Structure-Activity Relationship of Chalcones Against Influenza H1N1: Quantum Chemical Chemiometric Evaluation
Palavras-chave:
global pandemics, drugs, DFT, PCA
Resumo
It is well known that the influenza virus causes annual epidemics provoking thousands of deaths annually. Although there is already a vaccine for influenza, the virus mutates and acquires seasonal resistance to medicines. Therefore, due to the urgent need for new compounds with the inhibitory potential of the virus, many studies have presented several substances to avoid inhibitory activity to the enzyme responsible for the release of the virus into the respiratory tract. Here, a demonstrative calculation of theoretical and chemometric was performed studies of a set of eight chalcones with potential inhibition of the neuraminidase enzyme. It was performed calculations of electronic structure to determine the geometric and
electronic parameters using the theory of density functional at M06-2X/6-311++G(d,p) level calculation. The relationship between the structure of the compounds and their activity against the H1N1 influenza virus was accessed by principal component analysis and hierarchical cluster analysis. We hope that our results can help to explain the activities of chalcone analogs to model new compounds with influenza virus activity.
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1990;11:361–373.
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et al. A Study of Neolignan Compounds with Biological Activity
Against Paracoccidioides brasiliensis by Using Quantum Chemical
and Chemometric Methods. J Braz Chem Soc 2003;14:809–814.
34. Martins GR, Napolitano HB, Camargo LTFM, Camargo AJ.
Structure-activity relationship study of rutaecarpine analogous
active against central nervous system cancer. J Braz Chem Soc
2012;23:2183–2190.
35. Karelson M, Lobanov VS, Katritzky AR. Quantum-Chemical
Descriptors in QSAR/QSPR Studies. Chem Rev 1996;96:1027–1044.
36. Bhal SK. Understanding When to Use Log P & Log D. ACD/Labs -
Adv Chem Dev Inc Toronto, Canada 2019;3–6.
37. Österberg T, Norinder U. Prediction of drug transport processes
using simple parameters and PLS statistics - The use of ACD/logP
and ACD/ChemSketch descriptors. Eur J Pharm Sci 2001;12:327–
337.
38. Rice-Evans C, Miller N, Paganga G. Antioxidant properties of
phenolic compounds. Trends Plant Sci 1997;2:152–159.
39. Rosa GP, Seca AML, Barreto M do C, Silva AMS, Pinto DCGA.
Chalcones and flavanones bearing hydroxyl and/or methoxyl groups:
Synthesis and biological assessments. Appl Sci;9. Epub ahead of
print 2019. DOI: 10.3390/app9142846.
40. Yaeghoobi M, Frimayanti N, Chee CF, Ikram KK, Najjar BO, et
al. QSAR, in silico docking and in vitro evaluation of chalcone
derivatives as potential inhibitors for H1N1 virus neuraminidase.
Med Chem Res 2016;25:2133–2142.
influenza virus pandemic: A review. Vaccine 2010;28:4895–4902.
2. Hancock K, Veguilla V, Lu X, Zhong W, Butler EN, et al. Crossreactive antibody responses to the 2009 pandemic H1N1 influenza
virus. N Engl J Med 2009;361:1945–1952.
3. Le TT, Andreadakis Z, Kumar A, Roman RG, Tollefsen S, et al. The
COVID-19 vaccine development landscape. Nat Rev Drug Discov
2020;19:305–306.
4. Huang C, Wang Y, Li X, Ren L, Zhao J, et al. Clinical features of
patients infected with 2019 novel coronavirus in Wuhan, China.
Lancet 2020;395:497–506.
5. Organization WH, others. Coronavirus disease 2019 (COVID-19)
pandemic.
6. Organization WH, others. Coronavirus disease 2019 (COVID-19):
situation report, 72.
7. Qiu Y. Impacts of Social and Economic Factors on the Transmission
of Coronavirus Disease 2019 ( COVID-19 ) in China ∗. medRxiv
2020;2019:1–27.
8. Cui MY, Nie JX, Yan ZZ, Xiao MW, Lin D, et al. Design, synthesis,
bioactivity, and DFT calculation of 2-thiazolyl-hydrazone derivatives
as influenza neuraminidase inhibitors. Med Chem Res 2019;28:938–
947.
9. Li H, Li M, Xu R, Wang S, Zhang Y, et al. Synthesis, structure
activity relationship and in vitro anti-influenza virus activity of novel
polyphenol-pentacyclic triterpene conjugates. Elsevier Masson SAS.
Epub ahead of print 2019. DOI: 10.1016/j.ejmech.2018.12.006.
10. Li G, Zhao JY, Niu C, Nie LF, Dong CZ, et al. Structure–activity
relationship studies of 1-(1′-hydroxyalkyl)rupestonic acid methyl
esters against influenza viruses. Bioorganic Med Chem Lett
2017;27:1484–1487.
11. Neumann G, Noda T, Kawaoka Y. Emergence and pandemic
potential of swine-origin H1N1 influenza virus. Nature
2009;459:931–939.
12. Organization WH, others. Ten things you need to know about
pandemic influenza (update of 14 October 2005). Wkly Epidemiol
Rec Relev épidémiologique Hebd 2005;80:428–431.
13. Garten RJ, Davis CT, Russell CA, Shu B, Lindstrom S, et al.
Antigenic and genetic characteristics of swine-origin 2009
A(H1N1) influenza viruses circulating in humans. Science (80- )
2009;325:197–201.
14. Mercader AG, Pomilio AB. QSAR study of flavonoids and
biflavonoids as influenza H1N1 virus neuraminidase inhibitors. Eur J
Med Chem 2010;45:1724–1730.
15. Gao L, Zu M, Wu S, Liu AL, Du GH. 3D QSAR and docking study
of flavone derivatives as potent inhibitors of influenza H1N1 virus
neuraminidase. Bioorganic Med Chem Lett 2011;21:5964–5970.
16. Taylor NR, von Itzstein M. Molecular modeling studies on ligand
binding to sialidase from influenza virus and the mechanism of
catalysis. J Med Chem 1994;37:616–624.
17. Kim CU, Lew W, Williams MA, Liu H, Zhang L, et al. Influenza
neuraminidase inhibitors possessing a novel hydrophobic interaction
in the enzyme active site: design, synthesis, and structural analysis of
carbocyclic sialic acid analogues with potent anti-influenza activity.
J Am Chem Soc 1997;119:681–690.
18. Ison MG. Antivirals and resistance: influenza virus. Curr Opin Virol
2011;1:563–573.
19. Mu JX, Shi YX, Wu HK, Sun ZH, Yang MY, et al. Microwave
assisted synthesis, antifungal activity, DFT and SAR study of
1,2,4-triazolo[4,3-a]pyridine derivatives containing hydrazone
moieties. Chem Cent J 2016;10:1–9.
20. Dao TT, Nguyen PH, Lee HS, Kim E, Park J, et al. Chalcones as
novel influenza A (H1N1) neuraminidase inhibitors from Glycyrrhiza
inflata. Bioorganic Med Chem Lett 2011;21:294–298.
21. Alves CN, Pinheiro JC, Camargo AJ, Ferreira MMC, Romero
RAF, et al. A multiple linear regression and partial least squares
study of flavonoid compounds with anti-HIV activity. J Mol Struct
THEOCHEM 2001;541:81–88.
22. Camargo LTFM, Sena MM, Camargo AJ. A quantum chemical and
chemometrical study of indolo[2,1-b]quinazoline and their analogues
with cytotoxic activity against breast cancer cells. SAR QSAR
Environ Res 2009;20:537–549.
23. Worachartcheewan A, Nantasenamat C, Isarankura-Na-Ayudhya C,
Prachayasittikul V. QSAR Study of H1N1 Neuraminidase Inhibitors
from Influenza a Virus. Lett Drug Des Discov 2014;11:420–427.
24. Reed G. Feature Selection Methods in QSAR Studies. J AOAC Int
2012;95:5–24.
25. Vieira I, Camargo LTFM, Ribeiro L, Rodrigues ACC, Camargo AJ.
Structure–activity relationship of tacrine and its analogues in relation
to inhibitory activity against Alzheimer’s disease. J Mol Model;25.
Epub ahead of print 2019. DOI: 10.1007/s00894-019-3993-8.
26. Kohn W, Sham LJ. Self-consistent equations including exchange and
correlation effects. Phys Rev 1965;140:1133–1138.
27. Sharaf MA, Illman DL, Kowalski BR. Chemometrics. Wiley; 1986.
28. Stewart JJP. Optimization of parameters for semiempirical methods
II. Applications. J Comput Chem 1989;10:221–264.
29. Hypercube Inc. HyperChem, Release 7.0.
30. Zhao Y, Truhlar DG. The M06 suite of density functionals for main
group thermochemistry, thermochemical kinetics, noncovalent
interactions, excited states, and transition elements: two new
functionals and systematic testing of four M06-class functionals and
12 other function. Theor Chem Acc 2008;120:215–241.
31. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA,
et al. Gaussian 09, Revision A.02. Gaussian Inc Wallingford CT
2009;34:Wallingford CT.
32. Breneman CM, Wiberg KB. Determining atom-centered monopoles
from molecular electrostatic potentials. The need for high sampling
density in formamide conformational analysis. J Comput Chem
1990;11:361–373.
33. Camargo AJ, Honório KM, Mercadante R, Molfetta FA, Alves CN,
et al. A Study of Neolignan Compounds with Biological Activity
Against Paracoccidioides brasiliensis by Using Quantum Chemical
and Chemometric Methods. J Braz Chem Soc 2003;14:809–814.
34. Martins GR, Napolitano HB, Camargo LTFM, Camargo AJ.
Structure-activity relationship study of rutaecarpine analogous
active against central nervous system cancer. J Braz Chem Soc
2012;23:2183–2190.
35. Karelson M, Lobanov VS, Katritzky AR. Quantum-Chemical
Descriptors in QSAR/QSPR Studies. Chem Rev 1996;96:1027–1044.
36. Bhal SK. Understanding When to Use Log P & Log D. ACD/Labs -
Adv Chem Dev Inc Toronto, Canada 2019;3–6.
37. Österberg T, Norinder U. Prediction of drug transport processes
using simple parameters and PLS statistics - The use of ACD/logP
and ACD/ChemSketch descriptors. Eur J Pharm Sci 2001;12:327–
337.
38. Rice-Evans C, Miller N, Paganga G. Antioxidant properties of
phenolic compounds. Trends Plant Sci 1997;2:152–159.
39. Rosa GP, Seca AML, Barreto M do C, Silva AMS, Pinto DCGA.
Chalcones and flavanones bearing hydroxyl and/or methoxyl groups:
Synthesis and biological assessments. Appl Sci;9. Epub ahead of
print 2019. DOI: 10.3390/app9142846.
40. Yaeghoobi M, Frimayanti N, Chee CF, Ikram KK, Najjar BO, et
al. QSAR, in silico docking and in vitro evaluation of chalcone
derivatives as potential inhibitors for H1N1 virus neuraminidase.
Med Chem Res 2016;25:2133–2142.
Publicado
2023-05-08
Como Citar
Rezende, M. V. C. S., Neto, F. O. S., Camargo, A. J., & Camargo, L. T. F. M. (2023). Structure-Activity Relationship of Chalcones Against Influenza H1N1: Quantum Chemical Chemiometric Evaluation. Revista Processos Químicos, 16(32), 23-30. https://doi.org/10.19142/rpq.v18i32.664
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