pH-Responsive Aggregates from Double Hydrophilic Block Copolymers Carrying Zwitterionic Groups. Encapsulation of Antiparasitic Compounds for the Treatment of Leishmaniasis

Abstract

A series of well-defined poly[(ethylene oxide)-b-2-(dimethylamino)ethyl methacrylate] (PEO-b-PDMAEMA) diblock copolymers were synthesized by atom transfer radical polymerization (ATRP) techniques. Post-polymerization reactions were performed to transform a portion of the tertiary amine groups of the PDMAEpsilonMA into phosphorozwitterions. The aggregation behavior of the prepared zwitterionic block copolymers was investigated by static and dynamic light scattering techniques at 25 and 37 degrees C, in weakly basic and acidic aqueous solutions. Antiparasitic drugs used for the treatment of Leishmania were incorporated into the copolymer aggregates. The effect of the solution pH, the zwitterion content, temperature, and the quantity of the incorporated drug on the aggregation behavior of the copolymers was tested.

Complex coacervate core micelles

“…For C3Ms of PEO-g-PMAA and PDADMAC ρ was shown to decrease with increasing PDADMAC block length (as observed for Gaussian coils) [65]. See [69,90,120,141,143,176,217,232,239] for measurements on second virial coefficients, A 2 , of C3Ms.…”

“…Other oppositely charged species that have been incorporated into C3Ms are drugs, such as dendrimer porphyrin, [160][161][162][228][229][230] cisplatin, [163,164] dibucaine, [165] tetracaine, [165] procaine, [165] doxorubicin, [168] heparin, [231] miltephosine, [232] TCAN-26, [232] low molecular weight compounds other than drugs, such as ETC, [166] and pyranine, [234] Moloney leukemia virus, [233] and coordination polymers [181][182][183].…”

Micellization of copolymers via noncovalent interaction with TPPS and aggregation of TPPS

“…In acidic aqueous solution, the PEG-b-P4VP and PDMAEMAb-PNIPAM transform into neutral-cationic double hydrophilic block copolymers (DHBCs) due to protonation of the P4VP (pK a 4.5-4.7) [25] and PDMAEMA (pK a ~7.0) blocks [26]. Micellization of the two copolymers were performed in aqueous solution at pH 4.0 based on the noncovalent interactions of TPPS with P4VP and PDMAEMA.…”

Synthetic and Physicochemical Aspects of Advanced Stimuli‐Responsive Polymers

“…A series of well-defined PEO-block-PDMAEMA diblock copolymers were synthesized by ATRP techniques, followed by postpolymerization reactions to transform a portion of the tertiary amine groups of the PDMAEMA (poly(N,N-dimethylaminoethyl methacrylate) into phosphorozwitterions. Antiparasitic drugs used for the treatment of Leishmania were incorporated into the copolymer aggregates [115].…”

“…Generally, in multicomponent networks, the component with a low surface energy is located at the top surface, while the component with the high surface energy is hidden beneath. Following this concept, poly(2-ethylhexyl acrylate/arylic acid) (p(2EHA/AAc)) [115] elastomers were developed, in which aliphatic portions with the low surface energy components are located at the top layer. Upon pressure load, chain rearrangements occur, which allow the high surface energy chains (acid portion) to migrate to the surface; this process is facilitated by hydrogen-bonding that leads to enhanced adhesion.…”