Moulding calixarenes for biomacromolecule targeting

Abstract

After their successful use as a preorganized platform for the preparation of receptors for metal ions and small neutral molecules over the last 15 years, calixarenes are enjoying a renaissance of popularity as scaffolds for ligands that are able to efficiently and selectively target macromolecules such as proteins/enzymes, nucleic acids and lipids. This feature article summarizes the peculiar factors characterizing the calixarene structure and properties, as well as outlines the main rules that can be used to turn such macrocycles into efficient and successful ligands for these classes of biomacromolecules. Factors that affect the multivalent properties of calixarenes, such as the size, conformation and stereochemical presentation of binding groups or their amphiphilicity and hybrid character, are described in detail with the use of a few selected examples from the literature. Perspectives and applications of these ligands in bionanotechnology and nanomedicine, such as protein sensing and inhibition, gene-delivery, targeted drug-delivery and cell imaging, are also discussed.

Calix[4]arenes as Modulators of Energy-Dependent Cа2+- Accumulation and Functioning of the Electron Transport Chain in Smooth Muscle Mitochondria

“…У біохімічних і фізіологічних дослід-женнях останніх років значна увага при ді-ляється супрамолекулярним макроциклічним сполукам -калікс [4]аренам, а саме їх здат-ності модулювати перебіг катіон-транс-портувальних процесів в субклітинних струк турах [7]. У поле нашого зору увійшли калікс [4]арени -С-97, С-99, С-107, які мо-жуть впливати як на потенціал плазмалеми, у зв'язку з уабаїноподібним інгібуванням Na + ,К + -АТФазної активності, так і на потен-ціал внутрішньої мембрани мітохондрій клітин гладенького м'яза матки (міометрія).…”

New Amphiphilic Bowl-Shaped Receptors on the Basis of Calix[4]arenes in Cone Conformation: Synthesis, Self-Aggregation and Eosin Y Dye Binding

“…Solvents were purified according to standard methods. [11] p-tert-Butylcalix [4]arene, 5,17-ditert-butyl -11,23-dinitro-25,27-dibutyloxy-26,28-dihydroxycalix[4] arene (2) and N-propargyl-N,N,N-triethylammonium bromide were synthesized according to literature methods. [12][13][14] Microwave assisted reactions were carried out in the CEM Mars 5 Microwave Accelerated Reaction System.…”

“…We now report a new synthetic strategy for the synthesis of wide series of amphiphilic receptors through CuAAC reaction of calix [4]arene containing hydrophobic alkyl moieties on the lower rim and azide groups on the upper rim in cone configuration with several alkynes and study of self-aggregation of the synthesized bis-ammonium salt in aqueous media.…”

“…[1][2][3] Selective functionalization of both upper and lower rim in the cone conformation with maintaining the cavity for better host-guest interactions makes calixarenes one of the best platforms for the amphiphilic receptors design. The unique structure and a variety of stereoisomeric forms of calix [4]arene derivatives led to their wide applications in supramolecular chemistry. Their ability to form hostguest complexes and to bind both organic molecules and metal ions is successfully used in extraction; recognition of different substrates and as components of molecular devices.…”

“…Their ability to form hostguest complexes and to bind both organic molecules and metal ions is successfully used in extraction; recognition of different substrates and as components of molecular devices. [4][5][6] Furthermore, these macrocycles are indispensable in the design of biomimetic systems -artificial systems modeling at the molecular level or mimic the reaction and the processes occurring in living organisms. [7] The synthetic potential of calixarene platform can be essentially extended by click-chemistry.…”