Novel pyrene-calix[4]arene derivatives as highly sensitive sensors for nucleotides, DNA and RNA

Nikšić-Franjić, Ivana; Colasson, Benoit; Reinaud, Olivia; Višnjevac, Aleksandar; Piantanida, Ivo; Pavlović Saftić, Dijana

doi:10.1039/d3ra05696a

RSC Adv.

2023

DOI: 10.1039/d3ra05696a

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Novel pyrene-calix[4]arene derivatives as highly sensitive sensors for nucleotides, DNA and RNA

Ivana Nikšić-Franjić,

Benoit Colasson,

Olivia Reinaud

et al.

Abstract: Pyrene-armed calix[4]arene conjugates non-covalently bind to DNA/RNA, as well as to mononucleotides, with an amazing affinity.

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2024

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Novel Anthracene‐Appended Calix[4]triazacrown‐5 as an Effective Fluorescence Probe for Co²⁺ and Hazardous Cr₂O₇²⁻ Ions

Sayin

2024

Luminescence

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A new calix[4]triazacrown‐5–derived fluorescence chemosensor (AntUr‐AzClx) at cone conformation was synthesized to afford an effective fluorescent probe, which enables an enhancement in the fluorescence intensity specifically in the presence of Co2+ metal ions as well as a turnoff response for hazardous dichromate anions. 1H‐NMR, 13C‐NMR, ESI‐MS, and elemental analysis techniques were used to characterize the structure of the anthracene‐appended calix[4]triazacrown‐5 (AntUr‐AzClx). The metal ion–binding ability of AntUr‐AzClx was evaluated against Co2+, Ba2+, Ni2+, Pb2+, and Zn2+ ions. On the basis of various metal ion recognition phenomena, AntUr‐AzClx exhibited outstanding selectivity for only the Co2+ ion among other metal ions. Also, the calix[4]triazacrown‐5–derived fluorescence chemosensor showed high sensitivity towards the Co2+ ion with a very low limit of detection (LOD) 0.142 μmol L−1. In addition, anion binding abilities of AntUr‐AzClx against various anions such Cr2O72−, HCO3−, CO32−, NO3−, SO32−, SO42−, N3−, F−, and I− demonstrated that AntUr‐AzClx enables selective and highly sensitive detection of the Cr2O72− anion with an excellent LOD of 4.182 nmol L−1 in DMF/PBS (1/1, v/v; pH: 7.05). Furthermore, the calix[4]triazacrown‐5–derived fluorescence chemosensor displayed a significant sensing behavior to detect the presence of dichromate anions even in real samples.

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Novel Anthracene‐Appended Calix[4]triazacrown‐5 as an Effective Fluorescence Probe for Co²⁺ and Hazardous Cr₂O₇²⁻ Ions

Sayin

2024

Luminescence

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Transition Metals Coordination by Bis-imidazole-calix[4]arene Ligands with and Without Pyrene Units Grafted at the Large Rim

Nikšić-Franjić,

Pavlović Saftić,

Smrečki

et al. 2024

IJMS

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Herein, the presented results show that previously studied DNA/RNA-interacting bis-imidazole-calix[4]arene systems can, in aqueous solutions, efficiently bind a series of biorelevant transition metal cations by coordination with the two imidazole arms at the small rim of their macrocyclic basket. The SCXRD and NMR results structurally characterised the complexes formed by referent bis-imidazole-calix[4]arene with Cu2+ and Zn2+. In solid-state (crystal), the bis-anilino derivative/Cu2+ complex, only upon exposure to the air, undergoes intramolecular dehydrogenative coupling of two neighbouring aniline units, yielding an azo bridge at the large rim of the calix[4]arene basket. In the biorelevant aqueous solution, the comparison of fluorometric titrations of referent calix[4]arene, with its analogues having one or two pyrene units grafted at the opposite (large) rim, revealed moderate-to-strong affinity towards transition metal cations, and, more importantly, a strong impact of pyrene on the binding affinity towards some cations. The pyrene arm(s) significantly diminished the affinity of the calix[4]arene-imidazole ligand towards Cu+ and strongly increased the affinity towards divalent Co2+ and Cd2+ cations. Moreover, the fluorometric response of some studied derivatives was strappingly sensitive to cation type. Since the counter-anion plays only a marginal role, such a change in selectivity is attributed to the intramolecular interaction of pyrene(s) with the calix[4]arene-imidazole system, sterically controlling the metal cation binding site.

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Novel pyrene-calix[4]arene derivatives as highly sensitive sensors for nucleotides, DNA and RNA

Abstract: Pyrene-armed calix[4]arene conjugates non-covalently bind to DNA/RNA, as well as to mononucleotides, with an amazing affinity.

Cited by 2 publications

References 67 publications

Novel Anthracene‐Appended Calix[4]triazacrown‐5 as an Effective Fluorescence Probe for Co²⁺ and Hazardous Cr₂O₇²⁻ Ions

Novel Anthracene‐Appended Calix[4]triazacrown‐5 as an Effective Fluorescence Probe for Co²⁺ and Hazardous Cr₂O₇²⁻ Ions

Transition Metals Coordination by Bis-imidazole-calix[4]arene Ligands with and Without Pyrene Units Grafted at the Large Rim

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Novel pyrene-calix[4]arene derivatives as highly sensitive sensors for nucleotides, DNA and RNA

Abstract: Pyrene-armed calix[4]arene conjugates non-covalently bind to DNA/RNA, as well as to mononucleotides, with an amazing affinity.

Cited by 2 publications

References 67 publications

Novel Anthracene‐Appended Calix[4]triazacrown‐5 as an Effective Fluorescence Probe for Co2+ and Hazardous Cr2O72− Ions

Novel Anthracene‐Appended Calix[4]triazacrown‐5 as an Effective Fluorescence Probe for Co2+ and Hazardous Cr2O72− Ions

Transition Metals Coordination by Bis-imidazole-calix[4]arene Ligands with and Without Pyrene Units Grafted at the Large Rim

Contact Info

Product

Resources

About

Novel Anthracene‐Appended Calix[4]triazacrown‐5 as an Effective Fluorescence Probe for Co²⁺ and Hazardous Cr₂O₇²⁻ Ions

Novel Anthracene‐Appended Calix[4]triazacrown‐5 as an Effective Fluorescence Probe for Co²⁺ and Hazardous Cr₂O₇²⁻ Ions