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Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking.
Molecules. 2017 Aug 16; 22(8)M

Abstract

Sulfonamide derivatives serve as an important building blocks in the drug design discovery and development (4D) process. Ciprofloxacin-, sulfadiazine- and amantadine-based sulfonamides were synthesized as potent inhibitors of jack bean urease and free radical scavengers. Molecular diversity was explored and electronic factors were also examined. All 24 synthesized compounds exhibited excellent potential against urease enzyme. Compound 3e (IC50 = 0.081 ± 0.003 µM), 6a (IC50 = 0.0022 ± 0.0002 µM), 9e (IC50 = 0.0250 ± 0.0007 µM) and 12d (IC50 = 0.0266 ± 0.0021 µM) were found to be the lead compounds compared to standard (thiourea, IC50 = 17.814 ± 0.096 µM). Molecular docking studies were performed to delineate the binding affinity of the molecules and a kinetic mechanism of enzyme inhibition was propounded. Compounds 3e, 6a and 12d exhibited a mixed type of inhibition, while derivative 9e revealed a non-competitive mode of inhibition. Compounds 12a, 12b, 12d, 12e and 12f showed excellent radical scavenging potency in comparison to the reference drug vitamin C.

Authors+Show Affiliations

Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan. mrpervaiz@gmail.com.Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan. aamersaeed@yahoo.com.Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain. albericio@ukzn.ac.za. CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, University of Barcelona, 08028 Barcelona, Spain. albericio@ukzn.ac.za.Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan. fayazali@chem.qau.edu.pk.Department of Biological Sciences, College of Natural Sciences, Kongju National University, 56 Gongjudehak-Ro, Gongju, Chungnam 314-701, Korea. qamar.abbas.qau@gmail.com. Department of Physiology, University of Sindh, Jamshoro 76080, Pakistan. qamar.abbas.qau@gmail.com.Department of Biological Sciences, College of Natural Sciences, Kongju National University, 56 Gongjudehak-Ro, Gongju, Chungnam 314-701, Korea. mubashirhassan_gcul@yahoo.com.Department of Biological Sciences, College of Natural Sciences, Kongju National University, 56 Gongjudehak-Ro, Gongju, Chungnam 314-701, Korea. hussain_solangi@yahoo.com.Department of Biological Sciences, College of Natural Sciences, Kongju National University, 56 Gongjudehak-Ro, Gongju, Chungnam 314-701, Korea. dnalove@kongju.ac.kr.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28813027

Citation

Channar, Pervaiz Ali, et al. "Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking." Molecules (Basel, Switzerland), vol. 22, no. 8, 2017.
Channar PA, Saeed A, Albericio F, et al. Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking. Molecules. 2017;22(8).
Channar, P. A., Saeed, A., Albericio, F., Larik, F. A., Abbas, Q., Hassan, M., Raza, H., & Seo, S. Y. (2017). Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking. Molecules (Basel, Switzerland), 22(8). https://doi.org/10.3390/molecules22081352
Channar PA, et al. Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking. Molecules. 2017 Aug 16;22(8) PubMed PMID: 28813027.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking. AU - Channar,Pervaiz Ali, AU - Saeed,Aamer, AU - Albericio,Fernando, AU - Larik,Fayaz Ali, AU - Abbas,Qamar, AU - Hassan,Mubashir, AU - Raza,Hussain, AU - Seo,Sung-Yum, Y1 - 2017/08/16/ PY - 2017/07/05/received PY - 2017/08/09/accepted PY - 2017/8/17/entrez PY - 2017/8/17/pubmed PY - 2018/4/27/medline KW - drug derivatives KW - drug discovery KW - jack bean urease inhibition KW - kinetic mechanism KW - molecular docking KW - sulfonamides JF - Molecules (Basel, Switzerland) JO - Molecules VL - 22 IS - 8 N2 - Sulfonamide derivatives serve as an important building blocks in the drug design discovery and development (4D) process. Ciprofloxacin-, sulfadiazine- and amantadine-based sulfonamides were synthesized as potent inhibitors of jack bean urease and free radical scavengers. Molecular diversity was explored and electronic factors were also examined. All 24 synthesized compounds exhibited excellent potential against urease enzyme. Compound 3e (IC50 = 0.081 ± 0.003 µM), 6a (IC50 = 0.0022 ± 0.0002 µM), 9e (IC50 = 0.0250 ± 0.0007 µM) and 12d (IC50 = 0.0266 ± 0.0021 µM) were found to be the lead compounds compared to standard (thiourea, IC50 = 17.814 ± 0.096 µM). Molecular docking studies were performed to delineate the binding affinity of the molecules and a kinetic mechanism of enzyme inhibition was propounded. Compounds 3e, 6a and 12d exhibited a mixed type of inhibition, while derivative 9e revealed a non-competitive mode of inhibition. Compounds 12a, 12b, 12d, 12e and 12f showed excellent radical scavenging potency in comparison to the reference drug vitamin C. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/28813027/Sulfonamide_Linked_Ciprofloxacin_Sulfadiazine_and_Amantadine_Derivatives_as_a_Novel_Class_of_Inhibitors_of_Jack_Bean_Urease L2 - https://www.mdpi.com/resolver?pii=molecules22081352 DB - PRIME DP - Unbound Medicine ER -