TY - JOUR
T1 - Interactions of a water-soluble calix[4]arene with spermine
T2 - solution and solid-state characterisation
AU - D’Urso, Alessandro
AU - Brancatelli, Giovanna
AU - Hickey, Neal
AU - Farnetti, Erica
AU - De Zorzi, Rita
AU - Bonaccorso, Carmela
AU - Purrello, Roberto
AU - Geremia, Silvano
PY - 2016/1/13
Y1 - 2016/1/13
N2 - The octaanionic 5,11,17,23-tetrasulfonato-25,26,27,28-tetrakis(hydroxycarbonylmethoxy)-calix[4]arene (cone conformation) (C4TsTc) was investigated as a sensor for the biogenic tetracationic polyamine, spermine .(H4Spe4+). Fluorescence titration experiments of the water-soluble calixarene with spermine showed the formation of the 2:1 and 1:1 calixarene:spermine complexes in solution. The single crystal X-ray diffraction analysis of [(NaC4TsTc)4·(H4Spe)7] confirmed the formation of 2:1 and 1:1 calixarene:spermine species and showed that the water-soluble calixarene binds the spermine either by partially hosting it in the inner cavity or through the carboxylate groups on the lower rim. In order to investigate the effect of multivalent systems, supramolecular assemblies of octaanionic calixarene molecules templated by meso-tetrakis(4-N-methylpyridyl)porphyrin (H2T4) in different stoichiometric porphyrin:calixarene ratios (1:4 and 3:4) were also tested for spermine binding in solution. Fluorescence titration experiments with the 1:4 and 3:4 H2T4:C4TsTc supramolecular complexes showed that the multivalent assemblies are more sensitive to the presence of spermine than the calixarene alone.
AB - The octaanionic 5,11,17,23-tetrasulfonato-25,26,27,28-tetrakis(hydroxycarbonylmethoxy)-calix[4]arene (cone conformation) (C4TsTc) was investigated as a sensor for the biogenic tetracationic polyamine, spermine .(H4Spe4+). Fluorescence titration experiments of the water-soluble calixarene with spermine showed the formation of the 2:1 and 1:1 calixarene:spermine complexes in solution. The single crystal X-ray diffraction analysis of [(NaC4TsTc)4·(H4Spe)7] confirmed the formation of 2:1 and 1:1 calixarene:spermine species and showed that the water-soluble calixarene binds the spermine either by partially hosting it in the inner cavity or through the carboxylate groups on the lower rim. In order to investigate the effect of multivalent systems, supramolecular assemblies of octaanionic calixarene molecules templated by meso-tetrakis(4-N-methylpyridyl)porphyrin (H2T4) in different stoichiometric porphyrin:calixarene ratios (1:4 and 3:4) were also tested for spermine binding in solution. Fluorescence titration experiments with the 1:4 and 3:4 H2T4:C4TsTc supramolecular complexes showed that the multivalent assemblies are more sensitive to the presence of spermine than the calixarene alone.
KW - calixarene
KW - fluorescence titration
KW - Spermine
KW - supramolecular complexes
KW - X-ray crystallography
UR - http://www.scopus.com/inward/record.url?scp=84954287500&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84954287500&partnerID=8YFLogxK
U2 - 10.1080/10610278.2015.1125900
DO - 10.1080/10610278.2015.1125900
M3 - Article
AN - SCOPUS:84954287500
SP - 1
EP - 7
JO - Supramolecular Chemistry
JF - Supramolecular Chemistry
SN - 1061-0278
ER -