Synthesis of new 4-aminobenzoic acid (PABA) hydrazide-hydrazone/sulfonate hybrids and antimicrobial evaluation with ascorbic acid/salicylic acid/N-acetyl cysteine combinations

References

• Liu, G.; Stokes, J. M. A Brief Guide to Machine Learning for Antibiotic Discovery. Curr. Opin. Microbiol. 2022, 69, 102190. DOI: 10.1016/j.mib.2022.102190.
   PubMed Web of Science ®Google Scholar
• Guliy, O. I.; Zaitsev, B. D.; Smirnov, A. V.; Karavaeva, O. A.; Borodina, I. A. Prospects of Acoustic Sensor Systems for Antibiotic Detection. Biosens. Bioelect. 2022, 12, 100274. DOI: 10.1016/j.biosx.2022.100274.
   Google Scholar
• Qin, K.; Zhang, P.; Li, Z. Specific Detection of Antibiotic-Resistant Bacteria Using CRISPR/Cas9 Induced Isothermal Exponential Amplification Reaction (IEXPAR). Talanta 2023, 253, 124045. DOI: 10.1016/j.talanta.2022.124045.
   Web of Science ®Google Scholar
• Mohammed, E. H. M.; Lohan, S.; Tiwari, R. K.; Parang, K. Amphiphilic Cyclic Peptide [W4KR5]-Antibiotics Combinations as Broad-Spectrum Antimicrobial Agents. Eur. J. Med. Chem. 2022, 235, 114278. DOI: 10.1016/j.ejmech.2022.114278.
   PubMed Web of Science ®Google Scholar
• Pawlowski, A. C.; Johnson, J. W.; Wright, G. D. Evolving Medicinal Chemistry Strategies in Antibiotic Discovery. Curr. Opin. Biotechnol. 2016, 42, 108–117. DOI: 10.1016/j.copbio.2016.04.006.
   PubMed Web of Science ®Google Scholar
• Velkov, T.; Thompson, P. E.; Nation, R. L.; Li, J. Structure-Activity Relationships of Polymyxin Antibiotics. J. Med. Chem. 2010, 53, 1898–1916. DOI: 10.1021/jm900999h.
   PubMed Web of Science ®Google Scholar
• El-Etrawy, A. S.; Sherbiny, F. F. Design, Synthesis, Biological Evaluation and Molecular Modeling Investigation of New N'-(2-Thiouracil-5-Oyl) Hydrazone Derivatives as Potential anti-Breast Cancer and anti-Bacterial Agents. J. Mol. Struct. 2021, 1232, 129993. DOI: 10.1016/j.molstruc.2021.129993.
   Web of Science ®Google Scholar
• Han, M. İ.; İmamoğlu, N. Design, Synthesis, and Anticancer Evaluation of Novel Tetracaine Hydrazide-Hydrazones. ACS Omega 2023, 8, 9198–9211. DOI: 10.1021/acsomega.2c07192.
   PubMed Web of Science ®Google Scholar
• İnce, U.; Han, M. İ. Investigation of Antimicrobial Activity of Some Ethylparaben Hydrazide-Hydrazone Derivatives. Turk. J. Pharm. Sci. 2023, 20, 35–38. DOI: 10.4274/tjps.galenos.2022.57699.
   PubMed Web of Science ®Google Scholar
• Han, M. İ.; Gündüz, M. G.; Alçı, G.; Giovannuzzi, S.; Yuvalı, D.; Supuran, C. T.; Doğan, ŞD. Sulfonamides Linked to Sulfonate Esters via Hydrazone Functionality: Synthesis, Human Carbonic Anhydrase Inhibitory Activities, and Molecular Modeling Studies. New J. Chem. 2023, 47, 4267–4276. DOI: 10.1039/D2NJ05703D.
   Web of Science ®Google Scholar
• Han, M.; Yeşil Baysal, Ö. D.; Başaran, G. Ş.; Sezer, G.; Telci, D.; Küçükgüzel, Ş. Design, Synthesis and Anticancer Activity Studies of Novel 4-Butylaminophenyl Hydrazide-Hydrazones as Apoptotic Inducers. Tetrahedron 2022, 115, 132797. DOI: 10.1016/j.tet.2022.132797.
   Web of Science ®Google Scholar
• Koçak Aslan, E.; Han, M. İ.; Krishna, V. S.; Tamhaev, R.; Dengiz, C.; Doğan, ŞD.; Lherbet, C.; Mourey, L.; Tønjum, T.; Gündüz, M. G. Isoniazid Linked to Sulfonate Esters via Hydrazone Functionality: Design, Synthesis, and Evaluation of Antitubercular Activity. Pharmaceuticals (Basel) 2022, 15, 1301–1315. DOI: 10.3390/ph15101301.
   PubMedGoogle Scholar
• Han, M. I.; Atalay, P.; Tunç, C. Ü.; Ünal, G.; Dayan, S.; Aydın, O.; Küçükgüzel, S. G. Design and Synthesis of Novel (S)-Naproxen Hydrazide-Hydrazones as Potent VEGFR-2 Inhibitors and Their Evaluation in Vitro/in Vivo Breast Cancer Models. Bioorg. Med. Chem. 2021, 37, 116097. DOI: 10.1016/j.bmc.2021.116097.
   PubMed Web of Science ®Google Scholar
• Han, M. İ.; Atalay, P.; İmamoğlu, N.; Küçükgüzel, ŞG. Synthesis, Characterization and Anticancer Activity of Novel Hydrazide-Hydrazones Derived from Ethyl Paraben. jrp. 2020, 24, 341–349. DOI: 10.35333/jrp.2020.156.
   Google Scholar
• Han, M. İ.; Bekçi, H.; Uba, A. I.; Yıldırım, Y.; Karasulu, E.; Cumaoğlu, A.; Karasulu, H. Y.; Yelekçi, K.; Yılmaz, Ö.; Küçükgüzel, ŞG. Synthesis, Molecular Modeling, in Vivo Study, and Anticancer Activity of 1,2,4‐Triazole Containing Hydrazide–Hydrazones Derived from (S)‐Naproxen. Arch. Pharm. Chem. Life Sci. 2019, 352, 1800365. DOI: 10.1002/ardp.201800365.
   Web of Science ®Google Scholar
• Han, M. İ.; Bekçi, H.; Cumaoğlu, A.; Küçükgüzel, ŞG. Synthesis and Characterization of 1,2,4-Triazole Containing Hydrazide-Hydrazones Derived from (S)-Naproxen as Anticancer Agents. Marmara Pharm. J. 2018, 22, 559–569. DOI: 10.12991/jrp.2018.98.
   Google Scholar
• Han, M. İ.; Gürol, G.; Yildirim, T.; Kalayci, S.; Şahin, F.; Küçükgüzel, ŞG. Synthesis and Antibacterial Activity of New Hydrazide-Hydrazones Derived from Benzocaine. MPJ 2017, 21, 961–966. DOI: 10.12991/mpj.2017.34.
   Google Scholar
• Rollas, S.; Küçükgüzel, ŞG. Biological Activities of Hydrazone Derivatives. Molecules 2007, 12, 1910–1939. DOI: 10.3390/12081910.
   PubMed Web of Science ®Google Scholar
• Noshiranzadeh, N.; Heidari, A.; Haghi, F.; Bikas, R.; Lis, T. Chiral Lactic Hydrazone Derivatives as Potential Bioactive Antibacterial Agents: Synthesis, Spectroscopic, Structural and Molecular Docking Studies. J. Mol. Struct. 2017, 1128, 391–399. DOI: 10.1016/j.molstruc.2016.09.006.
   Web of Science ®Google Scholar
• Zhang, L.; Wen, B.; Bao, M.; Cheng, Y.; Mahmood, T.; Yang, W.; Chen, Q.; Lv, L.; Li, L.; Yi, J.; et al. Andrographolide Sulfonate is a Promising Treatment to Combat Methicillin-Resistant Staphylococcus aureus and Its Biofilms. Front. Pharmacol. 2021, 12, 720685. DOI: 10.3389/fphar.2021.720685.
   PubMed Web of Science ®Google Scholar
• Deng, Z.; Bheemanaboina, R. R. Y.; Luo, Y.; Zhou, C. H. Aloe Emodin-Conjugated Sulfonyl Hydrazones as Novel Type of Antibacterial Modulators against S. aureus 25923 through Multifaceted Synergistic Effects. Bioorg. Chem. 2022, 127, 106035. DOI: 10.1016/j.bioorg.2022.106035.
   PubMed Web of Science ®Google Scholar
• Özbek, N.; Özdemir, Ü. Ö.; Altun, A. F.; Şahin, E. Sulfonamide-Derived Hydrazone Compounds and Their Pd(II) Complexes: Synthesis, Spectroscopic Characterization, X-Ray Structure Determination, in Vitro Antibacterial Activity and Computational Studies. J. Mol. Struct. 2019, 1196, 707–719. DOI: 10.1016/j.molstruc.2019.07.016.
   Web of Science ®Google Scholar
• Adam, M. S. S.; Elsawy, H.; Sedky, A.; Makhlouf, M. M. Comparable Catalytic and Biological Behavior of Alternative Polar Dioxo-Molybdenum(VI) Schiff Base Hydrazone Chelates. J. Taiwan Ins. Chem. Eng. 2022, 136, 104425. DOI: 10.1016/j.jtice.2022.104425.
   Web of Science ®Google Scholar
• Adam, M. S. S.; Khalil, A.; Nickel I. I.; Copper, I. I.) And Vanadyl(II) Complexes with Tridentate Nicotinoyl Hydrazone Derivative Functionalized as Effective Catalysts for Epoxidation Processes and as Biological Reagents. J. Taiwan Ins. Chem. Eng. 2022, 132, 104192. DOI: 10.1016/j.jtice.2021.104192.
   Web of Science ®Google Scholar
• İhsan Han, M.; İnce, U.; Gündüz, M. G.; Coşkun, G. P.; Birgül, K.; Doğan, ŞD.; Küçükgüzel, ŞG. Synthesis, Antimicrobial Evaluation and Molecular Modeling Studies of Novel Thiosemicarbazides/Semicarbazides Derived from p-Aminobenzoic Acid. J. Mol. Struct. 2022, 1261, 132907. DOI: 10.1016/j.molstruc.2022.132907.
   Web of Science ®Google Scholar
• Shi, L.; Ge, H. M.; Tan, S. H.; Li, H. Q.; Song, Y. C.; Zhu, H. L.; Tan, R. X. Synthesis and Antimicrobial Activities of Schiff Bases Derived from 5-Chloro-Salicylaldehyde. Eur. J. Med. Chem. 2007, 42, 558–564. DOI: 10.1016/J.EJMECH.2006.11.010.
   PubMed Web of Science ®Google Scholar
• Abdulrab, S.; Mostafa, N.; Al‑Maweri, S. A.; Abada, H.; Halboub, E.; Alhadainy, H. A. Antibacterial and anti‑Inflammatory Efficacy of N‑Acetyl Cysteine in Endodontic Treatment: A Scoping Review. BMC Oral Health 2022, 22, 398–409. DOI: 10.1186/s12903-022-02433-6.
   PubMed Web of Science ®Google Scholar
• Sahoo, J.; Paidesetty, S. K. Antimicrobial, Analgesic, Antioxidant and in Silico Study of Synthesized Salicylic Acid Congeners and Their Structural Interpretation. Egyp. J. Bas. App. Sci. 2015, 2, 268–280. DOI: 10.1016/j.ejbas.2015.07.006.
   Google Scholar
• Rawal, B. D. Bactericidal Action of Ascorbic Acid on Pseudomonas Aeruginosa: Alteration of Cell Surface as a Possible Mechanism. Chemotherapy 1978, 24, 166–171. DOI: 10.1159/000237777.
   PubMed Web of Science ®Google Scholar
• Dinicola, S.; De Grazia, S.; Carlomagno, G.; Pintucci, J. P. N-Acetylcysteine as Powerful Molecule to Destroy Bacterial Biofilms. A Systematic Review. Eur. Rev. Med. Pharmacol. Sci. 2014, 18, 2942–2948.
   PubMed Web of Science ®Google Scholar
• Mogana, R.; Adhikari, A.; Tzar, M. N.; Ramliza, R.; Wiart, C. Antibacterial Activities of the Extracts, Fractions and Isolated Compounds from Canarium Patentinervium Miq. against Bacterial Clinical Isolates. BMC Complement. Med. Ther. 2020, 20, 55. DOI: 10.1186/s12906-020-2837-5.
   PubMedGoogle Scholar
• Sharma, P. C.; Sharma, D.; Sharma, A.; Saini, N.; Goyal, R.; Ola, M.; Chawla, R.; Thakur, V. K. Hydrazone Comprising Compounds as Promising anti-Infective Agents: Chemistry and Structure-Property Relationship. Mat. Tod. Chem. 2020, 18, 100349. DOI: 10.1016/j.mtchem.2020.100349.
   Web of Science ®Google Scholar
• Landini, G.; Di Maggio, T.; Sergio, F.; Docquier, J. D.; Rossolini, G. M.; Pallecchi, L. Effect of High N-Acetylcysteine Concentrations on Antibiotic Activity against a Large Collection of Respiratory Pathogens. Antimicrob. Agents Chemother. 2016, 60, 7513–7517. DOI: 10.1128/AAC.01334-16.
   PubMed Web of Science ®Google Scholar
• Clinical and Laboratory Standards Institute (CLSI). Performance Standards for Antimicrobial Susceptibility Testing, 2017.
   Google Scholar
• Clinical and Laboratory Standards Institute. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts: Approved Standard, 3rd ed.; Clinical and Laboratory Standards Institute: Wayne, PA, 2008, M 27–A3.
   Google Scholar