Positive variation of the MRI signal via intramolecular inclusion complexation of a C-2 functionalized β-cyclodextrin

Zgani, Ibrahim; Idriss, Hicham; Barbot, Cécile; Djedaïni‐Pilard, Florence; Petit, Samuel; Hubert‐Roux, Marie; Estour, François; Gouhier, Géraldine

doi:10.1039/c6ob02583h

Cited by 12 publications

(5 citation statements)

References 48 publications

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“…The same team studied the effect of the formation of inclusion complex on the MRI signal on similar structures. 90 They observed a signicant increase in MRI signal (+58% and +21% for perhydroxylated and permethylated CDs) during the formation of inter-and intramolecular inclusion complexes using a exible linker with hydrocynnamic acid and an adamantane acid molecules (Fig. 31).…”

Section: Acetate and Iminoacetate Ligandsmentioning

confidence: 94%

Cyclodextrins: promising scaffolds for MRI contrast agents

2021

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Section: Acetate and Iminoacetate Ligandsmentioning

confidence: 94%

Cyclodextrins: promising scaffolds for MRI contrast agents

2021

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“…The interaction of host and guest was determined by many technologies when hydrocinnamic and adamantine carboxylic acids were used as guest molecules [55]. Meanwhile, a γ -CD derivative, which was modified with pyrene carbonyl in DMF, exhibited remarkable excimer emission and formed a stable inclusion complex with 1-borneol [56].…”

Section: Two-position Modificationmentioning

confidence: 99%

Selective modifications at the different positions of cyclodextrins: a review ofstrategies

Liu¹,

Zhang²,

Tian³

2020

Turk J Chem

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Cyclodextrins (CDs) are natural, nontoxic, and biodegradable macrocyclic oligosaccharides. As supramolecular hosts, CDs have numerous applications in many aspects. However, nonsubstituted CDs have the disadvantages of solubility, unspecific recognition sites, and weak interactions with guest molecules. Therefore, new CD-based derivatives are successfully designed, synthesized, and widely used in various fields. This contribution outlines the research progress in CD derivatives. In particular, this review emphasizes the synthesis and application of CDs modified through functionalization in definite positions, random substitution, and reconstruction of the skeleton. At the end of this review, a summary and future directions are presented.Recently CDs have a wide range of applications in cancer treatment owing to the particularity of their different ring spaces. CDs could increase the solubility of anticancer flavonoids, such as curcumin and quercetin, which are very poorly soluble in water [41,42]. A novel CD complex of curcumin had superior attributes compared with free curcumin for cellular uptake and for antiproliferative and antiinflammatory activities, preferentially aggregating in the pancreas and possessing strong anticancer activity against pancreatic or tubulin surface cancer cells [41,43]. Similarly, the solubility of quercetin could be improved linearly with the increasing molality of CDs at the same temperature [44]. Selective modifications of CDs at definite positions Monosubstitution of CDsWhen natural CDs are unsuitable for a particular application, chemists begin to modify CDs to allow their derivatives to perform their intended function. To pursue an increasingly perfect structure, the idea of monosubstituted CD derivatives was conceived. However, the direct synthesis of single-isomer CD derivatives is challenging [45]. A single substitution has three possible isomers (Figure 2).

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“…6-O-Peracetylated-β-CDs were also synthesized to coordinate Gd 3+ in the axis of the macrocycle [30][31][32]. In particular, the effect of the second hydration sphere has been studied using the native and permethylated CDs.…”

Section: Introductionmentioning

confidence: 99%

Gd3+ Complexes Conjugated to Cyclodextrins: Hydroxyl Functions Influence the Relaxation Properties

et al. 2021

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In the search for improvement in the properties of gadolinium-based contrast agents, cyclodextrins (CDs) are interesting hydrophilic scaffolds with high molecular weight. The impact of the hydrophilicity of these systems on the MRI efficacy has been studied using five β-CDs substituted with DOTA or TTHA ligands which, respectively, allow for one (q = 1) or no water molecule (q = 0) in the inner coordination sphere of the Gd3+ ion. Original synthetic pathways were developed to immobilize the ligands at C-6 position of various hydroxylated and permethylated β-CDs via an amide bond. To describe the influence of alcohol and ether oxide functions of the CD macrocycle on the relaxation properties of the Gd3+ complexes, 1H Nuclear Magnetic Relaxation Dispersion (NMRD) profiles, and 17O transverse relaxation rates have been measured at various temperatures. The differences observed between the hydroxylated and permethylated β-CDs bearing non-hydrated GdTTHA complexes can be rationalized by a second sphere contribution to the relaxivity in the case of the hydroxylated derivatives, induced by hydrogen-bound water molecules around the hydroxyl groups. In contrast, for the DOTA analogs the exchange rate of the water molecule directly coordinated to the Gd3+ is clearly influenced by the number of hydroxyl groups present on the CD, which in turn influences the relaxivity and gives rise to a very complex behavior of these hydrophilic systems.

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Positive variation of the MRI signal via intramolecular inclusion complexation of a C-2 functionalized β-cyclodextrin

Cited by 12 publications

References 48 publications

Cyclodextrins: promising scaffolds for MRI contrast agents

Cyclodextrins: promising scaffolds for MRI contrast agents

Selective modifications at the different positions of cyclodextrins: a review ofstrategies

Gd3+ Complexes Conjugated to Cyclodextrins: Hydroxyl Functions Influence the Relaxation Properties

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