Novel water-soluble tetrasulfonatomethylcalix[4]resorcinarenes

Two amphiphilic water-soluble sulfonatomethylated calix[4]resorcinarene derivatives were studied by various 1 H NMR techniques ( 1 H NMR titration, 2D NOESY, NMR diffusion measurements). The derivative with methyl moieties at the lower rim (1) was found to be nonaggregated in the range 0 -10 mM in aqueous solutions. Lengthening of the lower rim substituent to pentyl (2) results in self-aggregation of 2 in aqueous solutions with the aggregation number varying from 3 at 1 mM to 20 at 10 mM. The 2D NOESY 1 H NMR spectroscopy data reveal an unusual head-to-tail packing mode in aqueous solutions, resulting from the cooperative effect of weak hydrophobic interactions. Binding of guests (tetramethylammonium and N-methylpyridinium) results in additional stabilization of the aggregates whilst the head-to-tail packing mode of the aggregate is retained.

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“…The hosts 1 and 2 were synthesized as recently reported [40]. Tetramethylammonium chloride (3Cl) was commercially available from "Lancaster".…”

Section: Methodsmentioning

confidence: 99%

Head-to-tail Aggregates of Sulfonatomethylated Calix[4]resorcinarene in Aqueous Solutions

Syakaev

Mustafina

Elistratova

et al. 2008

Supramolecular Chemistry

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“…Sulfonated calix[4]resorcinarenes SC(4)RC4 and SC(4)RC7 were prepared from the parent calix[4]resorcinarenes C(4)RC4 and C(4) RC7 using established procedures [22,32]. In brief, concentrated hydrochloric acid (12.5 mL) was added dropwise to a solution of either n-pentanal (for C(4)RC4) or n-octanal (for C(4)RC7) (90 mmol) and resorcinol (90 mmol) in ethanol (75 mL).…”

Section: Synthesis Of Sulfonated Calix[4]resorcinarenesmentioning

confidence: 99%

“…Kazakova et al first reported the synthesis of three sulfonated calix[4]resorcinarenes and their formation of 1:1 complexes with amino acids in aqueous media [22]. The group later reported a comparative study into the interactions of sulfonated calix[4]resorcinarenes bearing alkyl chains of either 1 carbon (methyl group) or 5 carbons (pentyl) on the lower rim with small molecules capable of multiple non-covalent interactions in aqueous media [23].…”

Section: Introductionmentioning

confidence: 99%

Investigation into Drug Solubilisation Potential of Sulfonated Calix[4]Resorcinarenes

Hoskins¹,

Papachristou²

2016

J Nanomed Nanotechnol

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“…Tetramethylenesulfonatocalix [4]resorcinarenes SCA1 and SCA2 were synthesized according to the procedure described earlier in ref 17. MY and MO were from Sigma-Aldrich (Moscow, Russia) and used as received.…”

Section: Methodsmentioning

confidence: 99%

Investigation of Tetramethylenesulfonated Calix[4]resorcinarene Interactions with Azo Dyes in Aqueous Solution

et al. 2010

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The interaction of a macrocycle's aggregates with a guest molecule has special interest due to the double role, both of macrocycle cavity and self-associates, in the binding of the guests. Here, we report on the interactions of nonaggregated methyl-substituted (SCA1) and aggregated penthyl-substituted (SCA2) tetramethylenesulfonated calix[4]resorcinarenes with pH indicators methyl yellow (MY) and methyl orange (MO) in aqueous solutions. It was found that the pH of aqueous solutions of SCA1 and SCA2 depends on their concentration; besides, variation of the concentration of SCA1 and SCA2 results in a shift of the absorption maxima and of pH-sensitive azo dyes. Association of the marocycles with azo dyes was demonstrated to follow a proton-transfer mechanism accompanied by protonation of the dyes; it was found that excess of the macrocycle in solution with the universal buffer background shifts the pK(a) values and stabilizes the protonated form of the dyes. Consideration of interactions of small dye molecules with large molecular associates, containing both individual and multimolecule binding sites, gives a closer approximation of synthetic biomimetics to their natural prototypes.

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Novel water-soluble tetrasulfonatomethylcalix[4]resorcinarenes

Cited by 77 publications

References 12 publications

Head-to-tail Aggregates of Sulfonatomethylated Calix[4]resorcinarene in Aqueous Solutions

Head-to-tail Aggregates of Sulfonatomethylated Calix[4]resorcinarene in Aqueous Solutions

Investigation into Drug Solubilisation Potential of Sulfonated Calix[4]Resorcinarenes

Investigation of Tetramethylenesulfonated Calix[4]resorcinarene Interactions with Azo Dyes in Aqueous Solution

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