Background: The reported rise in drug-resistant bacteria, as well as the prevalence of oxidative stress-related disorders, motivated the need for novel antimicrobial and antioxidants activity. The synthesis of gly-gly based dipeptides bearing sulphonamide functionalities is reported. Methodology: The base promoted reaction of appropriate substituted benzenesulphonyl chloride with L-glycine afforded compounds (3a-3b) and the condensation reaction of (3a-3b) with carboxamide derivatives gave the targeted products (7a-7b) using peptide coupling reagent. The characterization of compounds was done using 1HNMR, 13CNMR, FTIR and HRMS. Results: In the in vitro antimicrobial activity, compounds 7a (MIC 6.10 mg/mL), 7ai (MIC 7.01 mg/mL), 7b (MIC 7.42 mg/mL), 7bi (MIC 6.32 mg/mL) was most potent against S. aureus, B. subtilis, P. aeruginosa and E. coli respectively. Compounds 7a (MIC 6.90 mg/mL) and 7b (MIC 6.48 mg/mL) were most active against C. Albicans and A. Niger respectively. Compound 7a and 7bi (85.00% and 88.78% at 25mg/mL) exhibits excellent percentage inhibition antioxidant activities comparable with vitamin C (90.78% at 25mg/mL) and alsocompound 7bi had the best IC50 values of 0.7674 mg/mL. Conclusion: The synthesized compounds were found to be potent antibacterial, antifungal and antioxidant agents.
| Published in | American Journal of Applied Scientific Research (Volume 9, Issue 3) |
| DOI | 10.11648/j.ajasr.20230903.14 |
| Page(s) | 109-114 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2024. Published by Science Publishing Group |
Synthesis, Benzenesulphonamide, Dipeptide, Antimicrobial Activity, Antifungal Activity, Antioxidant Activity
| [1] | Sengupta S, Chattopadhyay M. K, Grossart H-P (2013). The multifaceted roles ofantibiotics and antibiotic resistance in nature. Front Microbiol.; 4: 47. |
| [2] | Randall C. P, Mariner K. R, Chopra I, O’Neill A. J (2013). The target ofdaptomycin is absent from Escherichia coli and other Gram-negative pathogens. Antimicrob Agents Chemother.; 57: 637–9. |
| [3] | Lobo, V.; Patil, A.; Phatak, A.; Chandra, N (2010). Free radicals, antioxidantsand functional foods: Impact on human health. Pharmacogn. Rev. 4, 118–126. |
| [4] | Akbarirad, H.; Gohari Ardabili, A.; Kazemeini, S. M.; Mousavi Khaneghah, A (2016). An overview on some of important sources of natural antioxidants. Int. Food Res. J., 23, 928–933. |
| [5] | Pham-Huy, L. A.; He, H.; Pham-Huy, C (2008). Free radicals, antioxidants in disease and health. Int J Biomed Sci, 4, 89-96. |
| [6] | Suleman, M.; Khan, A.; Baqi, A.; Kakar, M. S.; Samiullah.; Ayub, M (2018). Antioxidants, its role in preventing free radicals and infectious diseases in human body. Pure Appl. Biol, 7, 380- 388. |
| [7] | Ibrahim, M.; Khan, A.; Ikram, M.; Rehman, S.; Shah, M.; Nabi, H. H.; Achuchaogu, A. A (2017). In Vitro Antioxidant Properties of Novel Schiff Base Complexes. Asian J. Chem. Sci., 2, 1–12. |
| [8] | Zehiroglu, C.; OzturkSarikaya, S. B (2019). The importance of antioxidants and place in today’s scientific and technological studies. Journal of Food Science and Technology, 56, 4757-4774. |
| [9] | Nasr T, Bondock S, Eid S (2016). Design, synthesis, antimicrobial evaluation and molecular docking studies of some new 2, 3-dihydrothiazoles and 4-thiazolidinones containing sulfisoxazole. J Enzyme Inhib Med Chem. 2016; 31: 236-46. |
| [10] | Argyropoulou I, Geronikaki A, Vicini P, Zani F (2009). Synthesis and biological evaluation of sulfonamide thiazole and benzothiazole derivatives as antimicrobial agents. Arkivoc.; 6: 89-102. |
| [11] | Keche A. P, Hatnapure G. D, Tale RH, Rodge A. H, Birajdar S. S, Kamble VM (2012). A novel pyrimidine derivatives with aryl urea, thiourea and sulfonamide moieties: Synthesis, anti-inflammatory and antimicrobial evaluation. Bioorg Med ChemLett; 22: 3445-8. |
| [12] | Ghorab M. M, Ragab F. A, Hamed M. M (2009). Design, synthesis and anticancer evaluation of novel tetrahydroquinoline derivatives containing sulfonamide moiety. Eur J Med Chem; 44: 4211-7. |
| [13] | El-Sayed N. S, El-Bendary E. R, El-Ashry S. M, El-Kerdawy M. M (2001). Synthesis and antitumor activity of new sulfonamide derivatives of thiadiazolo[3,2-a] pyrimidines. Eur J Med Chem; 46: 3714-20. |
| [14] | Noaman E, Fahmy N, Yousri R, Shawi O, Ghazy M (2011). Evaluation of the antitumor and radiosynthetizing activity of a novel quinolone sulphonamide derivative (PIQSA) as a histone deacetylase inhibitor. J Cancer Ther; 2: 567-78. |
| [15] | Chen Z, Xu W, Liu K, Yang S, Fan H, Bhadury P. S, et al (2010). Synthesis and antiviral activity of 5-(4-chlorophenyl)1,3,4-thiadiazole sulfonamides. Molecules; 15: 9046-56. |
| [16] | Domínguez J. N, León C, Rodrigues J, Gamboa de Domínguez N, Gut J, Rosenthal P. J. (2005) Synthesis and antimalarial activity of sulfonamide chalcone derivatives. Farmaco; 60: 307-11. |
| [17] | Padmanilayam M, Scorneaux B, Dong Y, Chollet J, Matile H, Charman S. A, et al (2006). Antimalarial activity of N-alkyl amine, carboxamide, sulfonamide, and urea derivatives of a dispiro-1,2,4-trioxolane piperidine. Bioorg Med ChemLett; 16: 5542-5. |
| [18] | Wilkinson B. L, Bornaghi LF, Houston TA, Innocenti A, Vullo D, Supuran C. T, et al (2017). Carbonic anhydrase inhibitors: Inhibition of isozymes I, II, and IX with triazole-linked O-glycosides of benzene sulfonamides. J Med Chem; 50: 1651-7. |
| [19] | Sharma R, Soman S. S (2015). Design and synthesis of sulfonamide derivatives of pyrrolidine and piperidine as anti-diabetic agents. Eur J Med Chem; 90: 342-50. |
| [20] | Bag S, Tulsan R, Sood A, Cho H, Redjeb H, Zhou W, et al (2015). Sulfonamides as multifunctional agents for Alzheimer’s disease. Bioorg Med ChemLett; 25: 626-30. |
| [21] | Vincent, C. O (2005). Principles of Pharmaceutical application of Antimicrobial agent, Pharmaceutical Microbiology, [EL DEMART] (publisher) Enugu State Nigeria, 171-177. |
| [22] | Shen Q, Zhang B, Xu R, Wang Y, Ding X, Li P (2010). Antioxidant activity, in vitro of selenium-contained protein from the Se-enriched Bifidobacterium animalis. Anaer. 16 (4): 380-386. |
| [23] | Hennicke F, Grumbt M, Lermann U, Ueberschaar N, Palige K, Bottcher B (2013). Factors supporting cysteine tolerance and sulfite production in Candida albicans. Eukaryot Cell; 12 (4): 604-613. |
| [24] | Matuszewska, A., Jaszek, M., Stefaniuk, D., Ciszewski, T., Matuszewski, Ł. (2018). Anticancer, antioxidant, and antibacterial activities of low molecular weight bioactive subfractions isolated from cultures of wood degrading fungus Cerrenaunicolor. PLOSONE, 13 (6): e0197044–e0197044. |
APA Style
Ike Ozoemena Christian, Okoro Uchechukwu Christopher, Aguoma Chinedu Chris, Orjioke Nwakaego Marytheresa, Ugwu David Izuchukwu, et al. (2023). Synthesis, Antimicrobial and Antioxidant Properties of Gly-Gly Based Dipeptide. American Journal of Applied Scientific Research, 9(3), 109-114. https://doi.org/10.11648/j.ajasr.20230903.14
ACS Style
Ike Ozoemena Christian; Okoro Uchechukwu Christopher; Aguoma Chinedu Chris; Orjioke Nwakaego Marytheresa; Ugwu David Izuchukwu, et al. Synthesis, Antimicrobial and Antioxidant Properties of Gly-Gly Based Dipeptide. Am. J. Appl. Sci. Res. 2023, 9(3), 109-114. doi: 10.11648/j.ajasr.20230903.14
AMA Style
Ike Ozoemena Christian, Okoro Uchechukwu Christopher, Aguoma Chinedu Chris, Orjioke Nwakaego Marytheresa, Ugwu David Izuchukwu, et al. Synthesis, Antimicrobial and Antioxidant Properties of Gly-Gly Based Dipeptide. Am J Appl Sci Res. 2023;9(3):109-114. doi: 10.11648/j.ajasr.20230903.14
Share This Article
Twitter
Linked In
Facebook
Copy
Download@article{10.11648/j.ajasr.20230903.14,
author = {Ike Ozoemena Christian and Okoro Uchechukwu Christopher and Aguoma Chinedu Chris and Orjioke Nwakaego Marytheresa and Ugwu David Izuchukwu and Nweloke Regina Chinyere and Orie Kingsley John and Nsude Okechukwu Paul and Okoye Nebeolisa Johnson and Eze Cosmos Chibuike and Attah Solomon Izuchukwu and Ugwu Michael Chukwuemeka},
title = {Synthesis, Antimicrobial and Antioxidant Properties of Gly-Gly Based Dipeptide},
journal = {American Journal of Applied Scientific Research},
volume = {9},
number = {3},
pages = {109-114},
doi = {10.11648/j.ajasr.20230903.14},
url = {https://doi.org/10.11648/j.ajasr.20230903.14},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajasr.20230903.14},
abstract = {Background: The reported rise in drug-resistant bacteria, as well as the prevalence of oxidative stress-related disorders, motivated the need for novel antimicrobial and antioxidants activity. The synthesis of gly-gly based dipeptides bearing sulphonamide functionalities is reported. Methodology: The base promoted reaction of appropriate substituted benzenesulphonyl chloride with L-glycine afforded compounds (3a-3b) and the condensation reaction of (3a-3b) with carboxamide derivatives gave the targeted products (7a-7b) using peptide coupling reagent. The characterization of compounds was done using 1HNMR, 13CNMR, FTIR and HRMS. Results: In the in vitro antimicrobial activity, compounds 7a (MIC 6.10 mg/mL), 7ai (MIC 7.01 mg/mL), 7b (MIC 7.42 mg/mL), 7bi (MIC 6.32 mg/mL) was most potent against S. aureus, B. subtilis, P. aeruginosa and E. coli respectively. Compounds 7a (MIC 6.90 mg/mL) and 7b (MIC 6.48 mg/mL) were most active against C. Albicans and A. Niger respectively. Compound 7a and 7bi (85.00% and 88.78% at 25mg/mL) exhibits excellent percentage inhibition antioxidant activities comparable with vitamin C (90.78% at 25mg/mL) and alsocompound 7bi had the best IC50 values of 0.7674 mg/mL. Conclusion: The synthesized compounds were found to be potent antibacterial, antifungal and antioxidant agents.},
year = {2023}
}
TY - JOUR T1 - Synthesis, Antimicrobial and Antioxidant Properties of Gly-Gly Based Dipeptide AU - Ike Ozoemena Christian AU - Okoro Uchechukwu Christopher AU - Aguoma Chinedu Chris AU - Orjioke Nwakaego Marytheresa AU - Ugwu David Izuchukwu AU - Nweloke Regina Chinyere AU - Orie Kingsley John AU - Nsude Okechukwu Paul AU - Okoye Nebeolisa Johnson AU - Eze Cosmos Chibuike AU - Attah Solomon Izuchukwu AU - Ugwu Michael Chukwuemeka Y1 - 2023/07/24 PY - 2023 N1 - https://doi.org/10.11648/j.ajasr.20230903.14 DO - 10.11648/j.ajasr.20230903.14 T2 - American Journal of Applied Scientific Research JF - American Journal of Applied Scientific Research JO - American Journal of Applied Scientific Research SP - 109 EP - 114 PB - Science Publishing Group SN - 2471-9730 UR - https://doi.org/10.11648/j.ajasr.20230903.14 AB - Background: The reported rise in drug-resistant bacteria, as well as the prevalence of oxidative stress-related disorders, motivated the need for novel antimicrobial and antioxidants activity. The synthesis of gly-gly based dipeptides bearing sulphonamide functionalities is reported. Methodology: The base promoted reaction of appropriate substituted benzenesulphonyl chloride with L-glycine afforded compounds (3a-3b) and the condensation reaction of (3a-3b) with carboxamide derivatives gave the targeted products (7a-7b) using peptide coupling reagent. The characterization of compounds was done using 1HNMR, 13CNMR, FTIR and HRMS. Results: In the in vitro antimicrobial activity, compounds 7a (MIC 6.10 mg/mL), 7ai (MIC 7.01 mg/mL), 7b (MIC 7.42 mg/mL), 7bi (MIC 6.32 mg/mL) was most potent against S. aureus, B. subtilis, P. aeruginosa and E. coli respectively. Compounds 7a (MIC 6.90 mg/mL) and 7b (MIC 6.48 mg/mL) were most active against C. Albicans and A. Niger respectively. Compound 7a and 7bi (85.00% and 88.78% at 25mg/mL) exhibits excellent percentage inhibition antioxidant activities comparable with vitamin C (90.78% at 25mg/mL) and alsocompound 7bi had the best IC50 values of 0.7674 mg/mL. Conclusion: The synthesized compounds were found to be potent antibacterial, antifungal and antioxidant agents. VL - 9 IS - 3 ER -
Information
Email: