Preparation of inclusion complex of perfluorocarbon compound with β-cyclodextrin for ultrasound contrast agent

Yao, Yanjie; Liu, Xunwei; Liu, Tian; Zhou, Juan; Zhu, Jun; Sun, Gang; He, Dannong

doi:10.1039/c4ra12205d

Cited by 18 publications

(5 citation statements)

References 27 publications

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“…34−36 The only example that used the BCD/PFC inclusion complex for an US-related application was recently published. 37 In this work, PFC used for US imaging (FC-77) was complexed with BCD at different PFC/BCD ratios. Even though US imaging potential of the complex was shown, the size of the complex was reaching the micron level depending on the PFC/BCD ratio, resulting in one PFC chain having two BCD molecules in a complex.…”

Section: Introductionmentioning

confidence: 99%

“…Later, more work was published, for environmental purposes, to show the pollutant removal potential of the inclusion complex because some perfluorinated compounds, especially perfluoroalkyl carboxylic acid and perfluoroalkylsulfonates, are considered as a new class of persistent organic pollutants. In this regard, inclusion complex formation between BCD and different perfluoroalkyl carboxylic acids and their physicochemical characterization have been deeply studied. − The only example that used the BCD/PFC inclusion complex for an US-related application was recently published . In this work, PFC used for US imaging (FC-77) was complexed with BCD at different PFC/BCD ratios.…”

Section: Introductionmentioning

confidence: 99%

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Development of Acoustically Active Nanocones Using the Host–Guest Interaction as a New Histotripsy Agent

et al. 2019

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Histotripsy is a noninvasive and nonthermal ultrasound ablation technique, which mechanically ablates the tissues using very short, focused, high-pressured ultrasound pulses to generate dense cavitating bubble cloud. Histotripsy requires large negative pressures (≥28 MPa) to generate cavitation in the target tissue, guided by real-time ultrasound imaging guidance. The high cavitation threshold and reliance on real-time image guidance are potential limitations of histotripsy, particularly for the treatment of multifocal or metastatic cancers. To address these potential limitations, we have recently developed nanoparticle-mediated histotripsy (NMH) where perfluorocarbon (PFC)-filled nanodroplets (NDs) with the size of ∼200 nm were used as cavitation nuclei for histotripsy, as they are able to significantly lower the cavitation threshold. However, although NDs were shown to be an effective histotripsy agent, they pose several issues. Their generation requires multistep synthesis, they lack long-term stability, and determination of PFC concentration in the treatment dose is not possible. In this study, PFC-filled nanocones (NCs) were developed as a new generation of histotripsy agents to address the mentioned limitations of NDs. The developed NCs represent an inclusion complex of methylated β-cyclodextrin as a water-soluble analog of β-cyclodextrin and perfluorohexane (PFH) as more effective PFC derivatives for histotripsy. Results showed that NCs are easy to produce, biocompatible, have a size <50 nm, and have a quantitative complexation that allows us to directly calculate the PFH amount in the used NC dose. Results further demonstrated that NCs embedded into tissue-mimicking phantoms generated histotripsy cavitation “bubble clouds” at a significantly lower transducer amplitude compared to control phantoms, demonstrating the ability of NCs to function as effective histotripsy agents for NMH.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Development of Acoustically Active Nanocones Using the Host–Guest Interaction as a New Histotripsy Agent

et al. 2019

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“…And b-CD can be readily available from the enzymatic degradation of starch, which makes it possess excellent biocompatibility. [29][30][31][32] Because of its hydrophilic exterior and hydrophobic cavity, b-CD can form inclusion complexes with a wide range of organic molecules possessing a suitable shape and size in water spontaneously, [33][34][35][36] which brings the possibility of removing organic molecules from polluted water. Thus, b-CD has become a unique structural unit in the design and preparation of adsorbents employed in water treatment.…”

Section: Introductionmentioning

confidence: 99%

Surface immobilization of β-cyclodextrin on hybrid silica and its fast adsorption performance of p-nitrophenol from the aqueous phase

Shen

Zhu

et al. 2015

RSC Adv.

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“…These include a study of the effects of SPFO monomer–micelle exchange rates in the presence of CD, binding constant determination using native and substituted CDs, , the selective association of CD to SPFO in the presence of other hydrocarbon surfactants, and a study of hydrophobic effects on complex formation . It was recently demonstrated that complexation of SPFO by CDs is important to the biomedical field since these perfluorocarbon surfactants can be used as oxygen carriers, imaging contrast agents, delivery agents for pulmonary drugs, and genes. − The fate, transport pathways, and persistence of such recalcitrant materials are poorly understood, partly due to their unique surface activity, chemical mobility, and stability when compared with their hydrocarbon counterparts. In spite of the numerous solution studies that have reported the structure of the complexes of β-CD and SPFO, similar studies in the solid state were not reported.…”

Section: Introductionmentioning

confidence: 99%

Counterion Anchoring Effect on the Structure of the Solid-State Inclusion Complexes of β-Cyclodextrin and Sodium Perfluorooctanoate

et al. 2015

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Characterization of the structure and dynamics for the solid inclusion complexes (ICs) between β-cyclodextrin (β-CD; host) and sodium perfluorooctanoate (SPFO; guest) was carried out using 1H/19F/13C NMR spectroscopy. The 1:1 and 2:1 β-CD/SPFO solid complexes were prepared by a modified dissolution method. Evidence for the formation of β-CD/SPFO ICs was provided by 13C DP (direct polarization) and CP (cross-polarization) solid-state NMR spectroscopy with magic angle spinning (MAS) at 20 kHz. The complexation-induced shifts (CIS) of 1H/19F/13C nuclei between solution and the solid state for β-CD/SPFO complexes and the closely related complexes of β-CD/PFOA (perfluorooctanoic acid) were compared. The counterion effect for SPFO and PFOA was observed according to their variable structure and binding as inclusion compounds with β-CD. The effect of sodium versus hydronium counterions on the structure and dynamics of inclusion complexes for these systems was supported by DSC, TGA, FT-IR, and powder X-ray diffraction (PXRD). Simulations of the CF3 19F NMR with MAS at 25 kHz and selected dipolar coupling strengths were utilized in conjunction with deconvolution analyses of the experimental CF3 lineshapes to probe the dynamic properties of SPFO and its complexes with β-CD. The dynamics of the guest are influenced by the host/guest binding geometry and the stoichiometry of the complex, where free rotation of the CF3 group as well as rotations of the C–F bonds occur. 19F DP/MAS NMR results and spin–lattice (T 1) and spin–spin (T 2) relaxation times in the laboratory frame at variable temperatures in the solid phase indicate that the dynamics of SPFO in β-CD/SPFO complexes are unique compared to those of PFOA in β-CD/PFOA complexes, due to the role of counterion effects of the guest.

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Preparation of inclusion complex of perfluorocarbon compound with β-cyclodextrin for ultrasound contrast agent

Abstract: A novel FC-77/β-CD inclusion complex was prepared and used as a ultrasound imaging contract to enhance the ultrasonic echo signal.

Cited by 18 publications

References 27 publications

Development of Acoustically Active Nanocones Using the Host–Guest Interaction as a New Histotripsy Agent

Development of Acoustically Active Nanocones Using the Host–Guest Interaction as a New Histotripsy Agent

Surface immobilization of β-cyclodextrin on hybrid silica and its fast adsorption performance of p-nitrophenol from the aqueous phase

Counterion Anchoring Effect on the Structure of the Solid-State Inclusion Complexes of β-Cyclodextrin and Sodium Perfluorooctanoate

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