The influence of cationic tetrapropoxycalix[4]arene choline on protolytic equilibria of acid-base indicators in aqueous solutions

Mchedlov‐Petrossyan, Nikolay O.; Vodolazkaya, Natalya A.; Vilkova, L.N.; Soboleva, Olga; Kutuzova, L. V.; Rodik, Roman V.; Miroshnichenko, S. I.; Drapaylo, A.B.

doi:10.1016/j.molliq.2008.02.009

Cited by 18 publications

(31 citation statements)

References 28 publications

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“…For the reference compound CX3, the CMC value in water, 3.7 10 À4 m, was somewhat lower than that reported previously (2.5 10 À3 m) when using the dynamic light scattering (DLS) method. [30] As expected, calixarenes bearing longer alkyl chains showed much lower values of CMC in water, 4.8 10 À5 and 1.0 10 À5 m, for CX8 and CX8im, respectively (Table 1). Thus, the longer alkyl chains in calixarene derivatives favor stronger hydrophobic interactions than the shorter ones, thus promoting self-assembly at lower concentrations.…”

Section: Resultssupporting

confidence: 71%

“…[31] However, its studies showed that it forms micellar structures only at rather high concentrations (CMC near 2.5 mm) in water. [30] To improve the self-assembling ability of this molecule, we extended the length of the alkyl chains from propyl to octyl. Moreover, as a polar head group, we used either the original hydroxyethylammonium group or a N-methyl-imidazolium group, which shows high affinity to DNA.…”

Section: Resultsmentioning

confidence: 99%

“…[23,30] We expected that the new calixarenes CX8 and CX8im, bearing longer alkyl chains would also form micelles, but at lower CMC. To evaluate the CMC of these calixarenes we used a well-established method based on pyrene fluorescence.…”

Section: Resultsmentioning

confidence: 99%

“…[23,30] However, within this family of compounds only short-chain modified calixarenes have been reported, showing relatively high critical micellar concentrations (CMC) in the millimolar range. [30] Our present results show that calixarenes bearing long octyl chains can form micelles of 6 nm diameter at micromolar concentrations, which can further condense DNA into small and stable particles of about 50 nm diameter. These particles, which probably contain a single DNA molecule, exhibit promising transfection properties in cell culture.…”

Section: Introductionmentioning

confidence: 99%

“…[30] Figure 3. Fluorescence spectra of Nile Red in buffer (g) and bound to micelles of CX8 (10 mm) (a) or CX8/CT-DNA complexes (N/P = 2) (c).…”

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confidence: 99%

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Virus‐Sized DNA Nanoparticles for Gene Delivery Based on Micelles of Cationic Calixarenes

Rodik¹,

Klymchenko²,

Jain³

et al. 2011

Chemistry A European J

103

108

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Macrocyclic amphiphilic molecules based on calix[4]arenes are highly attractive for controlled supramolecular assembly of DNA into small nanoparticles, since they present a unique conical architecture and can bear multiple charged groups. In the present work, we synthesized new amphiphilic calixarenes bearing cationic groups at the upper rim and alkyl chains at the lower rim. Their self-assembly in aqueous solution was characterized by fluorescent probes, fluorescence correlation spectroscopy, dynamic light scattering, gel electrophoresis and atomic force microscopy. We found that calixarenes bearing long alkyl chains (octyl) self-assemble into micelles of 6 nm diameter at low critical micellar concentration and present the unique ability to condense DNA into small nanoparticles of about 50 nm diameter. In contrast, the short-chain (propyl) analogues that cannot form micelles at low concentrations failed to condense DNA, giving large polydisperse DNA complexes. Thus, formation of small DNA nanoparticles is hierarchical, requiring assembly of calixarenes into micellar building blocks that further co-assemble with DNA into small virus-sized particles. The latter showed much better gene transfection efficiency in cell cultures relative to the large DNA complexes with the short-chain analogues, which indicates that gene delivery of calixarene/DNA complexes depends strongly on their structure. Moreover, all cationic calixarenes studied showed low cytotoxicity. Thus, this work presents a two-step hierarchical assembly of small DNA nanoparticles for gene delivery based on amphiphilic cone-shaped cationic calixarenes.

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Section: Resultssupporting

confidence: 71%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…[30] Figure 3. Fluorescence spectra of Nile Red in buffer (g) and bound to micelles of CX8 (10 mm) (a) or CX8/CT-DNA complexes (N/P = 2) (c).…”

mentioning

confidence: 99%

See 3 more Smart Citations

Virus‐Sized DNA Nanoparticles for Gene Delivery Based on Micelles of Cationic Calixarenes

Rodik¹,

Klymchenko²,

Jain³

et al. 2011

Chemistry A European J

103

108

View full text Add to dashboard Cite

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

Ukhatskaya

Kurkov

Matthews

et al. 2013

Journal of Pharmaceutical Sciences

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Surface activity and self-aggregation ability of three cationic quaternized aminocalix[4]arenes

Ukhatskaya

Kurkov

Rodik³

et al. 2013

J Incl Phenom Macrocycl Chem

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The self-aggregation ability of three amphiphilic cationic calix[4]arenes possessing four quaternary amino groups (aminoCAs) was investigated using a variety of methods. All of the studied compounds possess high aggregation ability. Their critical aggregation concentration (CAC) values in water are in the 0.0009-0.04 % (w/v) concentration range. Several size populations of aggregates were detected by DLS for all three CAs, and restructuring of aggregates was observed to be dependent on concentration. Particles formed above CAC were attributed to formation of vesicular structures (vesicles). The coexistence of other type of aggregates (presumably micelles) with vesicles was observed in the aqueous solution of CAs 2 and 3 from concentrations of 0.5 and 0.8 % (w/v), respectively. The filtration procedure was found to be a significant factor since the obtained data from filtered and unfiltered samples was different. The particle sizes obtained by TEM measurements were somewhat correlated with the DLS data for unfiltered CAs solutions. An analysis of the aggregate composition was undertaken by a size-exclusion method using semi-permeable cellophane membranes with different MWCO. A negative deviation from linearity of permeability flux profile starting from 0.8 % (w/v) concentration of donor phase indicated that the fraction of large aggregates at this point is significant enough that the molecules could not easily permeate through the membranes. © 2013 Springer Science+Business Media Dordrecht

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The influence of cationic tetrapropoxycalix[4]arene choline on protolytic equilibria of acid-base indicators in aqueous solutions

Cited by 18 publications

References 28 publications

Virus‐Sized DNA Nanoparticles for Gene Delivery Based on Micelles of Cationic Calixarenes

Virus‐Sized DNA Nanoparticles for Gene Delivery Based on Micelles of Cationic Calixarenes

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

Surface activity and self-aggregation ability of three cationic quaternized aminocalix[4]arenes

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