Functional materials based on molecules with hydrogen-bonding ability: applications to drug co-crystals and polymer complexes

Abstract

The design, synthesis and property characterization of new functional materials has garnered interest in a variety of fields. Materials that are capable of recognizing and binding with small molecules have applications in sensing, sequestration, delivery and property modification. Specifically, recognition of pharmaceutical compounds is of interest in each of the aforementioned application areas. Numerous pharmaceutical compounds comprise functional groups that are capable of engaging in hydrogen-bonding interactions; thus, materials that are able to act as hydrogen-bond receptors are of significant interest for these applications. In this review, we highlight some crystalline and polymeric materials that recognize and engage in hydrogen-bonding interactions with pharmaceuticals or small biomolecules. Moreover, as pharmaceuticals often exhibit multiple hydrogen-bonding sites, many donor/acceptor molecules have been specifically designed to interact with the drug via such multiple-point hydrogen bonds. The formation of multiple hydrogen bonds not only increases the strength of the interaction but also affords unique hydrogen-bonded architectures.

Effect of TAT-DOX-PEG irradiated gold nanoparticles conjugates on human osteosarcoma cells

“…As it was mentioned in Materials and Methods section, DOX-PEG 500 -epoxy conjugates were used without purification in subsequent reactions with AuPEG 2000 -NH 2 or iAuPEG 2000 -NH 2 nanoparticles, meaning that the small amount of free doxorubicin added together with DOX-PEG 500 -epoxy conjugates can involve many hydrogen bonds with donor/acceptor moieties due to the presence of multiple hydroxyl and carbonyl groups in its composition, making possible its stabilization onto polymer chains surrounding the newly formed nanoconjugates, expressed by the codes: AuPEG 2000 -DOX, iAuPEG 2000 -DOX, AuPEG 2000 -TAT-DOX and iAuPEG 2000 -TAT-DOX. This finding was demonstrated before by Hutchins 39 when DOX formed hydrogen bonds with PEG moiety from PE-b-PEG copolymers. Under this circumstance, the "free" DOX is assumed to leave the carrier in the first step, prior to release of the drug in major amount, which was covalently bound onto the polymer layer of the gold nanoparticles.…”

In Situ Electrochemical Synthesis of a Conducting Polymer Composite for Multimetabolite Sensing

“…For instance, while a fluorescent dye labeled insulin could readily adhere on the p(EDOT‐ ran ‐EDOTOH) film surface, it does not show an affinity to pEDOT film (Figure S4, Supporting Information). Hydroxyl‐rich network of the copolymer enables hydrogen bonding and electrostatic interactions with biomolecules . Taken altogether, we conclude that p(EDOT‐ ran ‐EDOTOH) is the ideal polymer to incorporate enzymes via electropolymerization and for use in an OECT channel.…”

“…Hydroxylrich network of the copolymer enables hydrogen bonding and electrostatic interactions with biomolecules. [11,41,[46][47][48] Taken altogether, we conclude that p(EDOT-ran-EDOTOH) is the ideal polymer to incorporate enzymes via electropolymerization and for use in an OECT channel.…”

Rotational Spectroscopy Meets Quantum Chemistry for Analyzing Substituent Effects on Non-Covalent Interactions: The Case of the Trifluoroacetophenone-Water Complex

“…In this respect, the specificity of NCI-mediated mechanisms has been recently exploited to determine the absolute configuration of a selected enantiomer by introducing the so-called "chiral tag" method [5]. Among the possible interactions, hydrogen bond (HB) [6,7] is widespread in nature, frequently playing a fundamental role in life processes, e.g., by tuning nucleobase pairing in DNA and RNA, or in self-assembling processes in functional materials [8], organocatalysis [9] and many other situations. In this respect, HB features can be characterized by quantum-chemical methods [10][11][12] as well as by different spectroscopic techniques, such as the X-ray [13,14], NMR [14,15], IR [14,[16][17][18], Raman [17,18], ZEKE [19], REMPI [19] and microwave (MW) [20,21] spectroscopy.…”