Characterizing the Solvation Characteristics of Deep Eutectic Solvents Composed of Active Pharmaceutical Ingredients as a Hydrogen Bond Donor and/or Acceptor

Farooq, Muhammad Qamar; Abbasi, Nabeel Mujtaba; Smith, Emily A.; Petrich, Jacob W.; Anderson, Jared L.

doi:10.1021/acssuschemeng.1c08675

Title: Characterizing the Solvation Characteristics of Deep Eutectic Solvents Composed of Active Pharmaceutical Ingredients as a Hydrogen Bond Donor and/or Acceptor

Journal Article · 21 February 2022 · ACS Sustainable Chemistry & Engineering

DOI: https://doi.org/10.1021/acssuschemeng.1c08675 · OSTI ID:1856838

Farooq, Muhammad Qamar ^[1]; Abbasi, Nabeel Mujtaba ^[1];

^[1];

^[1]

Ames Lab., Ames, IA (United States); Iowa State Univ., Ames, IA (United States)

The formation of eutectic mixtures from active pharmaceutical ingredients (APIs) has emerged as an effective technique to develop liquid pharmaceutical formulations. API-based deep eutectic solvents (DESs) enhance the water solubility of APIs and avoid their recrystallization. The physico-chemical properties of API-DESs can be easily modulated by judicious selection of a hydrogen bond acceptor (HBA) or hydrogen bond donor (HBD) excipient that is mixed with the API. Solvation properties of API-DESs can help in understanding the role of ionic and non-ionic excipients towards the overall solvation interactions of these DESs. In this study, the solvation characteristics of three subclasses of API-DESs containing API-HBAs, API-HBDs, or API-HBAs and API-HBDs are investigated. Inverse gas chromatography is employed to study solute-solvent interactions of a variety of probe molecules for twenty different API-DESs. Among the API-DESs comprised of API-HBAs and carboxylic acid or diol-based HBDs, DESs containing diol-based HBDs exhibited stronger dipolar, hydrogen bond basicity, and hydrogen bond acidity interactions compared to carboxylic acid-based HBDs. No significant differences were observed in the solvation properties of DESs comprised of API HBAs and API HBDs. API-DESs comprised of the choline chloride HBA and API-HBDs exhibited stronger hydrogen bond acidity and dipolarity and weaker dispersive-type interactions among the DESs evaluated in this study. An in-depth evaluation of solvation properties for these DESs is important to completely exploit their potential in separation science as well as the fields of biomaterial science, pharmaceutical chemistry, and biotechnology.

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Research Organization:: Ames Laboratory (AMES), Ames, IA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-07CH11358

OSTI ID:: 1856838

Report Number(s):: IS-J--10,737

Journal Information:: ACS Sustainable Chemistry & Engineering, Journal Name: ACS Sustainable Chemistry & Engineering Journal Issue: 9 Vol. 10; ISSN 2168-0485

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Title: Characterizing the Solvation Characteristics of Deep Eutectic Solvents Composed of Active Pharmaceutical Ingredients as a Hydrogen Bond Donor and/or Acceptor

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