Exploiting Supramolecular Synthons in Designing Gelators Derived from Multiple Drugs

• Published in: Chemistry : a European journal Vol. 20; no. 47; pp. 15320 - 15324
• Main Authors: Roy, Rajdip, Deb, Jolly, Jana, Siddhartha Sankar, Dastidar, Parthasarathi
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 17.11.2014; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Amantadine; Amantadine - chemistry; Amantadine - pharmacology; Animals; Anti-Inflammatory Agents, Non-Steroidal - chemistry; Anti-Inflammatory Agents, Non-Steroidal - pharmacology; Biocompatibility; Biocompatible Materials - chemistry; Cell Line; Chemistry; crystal engineering; Diclofenac - chemistry; Diclofenac - pharmacology; Diffraction; Dinoprostone - metabolism; drug delivery; Drug therapy; Drugs; Gels - chemistry; Ingredients; Interferon-gamma - pharmacology; Lipopolysaccharides - toxicity; LMWGS; Macrophages - cytology; Macrophages - drug effects; Macrophages - metabolism; Mice; Nonsteroidal anti-inflammatory drugs; Rheology; Salicylates; Salicylates - chemistry; Salts - chemistry; Strategy; supramolecular gels; supramolecular synthons; X-rays; supramolecular synthons; LMWGS; drug delivery; crystal engineering; supramolecular gels
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201404965

A simple strategy for designing salt‐based supramolecular gelators comprised of various nonsteroidal anti‐inflammatory drugs (NSAIDs) and amantadine (AMN) (an antiviral drug) has been demonstrated using a supramolecular synthon approach. Single‐crystal and powder X‐ray diffraction established the existence of the well‐studied gel‐forming 1D supramolecular synthon, namely, primary ammonium monocarboxylate (PAM) synthon in all the salts. Remarkably five out of six salts were found to be capable of gelling methyl salicylate (MS)—an important ingredient in commercially available topical gels; one such selected biocompatible salt displayed an anti‐inflammatory response in prostaglandin E2 (PGE2) assay, thereby indicating their plausible biomedical applications. A supramolecular synthon approach enables an easy access (through salt formation) to a series of supramolecular gelators derived from nonsteroidal anti‐inflammatory drugs (NSAIDs) and amantadine. Biocompatibility and anti‐inflammatory response of the gelator salts indicate their plausible use in biomedical applications (see figure).