Synthesis, antioxidant and hypoglycemic assessment of new azo-sulfamethoxazole derivatives
Keywords:
Sulfamethoxazole, Azo, Antioxidant, Hypoglycemic, DiabetesAbstract
The link connecting oxidative stress and diabetes is unambiguous. From this perspective, this work was conducted to utilize sulfamethoxazole (SMZ) as a precursor to synthesize eight-based derivatives abbreviated as SMZ 1-8. Structural identification, carried out using the traditional spectroscopies, namely FTIR, 1H NMR, and 13C NMR, was ascertained the chemical frameworks of the synthesized derivatives. The antioxidant and hypoglycemic impacts of these derivatives were investigated to evaluate their potential as antidiabetic candidates. The antioxidant impact was assessed by following the capacity of the synthesized SMZ derivatives to track down DPPH- and hydroxyl-reactive species and subscribe an electron in a redox reaction. The hypoglycemic impact was evaluated in vitro versus yeast α-glucosidase and porcine α-amylase. The findings indicated that substituting the phenolic azo group for the primary amine moiety of SMZ caused a significant increase in the antioxidant and hypoglycemic effects. Also, the synthesized SMZ derivatives showed a similar style in their inhibitory efficacy throughout the employed assays. Additionally, SMZ-2 and SMZ-6 exhibited delightful antioxidant and hypoglycemic impacts that are exceedingly related to the applied standards. The authors stated that the synthesized SMZ derivatives, notably SMZ-2 and SMZ-6, were intriguing candidates for diabetes management and control due to their potent antioxidant and hypoglycemic activities.
Downloads
References
Radi R. Oxygen radicals, nitric oxide, and peroxynitrite: Redox pathways in molecular medicine. Proc Natl Acad Sci U S A 2018;115:5839–5848.
Chelombitko MA. Role of Reactive Oxygen Species in Inflammation: A Minireview. Moscow Univ Biol Sci Bull 2018;73:199–202.
Gulcin İ. Antioxidants and antioxidant methods: an updated overview. , 2020 doi:10.1007/s00204-020-02689-3.
Nejadmansouri M, Majdinasab M, Nunes GS, et al. An overview of optical and electrochemical sensors and biosensors for analysis of antioxidants in food during the last 5 years. , 2021 doi:10.3390/s21041176.
Dayma V, Chopra J, Sharma P, et al. Synthesis, antidiabetic, antioxidant and anti-inflammatory activities of novel hydroxytriazenes based on sulpha drugs. Heliyon 2020;6:e04787.
Song F, Jia W, Yao Y, et al. Oxidative stress, antioxidant status and DNA damage in patients with impaired glucose regulation and newly diagnosed type 2 diabetes. Clin Sci 2007;112:599–606.
Oluwafemi Omoniyi Oguntibeju. Type 2 diabetes mellitus, oxidative stress and inflammation: examining the links. Int J Physiol Pathophysiol Pharmacol 2019;11:45–63.
Ježek P, Jabůrek M, Plecitá-Hlavatá L. Contribution of Oxidative Stress and Impaired Biogenesis of Pancreatic β-Cells to Type 2 Diabetes. Antioxidants Redox Signal 2019;31:722–751.
Aljamali NM. Review in Azo Compounds and its Biological Activity. Biochem Anal Biochem 2015;04:1–4.
Benkhaya S, M’rabet S, El Harfi A. Classifications, properties, recent synthesis and applications of azo dyes. Heliyon 2020;6. doi:10.1016/j.heliyon.2020.e03271.
Mustafaa YF, Khalil R, Mohammed T. Effects of structural manipulation on the bioactivity of some coumarin-based products. Arch razi 2021;76:1297–1305.
Patil CJ, Nehete CA. The azo derivatives of salicylic acid. Int J Pharm Sci Rev Res 2015;33:248–256.
Kołaczek A, Fusiarz I, Lawecka J, et al. Biological activity and synthesis of sulfonamide derivatives: A brief review. Chemik 2014;68:620–628.
Strom BL, Schinnar R, Apter AJ, et al. Absence of Cross-Reactivity between Sulfonamide Antibiotics and Sulfonamide Nonantibiotics. N Engl J Med 2003;349:1628–1635.
Maity S, Mukherjee K, Banerjee A, et al. Inhibition of Porcine Pancreatic Amylase Activity by Sulfamethoxazole: Structural and Functional Aspect. Protein J 2016;35:237–246.
Ji Y, Chen X, Chen H, et al. Designing of acyl sulphonamide based quinoxalinones as multifunctional aldose reductase inhibitors. Bioorganic Med Chem 2019;27:1658–1669.
Mustafa YF, Mohammed NA. A promising oral 5-fluorouracil prodrug for lung tumor: Synthesis, characterization and releas. Biochem Cell Arch 2021;21:1991–1999.
Mustafa YF, Khalil RR, Mohammed ET. Synthesis and antitumor potential of new 7-halocoumarin-4-acetic acid derivatives. Egypt J Chem 2021;64:3711–3716.
Mustafa YF, Mohammed ET, Khalil RR. Synthesis, characterization, and anticoagulant activity of new functionalized biscoumarins. Egypt J Chem 2021;64:4461–4468.
Jumintono J, Alkubaisy S, Yánez Silva D, et al. Effect of cystamine on sperm and antioxidant parameters of ram semen stored at 4 °C for 50 hours. Arch Razi Inst 2021;76:981–989.
Oglah MK, Kahtan Bashir M, Fakri Mustafa Y, et al. Synthesis and biological activities of 3,5-disubstituted-4-hydroxycinnamic acids linked to a functionalized coumarin. Syst Rev Pharm 2020;11:717–725.
Mustafa YF, Mohammed ET, Khalil RR. Antioxidant and antitumor activities of methanolic extracts obtained from Red Delicious and Granny Smith apples’ seeds. Syst Rev Pharm 2020;11:570–576.
Bashir MK, Mustafa YF, Oglah MK. Synthesis and antitumor activity of new multifunctional coumarins. Period Tche Quim 2020;17:871–883.
Nejres AM, Ali HK, Behnam SP, et al. Potential effect of ammonium chloride on the optical physical properties of polyvinyl alcohol. Syst Rev Pharm 2020;11:726–732.
Mohammed ET, Mustafa YF. Coumarins from Red Delicious apple seeds : Extraction, phytochemical analysis, and evaluation as antimicrobial agents. Syst Rev Pharm 2020;11:64–70.
Tao Y, Zhang Y, Cheng Y, et al. Rapid screening and identification of α-glucosidase inhibitors from mulberry leaves using enzyme-immobilized magnetic beads coupled with HPLC/MS and NMR. Biomed Chromatogr 2013;27:148–155.
Krishnasamy G, Muthusamy K. In vitro evaluation of antioxidant and antidiabetic activities of Syzygium densiflorum fruits. Asian Pacific J Trop Dis 2015;5:912–917.
Mustafa YF, Bashir MK, Oglah MK. Original and innovative advances in the synthetic schemes of coumarin-based derivatives: A review. Syst Rev Pharm 2020;11:598–612.
Aldewachi H, Mustafa YF, Najm R, et al. Adulteration of Slimming Products and its Detection Methods. Syst Rev Pharm 2020;11:289–296.
Oglah MK, Mustafa YF. Synthesis, antioxidant, and preliminary antitumor activities of new curcumin analogues. J Glob Pharma Technol 2020;12:854–862.
Khalil RR, Mustafa YF. Phytochemical, antioxidant and antitumor studies of coumarins extracted from Granny Smith apple seeds by different methods. Syst Rev Pharm 2020;11:57–63.
Bashir MK, Mustafa YF, Oglah MK. Antitumor, antioxidant, and antibacterial activities of glycosyl-conjugated compounds: A review. Syst Rev Pharm 2020;11:175–187.
Mustafa YF, Oglah MK, Bashir MK. Conjugation of sinapic acid analogues with 5- Fluorouracil: Synthesis, preliminary cytotoxicity, and release study. Syst Rev Pharm 2020;11:482–489.
Mustafa YF, Abdulaziz NT. Biological potentials of hymecromone-based derivatives : A systematic review. Syst Rev Pharm 2020;11:438–452.
Mustafa YF, Abdulaziza NT, Jasima MH. 4-Methylumbelliferone and its derived compounds: A brief review of their cytotoxicity. Egypt J Chem 2021;64:1807–1816.
Mustafa YF, Bashir MK, Oglah MK, et al. Bioactivity of some natural and semisynthetic coumarin derived compounds. NeuroQuantology 2021;19:129–138.
Mustafa YF, Abdulaziz NT. Hymecromone and its products as cytotoxic candidates for brain cancer : A brief review. NeuroQuantology 2021;19:175–186.
Mustafa YF. Classical approaches and their creative advances in the synthesis of coumarins: A brief review. J Med Chem Sci 2021;4:612–625.
Mahmood AAJ, Mustafa YF, Abdulstaar M. New coumarinic azo-derivatives of metoclopramide and diphenhydramine: Synthesis and in vitro testing for cholinesterase inhibitory effect and protection ability against chlorpyrifos. Int Med J Malaysia 2014;13:3–12.
Mustafa YF, Khalil RR, Mohammed ET. Antimicrobial activity of aqueous extracts acquired from the seeds of two apples’ cultivars. Syst Rev Pharm 2020;11:382–387.
Mustafa YF, Kasim SM, Al-Dabbagh BM, et al. Synthesis, characterization and biological evaluation of new azo-coumarinic derivatives. Appl Nanosci 2021. doi:10.1007/s13204-021-01873-w.
Oueslati MH, Guetat A, Bouajila J, et al. Deverra tortuosa (Desf.) DC from Saudi Arabia as a new source of marmin and furanocoumarins derivatives with α-glucosidase, antibacterial and cytotoxic activities. Heliyon 2021;7. doi:10.1016/j.heliyon.2021.e06656.
Poovitha S, Parani M. In vitro and in vivo α-amylase and α-glucosidase inhibiting activities of the protein extracts from two varieties of bitter gourd (Momordica charantia L.). BMC Complement Altern Med 2016;16:1–8.
Kim YM, Wang MH, Rhee HI. A novel α-glucosidase inhibitor from pine bark. Carbohydr Res 2004;339:715–717.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2023 AVFT – Archivos Venezolanos de Farmacología y Terapéutica
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
