Aggregation behavior and in vitro biocompatibility study of octopus-shaped macromolecules based on tert-butylcalix[4]arenes

A series of products based on tert-butylcalix[4]arene have been synthesized by anionic polymerization of ethylene oxide. The resulting products are amphiphilic octopus-shaped macromolecules, consisting of a hydrophobic calix[4]arene core and four arms of hydrophilic poly(ethylene oxide) chains. In a...

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Bibliographic Details
Published in:International journal of pharmaceutics 2012-10, Vol.436 (1-2), p.410-417
Main Authors: Momekova, Denitsa, Budurova, Desislava, Drakalska, Elena, Shenkov, Stoycho, Momekov, Georgi, Trzebicka, Barbara, Lambov, Nikolay, Tashev, Emil, Rangelov, Stanislav
Format: Article
Language:English
Subjects:
aggregation behavior
aqueous solutions
Biocompatibility
Calixarenes
Calixarenes - chemistry
Calixarenes - pharmacology
Cell Line, Tumor
Cell Survival - drug effects
Cells, Cultured
Cytotoxicity
Erythrocytes - drug effects
Erythrocytes - physiology
ethylene oxide
Hemolysis
Hemolysis - drug effects
Humans
hydrodynamics
hydrophilicity
hydrophobicity
IL-2
interleukin-2
Interleukin-2 - metabolism
light scattering
Marine
PEO
Polyethylene Glycols - chemistry
Polyethylene Glycols - pharmacology
polymerization
Self-assembled structures
solubilization
T-lymphocytes
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Summary:A series of products based on tert-butylcalix[4]arene have been synthesized by anionic polymerization of ethylene oxide. The resulting products are amphiphilic octopus-shaped macromolecules, consisting of a hydrophobic calix[4]arene core and four arms of hydrophilic poly(ethylene oxide) chains. In aqueous solutions the polyoxyethylated tert-butylcalix[4]arenes were found to self-associate above certain CMC determined by dye solubilization technique. The light scattering study reveals that the polyoxyethylated tert-butylcalix[4]arenes form aggregates of narrow size distribution and hydrodynamic diameters ranging from about 155 to 245nm and aggregation numbers from tens to hundreds macromolecules per particle depending on the degree of polymerization of the PEO chains. An in vitro biocompatibility study showed that the tested compounds are practically devoid of intrinsic cytotoxic and hemolytic effects and moreover they failed to modulate the mitogen-induced interleukin-2 release from the human T-lymphocyte cell line Jurkat E6-1. Taken together the excellent in vitro biocompatibility profile and the favorable physicochemical characteristics of the tested polyoxyethylated calix[4]arenes give us reason to consider them as promising for further evaluation as drug delivery platforms.
ISSN:0378-5173
1873-3476
DOI:10.1016/j.ijpharm.2012.06.053