Host-guest properties of new water-soluble calixarenes derived from p-(chloromethyl) calixarenes

Arimura, Takashi; Nagasaki, Takeshi; Shinkai, Seiji; Matsuda, Tsutomu

doi:10.1021/jo00277a003

Cited by 86 publications

(107 citation statements)

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“…22) Other anionic water-soluble derivatives containing nitro, 23) phosphonic acid, 24) and carboxyl 25) moieties emerged, and the first example of a cationic water-soluble calixarene was reported by Shinkai et al 26) Other cationic calixarenes contain tetraalkylammonium groups and primary amines. [27][28][29] Neutral water-soluble calixarenes have been synthesized with sulfonamides, 30) sugars, 31) and polyoxyethylene. 32) In the development of water-soluble calixarenes, some hydrophilic-modified calixarenes were found to exhibit amphipathy and self-assemble into nano-aggregates in aqueous solutions, which were suitable for the delivery of hydrophobic antitumor drugs.…”

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confidence: 99%

Preparation and Characterization of Amphiphilic Calixarene Nanoparticles as Delivery Carriers for Paclitaxel

Zhao

Wang

Han

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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Two types of amphoteric calix[n]arene carboxylic acid (CnCA) derivative, i.e., calix[6]arene hexa-carboxylic acid (C 6 HCA) and calix[8]arene octo-carboxylic acid (C 8 OCA), were synthesized by introducing acetoxyls into the hydroxyls of calix[n]arene (n 6, 8). C 6 HCA and C 8 OCA nanoparticles (NPs) were prepared successfully using the dialysis method. CnCA NPs had regular spherical shapes with an average diameter of 180-220 nm and possessed negative charges of greater than 30 mV. C 6 HCA and C 8 OCA NPs were stable in 4.5% bovine serum albumin solutions and buffers (pH 5-9), with a low critical aggregation concentration value of 5.7 mg·L 1 and 4.0 mg·L 1 , respectively. C 6 HCA and C 8 OCA NPs exhibited good paclitaxel (PTX) loading capacity, with drug loading contents of 7.5% and 8.3%, respectively. The overall in vitro release behavior of PTX from the CnCA NPs was sustained, and C 8 OCA NPs had a slower release rate compared with C 6 HCA NPs. These favorable properties of CnCA NPs make them promising nanocarriers for tumortargeted drug delivery.Key words calix[n]arene carboxylic acid; nanoparticle; paclitaxel; tumor therapy Paclitaxel (PTX) is a well-known anticancer drug that is used primarily to treat lung, breast and ovarian cancers. Similar to most anticancer drugs, its poor solubility in water limits the clinical applications of PTX. Taxol, a widely used clinical formulation of paclitaxel, requires the use of Cremphor-EL as a solubilizer, which has been known to cause serious problems, including hypersensitivity reactions, neurotoxicity, and nephrotoxicity.1,2) Moreover, the lack of selectivity of PTX results in significant toxicity to noncancerous cells and severely impacts patients' quality of life. Therefore, there is a dire need for the development of a novel formulation that improves the solubility of PTX and decreases its side effects.Among various alternatives, nano-sized drug delivery system (nano-DDS) is one of the best choices. Nano-DDS not only greatly enhances the solubility of PTX without side effects, but it also promotes intra-tumoral drug accumulation through the enhanced permeability and retention (EPR) effect.3,4) Many nano-DDSs of PTX have been reported, and some of them have been marketed. Abraxane, a nanosuspension of paclitaxel encapsulated in human albumin was approved by the Food and Drug Administration (FDA) in 2005 for the treatment of metastatic breast cancer.5) A liposomebased PTX formulation, Lipusu, has been applied for the treatment of ovarian cancer in China.6) In addition to these approved drugs, a number of PTX nano-DDSs, such as polymeric nanoparticles (NPs), 7-9) inorganic NPs, 10) nano-emulsions, 11) carbon nanotubes, 12) and nanogels, 13) have been reported in preclinical studies. Although these novel PTX nano-DDSs exhibit varying levels of success, methods for improving the safety, stability and specificity of nano-DDS still warrant further research.Calixarenes have been used as an important class of macrocyclic host molecules in supramolecular chemistry.14) Becaus...

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confidence: 99%

Preparation and Characterization of Amphiphilic Calixarene Nanoparticles as Delivery Carriers for Paclitaxel

Zhao

Wang

Han

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Calix[n]arenes TAC n A (n = 4, 6, and 8) were prepared as per the literature procedure [31,32]. All the synthesized compounds were identified by IR 1 H NMR and FAB Mass spectroscopy as well as elemental analysis.…”

Section: Experimental Methodsmentioning

confidence: 99%

Calix[n]arenes mediated phase‐transfer catalytic synthesis of purine derivatives

Sharma

Kumar

Sahu

et al. 2008

Int J of Chemical Kinetics

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A new route was designed to achieve the synthesis of purine derivatives under phase-transfer catalysis conditions using calix[n]arenes TAC n A (n = 4, 6, and 8) as phasetransfer catalyst for the first time in this particular type of synthesis. The compounds were synthesized in excellent yields (70%-80%) and the structures were established on the basis of consistent IR, 1 H NMR, FAB-Mass, and elemental analyses data. Their purity has been ascertained by chromatographic resolution using acetonitrile, methanol, and water (50:30:20, v/v) as eluenting system. Moreover, the kinetics of the reaction was studied and it was found to obey first-order kinetics. Effect of various parameters, namely, temperature, amount of catalyst, stirring speed, and so on was also investigated. C

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“…It is very interesting to question whether the inclusion of chromophoric guests, most importantly fluorescent dyes, can affect their photophysical properties and, potentially, lead to unprecedented effects and, ultimately, new applications. In fact, numerous investigations have dealt with variations of fluorescent properties upon complexation [31][32][33][34]. In most cases, the effects of inclusion complexation are satisfactorily understood in terms of (i) the relocation of the fluorophore into the more hydrophobic environment of the host cavities or (ii) the geometrical confinement of the chromophore within the host.…”

Section: Supramolecular Assemblies and Host Moleculesmentioning

confidence: 99%

“…Solvatochromic probes have, in fact, been previously employed to determine the polarity of solvents [55] or inside macrocyclic hosts [31], or to assess hydrogen bond donor properties of the environment [55]. 1-Anilinonaphthalene-8-sulfonate is an example for a polarity-sensitive probe that has been applied to cyclodextrins [32,33] and water-soluble calixarenes [34] (Fig. 1), providing evidence for a hydrophobic environment inside these hosts (similar to alcohol : water mixtures, but with calixarenes being more hydrophobic).…”

Section: Supramolecular Assemblies and Host Moleculesmentioning

confidence: 99%

Squeezing Fluorescent Dyes into Nanoscale Containers—The Supramolecular Approach to Radiative Decay Engineering

Nau

Hennig

Koner

2007

Springer Series on Fluorescence

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Host-guest properties of new water-soluble calixarenes derived from p-(chloromethyl) calixarenes

Cited by 86 publications

References 0 publications

Preparation and Characterization of Amphiphilic Calixarene Nanoparticles as Delivery Carriers for Paclitaxel

Preparation and Characterization of Amphiphilic Calixarene Nanoparticles as Delivery Carriers for Paclitaxel

Calix[n]arenes mediated phase‐transfer catalytic synthesis of purine derivatives

Squeezing Fluorescent Dyes into Nanoscale Containers—The Supramolecular Approach to Radiative Decay Engineering

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