Functionalized cellulose as a matrix for the synthesis of library of molecular receptors useful for screening of compounds with anti-histamine activity

• Autorzy: Walczak M. E. , Frączyk J. , Kamiński Z. J. , Kolesińska B.
• Języki publikacji: EN

Abstrakty

EN

The library of molecular receptors was formed by self-organization of N-heptanoylated dipeptides anchored in the regular fashion via aminophenylamino- 1,3,5-triazine linker to the surface of cellulose membrane. SPOT method was used for the synthesis of peptide library. As C-terminal amino acids of peptide fragments were attached: Ala, Pro and Phe, while as a N-terminal amino acids were applied all natural amino acids. DMT/NMM/TosO- was selected as a coupling reagent for synthesis of library of N-heptanoylated dipeptides. These constructs were used as a tool for distinguishing pharmaceutically active compounds acting on histamine receptors. In the studies as active compounds were tested: Doxylamine and Difenhydramine with histamine agonist activity, Ranitidine and Cimetidine with antagonist activity as well as Histamine – natural ligand. The binding of colourless ligands was monitored by staining with Brilliant Black used as reporter dye and quantitative colour measurement was performed in 256 grade gray scale by using Image-Quant software. Substantial differences in the ability of interactions of agonists and antagonists with bounding pockets were observed with selected molecular receptors. From 60 elements library of molecular receptors were selected 12, which were able to distinguish between agonists or antagonists. It has been found that even small changes (Leu residue vs Val residue) in the structure of molecular receptor influenced specificity of agonist or antagonist binding.

Słowa kluczowe

EN

molecular receptors; immobilized peptides; binding pocket; agonist/antagonist; histamine receptors

• Wydawca: Polish Society for Biomaterials in Cracow
• Czasopismo: Engineering of Biomaterials
• Rocznik: 2017
• Tom: Vol. 20, no. 142
• Strony: 2--6
• Opis fizyczny: Bibliogr. 16 poz., rys., tab.

Twórcy

autor

Walczak M. E.

• Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland

autor

Frączyk J.

• Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland

autor

Kamiński Z. J.

• Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland

autor

Kolesińska B.

• Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland

Bibliografia

• [1] Langan P., Nishiyama Y., Chanzy H.: X-ray Structure of Mercerized Cellulose II at 1 Å Resolution. Biomacromolecules 2 (2001) 410-416.
• [2] Klemm D., Heublein B., Fink H.P., Bohn A.: Cellulose: fascinating biopolymer and sustainable raw material. Angew. Chem. Int. Ed. 44 (2005) 3358-3393.
• [3] Huang Y., Zhu C., Yang J., Nie Y., Chen C., Sun D.: Recent advances in bacterial cellulose. Cellulose 21 (2014) 1-30.
• [4] Wang B., Lv X., Chen S., Li Z., Sun X., Feng C., Wang H., Xu Y.: In vitro biodegradability of bacterial cellulose by cellulase in simulated body fluid and compatibility in vivo. Cellulose 23 (2016) 3187-3198.
• [5] Lu P., Hsieh Y.-L.: Preparation and properties of cellulose nanocrystals: Rods, spheres, and network. Carbohydrate Polymers 82 (2010) 329-336.
• [6] Beesley T.E.: Review of Chiral Stationary Phase Development and Chiral Applications. LCGC Europe 24 (2011) 270-276.
• [7] Voisin H., Bergström L., Liu P., Mathew A.P.: Nanocellulose- -Based Materials for Water Purification. Nanomaterials 7 (2017) doi:10.3390/nano7030057.
• [8] Kai H.K., Winkler D.F.H., Hancock R.E.W.: Peptide arrays on cellulose support: SPOT synthesis, a time and cost efficient method for synthesis of large numbers of peptides in a parallel and addressable fashion. Nature Protocols 2 (2007) 1333-1349.
• [9] Almeida I.F., Pereira T., Silva N.H.C.S., Gomes F.P., Silvestre A.J.D., Freire C.S.R., et al.: Bacterial cellulose membranes as drug delivery systems: An in vivo skin compatibility study. European Journal of Pharmaceutics and Biopharmaceutics 86 (2014) 332-336.
• [10] Kamel S., Ali, N., Jahangir K., Shah S. M., El-Gendy A. A.: Pharmaceutical significance of cellulose: a review. Express Polym. Lett. 2 (2008) 758-778.
• [11] Fraczyk J., Kolesinska B., Kaminski Z.J.: N-lipidated oligopeptides immobilized on cellulose as new type of organocatalysts. Comb. Chem. & HTS 16 (2013) 562-571.
• [12] Bak A., Daszykowski M., Kaminski Z.J., Kiec-Kononowicz K., Kuder K., Fraczyk J., Kolesinska, B., Ciosek P., Polanski J.: Probing an artificial polypeptide receptor library using a series of novel histamine H3 receptor ligands. Comb. Chem. & HTS 17 (2014) 141-156.
• [13] Fraczyk J., Kaminski Z.J.: Design, synthesis, and application of a library of supramolecular structures formed by N-lipidated peptides immobilized on cellulose. Artificial receptors. J. Comb. Chem. 10 (2008) 934-940.
• [14] Fraczyk J., Mrozek A., Kaminski Z.J.: Structure-activity relationship in binding ligands to library of artificial receptors: the search for biocompatible sensor. Bioelectrochemistry 80 (2010) 2-9.
• [15] Kolesinska B., Rozniakowski K.K., Fraczyk J., Relich I., Papini A.M., Kamiński Z.J.: The Effect of Counterion and Tertiary Amine on the Efficiency of N-Triazinylammonium Sulfonates in Solution and Solid-Phase Peptide Synthesis, Eur. J. Org. Chem. (2015) 401-408.
• [16] Nguyen B.T., Anslyn E.V.: Indicator- Displacement Assays. Coord. Chem. Rev. 250 (2006) 3118-3127.

Uwagi

Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2018).