Triostin A Derived Cyclopeptide as Architectural Template for the Alignment of Four Recognition Units1. Issue 4 (9th July 2014)

• Record Type: Journal Article
• Authors: Kotyrba, Ursula M.; Pröpper, Kevin; Sachs, Eike-F.; Myanovska, Anastasiya; Joppe, Tobias; Lissy, Friederike; Sheldrick, George M.; Koszinowski, Konrad; Diederichsen, Ulf
• Is Part Of: ChemistryOpen. Volume 3:Issue 4(2014:Aug.)
• Page Start: 152
• Page End: 160
• Publication Date: 2014-07-09
• Subjects: Chemistry -- Periodicals; 540; 540.5
• DOI: 10.1002/open.201400001
• Languages: English
• ISSNs: 2191-1363

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The DNA bisintercalator triostin A is structurally based on a disulfide‐bridged depsipeptide scaffold that provides preorganization of two quinoxaline units in 10.5 Å distance. Triostin A analogues are synthesized with nucleobase recognition units replacing the quinoxalines and containing two additional recognition units in between. Thus, four nucleobase recognition units are organized on a rigid template, well suited for DNA double strand interactions. The new tetra‐nucleobase binders are synthesized as aza‐TANDEM derivatives lacking the N‐methylation of triostin A and based on a cyclopeptide backbone. Synthesis of two tetra‐nucleobase aza‐TANDEM derivatives is established, DNA interaction analyzed by microscale thermophoresis, cytotoxic activity studied and a nucleobase sequence dependent self‐aggregation investigated by mass spectrometry.</p> </abstract>