New Glucosamine Derivatives Based Reducing Disaccharides via Schiff Reaction

Authors

DOI:

https://doi.org/10.24237/

Abstract

Due to the importance of glucosamine, this project aims to improve its role in medicinal and pharmaceutical applications and find new derivatives derived from glucosamine with useful and beneficial applications. We planned to couple two important glucosamine compounds, 6-deoxy-6-amino-D-glucose and 2-deoxy-2-amino-D-glucose, with two reducing disaccharides (D-lactose and D-maltose) via Schiff coupling because the two compounds, glucosamine and reducing disaccharides, have the required function groups for the Schiff reaction: the amine groups and the aldehyde groups. The synthesis of a series of four compounds was performed and subjected to spectroscopic characterization to prove their structure and purity. The biological activity was tested for two compounds; one of them shows excellent activity toward two kinds of gram-negative and gram-positive bacteria, which cannot be killed by penicillin.

Downloads

Download data is not yet available.

References

[1] R. Dalirfardouei, G. K. K. Jamialahmadi, Molecular mechanisms and biomedical applications of glucosamine as a potential multifunctional therapeutic agent, Life Sciences, 152, 21-29(2016), DOI(https://doi.org/10.1016/j.lfs.2016.03.028)

[2] G. A. Raciti , C. I. L. Ulianich, B. F. Vind, & M. Gaster, F. Andreozzi, M. Longo & R. Teperino, P. Ungaro, B. Di Jeso, P. Formisano, F. Beguinot, C. Miele, Glucosamine-induced endoplasmic reticulum stress affects GLUT4 expression via activating transcription factor 6 in rat and human skeletal muscle cells, Diabetologia, 53, 955–965(2010), DOI(https://doi.org/10.1007/s00125-010-1676-1)

[3] J. Salazar, L. B. Mervin Chávez, R. Añez, J. Rojas, V. Bermúdez, Glucosamine for Osteoarthritis: Biological Effects, Clinical Efficacy, and Safety on Glucose Metabolism, Arthritis, 1-14(2014), DOI(https://doi.org/10.1155/2014/432463)

[4] B. Liberek, A. M. Anna Osuch, R. Wakieć, S. Milewski, A. Wiśniewski, N-Alkyl derivatives of 2-amino-2-deoxy-d-glucose, Carbohydrate Research, 340(11), p. 1876-1884(2005), DOI(https://doi.org/10.1016/j.carres.2005.05.013)

[5] T. V. Ovchinnikova, A.V. P. Alexander, B. Tuzikov, N. V. Bovin, Synthesis of 1-BODIPY-labeled 2-amino-2-deoxy-d-glucose, substrate for acetyl-CoA:glucosaminide N-acetyltransferase, Mendeleev Communications, 25(6), 422-423(2015), DOI(https://doi.org/10.1016/j.mencom.2015.11.007)

[6] J. Yang, D. X. Xiaofeng, Ma, Recent Advances in Chemical Synthesis of Amino Sugars, Molecules, 28(12), (2023), DOI(https://doi.org/10.3390/molecules28124724)

[7] I. Serbian, E. P. Claudia Fischer, Hans-Peter Deigner, R. Csuk, n-Propyl 6-amino-2,6-dideoxy-2,2-difluoro-β-D-glucopyranoside is a good inhibitor for the β-galactosidase from E. coli., Medicinal Chemistry Research 30, 1099–1107(2021), DOI( https://doi.org/10.1007/s00044-021-02715-8)

[8] A. Fatangare, C. HanspeterSaluz, AlešSvatoš, 2-Deoxy-2-fluoro-D-glucosemetabolisminArabidopsisthaliana, Frontiers in Plant Science, 6, 1-12(2015), DOI(https://doi.org/10.3389/fpls.2015.00935)

[9] B. Pajak, E. Siwiak, M. Sołtyka, A. Priebe, R. Zieliński, I. Fokt, M. Ziemniak, A. Jaśkiewicz, R. Borowski, T. Domoradzki, 2-Deoxy-d-Glucose and Its Analogs: From Diagnostic to Therapeutic Agents, International Journal of Molecular Sciences, 21(1), (2020) DOI(https://doi.org/10.3390/ijms21010234)

[10] Y. Zhang, Q. Li, Z. Huang, B. Li, E. C. Nice, C. Huang, L. Wei, B. Zou1, Targeting Glucose Metabolism Enzymes in Cancer Treatment: Current and Emerging Strategies, Cancers (Basel), 14(19), (2022), DOI(https://doi.org/10.3390/cancers14194568)

[11] R. Singh, V. Gupta, A. Kumar, K. Singh, 2-Deoxy-D-Glucose: A Novel Pharmacological Agent for Killing Hypoxic Tumor Cells, Oxygen Dependence-Lowering in Covid-19, and Other Pharmacological Activities, Advances in Pharmacological and Pharmaceutical Sciences, 1-15(2023) DOI(https://doi.org/10.1155/2023/9993386)

[12] Y. S. Vidya , H. C. Manjunatha, S. Manjunatha, K. N. Sridhar, L. Seenappa, R. Munirathnam, 2-Deoxy-d-glucose functionalized zinc oxide nanodrug for kidney cancer treatment, Journal of Science: Advanced Materials and Devices, 8(3), 100587(2023), DOI(https://doi.org/10.1016/j.jsamd.2023.100587)

[13] T. MaruYama, H. Miyazaki, Y. Lim, J. Gu , M. Ishikawa, T. Yoshida, W. Chen, Y. Owada, H. Shibata, Pyrolyzed deketene curcumin controls regulatory T cell generation and gastric cancer metabolism cooperate with 2-deoxy-d-glucose, Frontiers in Immunology, 14, 1-13(2023), DOI(https://doi.org/10.3389/fimmu.2023.1049713)

[14] T. Li, X.Goa, L. Yang, Y. Shi, Q. Gao, Methyl 6-Amino-6-deoxy-d-pyranoside-Conjugated Platinum(II) Complexes for Glucose Transporter (GLUT)-Mediated Tumor Targeting: Synthesis, Cytotoxicity, and Cellular Uptake Mechanism, Chem Med Chem, 11(10), 1069-1077(2016), DOI(https://doi.org/10.1002/cmdc.201600079)

[15] A. Ozer, D. E. Yasa, D. H. Sahin, H. Turbayindir, E. Pehlivan, Z. E. Koc, Investigation of microwave assisted synthesis of Schiff Base derived Metal-Chelates by liquid invert sugar containing D-Glucose, Inorganic and Nano-Metal Chemistry, 1-12(2023), DOI(https://doi.org/10.1080/24701556.2023.2197885)

[16] S. Salman, I. İ Mahmood, L. Abd, New Bioactive Aromatic Indole Molecules with Monosaccharide Core. Journal of the Turkish Chemical Society, Section A: Chemistry, 9(3), 889-900(2023), DOI(https://doi.org/10.18596/jotcsa.1098055)

[17] Q. Weng, J. Yi, X. Chen, D. Luo, Y. Wang, W. Sun, J. Kang, Z. Han, Controllable Synthesis and Biological Application of Schiff Bases from d-Glucosamine and Terephthalaldehyde, ACS Omega, 5(38), 24864–24870(2020) DOI(https://doi.org/10.1021/acsomega.0c03591)

[18] D. Colombo, C. Gagliardi, M. Vetro, F. Ronchetti, M. Takasaki, T. Konoshima, N. Suzuki, H. Tokuda, New 6-amino-6-deoxy-glycoglycerolipids derived from 2-O-β-d-glucopyranosylglycerol: insights into the structure–activity relationship of glycoglycerolipids as anti-tumor promoters, Carbohydrate Research, 373, 64-74(2013), DOI(https://doi.org/10.1016/j.carres.2013.03.007)

[19] N. X. Vo, N. N. H. Le, T. D. P. Chu, H. L. Pham, K. X. An Dinh, U. T. T. Che, T. T. T. Ngo, T. T. Bui, Effectiveness and Safety of Glucosamine in Osteoarthritis: A Systematic Review, Pharmacy (Basel), 11(4), (2023), DOI(https://doi.org/10.3390/pharmacy11040117)

[20] J. Xie, Synthesis of new sugar amino acid derivatives of d-glucosamine, Carbohydrate Research, 338(5), 399-406(2003), DOI(https://doi.org/10.1016/S0008-6215(02)00487-1)

[21] E. Raczuk, B. Dmochowska, J. Samaszko-Fiertek, J. Madaj, Different Schiff Bases—Structure, Importance and Classification, Molecules, 27, (2022), DOI(https://doi.org/10.3390/molecules27030787)

[22] N. Ayad Abd AL-Qadir, N. Dheyaa Shaalan, Synthesis, Characterization, and Biological Activity of New Metal Ion Complexes with Schiff Base (Z)-3((E)-2-Hydroxybenzylidene) hydrazineylidene)indolin-2-one, Journal of Medicinal and Chemical Sciences, 6(7), 1660-1674(2023), DOI(10.26655/JMCHEMSCI.2023.7.16)

[23] S. K. Raju, S. Archana, Thiyagarajan, Divya Rama, Praveen Sekar and Shridharshini Kumar, Synthetic approaches of medicinally important Schiff bases: An updated Review, World Journal of Advanced Research and Review, 16(3), 838–852(2022), DOI(https://doi.org/10.30574/wjarr.2022.16.3.1394)

[24] D. B. Thuy, J. Campbell, C. T. Thuy, N. V. M. Hoang, P. V. Vinh, T. N. T. Nguyen, C. N. N. Minh, D. T. Pham, M. A. Rabaa, N. P. H. Lan, N. V. Hao, G. E. Thwaites, C. L. Thwaites, S. Baker, N. V. V. Chau, C. H. The, Colonization with Staphylococcus aureus and Klebsiella pneumoniae causes infections in a Vietnamese intensive care unit, Microbial Genomics, 7(2), (2021), DOI(https://doi.org/10.1099/mgen.0.000514)

[25] S. Namdari, F.A., Khademalhoseini A, Behzad-Behbahani A, Moaddeb A, Emergence of Highly Multidrug-Resistant Bacteria Isolated from Patients with Infections Admitted to Public Hospitals in Southwest Iran, Interdisciplinary Perspectives on Infectious Diseases, (2021), DOI(https://doi.org/10.1155/2021/5265379)

[26] S. Alfei, C. D. Piatti, G. Zuccari, A. M. Schito, Synthesis, Characterization and Broad-Spectrum Bactericidal Effects of Ammonium Methyl and Ammonium Ethyl Styrene-Based Nanoparticles, Nanomaterials (Basel), 12(16), (2022), DOI(https://doi.org/10.3390/nano12162743)

[27] A. Vasala, V. P. Hytönen,O. H. Laitinen, Modern Tools for Rapid Diagnostics of Antimicrobial Resistance, Frontiers in Cellular and Infection Microbiology, 10, 1-23(2020), DOI(https://doi.org/10.3389/fcimb.2020.00308)

[28] H. A. E. Obaid, Investigation of some physiological, biochemica characteristics and multiple antibiotic resistance of Staphylococcus aureus isolated from wound samples, Journal of Advanced Education and Sciences, 3(3), 9-16(2023)

[29] P. Goel, V. Galhotra, S. Makkar, J. Mohan, N. Bala, T. Kaur, An In Vitro Study Comparing the Antimicrobial Efficacy of 0.2% Chitosan, 3% Sodium Hypochlorite, 2% Chlorhexidine against Enterococcus faecalis, Alone and in Conjunction with Diode Laser, International Journal of Clinical Pediatric Dentistry, 15(1), 109–114(2022), DOI(https://doi.org/10.5005/jp-journals-10005-2351)

[30] S. Goud, S. Aravelli, S. Dronamraju, G. Cherukuri, P. Morishetty, Comparative Evaluation of the Antibacterial Efficacy of Aloe Vera, 3% Sodium Hypochlorite, and 2% Chlorhexidine Gluconate Against Enterococcus faecalis: An In Vitro Study, Cureus, 10(10), (2018), DOI(10.7759/cureus.3480)

Downloads

Published

2025-10-01

Issue

Vol. 3 No. 4 (2025)

Section

Articles

License

Copyright (c) 2025 CC BY 4.0

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

Ali Azeez, J. ., Salman, salih, & Baqir Ali, W. . (2025). New Glucosamine Derivatives Based Reducing Disaccharides via Schiff Reaction. Academic Science Journal, 3(4), 201-220. https://doi.org/10.24237/