Weak Interaction of the Antimetabolite Drug Methotrexate with a Cavitand Derivative

Abstract

Formation of inclusion complexes involving a cavitand derivative (as host) and an antimetabolite drug, methotrexate (as guest) was investigated by photoluminescence measurements in dimethyl sulfoxide solvent. Molecular modeling performed in gas phase reflects that, due to the structural reasons, the cavitand can include the methotrexate in two forms: either by its opened structure with free androsta-4-en-3-one-17α-ethinyl arms or by the closed form when all the androsta-4-en-3-one-17α-ethinyl arms play role in the complex formation. Experiments reflect enthalpy driven complex formation in higher temperature range while at lower temperature the complexes are stabilized by the entropy gain.

The Physical Chemistry and Chemical Physics (PCCP) Section of the International Journal of Molecular Sciences in Its Publications: The First 300 Thematic Articles in the First 3 Years

“…Articles [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 ] can be attributed to the first of the thematic areas indicated in the PCCP Section, and the distribution of these articles into the above categories is presented in Table 2 . As it can be seen, of the four types of articles established by the magazine’s standards ( Reviews , Originals, Communications , Editorials ), only the first two are presented here.…”

“…To the specifics of intermolecular interactions in systems containing surfactants, publications [ 4 , 12 , 18 ] were devoted; intermolecular interactions, in which the formation of hydrogen bonds plays a key role, are discussed to varying degrees in [ 5 , 23 , 25 ]. Two publications [ 7 , 19 ] provide data on the specific interactions in “guest-host” systems. Occasionally, there are works devoted to other aspects related to intermolecular interactions, in particular, to the formation of liquid crystal systems [ 8 ], supercooled bulk water [ 11 ], and liquid-liquid extraction aimed at separating individual heavy metals from aqueous solutions [ 10 ].…”

A New Application of Spin and Fluorescence Double-Sensor Molecules

“…It has also been documented how these nitroxides interact with certain proteins, such as BSA (Bovine Serum Albumin) [ 8 ], offering one more analytical tool. Fluorophores as light-sensitive molecules have been in the limelight of clinical research as well since many are used as antibacterial [ 9 ], antifungal [ 10 ], and chemotherapeutic agents [ 11 ]. Since pyrene is widely considered a useful compound for determining solvent environments, 3-hydroxymethyl-1-oxyl-4-(pyren-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1 H -pyrrole radical [ 12 ] ( Figure 1 , 1 ) was used in this study as a model molecule for a pharmaceutical agent in a system containing human serum albumin (HSA).…”

Weak Interactions of the Isomers of Phototrexate and Two Cavitand Derivatives

“…Therefore, in this work, the thermodynamic parameters of the interaction of PHX with tetrakis(androst-4-en-3-one-17α-ethinyl)-cavitand (TAC) and tetrakis(3,5-dicarboxylatophenoxy)-cavitand (TDC) ( Figure 2 ) were studied. TAC was synthesized as previously described [ 20 ]. The synthesis of TDC is based on the Williamson-type ether synthesis, reacting tetrabromo-cavitand [ 21 , 22 ] with dimethyl 5-hydroxyisophthalate, followed by the hydrolysis of the ester functionalities.…”