Fostering protein–calixarene interactions: from molecular recognition to sensing

Prata, José V.; Barata, Patrícia D.

doi:10.1039/c5ra19887a

Cited by 15 publications

(5 citation statements)

References 62 publications

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“…These synthetic receptors were successfully designed for the selective recognition of cyt c , ,− allowing its nanomolar specific detection . Recently, p -sulfonato-calix[4]arene was shown to act as “molecular glue” for the assembly and crystallization of cyt c on SAM-modified Au electrodes (Figure ).…”

Section: Technological Applications Of Cytochrome Cmentioning

confidence: 77%

Multifunctional Cytochrome c: Learning New Tricks from an Old Dog

et al. 2017

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Cytochrome c (cyt c) is a small soluble heme protein characterized by a relatively flexible structure, particularly in the ferric form, such that it is able to sample a broad conformational space. Depending on the specific conditions, interactions, and cellular localization, different conformations may be stabilized, which differ in structure, redox properties, binding affinities, and enzymatic activity. The primary function is electron shuttling in oxidative phosphorylation, and is exerted by the so-called native cyt c in the intermembrane mitochondrial space of healthy cells. Under pro-apoptotic conditions, however, cyt c gains cardiolipin peroxidase activity, translocates into the cytosol to engage in the intrinsic apoptotic pathway, and enters the nucleus where it impedes nucleosome assembly. Other reported functions include cytosolic redox sensing and involvement in the mitochondrial oxidative folding machinery. Moreover, post-translational modifications such as nitration, phosphorylation, and sulfoxidation of specific amino acids induce alternative conformations with differential properties, at least in vitro. Similar structural and functional alterations are elicited by biologically significant electric fields and by naturally occurring mutations of human cyt c that, along with mutations at the level of the maturation system, are associated with specific diseases. Here, we summarize current knowledge and recent advances in understanding the different structural, dynamic, and thermodynamic factors that regulate the primary electron transfer function, as well as alternative functions and conformations of cyt c. Finally, we present recent technological applications of this moonlighting protein.

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Section: Technological Applications Of Cytochrome Cmentioning

confidence: 77%

Multifunctional Cytochrome c: Learning New Tricks from an Old Dog

et al. 2017

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“…The above reports stimulated our interest to screen the ability of a series of fluorescent calix [4]arene platforms we have synthesized in the past, mostly designed as probes for nitroaromatic explosives [21,22], nitroaliphatic explosives and taggants [23,24], nitroanilines [25,26], and proteins [27], as sensors of transition metal ions, specifically Cu(II), Pb(II) and Hg(II). A particular family of calixarene derivatives having an oxacyclophane (OCP) unit tethered to the narrow rim of a calixarene unit [25], either as single-molecules (Calix-OCP-2-CBZ; Chart 1a) [28] or integrated in a polymer (Calix-OCP-PPE; Chart 1b) [26] was envisaged as having potential for transition metal ions recognition.…”

Section: Introductionmentioning

confidence: 99%

Highly Sensitive and Selective Fluorescent Probes for Cu(II) Detection Based on Calix[4]arene-Oxacyclophane Architectures

et al. 2020

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A new topological design of fluorescent probes for sensing copper ion is disclosed. The calix[4]arene-oxacyclophane (Calix-OCP) receptor, either wired-in-series in arylene-alt-ethynylene conjugated polymers or standing alone as a sole molecular probe, display a remarkable affinity and selectivity for Cu(II). The unique recognition properties of Calix-OCP system toward copper cation stem from its pre-organised cyclic array of O-ligands at the calixarene narrow rim, which is kept in a conformational rigid arrangement by a tethered oxacyclophane sub-unit. The magnitude of the binding constants (Ka = 5.30 − 8.52 × 104 M−1) and the free energy changes for the inclusion complexation (−ΔG = 27.0 − 28.1 kJmol−1), retrieved from fluorimetric titration experiments, revealed a high sensitivity of Calix-OCP architectures for Cu(II) species. Formation of supramolecular inclusion complexes was evidenced from UV-Vis spectroscopy. The new Calix-OCP-conjugated polymers (polymers 4 and 5), synthesized in good yields by Sonogashira–Hagihara methodologies, exhibit high fluorescence quantum yields (ΦF = 0.59 − 0.65). Density functional theory (DFT) calculations were used to support the experimental findings. The fluorescence on–off behaviour of the sensing systems is tentatively explained by a photoinduced electron transfer mechanism.

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“…In this context, several calixarene architectures, a benchmark in supramolecular chemistry [3,4], stands out as supramolecular hosts able to act as receptors for a wide range of guests (e.g., neutral and ionic molecular species). Some examples of highly sensitive and selective chemosensors for detection of explosives [5], pollutants [6] and proteins [7] based on fluorescent calixarenes structures have been reported by our investigation group.…”

Section: Introductionmentioning

confidence: 89%

A New Fluorescent Calixarene Dimer: Synthesis, Optical Properties, and Sensory Applications

Costa

Barata

Costa

et al. 2020

The 24th International Electronic Conference on Synthetic Organic Chemistry

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A new fluorogenic bis-calix[4]arene-carbazole compound (3) with an enlarged intramolecular cavity able to be involved in host:guest chemistry with large organic guests was designed. Its synthesis was accomplished for the first time using a Sonogashira-Hagihara crosscoupling reaction in the final step. The calixarene receptor was structurally characterized by FTIR and 1 H/ 13 C/2D NMR techniques and its photophysical properties evaluated. The ability of 3 to form supramolecular complexes with fullerenes (C60 and C70) was evaluated through fluorimetric titration experiments. The value of the binding constants (K3:C60 = 1.39x10 5 M −1 and K3:C70= 6.88x10 4 M −1), and the free energy changes for the inclusion complexation (G3:C60 = −29.33 kJ/mol and G3:C70 = −27.60 kJ/mol), revealed a high sensitivity of the calixarene-carbazole host for both fullerenes. The host molecule shown to be particularly selective towards fullerene C60.

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Fostering protein–calixarene interactions: from molecular recognition to sensing

Abstract: An highly selective direct sensing of cytochrome c by a bis-calix[4]arene-carbazole conjugate (CCC-1) in aqueous-based medium at nanomolar levels is disclosed. An electron transfer (ET) between complexed partners mediates the sensory event.

Cited by 15 publications

References 62 publications

Multifunctional Cytochrome c: Learning New Tricks from an Old Dog

Multifunctional Cytochrome c: Learning New Tricks from an Old Dog

Highly Sensitive and Selective Fluorescent Probes for Cu(II) Detection Based on Calix[4]arene-Oxacyclophane Architectures

A New Fluorescent Calixarene Dimer: Synthesis, Optical Properties, and Sensory Applications

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