INVESTIGATION OF INTERACTION OF PILLARARENE WITH DNA OLIGONUCLEOTIDE BY NMR SPECTROSCOPY METHOD
Abstract and keywords
Abstract (English):
The project is destined at the engineering of new promising supramolecular structures for medical and biological applications that have the ability to bind and/or compact DNA molecules. The fundamental novelty of the project is the using of new macrocyclic compounds - pillar[5]arenas, which can work as containers for drug delivery, including genetic diagnostics and pharmacology. High-resolution NMR spectroscopy and NMR diffusometry were used to study the ability of 4,8,14,18,23,26,28,31,32,35- decakis-[(N-(2', 2', 2'-triethylaminoethyl) - carbamoylmethoxy] -pillar[5]arene decay iodide to interact with the palindromic DNA decamer. The completely assigned of the NMR spectra of the oligonucleotide and the pillar[5]arene was carried out using the two-dimensional homo- and hetero-nuclear NMR spectra: COSY, TOCSY, NOESY, HSQC, HMBC. The hydrodynamic radius of the pillar[5]arene is determined, which is in good agreement with the theoretically calculated one. The formation of the molecular complex pillar[5]arene with a DNA oligonucleotide is confirmed by measurements of the coefficients of self-diffusion of molecules in free form and in a complex.

Keywords:
illar[5]arene, DNA, supramolecular associates, structure, NMR spectroscopy
Text
Publication text (PDF): Read Download
References

1. Ogoshi T., Yamagishi T., Nakamoto Y. Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry. Chemical Reviews, 2016, vol. 116, pp. 7923-8002.

2. Li C., Chen S., Li J., Han K., Xu M., Hu B., Jia X. Novel neutral guest recognition and interpenetrated complex formation from pillar[5]arenes. Chem. Commun., 2011, vol. 47, no. 40, pp. 11294-11296

3. Cao D., Meier H. Pillar[n]arenes - a novel, highly promising class of macrocyclic host molecules. Asian J. Org. Chem., 2014, vol. 3, pp. 244-262.

4. Orts J., Bartoschek S., Griesinger C., Monecke P., Carlomagno T. An NMR-based scoring function improves the accuracy of binding pose predictions by docking by two orders of magnitude. Journal of Biomolecular NMR, 2012, vol. 52, pp. 23-30.

5. Yakimova L., Shurpik D., Gilmanova L., Makhmutova A., Rakhimbekova A., Stoikov I. Highly selective binding of methyl orange dye by cationic water-soluble pillar[5]arenes. Organic and Biomolecular Chemistry, 2016, vol. 14, pp. 4233- 4238.

6. Khairutdinov B., Ermakova E., Sitnitsky A., Stoikov I., Zuev Y. Supramolecular complex formed by DNA oligonucleotide and thiacalix[4]arene. NMR-spectroscopy and molecular docking. Journal of Molecular Structure, 2014, vol. 1074. pp. 126-133.


Login or Create
* Forgot password?