Acyclic Cucurbit[<i>n</i>]uril Dendrimers

Sigwalt, David; Ahlbrand, Sarah E.; Zhang, Mingming; Vinciguerra, Brittany; Briken, Volker; Isaacs, Lyle

doi:10.1021/acs.orglett.5b03145

Cited by 5 publications

(3 citation statements)

References 53 publications

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“…Therefore, the intervention of CB[7] can help reduce the side effects of PEI, and it will not affect the efficiency of gene delivery. In addition, Sigwalt et al also proposed that dendrimer gene vectors consisting of acyclic CB derivatives can display higher gene transfection rates …”

Section: Applications Of Cb Homologuesmentioning

confidence: 99%

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Cucurbituril-Oriented Nanoplatforms in Biomedical Applications

Cheng

Luo

Liu

et al. 2020

ACS Appl. Bio Mater.

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Cucucrbituril (CB) belongs to a family of macrocycles that are easily accessible. Their structural specificity provides excellent molecular recognition capabilities, with the ability to be readily chemically modified. Because of these properties, researchers have found CB to be a useful molecular carrier for delivering drug molecules and therapeutic biomolecules. Their significance lies in the fact that CB not only increases the solubility and stability of an encapsulated guest but also provides the possibility to achieve targeted delivery of the guest molecule. Therefore, the emergence of CB undoubtedly provides opportunities for the development of targeted drug delivery in an era where intelligent drugs have attracted considerable attention. It has also been found that CB can enhance fluorescent dyes, allowing the preparation of biosensors with enhanced sensitivity for use in clinical settings. In the present review, the acquisition, properties, and structural modifications of CB are first comprehensively described, and then the value of this macrocycle in applications within the medical field is discussed. In addition, we have also summarized patent applications of CB in this field over recent years, aiming to illustrate the current status of developments of this molecule. Finally, we discuss the challenges faced by CB in the medical field and future trends in its development.

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Section: Applications Of Cb Homologuesmentioning

confidence: 99%

“…In addition, Sigwalt et al also proposed that dendrimer gene vectors consisting of acyclic CB derivatives can display higher gene transfection rates. 173 Therefore, CB has potential value in improving gene transfection efficiency and providing targeted gene therapy, representing a new method in this regard.…”

Section: Applications Of Cb Homologuesmentioning

confidence: 99%

Cucurbituril-Oriented Nanoplatforms in Biomedical Applications

Cheng

Luo

Liu

et al. 2020

ACS Appl. Bio Mater.

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“…Based on this observation, we recently prepared cationic acyclic cucurbit[n]uril dendrimers and demonstrated their ability to bind to and compact plasmid DNA although, unfortunately, gene transfection ability was quite modest. 28 Previous supramolecular researchers have shown that polycationic receptors are capable of recognizing nucleotide anions in aqueous solution due to electrostatic and other non-covalent interactions. 29 Within the CB[n] field, bambusurils and related compounds are known to be potent receptors for anions in water.…”

Section: Introductionmentioning

confidence: 99%

Cationic acyclic cucurbit[n]uril-type containers: synthesis and molecular recognition toward nucleotides

Sigwalt

Zavalij

Isaacs

2016

Supramolecular Chemistry

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We report the synthesis of M2NH3 which is a tetracationic analogue of our prototypical acyclic CB[n]-type molecular container M2. Both M1NH3 and M2NH3 possess excellent solubility in D2O and do not undergo intermolecular self-association processes that would impinge on their molecular recognition properties. Compounds M1NH3 and M2NH3 do, however, undergo an intramolecular self-complexation process driven by ion-dipole interactions between the ureidyl C=O portals and the OCH2CH2NH3 arms along with inclusion of one aromatic wall in its own hydrophobic cavity. The Ka values for M1NH3 and M2NH3 toward seven nucleotides were determined by 1H NMR titration and found to be quite modest (Ka in the 102 – 103 M−1 range) although M2NH3 is slightly more potent. The more highly charged guests (e.g. ATP) form stronger complexes with M1NH3 and M2NH3 than the less highly charged guest (e.g. ADP, AMP). The work highlights the dominant influence of the ureidyl C=O portals on the molecular recognition behavior of acyclic CB[n]-type receptors and suggests routes (e.g. more highly charged arms) to enhance their recognition behavior toward anions.

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