Synthesis of Macrocyclic Hexaoxazole (6OTD) Dimers, Containing Guanidine and Amine Functionalized Side Chains, and an Evaluation of Their Telomeric G4 Stabilizing Properties

Structure-activity relationship studies were carried out on macrocyclic hexaoxazole (6OTD) dimers, whose core structure stabilizes telomeric G-quadruplexes (G4). Two new 6OTD dimers having side chain amine and guanidine functional groups were synthesized and evaluated for their stabilizing ability a...

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Autores principales: Iida, Keisuke, Tera, Masayuki, Hirokawa, Takatsugu, Shin-ya, Kazuo, Nagasawa, Kazuo
Formato: Texto
Lenguaje:English
Publicado: SAGE-Hindawi Access to Research 2010
Materias:
Research Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2911606/
https://www.ncbi.nlm.nih.gov/pubmed/20700415
http://dx.doi.org/10.4061/2010/217627
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author Iida, Keisuke
Tera, Masayuki
Hirokawa, Takatsugu
Shin-ya, Kazuo
Nagasawa, Kazuo
author_facet Iida, Keisuke
Tera, Masayuki
Hirokawa, Takatsugu
Shin-ya, Kazuo
Nagasawa, Kazuo
author_sort Iida, Keisuke
collection PubMed
description Structure-activity relationship studies were carried out on macrocyclic hexaoxazole (6OTD) dimers, whose core structure stabilizes telomeric G-quadruplexes (G4). Two new 6OTD dimers having side chain amine and guanidine functional groups were synthesized and evaluated for their stabilizing ability against a telomeric G4 DNA sequence. The results show that the 6OTD dimers interact with the DNA to form 1:1 complexes and stabilize the antiparallel G4 structure of DNA in the presence of potassium cation. The guanidine functionalized dimer displays a potent stabilizing ability of the G4 structure, as determined by using a FRET melting assay (ΔT (m) = 14°C).
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spelling pubmed-29116062010-08-10 Synthesis of Macrocyclic Hexaoxazole (6OTD) Dimers, Containing Guanidine and Amine Functionalized Side Chains, and an Evaluation of Their Telomeric G4 Stabilizing Properties Iida, Keisuke Tera, Masayuki Hirokawa, Takatsugu Shin-ya, Kazuo Nagasawa, Kazuo J Nucleic Acids Research Article Structure-activity relationship studies were carried out on macrocyclic hexaoxazole (6OTD) dimers, whose core structure stabilizes telomeric G-quadruplexes (G4). Two new 6OTD dimers having side chain amine and guanidine functional groups were synthesized and evaluated for their stabilizing ability against a telomeric G4 DNA sequence. The results show that the 6OTD dimers interact with the DNA to form 1:1 complexes and stabilize the antiparallel G4 structure of DNA in the presence of potassium cation. The guanidine functionalized dimer displays a potent stabilizing ability of the G4 structure, as determined by using a FRET melting assay (ΔT (m) = 14°C). SAGE-Hindawi Access to Research 2010-05-24 /pmc/articles/PMC2911606/ /pubmed/20700415 http://dx.doi.org/10.4061/2010/217627 Text en Copyright © 2010 Keisuke Iida et al. https://creativecommons.org/licenses/by/3.0/ This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Article
Iida, Keisuke
Tera, Masayuki
Hirokawa, Takatsugu
Shin-ya, Kazuo
Nagasawa, Kazuo
Synthesis of Macrocyclic Hexaoxazole (6OTD) Dimers, Containing Guanidine and Amine Functionalized Side Chains, and an Evaluation of Their Telomeric G4 Stabilizing Properties
title Synthesis of Macrocyclic Hexaoxazole (6OTD) Dimers, Containing Guanidine and Amine Functionalized Side Chains, and an Evaluation of Their Telomeric G4 Stabilizing Properties
title_full Synthesis of Macrocyclic Hexaoxazole (6OTD) Dimers, Containing Guanidine and Amine Functionalized Side Chains, and an Evaluation of Their Telomeric G4 Stabilizing Properties
title_fullStr Synthesis of Macrocyclic Hexaoxazole (6OTD) Dimers, Containing Guanidine and Amine Functionalized Side Chains, and an Evaluation of Their Telomeric G4 Stabilizing Properties
title_full_unstemmed Synthesis of Macrocyclic Hexaoxazole (6OTD) Dimers, Containing Guanidine and Amine Functionalized Side Chains, and an Evaluation of Their Telomeric G4 Stabilizing Properties
title_short Synthesis of Macrocyclic Hexaoxazole (6OTD) Dimers, Containing Guanidine and Amine Functionalized Side Chains, and an Evaluation of Their Telomeric G4 Stabilizing Properties
title_sort synthesis of macrocyclic hexaoxazole (6otd) dimers, containing guanidine and amine functionalized side chains, and an evaluation of their telomeric g4 stabilizing properties
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2911606/
https://www.ncbi.nlm.nih.gov/pubmed/20700415
http://dx.doi.org/10.4061/2010/217627
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