Synthesis of homologous series of surfactants from renewable resources, structure–properties relationship, surface active performance, evaluation of their antimicrobial and anticancer potentialities

• Published in: Scientific reports Vol. 14; no. 1; pp. 13201 - 24
• Main Authors: Abdelaziz, Shimaa A., Ahmed, Entesar M., Sadek, M.
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 08-06-2024; Nature Publishing Group; Nature Portfolio
• Subjects: 631/92/72/1202; 631/92/72/1204; 639/638/403/931; Amino acids; Amino Acids - chemistry; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Antibacterial activity; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Antitumor activity; Bacteria; Biological activity; Cancer; Cell Line, Tumor; Cysteine; Esters; Esters - chemical synthesis; Esters - chemistry; Esters - pharmacology; Foaming; Glucosyl ester; Gram-negative bacteria; Gram-positive bacteria; Hepatocytes; Humanities and Social Sciences; Humans; Hydrophile-lipophile balance (HLB); Magnetic resonance spectroscopy; Microbial Sensitivity Tests; multidisciplinary; NMR; Nuclear magnetic resonance; Physicochemical properties; Renewable resources; Science; Science (multidisciplinary); Structure-Activity Relationship; Surface active performance; Surface-Active Agents - chemical synthesis; Surface-Active Agents - chemistry; Surface-Active Agents - pharmacology; Surfactant; Surfactants; Sustainable yield; Tumor cell lines; Surface active performance; Antitumor activity; Cysteine; Surfactant; Hydrophile-lipophile balance (HLB); Glucosyl ester
• ISSN: 2045-2322; 2045-2322
• DOI: 10.1038/s41598-024-62905-3

Sugar esters display surface-active properties, wetting, emulsifying, and other physicochemical phenomena following their amphipathic nature and recognize distinct biological activity. The development of nutritional pharmaceuticals and other applications remains of great interest. Herein, three novel homologous series of several
N-
mono-fatty acyl amino acid glucosyl esters were synthesized, and their physicochemical properties and biological activities were evaluated. The design and preparation of these esters were chemically performed via the reaction of glucose with different fatty acyl amino acids as renewable starting materials, with the suggestion that they would acquire functional characteristics superior and competitive to certain conventional surfactants. The synthesized products are characterized using FTIR,
1
H-NMR, and
13
C-NMR spectroscopy. Further, their physicochemical properties, such as HLB, CMC, Γ
max
, γ
CMC
, and A
min,
were determined. Additionally, their antimicrobial and anticancer efficiency were assessed. The results indicate that the esters' molecular structure, including the acyl chain length and the type of amino acid, significantly influences their properties. The measured HLB ranged from 8.84 to 12.27, suggesting their use as oil/water emulsifiers, wetting, and cleansing agents. All esters demonstrate promising surface-active characteristics, with moderate to high foam production with good stability. Notably, compounds 6-
O-
(
N
-dodecanoyl, tetradecanoyl cysteine)-glucopyranose (
34, 35
), respectively and 6-
O
-(
N-
12-hydroxy-9-octadecenoyl cysteine)-glucopyranose (
38
) display superior foamability. Wetting efficiency increased with decreasing the chain length of the acyl group. The storage results reveal that increasing the fatty acyl hydrophobe length enhances the derived emulsion's stability for up to 63 days. Particularly, including cysteine in these glucosyl esters improves wetting, foaming, and emulsifying potentialities. Furthermore, the esters exhibit antibacterial activity against several tested Gram-positive and Gram-negative bacteria and fungi. On the other hand, they show significant antiproliferative effects on some liver tumor cell lines. For instance, compounds 6
-O
-(
N-
12-hydroxy-9-octadecenoylglycine)-glucopyranose (
28
), 6-
O
-(
N
-dodecanoyl, hexadecanoyl, 9
-
octadecenoyl and 12-hydroxy-9-octadecenoylvaline)
-
glucopyranose (
29
,
31
,
32
and
33
), respectively in addition to the dodecanoyl, hexadecanoyl, 9-octadecenoyl and 12-hydroxy-9-octadecenoyl cysteine glucopyranose (
34
,
36
,
37
and
38
), respectively significantly inhibit the examined cancer cells.