Detection of sulfate surface-active substances via fluorescent response using new amphiphilic thiacalix[4]arenes bearing cationic headgroups with Eosin Y dye

Thiacalix[4]arene’s Lower Rim Derivatives: Synthesis and Supramolecular Properties

“…[96] Anionic dye Eosin Y (EY) forms the associates with positive charged thiacalixarenes 116, shifts CAC to the low concentration region (2 µM) and decreases nanoaggregates size up to 90 nm. [92] An addition of EY (10 mol %) to thiacalixarene 116 solution leads to the decrease of aggregates surface charge from ∼ +45 to +20 mV. Thus, the anionic dye partly compensates the positive surface charge of the aggregates and their size decreases due to the less repulsion between head groups of thiacalixarene amphiphiles.…”

“…[93] Second, such thin thiacalix [4]arene films are stable in aqueous solution in the presence of biological active compounds such as dihydroquercetin up to pH 5.0, but cytochrome c is extracted by ascorbic acid from TCA films very intensively. 100: R'=(CH 2 ) 3 Br, Alk=C 14 H 29 ; [87] 101: R'=(CH 2 ) 2 Br, Alk=C 14 H 29 ; [87] 102: R'=(CH 2 ) 3 N 3 , Alk=C 14 H 29 ; [87] 103: R'=(CH 2 ) 2 N 3 , Alk=C 14 H 29 ; [87] 104: R'=(CH 2 ) 3 N 3 , Alk=C 4 H 9 , C 8 H 17 , C 14 H 29 ; [88] 105: R'=(CH 2 ) 3 N 3 , Diynyl=CH 2 C≡C-C≡C-C 6 H 5 ; [70] B: 106: n=3; Y=COOH, Z=COOH, Alk=C 4 H 9 ,C 8 H 17 , C 14 H 29 ; [87] 107: n=3; Y=CH 2 NH 2 , Z=H, Alk=C 14 H 29 ; [87] 108: n=3; Y=CH 2 OH, Z=H, Alk=C 14 H 29 ; [87] 109: n=3; Y=CH 2 N + (Et) 3 Br -, Z=H, Alk=C 4 H 9 , C 8 H 17 , C 14 H 29 ; [88] 110: n=3; Y=CH 2 С 6 H 5 , Z=H, Diynyl=CH 2 C≡C-C≡C-C 6 H 5 ; [70] 111: n=3; Y=CH 2 NH 2 , Z=H, Diynyl=CH 2 C≡C-C≡C-C 6 H 5 ; [70] 112: n=3; Y=COOH, Z=COOH, Diynyl=CH 2 C≡C-C≡C-C 6 H 5 ; [70] 113: n=3; Y=phtalimide, Z=H, Diynyl=CH 2 C≡C-C≡C-C 6 H 5 ; [70] [92] 99: Alkynyl=-CH 2 C≡CH, Alk=C 4 H 9 , C 8 H 17 , C 14 H 29 ; [68] A: 117: n=1; X=Bn, Alk=C 4 H 9 , C 8 H 17 , C 14 H 29 ; [68] 118: n=1; X=p-NO 2 C 6 H 4 , Alk=C 4 H 9 , C 8 H 17 , C 14 H 29 ; [68] 119: n=1; X=Bn, Alk=C 4 H 9 , C 8 H 17 , C 14 H 29 ; [68] 120: n=1; X=2,4,6-trichlorophenyl, Alk=C 4 H 9 ; [68] 121: n=1; X=p-MeOC 6 H 4 , Alk=C 4 H 9 ; [68] 122: n=1; X=CH 2 C(O)O-t-Bu, Alk=C 4 H 9 ; [68] Scheme 10. New type of ligands on the basis of thiacalix [4]arene platform in 1,3-alternate conformation was designed for gold surface functionalization.…”

“…[92] According to DLS data the diameter of these aggregates is around 130 nm. Their electrokinetic potential corresponds to the positive charge of the headgroups of thiacalixarene derivatives and is about +40 mV, which corresponds to the moderately stable colloids.…”

“…Addition of all synthesized macrocycles 115, 116 below the critical aggregation concentration (CAC) does not lead to a significant change in the size of the calf thymus DNA, while at the concentrations higher than CAC a significant compression of DNA in 2-5 times is observed. [91,92] Increased lipophilicity of the macrocycles leads to the formation of more compact lipoplex.…”

“…New water-soluble amphiphilic derivatives of p-tertbutylthiacalix [4]arene in 1,3-alternate stereoisomeric form with different length of O-alkyl chains 115, 116 (C 4 , C 8 , C 14 ) containing polycationic fragments were studied [91,92] to discover efficient carries capable of compacting, protecting, transporting, and delivering nucleic acids and proteins into the cell. It is noteworthy that amphiphilic gene vectors based on calixarenes are presented only in cone stereoisomeric form, [89,90] while 1,3-alternate also allows to achieve a spatial separation between hydrophilic and hydrophobic moieties of macrocycle.…”