Synthetic Guaiacol Derivatives as Promising Myeloperoxidase Inhibitors Targeting Atherosclerotic Cardiovascular Disease.
Animals
Antioxidants
/ chemical synthesis
Atherosclerosis
/ drug therapy
Benzothiazoles
/ antagonists & inhibitors
Biphenyl Compounds
/ antagonists & inhibitors
Cardiovascular Diseases
/ drug therapy
Cell Survival
/ drug effects
Cells, Cultured
Dose-Response Relationship, Drug
Enzyme Inhibitors
/ chemical synthesis
Guaiacol
/ chemical synthesis
Humans
Interleukin-1beta
/ antagonists & inhibitors
Lipopolysaccharides
/ antagonists & inhibitors
Mice
Molecular Docking Simulation
Molecular Structure
Peroxidase
/ antagonists & inhibitors
Picrates
/ antagonists & inhibitors
RAW 264.7 Cells
Structure-Activity Relationship
Sulfonic Acids
/ antagonists & inhibitors
Tumor Necrosis Factor-alpha
/ antagonists & inhibitors
chlorotyrosine
heme protein
hypochlorous acid
low-density lipoprotein (LDL)
myeloperoxidase
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
03 07 2020
03 07 2020
Historique:
received:
11
02
2020
revised:
03
05
2020
pubmed:
6
5
2020
medline:
16
6
2021
entrez:
6
5
2020
Statut:
ppublish
Résumé
Myeloperoxidase (MPO) is known to cause oxidative stress and inflammation leading to cardiovascular disease (CVD) complications. MPO-mediated oxidation of lipoproteins leads to dysfunctional entities altering the landscape of lipoprotein functionality. The specificity of guaiacol derivatives toward preventing MPO-mediated oxidation to limit MPO's harmful effects is unknown. Diligent in silico studies were accomplished for a portfolio of compounds with guaiacol as a building block. The compounds' activity toward MPO inhibition was also validated. The role of these chemical entities in controlling MPO-mediated oxidation of lipoproteins (LDL and HDL) was shown to agree with our approach of developing powerful MPO inhibitors. The mechanism of MPO inhibition was demonstrated to be reversible in nature. This study reveals that there is great potential for guaiacol derivatives as therapeutics for CVD by modulating lipid profiles, reducing atherosclerotic plaque burden, and subsequently optimizing cardiovascular functions.
Identifiants
pubmed: 32368837
doi: 10.1002/cmdc.202000084
doi:
Substances chimiques
Antioxidants
0
Benzothiazoles
0
Biphenyl Compounds
0
Enzyme Inhibitors
0
Interleukin-1beta
0
Lipopolysaccharides
0
Picrates
0
Sulfonic Acids
0
Tumor Necrosis Factor-alpha
0
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
28752-68-3
Guaiacol
6JKA7MAH9C
1,1-diphenyl-2-picrylhydrazyl
DFD3H4VGDH
MPO protein, human
EC 1.11.1.7
Peroxidase
EC 1.11.1.7
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1187-1199Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
J. Soubhye, I. Aldib, B. Elfving, M. Gelbcke, P. G. Furtmüller, M. Podrecca, R. Conotte, J.-M. Colet, A. Rousseau, F. Reye, J. Med. Chem. 2013, 56, 3943-3958.
A. C. Carr, E. A. Decker, Y. Park, B. Frei, Free Radical Biol. Med. 2001, 31, 62-72.
S. J. Nicholls, S. L. Hazen, Arterioscler. Thromb. Vasc. Biol. 2005, 25, 1102-1111.
J. Arnhold, J. Flemmig, Arch. Biochem. Biophys. 2010, 500, 92-106.
S. Fu, H. Wang, M. Davies, R. Dean, J. Biol. Chem. 2000, 275, 10851-10858.
A. C. Carr, M. R. McCall, B. Frei, Arterioscler. Thromb. Vasc. Biol. 2000, 20, 1716-1723.
C. Delporte, P. Van Antwerpen, L. Vanhamme, T. Roumeguère, K. Zouaoui Boudjeltia, Mediators Inflammation 2013, 2013.
S. E. Recabarren, A. Lobos, V. Torres, R. Oyarzo, T. Sir-Petermann, Biol. Res. 2004, 37, 371-384.
K. Irani, Circ. Res. 2000, 87, 179-183.
H. Kaneto, N. Katakami, M. Matsuhisa, T. Matsuoka, Mediators Inflammation 2010, 2010.
K. Shi, Z. Gao, T.-Q. Shi, P. Song, L.-J. Ren, H. Huang, X.-J. Ji, Front. Microbiol. 2017, 8, 793.
G. Barrera, ISRN Oncol. 2012, 2012.
H. Ma, Nat. Sci. 2004, 2, 17-21.
A. Taleb, S. Tsimikas, Expert Rev. Cardiovasc. Ther. 2012, 10, 399-402.
S. Oravec, J. Mikl, K. Gruber, E. Dostal in Lipoproteins-Role in Health and Disease (Ed.: G. Kostner, F. Sasa), IntechOpen, 2012, pp. 73-94.
J. A. Leopold, J. Loscalzo, Drug Discovery Today Ther. Strategies 2008, 5, 5-13.
R. Namiri-Kalantari, F. Gao, A. Chattopadhyay, A. A. Wheeler, K. D. Navab, R. Farias-Eisner, S. T. Reddy, BioFactors 2015, 41, 153-159.
B. Shao, M. N. Oda, J. F. Oram, J. W. Heinecke, Chem. Res. Toxicol. 2009, 23, 447-454.
C. Capeillère-Blandin, Biochem. J. 1998, 336, 395-404.
M. G. Carnuta, C. S. Stancu, L. Toma, G. M. Sanda, L. S. Niculescu, M. Deleanu, A. C. Popescu, M. R. Popescu, A. Vlad, D. R. Dimulescu, Sci. Rep. 2017, 7, 7295.
V. S. Kamanna, S. H. Ganji, M. L. Kashyap, Curr. Cardiovasc. Risk Rep. 2013, 7, 102-107.
M. G. Traber, J. F. Stevens, Free Radical Biol. Med. 2011, 51, 1000-1013.
S. Uesugi, J. Ishihara, H. Iso, N. Sawada, R. Takachi, M. Inoue, S. Tsugane, Eur. J. Clin. Nutr. 2017, 71, 1179.
S. Sen Gupta, M. Ghosh, J. Anal. Methods Chem. 2013, 2013.
A. Lugasi, Acta Biol. Szeged. 2003, 47, 119-125.
B. Saranya, T. Sulfikarali, S. Chindhu, A. M. Muneeb, N. K. Leela, T. J. Zachariah, J. Spices Aromat. Crop. 2017, 26, 27-32.
C. A. Narasimhulu, K. Y. Burge, M. Doomra, A. Riad, S. Parthasarathy, Sci. Rep. 2018, 8, 12270.
R. Desikan, C. A. Narasimhulu, B. Khan, S. Rajagopalan, S. Parthasarathy in Mechanisms of Vascular Defects in Diabetes Mellitus (Eds.: C. C. Kartha, S. Ramachandran, R. Pillai), Springer, 2017, pp. 535-571.
L. Gan, M. Lagerström-Fermér, H. Ericsson, K. Nelander, E. Lindstedt, E. Michaëlsson, M. Kjaer, M. Heijer, C. Whatling, R. Fuhr, Br. J. Clin. Pharmacol. 2019, 85, 762-770.
E. Hernández-Vázquez, A. Chávez-Riveros, A. Nieto-Camacho, L. D. Miranda, ChemMedChem 2019, 14, 132-146.
S. C. Gupta, S. Prasad, J. H. Kim, S. Patchva, L. J. Webb, I. K. Priyadarsini, B. B. Aggarwal, Nat. Prod. Rep. 2011, 28, 1937-1955.
W.-H. Lee, C.-Y. Loo, M. Bebawy, F. Luk, R. S. Mason, R. Rohanizadeh, Curr. Neuropharmacol. 2013, 11, 338-378.
B. G. Gimenez, M. S. Santos, M. Ferrarini, J. P. S. Fernandes, Die Pharm. Int. J. Pharm. Sci. 2010, 65, 148-152.
L. Z. Benet, C. M. Hosey, O. Ursu, T. I. Oprea, Adv. Drug Delivery Rev. 2016, 101, 89-98.
A. S. Kalgutkar, A. B. Marnett, B. C. Crews, R. P. Remmel, L. J. Marnett, J. Med. Chem. 2000, 43, 2860-2870.
S. Son, B. A. Lewis, J. Agric. Food Chem. 2002, 50, 468-472.
A. L. Simplício, J. M. Clancy, J. F. Gilmer, Molecules 2008, 13, 519-547.
I. Aldib, M. Gelbcke, J. Soubhye, M. Prévost, P. G. Furtmüller, C. Obinger, B. Elfving, I. C. Alard, G. Roos, C. Delporte, Eur. J. Med. Chem. 2016, 123, 746-762.
J. Huang, F. Smith, J. R. Panizzi, D. C. Goodwin, P. Panizzi, Arch. Biochem. Biophys. 2015, 570, 14-22.
L. V. Forbes, T. Sjögren, F. Auchère, D. W. Jenkins, B. Thong, D. Laughton, P. Hemsley, G. Pairaudeau, R. Turner, H. Eriksson, J. Biol. Chem. 2013, 288, 36636-36647.
G. S. Basarab, P. Brassil, P. Doig, V. Galullo, H. B. Haimes, G. Kern, A. Kutschke, J. McNulty, V. J. A. Schuck, G. Stone, J. Med. Chem. 2014, 57, 9078-9095.
P. M. Bozeman, D. B. Learn, E. L. Thomas, J. Immunol. Methods 1990, 126, 125-133.
P. Jayaraj, C. A. Narasimhulu, A. Maiseyeu, R. Durairaj, S. Rao, S. Rajagopalan, S. Parthasarathy, R. Desikan, Future Med. Chem. 2020, 12, 95-110.
J. Fruebis, S. Parthasarathy, D. Steinberg, Proc. Mont. Acad. Sci. 1992, 89, 10588-10592.
O. Meilhac, M. Zhou, N. Santanam, S. Parthasarathy, J. Lipid Res. 2000, 41, 1205-1213.
J. K. Baird, S. L. Hoffman, Clin. Infect. Dis. 2004, 39, 1336-1345.
A. Baker, F. D. Northrop, H. Miedema, G. R. Devine, J. M. Davies, Mycopathologia 2002, 153, 25.
Y. Chi, K. Li, Q. Yan, S. Koizumi, L. Shi, S. Takahashi, Y. Zhu, H. Matsue, M. Takeda, M. Kitamura, J. Pharmacol. Exp. Ther. 2011, 339, 257-266.
E. M. Lago, M. P. Silva, T. G. Queiroz, S. F. Mazloum, V. C. Rodrigues, P. U. Carnaúba, P. L. Pinto, J. A. Rocha, L. L. G. Ferreira, A. D. Andricopulo, EBioMedicine 2019, 43, 370-379.
H. Sato, V. T. G. Chuang, K. Yamasaki, N. Yamaotsu, H. Watanabe, K. Nagumo, M. Anraku, D. Kadowaki, Y. Ishima, S. Hirono, PLoS One 2014, 9.
A. J. Kettle, C. C. Winterbourn, Biochem. Pharmacol. 1991, 41, 1485-1492.
J.-F. Tang, X.-H. Lv, X.-L. Wang, J. Sun, Y.-B. Zhang, Y.-S. Yang, H.-B. Gong, H.-L. Zhu, Bioorg. Med. Chem. 2012, 20, 4226-4236.
K. R. Houser, D. K. Johnson, F. T. Ishmael, J. Inflammation 2012, 9, 6.
H. S. Youn, J. K. Lee, Y. J. Choi, S. I. Saitoh, K. Miyake, D. H. Hwang, J. Y. Lee, Biochem. Pharmacol. 2008, 75, 494-502.
K. Selvarajan, C. A. Narasimhulu, R. Bapputty, S. Parthasarathy, J. Med. Food 2015, 18, 393-402.
T. R. Helgren, T. J. Hagen, J. Chem. Educ. 2017, 94, 345-349.
J. Shen, F. Cheng, Y. Xu, W. Li, Y. Tang, J. Chem. Inf. Model. 2010, 50, 1034-1041.
L. A. Marquez, H. B. Dunford, Biochemistry 1997, 36, 9349-9355.
N. Santanam, S. Parthasarathy, J. Clin. Invest. 1995, 95, 2594-2600.
B. J. Auerbach, J. S. Kiely, J. A. Cornicelli, Anal. Biochem. 1992, 201, 375-380.
N. Khan-Merchant, M. Penumetcha, O. Meilhac, S. Parthasarathy, J. Nutr. 2002, 132, 3256-3262.
P. Deme, C. A. Narasimhulu, S. Parthasarathy, J. Med. Food 2019, 22, 861-873.