Study of Interaction of Glycerol Cryoprotectant and Its Derivatives with Dimethylacetamide in Aqueous Solution Using Fluorescent Probes
DOI:
https://doi.org/10.15407/cryo31.02.139Ключевые слова:
glycerol, oxyethylated derivatives, dimethylacetamide, cryoprotectants, mixtures, membranotropy, 3-hydroxy-4´- (N, N dimethylaminoflavone), fluorescenceАннотация
In this paper we have studied the interaction of the mixtures of glycerol (GL) and its oxyethylated derivatives (OEG) with polymerization degree n = 3, 25 and 30 with dimethylacetamide (DMAc) in aqueous solution using 3-hydroxy-4´-(N, N dimethylaminoflavone) fluorescent probe. The combination of GL and its oxyethylated derivatives with DMAc was found to reduce the membranotropy of certain cryoprotective agents, forming a mixture. The combination of both GL and its low molecular weight derivative (OEGn=3) with DMAc reduced the membranotropy of the latter. At the same time, combining GL derivatives of high molecular weight (OEGn=25 and OEGn=30) with DMAc diminished the membranotropy of OEG. The OEGn=30 at concentrations above 1 wt.% was shown to form the micellar-type structures or micellar associates in aqueous solution. This enabled suggesting the membranotropic ability of high molecular weight OEG associates to be stipulated by possible interaction of their nonpolar segments with nonpolar sites on biomembrane surface. Structural rearrangements of molecular associates in aqueous solutions of low and high molecular weight cryoprotectant mixtures were designated as the experimentally established mechanism of cytotoxicity reduction in combined cryoprotective media.
Probl Cryobiol Cryomed 2021; 31(2): 139–150
Библиографические ссылки
Bakaltcheva IB, Odeyale CO, Spargo BJ. Effects of alkanols, alkanediols and glycerol on red blood cell shape and hemolysis. Biochim Biophys Acta. 1996; 1280: 73-80. CrossRef
Bondar OP, Pivovarenko VG, Rowe ES. Flavonols - new fluorescent membrane probes for studying the interdigitation of lipid bilayers. Biochim Biophys Acta. 1998; 1369(1): 119-30. CrossRef
Chattoraj S, Chowdhury R, Ghosh S, Bhattacharyya K. Heterogeneity in binary mixtures of dimethyl sulfoxide and glycerol: fluorescence correlation spectroscopy. J Chem Phys[Internet]. 2013 Jun 07 [cited 2019 Feb 12]; 138(21): 214507. 11 Available from: https://aip.scitation.org/doi/10.1063/1.4808217 CrossRef
Chekanova VV, Pakhomova YuS, Kompaniets AM. [Micelle formation in solutions of ethoxylated glycerols and combined media based on them]. Bulletin of V.N. Karazin Kharkiv National University. Series 'Chemistry' 2016; 26: 40-4. Russian.
Demchenko AP, Ercelen S, Rochal AD, et al. Excited-state proton transfer reaction in a new benzofuryl 3-hydroxychromone derivative: the influence of low-polar solvents. Polish J Chem. 2002; 76(9): 1287-99.
Douhal A, Roshal AD, Organero JA. Stepwise interactions, sodium ion photoejection and proton-transfer inhibition in a crown-ether and proton-transfer dye. Chemical Physics Letters 2003; 381(3-4): 519-25. CrossRef
Duportail G, Klymchenko A, Mely I, et al. Neutral fluorescence probe with strong ratiometric response to surface charge of phospholipid membranes. FEBS Letters. 2001; 508 (2): 196- 200. CrossRef
Dutheil D, Underhaug Gjerde A, Petit-Paris I, et al. Polyethylene glycols interact with membrane glycerophospholipids: is this part of their mechanism for hypothermic graft protection. J Chem Biol. 2009, 2(1), 39-49. CrossRef
Ercelen S, Klymchenko AS, Demchenko AP. Ultrasensitive fluorescent probe for the hydrophobic range of solvent polarities. Anal Chim Acta 2002; 464(2): 273-87. CrossRef
Fahy GM. Cryoprotectant toxicity neutralization. Cryobiology 2010; 60(3): 45-53. CrossRef
Grischenko VI, Dyubko TS, Pivovarenko VG, Linnik TP, inventors; Institute for Problems of Cryobiology and Cryomedicine NAS Ukraine, assignee. [Method for determining membranotropic activity]. Patent № 13838 . 2006 Apr 17. Ukrainian.
Holmberg K. Surfactants and polymers in aqueous solutions. Chichester: John Wiley and Sons; 2002. 545p. CrossRef
Indra S, Biswas R. How heterogeneous are trehalose / glycerol cryoprotectant mixtures? A combined time-resolved fluorescence and computer simulation investigation. J Phys Chem B. 2016, 3; 120(43): 11214-28. CrossRef
Klymchenko AS, Duportail G, Turan O, et. Novel two-band ratiometric fluorescence probes with different location and orientation in phospholipid membranes. Chem Biol. 2002; 9(11): 1199-208. CrossRef
Klymchenko AS, Mely Y, Demchenko AP, et al. Simultaneous probing of hydration and polarity of lipid bilayers with 3-hydroxyflavone fluorescent dyes. Biochim Biophys Acta 2004; 1665(1-2): 6-19. CrossRef
Kompaniets AM, Nikolenko OV, Chekanova VV, Yesipova YuS. Cryoprotective efficiency of media based on oxyethyl derivatives of polyols during freezing of human erythrocytes. Problems of Cryobiology. 2008; 18(3): 299-301. Full Text
Kompaniets AM, Chekanova VV, Nikolenko AV, et al. [Synthesis, physic-chemical properties of hydroxyethyl glycerol derivatives. Cryoprotective environments based on combination of cryoprotectants for freezing biological objects. In: Goltsev AN, editor [Actual problems of cryobiology and cryomedicine]. Kharkiv; 2012. p. 26-73. Russian.
Mitrus I, Smagur A, Fidyk W, et al. Reduction of DMSO concentration in cryopreservation mixture from 10% to 7.5% and 5% has no impact on engraftment after autologous peripheral blood stem cell transplantation: results of a prospective, randomized study. Bone Marrow Transplant. 2018, 53(3):274- 80. CrossRef
McMorrow D, Kasha M. Proton-transfer spectroscopy of 3-hydroxyflavone in an isolated-site crystal matrix. Proc Natl Acad Sci USA 1984; 81(11): 3375-8. CrossRef
Pakhomova YuS, Chekanova VV, Kompaniets AM. Cryoprotective properties of solutions based on non-penetrative OEG n=25 combined with penetrating cryoprotectants during freezing of human erythrocytes. Probl Cryobiol Cryomed. 2013; 23(1): 26-39. Full Text
Pakhomova YuS, Kompaniets AM, Kuleshova LG. Transformation of erythrocytes during cryopreservation with oxyethylated glycerol derivation with n=25 and n=30 polymerization degree. Probl Cryobiol Cryomed 2016; 24(4):349-60. CrossRef
Pivovarenko VG [Design of fluorescent probes based on 3-hydroxychromones and analogs.] Ukrainica Bioorganica Acta. 2002; 1 (1); 40-9. Ukrainian
Roshal AD, Dyubko TS, Linnik TP. [4' -dimethylaminofl avone − a new fl uorescent probe to evaluate the cryoprotective properties of organic substances in aqueous solutions]. Biophysical Bulletin of V.N. Karazin Kharkiv National University. 2005; 2(16): 106-11. Russian
Rusanov AI. [Micelle formation in surfactant solutions]. St. Petersburg: Khimia; 1992. 528 p. Russian.
Smith MA, Neumann RM, Webb RA. A modification of the Algar-Flynn-Oyamada preparation of flavonols. J Heteroc Chem 1968; 5(3): 425-6. CrossRef
Yushchenko DA, Shvadchak VV, Klymchenko AS, et al. Modulation of excited-state intramolecular proton transfer by viscosity in protic media. The J Phys Chem A. 2007; 111(42); 10435-8. CrossRef
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