Assembling Multiporphyrin Stacks Inside the DNA Double Helix

Vybornyi, Mykhailo; Nussbaumer, Alina L.; Langenegger, Simon M.; Häner, Robert (2014). Assembling Multiporphyrin Stacks Inside the DNA Double Helix. Bioconjugate chemistry, 25(10), pp. 1785-1793. American Chemical Society 10.1021/bc500297e

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Double stranded DNA hybrids containing up to four consecutive, face-to-face stacked porphyrins are described. Non-nucleosidic, 5,15-bisphenyl-substituted porphyrin building blocks were incorporated into complementary oligonucleotide strands. Upon hybridization multiple porphyrins are well accommodated inside the DNA scaffold without disturbing the overall B-DNA structure. The formation of double strands containing up to four free base porphyrins is enabled without compromising duplex stability. UV/vis, fluorescence, and CD spectroscopy demonstrate the formation of porphyrins H-aggregates inside the DNA double helix and provide evidence for the existence of strong excitonic coupling between interstrand stacked porphyrins. H-aggregation results in considerable fluorescence quenching. Most intense CD effects are observed in stacks containing four porphyrins. The findings demonstrate the value of DNA for the controlled formation of molecularly defined porphyrin aggregates.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Vybornyi, Mykhailo; Nussbaumer, Alina Laura; Langenegger, Simon Matthias and Häner, Robert

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

1043-1802

Publisher:

American Chemical Society

Funders:

[UNSPECIFIED] Universität Bern
[UNSPECIFIED] Schweizerischer Nationalfonds

Language:

English

Submitter:

Robert Häner

Date Deposited:

20 Oct 2014 08:06

Last Modified:

26 Aug 2015 15:12

Publisher DOI:

10.1021/bc500297e

BORIS DOI:

10.7892/boris.58872

URI:

https://boris.unibe.ch/id/eprint/58872

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