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 (2023) Novel pyrene-calix[4]arene derivatives as highly sensitive sensors for nucleotides, DNA and RNA. RSC Advances, 13 (39). pp. 27423-27433. ISSN 2046-2069

PDF - Published Version - article Available under License Creative Commons Attribution. Download (1MB)

Abstract

Covalent functionalization of a calix[4]arene with one or two pyrene arms at one rim and two imidazoles at the opposite rim of the macrocyclic basket, yields fluorescent conjugates characterized by intramolecular pyrene-calixarene exciplex emission of a mono-pyrene conjugate, whereas the bis-pyrene derivative exhibits pyrene excimer fluorescence. The pyrene emission in these novel compounds is shown to be sensitive to non-covalent interactions with both mono- and polynucleotides. Pyrene-calixarene conjugates, acting as host molecules, strongly interact with nucleotides, as monitored by moderate emission quenching, reaching 0.1 μM affinities, comparable to some of the most effective supramolecular sensors for nucleotides. These compounds are efficiently inserted into ds-DNA/RNA grooves, with a high, 0.1–1 μM affinity, not influencing significantly any of the ds-polynucleotide native properties, whereby complete emission quenching allows the detection of DNA at nM concentration.

Item Type:	Article
Uncontrolled Keywords:	calix[4]arene - pyrene derivatives; pyrene excimer/exciplex; nucleotide binding; DNA/RNA recognition; fluorescence
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry Division of Physical Chemistry
Projects:	Project title Project leader Project code Project type Biomimetički “funnel” i “bowl” supramolekularni sustavi za selektivno prepoznavanje DNA/RNA-CALIXDNA / CALIXDNA Aleksandar Višnjevac IP-2020-02-3786 HRZZ Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteina-BioMultiChromoProbes Ivo Piantanida IP-2018-01-5475 HRZZ
Depositing User:	Ivana Vuglec
Date Deposited:	16 Apr 2026 06:01
URI:	http://fulir.irb.hr/id/eprint/11723
DOI:	10.1039/d3ra05696a

Actions (login required)

View Item