in chemical switches, and the ability to create ditopic ligands with binding sites at the rims . Moreover, many of the nitrogen‐containing CAs possess inherent antifungal, antibacterial, or antiviral activity . Not surprisingly, many studies describe the advantages of incorporating CAs into DDSs, though as of yet only a few report CA‐modified IONPs.…”

Section: Organic Macrocyclesmentioning

confidence: 99%

Design of Organic Macrocycle‐Modified Iron Oxide Nanoparticles for Drug Delivery

Škorjanc

Benyettou

Olsen

et al. 2017

Chemistry A European J

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Paul Ehrlich's vision of a "magic bullet" cure for disease inspires the modern design of nanocarriers whose purpose is to deliver drug cargo to specific sites in the body while circumventing endogenous immunological clearance mechanisms. Iron oxide nanoparticles (IONPs) have emerged as particularly promising nanocarriers because of their biodegradability, ability to be guided magnetically to sites of pathology, mediation of hyperthermic therapy, and imaging capabilities. In this review, we focus on the design and drug-delivery aspects of IONPs coated with organic macrocycles (crown ethers, cyclodextrins, calix[n]arenes, cucurbit[n]urils, or pillar[n]arenes), which, by means of reversible complexation, allow for the convenient loading and release of drug molecules. Macrocycles can be attached to IONPs indirectly or directly. Indirect attachment requires the use of small organic linking molecules or conjugation to shell materials. Direct attachment requires neither. We discuss in detail drug release from the macrocycles, highlighting mechanisms that depend on external stimuli such as changes in pH, the competitive binding of ions or small molecules, or the application of ultrasound or electromagnetic radiation.

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Encapsulation of Drug Molecules into Calix[n]arene Nanobaskets. Role of Aminocalix[n]arenes in Biopharmaceutical Field

Cited by 58 publications

References 145 publications

Developmental and organ-specific toxicity of cucurbit[7]uril: in vivo study on zebrafish models

Developmental and organ-specific toxicity of cucurbit[7]uril: in vivo study on zebrafish models

The ex vivo neurotoxic, myotoxic and cardiotoxic activity of cucurbituril-based macrocyclic drug delivery vehicles

Design of Organic Macrocycle‐Modified Iron Oxide Nanoparticles for Drug Delivery

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