Structure-based scoring of anthocyanins and molecular modeling of PfLDH, PfDHODH, and PfDHFR reveal novel potential P. falciparum inhibitors

Ariey, 2014, A molecular marker of artemisinin-resistant Plasmodium falciparum malaria, Nature, 505, 50, 10.1038/nature12876 Owoloye, 2021, Prevalence of potential mediators of artemisinin resistance in African isolates of Plasmodium falciparum, Malar J, 20, 451, 10.1186/s12936-021-03987-6 Ocan, 2019, K13-propeller gene polymorphisms in Plasmodium falciparum parasite population in malaria affected countries: a systematic review of prevalence and risk factors, 18, 1 Saxena, 2019, Multiple e-pharmacophore modelling pooled with high-throughput virtual screening, docking and molecular dynamics simulations to discover potential inhibitors of Plasmodium falciparum lactate dehydrogenase (PfLDH), 37, 1783 Joshi, 2022, Highly potent anti-malarial activity of benzopyrano (4, 3-b) benzopyran derivatives and in silico interaction analysis with putative target Plasmodium falciparum lactate dehydrogenase, 40, 5159 Owoloye, 2020, Molecular docking analysis of Plasmodium falciparum dihydroorotate dehydrogenase towards the design of effective inhibitors, Bioinformation, 16, 672, 10.6026/97320630016672 Ibrahim, 2022, Virtual screening and molecular dynamic simulations of the antimalarial derivatives of 2-anilino 4-amino substituted quinazolines docked against a Pf-DHODH protein target, 23, 1 O.A.J.J.o.A.P.S, 2021, Exploring the potentials of selected bioactive compounds isolated from Piper guineense Schumach. & Thonn. leaf toward identification of novel PfDHFR and PfDHODH inhibitors as antimalaria agents, 11, 153 Balogun, 2020, In silico anti-malaria activity of quinolone compounds against Plasmodium falciparum dihydrofolate reductase (PfDHFR), 29, 10 Lang-Unnasch, 1998, Metabolic changes of the malaria parasite during the transition from the human to the mosquito host, Annu Rev Microbiol, 52, 561, 10.1146/annurev.micro.52.1.561 Singh, 2018, Molecular docking analysis of Pyrimethamine derivatives with Plasmodium falciparum dihydrofolate reductase, 14, 232 Schnell, 2004, Structure, dynamics, and catalytic function of dihydrofolate reductase, Annu Rev Biophys Biomol Struct, 33, 119, 10.1146/annurev.biophys.33.110502.133613 Kompis, 2005, DNA and RNA synthesis: antifolates, Chemical reviews, 105, 593, 10.1021/cr0301144 Nzila, 2006, Inhibitors of de novo folate enzymes in Plasmodium falciparum, Drug Discov Today, 11, 939, 10.1016/j.drudis.2006.08.003 da Cunha, 2005, The search for new DHFR inhibitors: a review of patents, January 2001–February 2005, Expert Opin Ther Pat, 15, 967, 10.1517/13543776.15.8.967 Anderson, 2005, Targeting DHFR in parasitic protozoa, Drug Discov Today, 10, 121, 10.1016/S1359-6446(04)03308-2 Rastelli, 2000, Interaction of pyrimethamine, cycloguanil, WR99210 and their analogues with Plasmodium falciparum dihydrofolate reductase: structural basis of antifolate resistance, Bioorg Med Chem, 8, 1117, 10.1016/S0968-0896(00)00022-5 Shamshad, 2022, 1 Avilés, 2008, Isolated swine heart ventricle perfusion model for implant assisted-magnetic drug targeting, Int J Pharm, 361, 202, 10.1016/j.ijpharm.2008.05.027 Pavadai, 2016, Identification of new human malaria parasite Plasmodium falciparum dihydroorotate dehydrogenase inhibitors by pharmacophore and structure-based virtual screening, J Chem Inf Model, 56, 548, 10.1021/acs.jcim.5b00680 Hoelz, 2018, Plasmodium falciparum dihydroorotate dehydrogenase: a drug target against malaria, Future Med Chem, 10, 1853, 10.4155/fmc-2017-0250 Singh, 2017, Dihydroorotate dehydrogenase: a drug target for the development of antimalarials, Eur J Med Chem, 125, 640, 10.1016/j.ejmech.2016.09.085 Vaidya, 2009, Mitochondrial evolution and functions in malaria parasites, Annu Rev Microbiol, 63, 249, 10.1146/annurev.micro.091208.073424 Phillips, 2017, Medicinal chemistry case history: discovery of the dihydroorate dehydrogenase inhibitor DSM265 as an antimalarial drug candidate, 544 Gardner, 2002, Genome sequence of the human malaria parasite Plasmodium falciparum, Nature, 419, 498, 10.1038/nature01097 Phillips, 2008, Triazolopyrimidine-based dihydroorotate dehydrogenase inhibitors with potent and selective activity against the malaria parasite Plasmodium falciparum, J Med Chem, 51, 3649, 10.1021/jm8001026 Booker, 2010, Novel inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase with anti-malarial activity in the mouse model, J Biol Chem, 285, 33054, 10.1074/jbc.M110.162081 Phillips, 2015, A long-duration dihydroorotate dehydrogenase inhibitor (DSM265) for prevention and treatment of malaria, Sci Transl Med, 7, 296ra111, 10.1126/scitranslmed.aaa6645 Pascual-Teresa, 2010, Flavanols and anthocyanins in cardiovascular health: a review of current evidence, Int J Mol Sci, 11, 1679, 10.3390/ijms11041679 Riaz, 2016 Mohammadi Pour, 2019, The signaling pathways, and therapeutic targets of antiviral agents: focusing on the antiviral approaches and clinical perspectives of anthocyanins in the management of viral diseases, Front Pharmacol, 10, 1207, 10.3389/fphar.2019.01207 Akinnusi, 2022, Molecular binding studies of anthocyanins with multiple antiviral activities against SARS-CoV-2, Bull Natl Res Cent, 46, 1, 10.1186/s42269-022-00786-0 Maestro, S.J.N.Y., NY, Llc. 2017. Conners, 2005, Mapping the binding site for gossypol-like inhibitors of Plasmodium falciparum lactate dehydrogenase, Mol Biochem Parasitol, 142, 137, 10.1016/j.molbiopara.2005.03.015 Pippione, 2019, Hydroxyazole scaffold-based Plasmodium falciparum dihydroorotate dehydrogenase inhibitors: synthesis, biological evaluation and X-ray structural studies, Eur J Med Chem, 163, 266, 10.1016/j.ejmech.2018.11.044 Vanichtanankul, 2012, Combined spatial limitation around residues 16 and 108 of Plasmodium falciparum dihydrofolate reductase explains resistance to cycloguanil, Antimicrob Agents Chemother, 56, 3928, 10.1128/AAC.00301-12 Friesner, 2004, Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy, J Med Chem, 47, 1739, 10.1021/jm0306430 Alamri, 2019, Pharmacophore and docking-based sequential virtual screening for the identification of novel Sigma 1 receptor ligands, 15, 586 Daina, 2017, SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules, Sci Rep, 7, 1, 10.1038/srep42717 Giordanetto, 2014, Macrocyclic drugs and clinical candidates: what can medicinal chemists learn from their properties?, J Med Chem, 57, 278, 10.1021/jm400887j Ertl, 2009, Estimation of synthetic accessibility score of drug-like molecules based on molecular complexity and fragment contributions, J Cheminf, 1, 1, 10.1186/1758-2946-1-8 Tripathi, 2019, Bioavailability prediction of phytochemicals present in Calotropis procera (Aiton) R, Br. by using Swiss-ADME tool, 131, 147 Granchi, 2010, Inhibitors of lactate dehydrogenase isoforms and their therapeutic potentials, Curr Med Chem, 17, 672, 10.2174/092986710790416263 Choi, 2007, Design, synthesis, and biological evaluation of Plasmodium falciparum lactate dehydrogenase inhibitors, J Med Chem, 50, 3841, 10.1021/jm070336k Brandao, 2018, Antimalarial naphthoquinones. Synthesis via click chemistry, in vitro activity, docking to PfDHODH and SAR of lapachol-based compounds, 145, 191 Wright, 2020, Application of the ESMACS binding free energy protocol to a multi‐binding site lactate, Dehydogenase A Ligand Dataset, 3 Bagchi, 2019, vol. 13, 3591 Bagchi, 2019, In-vitro blood-brain barrier models for drug screening and permeation studies: an overview, Drug Des Dev Ther, 13, 3591, 10.2147/DDDT.S218708 Gao, 2002, Optimizing higher throughput methods to assess drug-drug interactions for CYP1A2, CYP2C9, CYP2C19, CYP2D6, rCYP2D6, and CYP3A4 in vitro using a single point IC50, J Biomol Screen, 7, 373 Zhao, 2021, Cytochrome P450 enzymes and drug metabolism in humans, 22, 12808 Finch, 2014, P-glycoprotein and its role in drug-drug interactions, Aust Prescr, 37, 137, 10.18773/austprescr.2014.050 Lipinski, 2004, Lead-and drug-like compounds: the rule-of-five revolution, Drug Discov Today Technol, 1, 337, 10.1016/j.ddtec.2004.11.007 Doak, 2014, Oral druggable space beyond the rule of 5: insights from drugs and clinical candidates, Chemistry & biology, 21, 1115, 10.1016/j.chembiol.2014.08.013 Veber, 2002, Molecular properties that influence the oral bioavailability of drug candidates, J Med Chem, 45, 2615, 10.1021/jm020017n Mignani, 2018, Present drug-likeness filters in medicinal chemistry during the hit and lead optimization process: how far can they be simplified?, Drug Discov Today, 23, 605, 10.1016/j.drudis.2018.01.010 Savjani, 2012