Dimeric calixarenes: a new family of major-groove binders

Chemistry : a European Journal
Wenbin HuThomas Schrader

Abstract

A new class of potent DNA binding agents is presented. Dimeric calix[4]arenes with cationic groups at their upper rims and flexible alkyl bridges can be synthesized from triply acyl-protected calix[4]arene tetramines in relatively short synthetic sequences (3-5 steps). The compounds attach themselves to double-stranded nucleic acids in a noncovalent fashion, with micro- to nanomolar affinities. Guanidinium headgroups with their extended hydrogen-bonding "fingers" are more powerful than ammonium groups, and the benzylamine series is superior to the anilinium series (see below). The new ligands easily distinguish between RNA and various DNA types, and produce characteristic changes in UV/Vis, fluorescence, CD, as well as NMR spectra. Especially extended oligonucleotides of more than 100 base pairs are bound with affinities increasing from RNA (10 μM K(d))<AT-rich (1 μM)<GC-rich DNA double strands (100-10 nM). Ethidium bromide displacement studies confirm this order. CE(50) values are remarkably low (1-4 μM), and are more than 300 times lower than that of spermine, which is a typical backbone binder. Stoichiometries are rather high (one calixarene dimer per two BP), suggesting a potential aggregation of bound ligands inside the ma...Continue Reading

References

May 7, 1982·Science·D J PatelK Itakura
Oct 28, 1998·Proceedings of the National Academy of Sciences of the United States of America·L A DickinsonP B Dervan
Apr 17, 2003·Angewandte Chemie·Derk JoesterFrançois Diederich
Dec 16, 2003·Chemical Society Reviews·M Eugenio VázquezJ L Mascareñas
Dec 22, 2004·Chemistry & Biology·Winston C Tse, Dale L Boger
Jan 11, 2005·Current Medicinal Chemistry·Tatiana Da RosBarbara Cacciari
Jan 4, 2006·Biochemistry·Anatoly I DraganPeter L Privalov
Mar 21, 2006·Angewandte Chemie·Reza Zadmard, Thomas Schrader
Oct 24, 2006·Journal of Molecular Biology·Peter L PrivalovConceição A S A Minetti
Feb 1, 2007·Chemical Society Reviews·Michael J Hannon
May 29, 2008·Doklady. Biochemistry and Biophysics·I B MertsalovD A Kulikova
Aug 30, 2008·Journal of Molecular Recognition : JMR·Sasa Bjelić, Ilian Jelesarov
May 14, 2009·Proceedings of the National Academy of Sciences of the United States of America·Vera MartosJavier de Mendoza
Mar 2, 2001·Angewandte Chemie·Michael J HannonAlison Rodger

❮ Previous
Next ❯

Citations

Apr 18, 2013·Nature Communications·Valentina BagnacaniRocco Ungaro
Aug 20, 2015·Chemical Communications : Chem Comm·Marta GiulianiAlessandro Casnati
Mar 29, 2014·Chemistry : a European Journal·Andrew G CairnsRichard C Hartley
Oct 4, 2012·Chemical Society Reviews·Satish Balasaheb Nimse, Taisun Kim
Nov 14, 2012·Chemical Communications : Chem Comm·Vanessa RullaudPatrick Shahgaldian
Jan 23, 2020·Angewandte Chemie·Yu-Chen PanDong-Sheng Guo
Jul 17, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Vanessa RullaudPatrick Shahgaldian

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.