60
Views
3
CrossRef citations to date
0
Altmetric
Research Article

Antimicrobial, Anticancer and Immunomodulatory Potential of New Quinazolines Bearing Benzenesulfonamide Moiety

ORCID Icon, , ORCID Icon & ORCID Icon
Pages 275-290 | Received 07 Dec 2022, Accepted 24 Jan 2023, Published online: 09 Mar 2023

References

  • Fleming A . On the antibacterial action of cultures of a penicillium, with special reference to their use in the isolation of B. influenzae. Br. J. Exp. Pathol.10(3), 226 (1929).
  • Resistance ROA . Antimicrobial resistance: tackling a crisis for the health and wealth of nations. Review on Antimicrobial Resistance. 3 (2014).
  • Tacconelli E , MagriniN, KahlmeterG, SinghN. Global priority list of antibiotic-resistant bacteria to guide research, discovery, and development of new antibiotics. World Health Organization27, 318–327 (2017).
  • World Malaria Report 2015. World Health Organization, Geneva, Switzerland (2016).
  • Johns Hopkins Corona Virus Resource Center . https://coronavirus.jhu.edu
  • Loomba PS , TanejaJ, MishraB. Methicillin and vancomycin resistant S. aureus in hospitalized patients. J. Glob. Infect. Dis.2(3), 275 (2010).
  • Ormerod LP . Multidrug-resistant tuberculosis (MDR-TB): epidemiology, prevention and treatment. Br. Med. Bull.73(1), 17–24 (2005).
  • Arnold RS , ThomKA, SharmaS, PhillipsM, JohnsonJK, MorganDJ. Emergence of klebsiella pneumoniae carbapenemase (KPC)-producing bacteria. South. Med. J.104(1), 40 (2011).
  • Dias FR , NovaisJS, DevillartTADNSet al. Synthesis and antimicrobial evaluation of amino sugar-based naphthoquinones and isoquinoline-5, 8-diones and their halogenated compounds. Eur. J. Med. Chem.156, 1–12 (2018).
  • Opintan JA , NewmanMJ. Prevalence of antimicrobial resistant pathogens from blood cultures: results from a laboratory based nationwide surveillance in Ghana. Antimicrob. Res. Infect. Control6(1), 1–6 (2017).
  • Mehrad B , ClarkNM, ZhanelGG, LynchIii JP. Antimicrobial resistance in hospital-acquired Gram-negative bacterial infections. Chest147(5), 1413–1421 (2015).
  • Kanj SS , KanafaniZA. Current concepts in antimicrobial therapy against resistant Gram-negative organisms: extended-spectrum β-lactamase–producing enterobacteriaceae, carbapenem-resistant enterobacteriaceae, and multidrug-resistant Pseudomonas aeruginosa. Mayo Clin. Proc.86(3), 250–259 (2011).
  • Andreassen AES , JacobsenCM, DeBlasio B, WhiteR, KristiansenIS, ElstrømP. The impact of methicillin-resistant S. aureus on length of stay, readmissions and costs: a register based case–control study of patients hospitalized in Norway. Antimicrob. Res. Infect. Control6(1), 74 (2017).
  • Braine T . Race against time to develop new antibiotics.Bullet. WHO89(2), 88–89 (2011).
  • Santos R , UrsuO, GaultonAet al. A comprehensive map of molecular drug targets. Nat. Rev. Drug Discov.16(1), 19–34 (2017).
  • Chellat MF , RagužL, RiedlR. Targeting antibiotic resistance. Angew. Chem. Int. Ed.55(23), 6600–6626 (2016).
  • Singh SB , YoungK, SilverLL. What is an “ideal” antibiotic? Discovery challenges and path forward. Biochem. Pharmacol.133, 63–73 (2017).
  • Richter MF , HergenrotherPJ. The challenge of converting Gram-positive-only compounds into broad-spectrum antibiotics. Ann. NY Acad. Sci.1435(1), 18 (2019).
  • Viegas-Junior C , DanuelloA, DaSilva Bolzani V, BarreiroEJ, FragaCaM. Molecular hybridization: a useful tool in the design of new drug prototypes. Curr. Med. Chem.14(17), 1829–1852 (2007).
  • Barreiro EJ , FragaCA, MirandaAL, RodriguesCR. Medicinal chemistry of n-acylhydrazones: novel lead-compounds of analgesic, antiinflammatory and antithrombotic drugs. Química Nova25(1), 129–148 (2002).
  • Ghorab MM , SolimanAM, BuaS, SupuranCT. Biological evaluation, radiosensitizing activity and structural insights of novel halogenated quinazoline-sulfonamide conjugates as selective human carbonic anhydrases IX/XII inhibitors. Bioorg. Chem.107, 104618 (2021).
  • Casini A , ScozzafavaA, SupuranCT. Sulfonamide derivatives with protease inhibitory action as anticancer, anti-inflammatory and antiviral agents. Expert Opin. Ther. Pat.12(9), 1307–1327 (2002).
  • Gündüz MG , TahirMN, ArmakovićS, KoçakCÖ, ArmakovićSJ. Design, synthesis and computational analysis of novel acridine-(sulfadiazine/sulfathiazole) hybrids as antibacterial agents. J. Mol. Struct.1186, 39–49 (2019).
  • Ghorab MM , El-GabyMS, SolimanAM, AlsaidMS, Abdel-AzizMM, ElaasserMM. Synthesis, docking study and biological evaluation of some new thiourea derivatives bearing benzenesulfonamide moiety. Chem. Cent. J.11(1), 1–12 (2017).
  • Ghorab MM , RagabFA, HeibaHI, SolimanAM. Design and synthesis of some novel 4-chloro-N-(4-(1-(2-(2-cyanoacetyl) hydrazono) ethyl) phenyl) benzenesulfonamide derivatives as anticancer and radiosensitizing agents. Eur. J. Med. Chem.117, 8–18 (2016).
  • Quesada I , NadalA, SoriaB. Different effects of tolbutamide and diazoxide in alpha, beta-, and delta-cells within intact islets of Langerhans. Diabetes48(12), 2390–2397 (1999).
  • Soliman AM , MekkawyMH, KaramHM, HigginsM, Dinkova-KostovaAT, GhorabMM. Novel iodinated quinazolinones bearing sulfonamide as new scaffold targeting radiation induced oxidative stress. Bioorg. Med. Chem. Lett.42, 128002 (2021).
  • Lubenets V , KarpenkoO, PonomarenkoM, ZahoriyG, KrychkovskaA, NovikovV. Development of new antimicrobial compositions of thiosulfonate structure. Chemistry Chem. Technol.67(2), 119–124 (2013).
  • Lubenets V , VasylyukS, MonkaNet al. Synthesis and antimicrobial properties of 4-acylaminobenzenethiosulfoacid S-esters. Saudi Pharm. J.25(2), 266–274 (2017).
  • Ghorab MM , AlsaidMS, SolimanAM, RagabFA. VEGFR-2 inhibitors and apoptosis inducers: synthesis and molecular design of new benzo [g] quinazolin bearing benzenesulfonamide moiety. J. Enzyme Inhib. Med. Chem.32(1), 893–907 (2017).
  • Soliman AM , AlqahtaniAS, GhorabMM. Novel sulfonamide benzoquinazolinones as dual EGFR/HER2 inhibitors, apoptosis inducers and radiosensitizers. J. Enzyme Inhib. Med. Chem.34(1), 1030–1040 (2019).
  • Soliman AM , GhorabMM, BuaS, SupuranCT. Iodoquinazolinones bearing benzenesulfonamide as human carbonic anhydrase I, II, IX and XII inhibitors: synthesis, biological evaluation and radiosensitizing activity. Eur. J. Med. Chem.200, 112449 (2020).
  • Soliman AM , KaramHM, MekkawyMH, HigginsM, Dinkova-KostovaAT, GhorabMM. Radiomodulatory effect of a non-electrophilic NQO1 inducer identified in a screen of new 6, 8-diiodoquinolin-4 (3H)-ones carrying a sulfonamide moiety. Eur. J. Med. Chem.200, 112467 (2020).
  • Soliman AM , KaramHM, MekkawyMH, GhorabMM. Antioxidant activity of novel quinazolinones bearing sulfonamide: potential radiomodulatory effects on liver tissues via NF-κB/PON1 pathway. Eur. J. Med. Chem.197, 112333 (2020).
  • Dinakaran M , SelvamP, DeclercqE, SridharSK. Synthesis, antiviral and cytotoxic activity of 6-bromo-2, 3-disubstituted-4 (3H)-quinazolinones. Biol. Pharm. Bull.26(9), 1278–1282 (2003).
  • Chevalier J , MahamoudA, BaiticheMet al. Quinazoline derivatives are efficient chemosensitizers of antibiotic activity in Enterobacter aerogenes, Klebsiella pneumoniae and Pseudomonas aeruginosa resistant strains. Int. J. Antimicrob. Agents36(2), 164–168 (2010).
  • Mahamoud A , ChevalierJ, BaiticheM, AdamE, PagesJ-M. An alkylaminoquinazoline restores antibiotic activity in Gram-negative resistant isolates. Microbiology157(2), 566–571 (2011).
  • Ghorab MM , AlqahtaniAS, SolimanAM, AskarAA. Novel N-(substituted) thioacetamide quinazolinone benzenesulfonamides as antimicrobial agents. Int. J. Nanomedicine15, 3161 (2020).
  • Devi KA , SarangapaniM. Synthesis and antimicrobial activity of some quinazolinones derivatives. Int. J. Drug Dev. Res.4(3), 324–327 (2012).
  • Lu W , BaigIA, SunH-Jet al. Synthesis, crystal structure and biological evaluation of substituted quinazolinone benzoates as novel antituberculosis agents targeting acetohydroxyacid synthase. Eur. J. Med. Chem.94, 298–305 (2015).
  • Maddry JA , ChenX, JonssonCBet al. Discovery of novel benzoquinazolinones and thiazoloimidazoles, inhibitors of influenza H5N1 and H1N1 viruses, from a cell-based high-throughput screen. J. Biomol. Screening16(1), 73–81 (2011).
  • Ghorab MM , IsmailZH, RadwanAA, AbdallaM. Synthesis and pharmacophore modeling of novel quinazolines bearing a biologically active sulfonamide moiety. Acta Pharm.63(1), 1–18 (2013).
  • Prasad KS , KumarLS, ChandanS, JayalakshmiB, RevanasiddappaHD. Diorganotin (IV) complexes of biologically potent 4 (3H)-quinazolinone derived Schiff bases: synthesis, spectroscopic characterization, DNA interaction studies and antimicrobial activity. Spectrochimica Acta A Mol. Biomol. Spectrosc.81(1), 276–282 (2011).
  • Jafari E , KhajoueiMR, HassanzadehF, HakimelahiGH, KhodarahmiGA. Quinazolinone and quinazoline derivatives: recent structures with potent antimicrobial and cytotoxic activities. Res. Pharm. Sci.11(1), 1 (2016).
  • Asadi P , KhodarahmiG, Jahanian-NajafabadiA, SaghaieL, HassanzadehF. Biologically active heterocyclic hybrids based on quinazolinone, benzofuran and imidazolium moieties: synthesis, characterization, cytotoxic and antibacterial evaluation. Chem. Biodivers.14(4), e1600411 (2017).
  • Gatadi S , GourJ, ShuklaMet al. Synthesis and evaluation of new 4-oxoquinazolin-3 (4H)-yl) benzoic acid and benzamide derivatives as potent antibacterial agents effective against multidrug resistant Staphylococcus aureus. Bioorg. Chem.83, 569–579 (2019).
  • Malasala S , AhmadMN, GourJet al. Synthesis, biological evaluation and molecular modelling insights of 2-arylquinazoline benzamide derivatives as anti-tubercular agents. J. Mol. Struct.1218, 128493 (2020).
  • Dokla EM , AbutalebNS, MilikSNet al. Development of benzimidazole-based derivatives as antimicrobial agents and their synergistic effect with colistin against Gram-negative bacteria. Eur. J. Med. Chem.186, 111850 (2020).
  • Rajendran S , KhanMM, GraciaF, QinJ, GuptaVK, ArumainathanS. Ce 3+-ion-induced visible-light photocatalytic degradation and electrochemical activity of ZnO/CeO 2 nanocomposite. Sci. Rep.6, 31641 (2016).
  • Lokina S , StephenA, KaviyarasanV, ArulvasuC, NarayananV. Cytotoxicity and antimicrobial activities of green synthesized silver nanoparticles. Eur. J. Med. Chem.76, 256–263 (2014).
  • Singh R , LillardJWJr. Nanoparticle-based targeted drug delivery. Exp. Mol. Pathol.86(3), 215–223 (2009).
  • Sukhdev A , ChallaM, NarayaniLet al. Synthesis, phase transformation, and morphology of hausmannite Mn3O4 nanoparticles: photocatalytic and antibacterial investigations. Heliyon6(1), e03245 (2020).
  • Kołodziejczak-Radzimska A , JesionowskiT. Zinc oxide – from synthesis to application: a review. Materials7(4), 2833–2881 (2014).
  • Makaremi M , LimCX, PasbakhshPet al. Electrospun functionalized polyacrylonitrile–chitosan bi-layer membranes for water filtration applications. RSC Adv.6(59), 53882–53893 (2016).
  • Wang Y , ZhangQ, ZhangC-L, LiP. Characterisation and cooperative antimicrobial properties of chitosan/nano-ZnO composite nanofibrous membranes. Food Chem.132(1), 419–427 (2012).
  • Askar AA , SelimMS, El-SaftySA, HashemAI, SelimMM, ShenashenMA. Antimicrobial and immunomodulatory potential of nanoscale hierarchical one-dimensional zinc oxide and silicon carbide materials. Mater. Chem. Phys.263, 124376 (2021).
  • Sahu A , KwonI, TaeG. Improving cancer therapy through the nanomaterials-assisted alleviation of hypoxia. Biomaterials228, 119578 (2020).
  • Rivera G , ShahSSA, Arrieta-BaezD, PalosI, MongueA, Sanchez-TorresLE. Esters of quinoxaline 1,4-di-N-oxide with cytotoxic activity on tumor cell lines based on NCI-60 panel. Iran. J. Pharm. Res.16(3), 953 (2017).
  • Salem MA , RagabA, AskarAA, El-KhalafawyA, MakhloufAH. One-pot synthesis and molecular docking of some new spiropyranindol-2-one derivatives as immunomodulatory agents and in vitro antimicrobial potential with DNA gyrase inhibitor. Eur. J. Med. Chem.188, 111977 (2020).
  • Ghorab MM , SolimanAM, AlsaidMS, AskarAA. Synthesis, antimicrobial activity and docking study of some novel 4-(4, 4-dimethyl-2, 6-dioxocyclohexylidene) methylamino derivatives carrying biologically active sulfonamide moiety. Arab. J. Chemistry. 13(1) (2017).
  • El Ella DAA , GhorabMM, HeibaHI, SolimanAM. Synthesis of some new thiazolopyrane and thiazolopyranopyrimidine derivatives bearing a sulfonamide moiety for evaluation as anticancer and radiosensitizing agents. Med. Chem. Res.21(9), 2395–2407 (2012).
  • Cappuccino J , ShermanN. Microbiology, Laboratory Manual.Pearson Education, Inc., New Delhi, India, 282–283 (2004).
  • Cooper K . The theory of antibiotic inhibition zones. Analytical Microbiology1–86 (1963).
  • Swidan K , ElSherbiny G, MansourA, El-HawM, AskarA, El-BadryM. Antibacterial evaluation of Punica granatum as therapeutic agents against multi drug resistance bacteria isolated from infertile male's semen. Al-Azhar Int. Med. J.1(2), 125–132 (2020).
  • El-Sherbiny GM , El-BatalA, El-SherbinyI. Antibacterial potential with molecular docking study against multi-drug resistant bacteria and Mycobacterium tuberculosis of streptomycin produced by Streptomyces atroverins, strain Askar-SH50. J. Chem. Pharm. Res9, 189–208 (2017).
  • Alnassar HS , HelalMH, AskarAA, MasoudDM, AbdallahAE. Pyridine azo disperse dye derivatives and their selenium nanoparticles (SeNPs): synthesis, fastness properties, and antimicrobial evaluations. Int. J. Nanomed.14, 7903 (2019).
  • Abdel-Khalek E , RayanD, AskarAA, MaksoudMA, El-BahnasawyH. Synthesis and characterization of SrFeO 3-δ nanoparticles as antimicrobial agent. J. Sol-Gel Sci. Technol.97(1), 27–38 (2021).
  • Mosmann T . Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods65(1–2), 55–63 (1983).
  • Akbay P , CalisI, ÜndegerÜ, BasaranN, BasaranAA. In vitro immunomodulatory activity of verbascoside from Nepeta ucrainica L. Phytother. Res.16(6), 593–595 (2002).
  • Akbay P , BasaranAA, UndegerU, BasaranN. In vitro immunomodulatory activity of flavonoid glycosides from Urtica dioica L. Phytother. Res. Eval.17(1), 34–37 (2003).
  • Zhang W-N , GongL-L, LiuYet al. Immunoenhancement effect of crude polysaccharides of Helvella leucopus on cyclophosphamide-induced immunosuppressive mice. J. Funct. Foods69, 103942 (2020).
  • Ayeka PA , BianY, GithaigaPM, ZhaoY. The immunomodulatory activities of licorice polysaccharides (Glycyrrhiza uralensis Fisch.) in CT 26 tumor-bearing mice. BMC Complement. Altern. Med.17(1), 1–9 (2017).
  • Ragab A , FouadSA, AliOAAet al. Sulfaguanidine hybrid with some new pyridine-2-one derivatives: design, synthesis, and antimicrobial activity against multidrug-resistant bacteria as dual DNA gyrase and DHFR inhibitors. Antibiotics10(2), 162 (2021).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.