Synthesis, characterization and potential application of hydrophobically modified carrageenan derivatives as pharmaceutical excipients

Selma Toumi; Madiha Melha Yahoum; Sonia Lefnaoui; Abdelkader Hadjsadok

doi:10.1016/j.carbpol.2020.116997

Synthesis, characterization and potential application of hydrophobically modified carrageenan derivatives as pharmaceutical excipients

Carbohydr Polym. 2021 Jan 1:251:116997. doi: 10.1016/j.carbpol.2020.116997. Epub 2020 Aug 29.

Authors

Selma Toumi¹, Madiha Melha Yahoum², Sonia Lefnaoui³, Abdelkader Hadjsadok⁴

Affiliations

¹ Laboratory of experimental Biology and Pharmacolgy, University of Medea, Nouveau pôle urbain, Medea University, 26000 Medea, Algeria; Faculty of Sciences, University of Medea, Nouveau pôle urbain, Medea University, 26000 Medea, Algeria; Laboratory of Biomaterials and Transport Phenomena (LBMPT), University of Medea, Nouveau pôle urbain, Medea University, 26000 Medea, Algeria.
² Faculty of Sciences, University of Medea, Nouveau pôle urbain, Medea University, 26000 Medea, Algeria; Materials and Environmental Laboratory (LME), University of Medea, Nouveau pôle urbain, Medea University, 26000 Medea, Algeria. Electronic address: madinayahoum@gmail.com.
³ Laboratory of experimental Biology and Pharmacolgy, University of Medea, Nouveau pôle urbain, Medea University, 26000 Medea, Algeria; Faculty of Sciences, University of Medea, Nouveau pôle urbain, Medea University, 26000 Medea, Algeria.
⁴ Functional Analysis of Chemical Processes Laboratory, Chemical Engineering Department, Saad Dahlab University, BP 270, 09000, Blida, Algeria.

PMID: 33142566
DOI: 10.1016/j.carbpol.2020.116997

Abstract

New amphiphilic derivatives of kappa-carrageenan (KC) were synthesized by hydrophobic modification with octyl chloride. Two different methods based on microwave and conventional heating were used. All KC derivatives (KCRs) were characterized by different techniques. The FT-IR and ¹HNMR studies demonstrated that the octyl groups were effectively grafted onto KC backbone and confirmed that the derivative KCRMM, obtained by microwave heating, presented a higher degree of substitution (DS = 0.77) compared to KCRCM (0.45). The amphiphilic character investigation also revealed that KCRMM exhibited a lower critical aggregation concentration (CAC) value of 0.13% w/v than KCRCM (0.15%). Furthermore, KCRs greatly improved the stability of oil/water emulsions as the droplet size decreased with increasing DS. Unlike the conventional heating method, novel derivatives with a higher DS, greater amphiphilic character, and an improved emulsifying power were obtained by microwave-assisted synthesis. These derivatives could potentially be used in food, cosmetics, or as excipients in pharmaceutics.

Keywords: Critical aggregation concentration; Emulsion stability; Hydrophobic modification; Kappa-carrageenan; Octyl chloride; Rheology.

MeSH terms

Carrageenan / chemical synthesis*
Carrageenan / chemistry
Carrageenan / ultrastructure
Drug Stability
Dynamic Light Scattering
Excipients / chemical synthesis*
Excipients / chemistry
Hot Temperature
Humans
Hydrophobic and Hydrophilic Interactions
Magnetic Resonance Spectroscopy
Microscopy, Electron, Scanning
Molecular Weight
Particle Size
Rheology
Spectroscopy, Fourier Transform Infrared
Surface-Active Agents
Thermodynamics
X-Ray Diffraction

Substances

Excipients
Surface-Active Agents
Carrageenan