ABSTRACT

This study is the first report on the solubilizing effect of O-phosphorylated calix[n]arene that form complexes with neutral molecules such as nifedipine, niclosamide and furosemide by host-guest complexation. This complexation studies were carried out by using the phase solubility technique. From the obtained results, it was observed that the solubility of guest molecules such as nifedipine, niclosamide and furosemide was significantly increased in the presence of host molecules 1-5. The increase in solubility of drugs by the calixarene host 1-5 was most probably due to inclusion complexation between drug molecules and cavities of the calixarene skeleton similar to drug:cyclodextrin complexes.

Compounds

#	Formula	Name
1	C12H11ClN2O5S	5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid
2	H2O	water
3	C44H56Na4O16P4	tetrasodium 1(5),3(5),5(5),7(5)-tetra-tert-butyl-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-1(2),3(2),5(2),7(2)-tetrayl tetrakis(hydrogen phosphate)
4	C28H24Na4O16P4	tetrasodium 1,3,5,7(1,3)-tetrabenzenacyclooctaphane-1(2),3(2),5(2),7(2)-tetrayl tetrakis(hydrogen phosphate)
5	C44H56Na2O10P2	disodium 1(5),3(5),5(5),7(5)-tetra-tert-butyl-3(2),7(2)-dihydroxy-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-1(2),5(2)-diyl bis(hydrogen phosphate)
6	C28H24Na2O10P2	disodium 3(2),7(2)-dihydroxy-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-1(2),5(2)-diyl bis(hydrogen phosphate)
7	C88H112Na8O32P8	octasodium 1(5),3(5),5(5),7(5),9(5),11(5),13(5),155-octa-tert-butyl-1,3,5,7,9,11,13,15(1,3)-octabenzenacyclohexadecaphane-1(2),3(2),5(2),7(2),9(2),11(2),13(2),15(2)-octayl octakis(hydrogen phosphate)
8	C17H18N2O6	dimethyl 4-(2-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
9	C13H8Cl2N2O4	5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide

Datasets

The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type	Compound-#	Property	Variable	Constraint	Phase	Method	#Points
POMD	1 2 3	Molality, mol/kg - 1 ; Liquid	Molality, mol/kg - 3; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 1	HPLC	4
POMD	1 2 4	Molality, mol/kg - 1 ; Liquid	Molality, mol/kg - 4; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 1	HPLC	4
POMD	1 2 5	Molality, mol/kg - 1 ; Liquid	Molality, mol/kg - 5; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 1	HPLC	4
POMD	1 2 6	Molality, mol/kg - 1 ; Liquid	Molality, mol/kg - 6; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 1	HPLC	4
POMD	1 2 7	Molality, mol/kg - 1 ; Liquid	Molality, mol/kg - 7; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 1	HPLC	4
POMD	2 8 3	Molality, mol/kg - 8 ; Liquid	Molality, mol/kg - 3; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 8	HPLC	4
POMD	2 8 4	Molality, mol/kg - 8 ; Liquid	Molality, mol/kg - 4; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 8	HPLC	4
POMD	2 8 5	Molality, mol/kg - 8 ; Liquid	Molality, mol/kg - 5; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 8	HPLC	4
POMD	2 8 6	Molality, mol/kg - 8 ; Liquid	Molality, mol/kg - 6; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 8	HPLC	4
POMD	2 8 7	Molality, mol/kg - 8 ; Liquid	Molality, mol/kg - 7; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 8	HPLC	4
POMD	9 2 3	Molality, mol/kg - 9 ; Liquid	Molality, mol/kg - 3; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 9	HPLC	4
POMD	9 2 4	Molality, mol/kg - 9 ; Liquid	Molality, mol/kg - 4; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 9	HPLC	4
POMD	9 2 5	Molality, mol/kg - 9 ; Liquid	Molality, mol/kg - 5; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 9	HPLC	4
POMD	9 2 6	Molality, mol/kg - 9 ; Liquid	Molality, mol/kg - 6; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 9	HPLC	4
POMD	9 2 7	Molality, mol/kg - 9 ; Liquid	Molality, mol/kg - 7; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid Crystal - 9	HPLC	4

Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

Phase solubility studies of poorly soluble drug molecules by using O-phosphorylated calixarenes as drug solubilizing agents

Bayrakci, M.[Mevlut], Ertul, S.[Seref], Yilmaz, M.[Mustafa]

ABSTRACT