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

El-Sayed, Naglaa Salem; Hashem, Amr H.; Kamel, Samir

doi:10.1016/j.carbpol.2021.118823

Cited by 14 publications

(13 citation statements)

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“…Therefore, this dose was chosen to study the toxicological, antiangiogenic, and immunomodulatory actions, as well as the modulation of oxidative stress in the EAC model. Our findings are consistent with literature reports which have shown the antitumor potential of other acridine derivatives, including alkylamino-acridine derivatives (Cholewiński et al, 2011), spiro-acridines (Silva et al, 2019;, and 9aminoacridine derivatives (Belmont and Dorange, 2008;Mangueira et al, 2017;Kozurkova et al, 2020;Kumar et al, 2013;Rupar et al, 2020;El-Sayed et al, 2022).…”

Section: Figuresupporting

confidence: 93%

“…It was the first synthetic topoisomerase II poison approved for clinical use ( Rupar et al, 2020 ). Literature reports have shown the effects of 9-aminoacridine derivatives, based on amsacrine scaffold, as potential anticancer drugs ( Belmont and Dorange, 2008 ; Kozurkova et al, 2020 ; Kumar et al, 2013 ; Rupar et al, 2020 ; El-Sayed et al, 2022 ). Additionally, the mechanism of action for 9-aminoacridine-based anticancer drugs involves cell cycle arrest and apoptosis induction ( Sun et al, 2015 ), and effects on the PI3K/AKT/mTOR, NF-κB and p53 signaling pathways ( Guo et al, 2008 ; Guo et al, 2009 ).…”

Section: Introductionmentioning

confidence: 99%

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A 9-aminoacridine derivative induces growth inhibition of Ehrlich ascites carcinoma cells and antinociceptive effect in mice

Mangueira

Sousa²,

Batista³

et al. 2022

Front. Pharmacol.

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Acridine derivatives have been found with anticancer and antinociceptive activities. Herein, we aimed to evaluate the toxicological, antitumor, and antinociceptive actions of N’-(6-chloro-2-methoxyacridin-9-yl)-2-cyanoacetohydrazide (ACS-AZ), a 9-aminoacridine derivative with antimalarial activity. The toxicity was assessed by acute toxicity and micronucleus tests in mice. The in vivo antitumor effect of ACS-AZ (12.5, 25, or 50 mg/kg, intraperitoneally, i.p.) was determined using the Ehrlich tumor model, and toxicity. The antinociceptive efficacy of the compound (50 mg/kg, i.p.) was investigated using formalin and hot plate assays in mice. The role of the opioid system was also investigated. In the acute toxicity test, the LD50 (lethal dose 50%) value was 500 mg/kg (i.p.), and no detectable genotoxic effect was observed. After a 7-day treatment, ACS-AZ significantly (p < 0.05) reduced tumor cell viability and peritumoral microvessels density, suggesting antiangiogenic action. In addition, ACS-AZ reduced (p < 0.05) IL-1β and CCL-2 levels, which may be related to the antiangiogenic effect, while increasing (p < 0.05) TNF-α and IL-4 levels, which are related to its direct cytotoxicity. ACS-AZ also decreased (p < 0.05) oxidative stress and nitric oxide (NO) levels, both of which are crucial mediators in cancer known for their angiogenic action. Moreover, weak toxicological effects were recorded after a 7-day treatment (biochemical, hematological, and histological parameters). Concerning antinociceptive activity, ACS-AZ was effective on hotplate and formalin (early and late phases) tests (p < 0.05), characteristic of analgesic agents with central action. Through pretreatment with the non-selective (naloxone) and μ1-selective (naloxonazine) opioid antagonists, we observed that the antinociceptive effect of ACS-AZ is mediated mainly by μ1-opioid receptors (p < 0.05). In conclusion, ACS-AZ has low toxicity and antitumoral activity related to cytotoxic and antiangiogenic actions that involve the modulation of reactive oxygen species, NO, and cytokine levels, in addition to antinociceptive properties involving the opioid system.

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Section: Figuresupporting

confidence: 93%

Section: Introductionmentioning

confidence: 99%

A 9-aminoacridine derivative induces growth inhibition of Ehrlich ascites carcinoma cells and antinociceptive effect in mice

Mangueira

Sousa²,

Batista³

et al. 2022

Front. Pharmacol.

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“…In addition, Gum Arabic (GA) is a natural tree gum exudate that has a complex polysaccharide structure and is well known for its biodegradability, biocompatibility and water solubility [25] . GA remarkable rheological and emulsifying properties play critical role in stabilization of GO [26] , while its highly branched structure offers multiple carboxyl (–COOH) and hydroxyl (–OH) groups for attachment with various drugs [ 27 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

Green decoration of graphene oxide Nano sheets with gelatin and gum Arabic for targeted delivery of doxorubicin

Hasanin¹,

Taha²,

Abdou³

et al. 2022

Biotechnology Reports

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“…1,31 ATR-FTIR, 3,21,27,[33][34][35][36] NMR, 35 and UV/Vis absorption 21 spectra have been recorded of products of the periodate oxidation of gum arabic and the extent of the reaction followed using iodometric titrations. 22,28 The amount of aldehyde formed in the product was quantified using hydroxylamine hydrochloride 3,[35][36][37][38] and 2,4-dinitrophenylhydrazine 22,34 titrations, or a TNBS assay. 39 Removal of the iodate by-product is usually achieved by dialysis, 3,21,22,27,28,33,36,[38][39][40][41] or precipitation in ethanol 35 or acetone 34 and washing with water.…”

Section: Introductionmentioning

confidence: 99%

“…22,28 The amount of aldehyde formed in the product was quantified using hydroxylamine hydrochloride 3,[35][36][37][38] and 2,4-dinitrophenylhydrazine 22,34 titrations, or a TNBS assay. 39 Removal of the iodate by-product is usually achieved by dialysis, 3,21,22,27,28,33,36,[38][39][40][41] or precipitation in ethanol 35 or acetone 34 and washing with water.…”

Section: Introductionmentioning

confidence: 99%

Formation of substituted dioxanes in the oxidation of gum arabic with periodate

Siebe

Sardjan

Massmann

et al. 2022

Preprint

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Renewable polysaccharide feedstocks are of interest in bio-based food packaging, coatings and hydrogels. Their physical properties often need to be tuned by chemical modification, e.g. by oxidation using periodate, to introduce carboxylic acid, ketone or aldehyde functional groups. The reproducibility required for application on an industrial scale, however, is challenged by uncertainty about the composition of product mixtures obtained and of the precise structural changes that the reaction with periodate induces. Here, we show that despite the structural diversity of gum arabic, primarily rhamnose and arabinose subunits undergo oxidation, whereas (inchain) galacturonic acids are unreactive towards periodate. Using model sugars, we show that periodate preferentially oxidises the anti 1,2-diols in the rhamnopyranoside monosaccharides present as terminal groups in the biopolymer. While formally oxidation of vicinal diols results in the formation of two aldehyde groups, only traces of aldehydes are observed in solution, with the main final products obtained being substituted dioxanes, both in solution and in the solid state. The substituted dioxanes form most likely by the intramolecular reaction of one aldehyde with a nearby hydroxyl group, followed by hydration of the remaining aldehyde to form a geminal diol. The absence of significant amounts of aldehyde functional groups in the modified polymer impacts crosslinking strategies currently attempted in the preparation of renewable polysaccharide-based materials.

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

Cited by 14 publications

References 47 publications

A 9-aminoacridine derivative induces growth inhibition of Ehrlich ascites carcinoma cells and antinociceptive effect in mice

A 9-aminoacridine derivative induces growth inhibition of Ehrlich ascites carcinoma cells and antinociceptive effect in mice

Green decoration of graphene oxide Nano sheets with gelatin and gum Arabic for targeted delivery of doxorubicin

Formation of substituted dioxanes in the oxidation of gum arabic with periodate

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