DNA-based assemblies with bischromophoric styryl dye-chromene conjugates and cucurbit[7]uril

Polina S Perevozchikova; Ekaterina Y Chernikova; Nikolai E Shepel; Olga A Fedorova; Yuri V Fedorov

doi:10.1016/j.saa.2022.121971

DNA-based assemblies with bischromophoric styryl dye-chromene conjugates and cucurbit[7]uril

Spectrochim Acta A Mol Biomol Spectrosc. 2023 Feb 5:286:121971. doi: 10.1016/j.saa.2022.121971. Epub 2022 Oct 13.

Authors

Polina S Perevozchikova¹, Ekaterina Y Chernikova², Nikolai E Shepel², Olga A Fedorova³, Yuri V Fedorov²

Affiliations

¹ Laboratory of Photoactive Supramolecular Systems, A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova st. 28, 119991 Moscow, Russia; Department of Fine Organic Synthesis and Chemistry of Dyes, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya Square 9, 125047 Moscow, Russia. Electronic address: polina-krasnoperova@mail.ru.
² Laboratory of Photoactive Supramolecular Systems, A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova st. 28, 119991 Moscow, Russia.
³ Laboratory of Photoactive Supramolecular Systems, A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova st. 28, 119991 Moscow, Russia; Department of Fine Organic Synthesis and Chemistry of Dyes, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya Square 9, 125047 Moscow, Russia. Electronic address: fedorova@ineos.ac.ru.

PMID: 36288627
DOI: 10.1016/j.saa.2022.121971

Abstract

Novel conjugates consist of 4-styrylpyridinium dye and 2,2-diphenyl-2H-chromene moiety were obtained, and their affinity to double stranded DNA and cucurbit[7]uril was investigated. With a combination of absorption, fluorescence and circular dichroism spectroscopies as well as MALDI-TOF mass spectrometry, we demonstrate that these compounds can interact with macromolecules to form of the supramolecular assemblies due to two suitable binding sites. The ternary complex is formed as a result of the intercalation of a positively charged styryl part between DNA base pairs, while cucurbit[7]uril is located on the alkyl chain between two moieties of conjugate. All these findings provide valuable information into controlling the interaction between organic molecules, DNA and cucurbit[7]uril.

Keywords: 2H-chromene; Conjugate; Cucurbit[7]uril; DNA; Styryl dye.

MeSH terms

Benzopyrans
Bridged-Ring Compounds* / chemistry
DNA
Imidazoles* / chemistry

Substances

cucurbit(7)uril
Bridged-Ring Compounds
Imidazoles
DNA
Benzopyrans