Preparation and characterization of Gum Arabic Schiff's bases based on 9-aminoacridine with in vitro evaluation of their antimicrobial and antitumor potentiality

• Published in: Carbohydrate polymers 2022-02, Vol.277, p.118823-118823, Article 118823
• Main Authors: El-Sayed, Naglaa Salem, Hashem, Amr H., Kamel, Samir
• Format: Article
• Language: English
• Subjects: 9-Aminoacridine; Aminacrine - chemical synthesis; Aminacrine - chemistry; Aminacrine - pharmacology; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antimicrobial activity; Antineoplastic Agents, Phytogenic - chemical synthesis; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - pharmacology; Antitumor activity; Bacillus subtilis - drug effects; Caco-2 Cells; Candida albicans - drug effects; Cell Proliferation - drug effects; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Escherichia coli - drug effects; Gum Arabic; Humans; Imine linkage; Microbial Sensitivity Tests; Molecular Structure; Pseudomonas aeruginosa - drug effects; Schiff Bases - chemical synthesis; Schiff Bases - chemistry; Schiff Bases - pharmacology; Staphylococcus aureus - drug effects; Structure-Activity Relationship
• ISSN: 0144-8617; 1879-1344
• DOI: 10.1016/j.carbpol.2021.118823

The conjugation between drug and biopolymers through an easily hydrolysable bond such as ester linkage, disulfide linkage, or imine-bond have been extensively employed to control the drug release pattern and improve its bioavailability. This work described the conjugation of 9-aminoacridine (9-AA) to Gum Arabic (GA) via Schiff's base, as a pH-responsive bond. First, GA was oxidized to Arabic Gum dialdehyde (AGDA), then a different amount of 9-AA (10, 25, and 50 mg 9-AA) was coupled to defined amount of AGDA, the coupling was confirmed by elemental analysis and different spectroscopic tools. In addition, the physical features of Schiff's base conjugates including surface morphology, thermal stability, and crystalline structure were examined. The thermogravimetric analysis revealed that the incorporation of 9-AA slightly improved the thermal stability. The coupling of 9-AA to AGDA dramatically enhanced its in vitro antimicrobial and antitumor activities. All conjugates exhibited broad-spectrum activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, and Candida albicans. Moreover, AGA 25 and AGA 50 demonstrated promising capability to suppress the proliferation of human colon cancer cell line (Caco-2), with IC50 190.10 and 180.80 μg/mL respectively. [Display omitted]