Governing the DNA-binding mode of styryl dyes by the length of their alkyl substituents – from intercalation to major groove binding

Literature Information

Publication Date 2017-12-14
DOI 10.1039/C7OB02736B
Impact Factor 3.876
Authors

Nikolai I. Sosnin, Olga A. Fedorova, Heiko Ihmels


View Original

Abstract

A series of monomeric and homodimeric 4-alkoxystyryl(pyridinium) dyes was synthesized and their DNA-binding properties were investigated. We found that the length of the alkyl substituent has a crucial influence on the binding mode of the dyes, although the structure of the DNA-binding unit is the same for all compounds. Remarkably, mono- and bis-styryl derivatives comprising an oxodecyl chain represent the rare examples of small molecules that bind to the major groove of DNA. We have also demonstrated that the dyes, except the monostyryl dye with a bromopropyl substituent, form chiral aggregates in the presence of double-stranded DNA.

Related Literature

A method for finding the ridge between saddle points applied to rare event rate estimates

Jón Bergmann Maronsson, Hannes Jónsson, Tejs Vegge

2011-12-22 Paper

DOI: 10.1039/C2CP23421A

Optically probing nanoemulsion compositions

Xiaoming Zhu, Michael M. Fryd, Jung-Ren Huang

2012-01-16 Paper

DOI: 10.1039/C2CP23007K

Laser pulse trains for controlling excited state dynamics of adenine in water

Jens Petersen, Matthias Wohlgemuth, Bernhard Sellner, Roland Mitrić

2012-01-17 Paper

DOI: 10.1039/C2CP24002E

Adsorption of water and carbon dioxide on hematite and consequences for possible hydrate formation

Bjørn Kvamme, Tatiana Kuznetsova, Pilvi-Helina Kivelæ

2012-01-09 Paper

DOI: 10.1039/C2CP23810A

Back cover

Front/Back Matter

DOI: 10.1039/C2CP90009B

Interfacial electron transfer dynamics in dye-modified graphene oxide nanosheets studied by single-molecule fluorescence spectroscopy

Takashi Tachikawa, Shi-Cong Cui, Mamoru Fujitsuka, Tetsuro Majima

2012-02-02 Paper

DOI: 10.1039/C2CP23317G

Identification of a thermally activated process in the Cy3 photobleaching mechanism

A. L. Jouonang, P. Didier, Y. Mély

2011-12-21 Paper

DOI: 10.1039/C2CP22334A

Inside front cover

Front/Back Matter

DOI: 10.1039/C2CP90033E

Reorganization energy and pre-exponential factor from temperature-dependent experiments in electron transfer reactions. A typical example: the reduction of tert-nitrobutane

Cyrille Costentin, Cyril Louault, Marc Robert, Vincent Rogé, Jean-Michel Savéant

2011-12-16 Communication

DOI: 10.1039/C2CP23050J

Losartan's affinity to fluid bilayers modulates lipid–cholesterol interactions

P. Zoumpoulakis, G. Pabst, T. Mavromoustakos, M. Rappolt

2012-02-17 Paper

DOI: 10.1039/C2CP40134G

You might also like

Compound Q&A

What are the main uses of (3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8)?

(3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8) is primari...

79066-03-8(3.beta.)-3-Hydroxy-...
Compound Q&A

What regulatory guidelines apply to 5-(aminomethyl)-2-methoxyphenol (CAS: 89702-89-6)?

5-(Aminomethyl)-2-methoxyphenol (CAS: 89702-89-6) is classified under GHS as a s...

89702-89-65-(aminomethyl)-2-me...
Compound Q&A

What is Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7)?

Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7) is a heterocyclic organic compo...

28981-13-7Thieno[2,3-c]pyridin...
Compound Q&A

Is 1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride (CAS: 1185311-28-7) safe?

1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride is generally ...

1185311-28-71-[(6-Methoxy-3-pyri...
Compound Q&A

What regulatory guidelines apply to [(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2)?

[(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2) is regulated und...

146404-58-2[(2E)-3-Phenyl-2-pro...
Compound Q&A

What regulatory guidelines apply to 6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7)?

6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7) falls under the scope of the Glob...

1620515-86-76-Bromo-7-methoxyqui...
Compound Q&A

What industries use (2R)-1-(1-Benzofuran-2-yl)-N-propyl-2-pentanamine (CAS: 260550-89-8)?

This compound is primarily used in the pharmaceutical industry for the developme...

260550-89-8(2R)-1-(1-Benzofuran...
1228013-15-71-Ethyl-7-[2-methyl-...
Compound Q&A

Are there alternatives to {5-(Acryloylamino)-2-[(dimethylamino)methyl]phenyl}boronic acid (CAS: 1217500-78-1) in synthesis?

Alternative reagents such as 2-[(dimethylamino)methyl]phenylboronic acid or rela...

1217500-78-1{5-(Acryloylamino)-2...
Compound Q&A

What is 3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2)?

3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2) is an organic compound with the...

310881-48-23-(Piperidin-4-yloxy...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.