New Peptide Derived Antimalaria and Antimicrobial Agents Bearing Sulphonamide Moiety

Overview

Journal J Enzyme Inhib Med Chem

Specialty Biochemistry

Date 2019 Aug 9

PMID 31392901

Citations 5

Authors

D I Ugwuja

U C Okoro

S S Soman

R Soni

S N Okafor

D I Ugwu

Affiliations

Soon will be listed here.

Abstract

Fourteen novel dipeptide carboxamide derivatives bearing benzensulphonamoyl propanamide were synthesized and characterized using H NMR, C NMR, FTIR and MS spectroscopic techniques. antimalarial and antimicrobial studies were carried out on these synthesized compounds. Molecular docking, haematological analysis, liver and kidney function tests were also evaluated to assess the effect of the compounds on the organs. At 200 mg/kg body weight, inhibited the multiplication of the parasite by 81.38% on day 12 of post-treatment exposure. This was comparable to the 82.34% reduction with artemisinin. The minimum inhibitory concentration (MIC) in µM ranged from 0.03 to 2.34 with having MIC of 0.03 µM against The antibacterial activity of the compounds against some clinically isolated bacteria strains showed varied activities with some of the new compounds showing better activities against the bacteria and the fungi more than the reference drug ciprofloxacin and fluconazole.

Citing Articles

Facile synthesis of new -(aminocycloalkylene)amino acid compounds using chiral triflate esters with -Boc-aminopyrrolidines and -Boc-aminopiperidines.

Matuleviciute G, Kleiziene N, Rackauskiene G, Martynaitis V, Bieliauskas A, Sachleviciute U RSC Adv. 2023; 13(31):21378-21394.

PMID: 37469966 PMC: 10353522. DOI: 10.1039/d3ra03060a.

In pursuit of new anti-malarial candidates: novel synthesized and characterized pyrano-benzodioxepin analogues attenuated replication in malaria-infected mice.

Atolani O, Sulaiman F, Hamid A, Alayo A, Akina A, Oloriegbe S Heliyon. 2021; 7(12):e08517.

PMID: 34934836 PMC: 8661026. DOI: 10.1016/j.heliyon.2021.e08517.

New sulphonamide pyrolidine carboxamide derivatives: Synthesis, molecular docking, antiplasmodial and antioxidant activities.

Onoabedje E, Ibezim A, Okoro U, Batra S PLoS One. 2021; 16(2):e0243305.

PMID: 33626047 PMC: 7904193. DOI: 10.1371/journal.pone.0243305.

Novel Leu-Val Based Dipeptide as Antimicrobial and Antimalarial Agents: Synthesis and Molecular Docking.

Ezugwu J, Okoro U, Ezeokonkwo M, Bhimapaka C, Okafor S, Ugwu D Front Chem. 2020; 8:583926.

PMID: 33330372 PMC: 7732421. DOI: 10.3389/fchem.2020.583926.

Synthesis, molecular docking, antiplasmodial and antioxidant activities of new sulfonamido-pepetide derivatives.

Onoabedje E, Ibezim A, Okoro U, Batra S Heliyon. 2020; 6(9):e04958.

PMID: 33005786 PMC: 7519377. DOI: 10.1016/j.heliyon.2020.e04958.

References

Parai M, Panda G, Srivastava K, Puri S . Design, synthesis and antimalarial activity of benzene and isoquinoline sulfonamide derivatives. Bioorg Med Chem Lett. 2007; 18(2):776-81. DOI: 10.1016/j.bmcl.2007.11.038. View

de Souza N, de Andrade I, Carneiro P, Jardim G, de Melo I, da Silva Junior E . Blood shizonticidal activities of phenazines and naphthoquinoidal compounds against Plasmodium falciparum in vitro and in mice malaria studies. Mem Inst Oswaldo Cruz. 2014; 109(5):546-52. PMC: 4156448. DOI: 10.1590/0074-0276130603. View

Krungkrai J, Scozzafava A, Reungprapavut S, Krungkrai S, Rattanajak R, Kamchonwongpaisan S . Carbonic anhydrase inhibitors. Inhibition of Plasmodium falciparum carbonic anhydrase with aromatic sulfonamides: towards antimalarials with a novel mechanism of action?. Bioorg Med Chem. 2004; 13(2):483-9. DOI: 10.1016/j.bmc.2004.10.015. View

Craik D, Fairlie D, Liras S, Price D . The future of peptide-based drugs. Chem Biol Drug Des. 2012; 81(1):136-47. DOI: 10.1111/cbdd.12055. View

Day T, Greenfield S . Bioactivity of a peptide derived from acetylcholinesterase in hippocampal organotypic cultures. Exp Brain Res. 2003; 155(4):500-8. DOI: 10.1007/s00221-003-1757-1. View

Martyn D, Cortese J, Tyndall E, Dick J, Mazitschek R, Munoz B . Antiplasmodial activity of piperazine sulfonamides. Bioorg Med Chem Lett. 2009; 20(1):218-21. DOI: 10.1016/j.bmcl.2009.10.130. View

Krungkrai J, Krungkrai S, Supuran C . Carbonic anhydrase inhibitors: inhibition of Plasmodium falciparum carbonic anhydrase with aromatic/heterocyclic sulfonamides-in vitro and in vivo studies. Bioorg Med Chem Lett. 2008; 18(20):5466-71. DOI: 10.1016/j.bmcl.2008.09.030. View

Ugwu D, Okoro U, Ukoha P, Gupta A, Okafor S . Novel anti-inflammatory and analgesic agents: synthesis, molecular docking and in vivo studies. J Enzyme Inhib Med Chem. 2018; 33(1):405-415. PMC: 7011796. DOI: 10.1080/14756366.2018.1426573. View

Ekoue-Kovi K, Yearick K, Iwaniuk D, Natarajan J, Alumasa J, de Dios A . Synthesis and antimalarial activity of new 4-amino-7-chloroquinolyl amides, sulfonamides, ureas and thioureas. Bioorg Med Chem. 2008; 17(1):270-83. PMC: 2647815. DOI: 10.1016/j.bmc.2008.11.009. View

10.

Izuchukwu U, Chris O, Izuchukwu U . Synthesis of N-aryl substituted p-toluenesulphonamides via nickel catalyzed amidation reaction and their antibacterial, antifungal and antioxidant activities evaluation. Pak J Pharm Sci. 2018; 31(4):1209-1216. View

11.

REITMAN S, Frankel S . A colorimetric method for the determination of serum glutamic oxalacetic and glutamic pyruvic transaminases. Am J Clin Pathol. 1957; 28(1):56-63. DOI: 10.1093/ajcp/28.1.56. View

12.

Scozzafava A, Carta F, Supuran C . Secondary and tertiary sulfonamides: a patent review (2008 - 2012). Expert Opin Ther Pat. 2012; 23(2):203-13. DOI: 10.1517/13543776.2013.742065. View

13.

Petit J, Meurice N, Kaiser C, Maggiora G . Softening the Rule of Five--where to draw the line?. Bioorg Med Chem. 2012; 20(18):5343-51. PMC: 4209914. DOI: 10.1016/j.bmc.2011.11.064. View

14.

Veber D, Johnson S, Cheng H, Smith B, Ward K, Kopple K . Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem. 2002; 45(12):2615-23. DOI: 10.1021/jm020017n. View

15.

Ugwu D, Okoro U, Ukoha P, Okafor S, Ibezim A, Kumar N . Synthesis, characterization, molecular docking and in vitro antimalarial properties of new carboxamides bearing sulphonamide. Eur J Med Chem. 2017; 135:349-369. DOI: 10.1016/j.ejmech.2017.04.029. View

16.

Sinha S, Medhi B, Sehgal R . Challenges of drug-resistant malaria. Parasite. 2014; 21:61. PMC: 4234044. DOI: 10.1051/parasite/2014059. View

17.

Posner G, Maxwell J, ODowd H, Krasavin M, Xie S, Shapiro T . Antimalarial sulfide, sulfone, and sulfonamide trioxanes. Bioorg Med Chem. 2000; 8(6):1361-70. DOI: 10.1016/s0968-0896(00)00079-1. View

18.

Peters W . The chemotherapy of rodent malaria, XXII. The value of drug-resistant strains of P. berghei in screening for blood schizontocidal activity. Ann Trop Med Parasitol. 1975; 69(2):155-71. View

19.

Cox F . History of the discovery of the malaria parasites and their vectors. Parasit Vectors. 2010; 3(1):5. PMC: 2825508. DOI: 10.1186/1756-3305-3-5. View

20.

Primas N, Verhaeghe P, Cohen A, Kieffer C, Dumetre A, Hutter S . A new synthetic route to original sulfonamide derivatives in 2-trichloromethylquinazoline series: a structure-activity relationship study of antiplasmodial activity. Molecules. 2012; 17(7):8105-17. PMC: 6269066. DOI: 10.3390/molecules17078105. View