Influence of perylenediimide–pyrene supramolecular interactions on the stability of DNA-based hybrids: Importance of electrostatic complementarity

Winiger, Christian B.; Langenegger, Simon Matthias; Khorev, Oleg; Häner, Robert (2014). Influence of perylenediimide–pyrene supramolecular interactions on the stability of DNA-based hybrids: Importance of electrostatic complementarity. Beilstein journal of organic chemistry, 10, pp. 1589-1595. Beilstein-Institut 10.3762/bjoc.10.164

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Aromatic pi–pi stacking interactions are ubiquitous in nature, medicinal chemistry and materials sciences. They play a crucial role in the stacking of nucleobases, thus stabilising the DNA double helix. The following paper describes a series of chimeric DNA–polycyclic aromatic hydrocarbon (PAH) hybrids. The PAH building blocks are electron-rich pyrene and electron-poor perylenediimide (PDI), and were incorporated into complementary DNA strands. The hybrids contain different numbers of pyrene–PDI interactions that were found to directly influence duplex stability. As the pyrene–PDI ratio approaches 1:1, the stability of the duplexes increases with an average value of 7.5 °C per pyrene–PDI supramolecular interaction indicating the importance of electrostatic complementarity for aromatic pi–pi stacking interactions.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry
04 Faculty of Medicine > Pre-clinic Human Medicine > BioMedical Research (DBMR) > Unit Childrens Hospital > Forschungsgruppe Nephrologie / Hypertonie
04 Faculty of Medicine > Department of Dermatology, Urology, Rheumatology, Nephrology, Osteoporosis (DURN) > Clinic of Nephrology and Hypertension

UniBE Contributor:

Langenegger, Simon Matthias; Khorev, Oleg and Häner, Robert

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry
600 Technology > 610 Medicine & health

ISSN:

1860-5397

Publisher:

Beilstein-Institut

Funders:

[UNSPECIFIED] Universität Bern
[UNSPECIFIED] Schweizerischer Nationalfonds

Language:

English

Submitter:

Robert Häner

Date Deposited:

22 Aug 2014 08:16

Last Modified:

18 Feb 2015 04:11

Publisher DOI:

10.3762/bjoc.10.164

BORIS DOI:

10.7892/boris.54883

URI:

https://boris.unibe.ch/id/eprint/54883

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