{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T07:46:51Z","timestamp":1791013611704,"version":"4.1.0"},"reference-count":42,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2021,9,11]],"date-time":"2021-09-11T00:00:00Z","timestamp":1631318400000},"content-version":"am","delay-in-days":314,"URL":"http:\/\/www.elsevier.com\/open-access\/userlicense\/1.0\/"},{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"funder":[{"DOI":"10.13039\/501100010747","name":"Consejo Nacional de Ciencia, Tecnolog\u00eda e Innovaci\u00f3n Tecnol\u00f3gica","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100010747","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002848","name":"Comisi\u00f3n Nacional de Investigaci\u00f3n Cient\u00edfica y Tecnol\u00f3gica","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100002848","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic Chemistry"],"published-print":{"date-parts":[[2020,11]]},"DOI":"10.1016\/j.bioorg.2020.104243","type":"journal-article","created":{"date-parts":[[2020,8,27]],"date-time":"2020-08-27T21:47:11Z","timestamp":1598564831000},"page":"104243","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":14,"special_numbering":"C","title":["Correlation study on methoxylation pattern of flavonoids and their heme-targeted antiplasmodial activity"],"prefix":"10.1016","volume":"104","author":[{"given":"Sergio","family":"Ortiz","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pedro G.","family":"V\u00e1squez-Ocm\u00edn","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sandrine","family":"Cojean","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chouaha","family":"Bouzidi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sylvie","family":"Michel","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bruno","family":"Figad\u00e8re","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rapha\u00ebl","family":"Grougnet","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sabrina","family":"Boutefnouchet","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexandre","family":"Maciuk","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.bioorg.2020.104243_b0005","doi-asserted-by":"crossref","first-page":"723","DOI":"10.1016\/S0140-6736(13)60024-0","article-title":"Malaria","volume":"383","author":"White","year":"2014","journal-title":"The Lancet."},{"key":"10.1016\/j.bioorg.2020.104243_b0010","unstructured":"World malaria report 2019, (n.d.). (accessed January 17, 2020). https:\/\/www.who.int\/publications-detail\/world-malaria-report-2019."},{"key":"10.1016\/j.bioorg.2020.104243_b0015","doi-asserted-by":"crossref","first-page":"156","DOI":"10.1038\/nm.3073","article-title":"Malaria biology and disease pathogenesis: Insights for new treatments","volume":"19","author":"Miller","year":"2013","journal-title":"Nat. Med."},{"key":"10.1016\/j.bioorg.2020.104243_b0020","doi-asserted-by":"crossref","first-page":"961","DOI":"10.1084\/jem.173.4.961","article-title":"Hemoglobin degradation in the human malaria pathogen Plasmodium falciparum: a catabolic pathway initiated by a specific aspartic protease","volume":"173","author":"Goldberg","year":"1991","journal-title":"J. Experim. Medicine"},{"key":"10.1016\/j.bioorg.2020.104243_b0025","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1016\/j.molbiopara.2007.11.005","article-title":"Haemozoin formation","volume":"157","author":"Egan","year":"2008","journal-title":"Mol. Bioch. Parasitol."},{"key":"10.1016\/j.bioorg.2020.104243_b0030","doi-asserted-by":"crossref","first-page":"5231","DOI":"10.1021\/jm400282d","article-title":"Quinoline Drug-Heme interactions and implications for antimalarial cytostatic versus cytocidal activities","volume":"56","author":"Gorka","year":"2013","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104243_b0035","doi-asserted-by":"crossref","first-page":"63","DOI":"10.2174\/1386207053328101","article-title":"Targeting the hemozoin synthesis pathway for new antimalarial drug discovery: technologies for in vitro beta-hematin formation assay","volume":"8","author":"Tekwani","year":"2005","journal-title":"Comb Chem High Throughput Screen."},{"key":"10.1016\/j.bioorg.2020.104243_b0040","doi-asserted-by":"crossref","first-page":"4899","DOI":"10.1021\/cr078274t","article-title":"Interplay between Malaria, crystalline hemozoin formation, and antimalarial drug action and design","volume":"108","author":"Weissbuch","year":"2008","journal-title":"Chem. Rev."},{"key":"10.1016\/j.bioorg.2020.104243_b0045","doi-asserted-by":"crossref","first-page":"1437","DOI":"10.4155\/fmc.13.113","article-title":"Hemozoin and antimalarial drug discovery","volume":"5","author":"Fong","year":"2013","journal-title":"Future Med. Chemistry."},{"key":"10.1016\/j.bioorg.2020.104243_b0050","doi-asserted-by":"crossref","first-page":"1378","DOI":"10.3390\/molecules15031378","article-title":"Biological actions of Artemisinin: Insights from medicinal chemistry studies","volume":"15","author":"Li","year":"2010","journal-title":"Molecules"},{"key":"10.1016\/j.bioorg.2020.104243_b0055","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.fitote.2017.01.012","article-title":"Heme-binding activity of methoxyflavones from Pentzia monodiana Maire (Asteraceae)","volume":"118","author":"Ortiz","year":"2017","journal-title":"Fitoterapia"},{"key":"10.1016\/j.bioorg.2020.104243_b0060","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1016\/j.ejmech.2015.01.012","article-title":"Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae)","volume":"93","author":"Mai","year":"2015","journal-title":"Europ. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104243_b0065","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1007\/BF02976690","article-title":"Synthesis and PGE2 inhibitory activity of 5,7-Dihydroxyflavones and their O-Methylated flavone analogs","volume":"26","author":"Dao","year":"2003","journal-title":"Arch. Pharm. Res."},{"key":"10.1016\/j.bioorg.2020.104243_b0070","doi-asserted-by":"crossref","unstructured":"W.L. Whaley, J.-T. Tseng, J.D. Rummel, C.L. Wommack, Monohydroxyflavones: distribution coefficients and affinities for Reverse-Phase (C18) and immobilized artificial membrane (IAM) adsorbents, Nat. Prod. Commun., 2 (2007) 1934578X0700201005. https:\/\/doi.org\/10.1177\/1934578X0700201005.","DOI":"10.1177\/1934578X0700201005"},{"key":"10.1016\/j.bioorg.2020.104243_b0075","doi-asserted-by":"crossref","first-page":"7175","DOI":"10.1021\/la0606502","article-title":"Interactions of Genistein and related isoflavones with lipid micelles","volume":"22","author":"Whaley","year":"2006","journal-title":"Langmuir."},{"key":"10.1016\/j.bioorg.2020.104243_b0080","doi-asserted-by":"crossref","first-page":"1075","DOI":"10.1006\/bbrc.2000.3592","article-title":"Interaction of Chloroquine and its analogues with Heme: An isothermal titration calorimetric study","volume":"276","author":"Bachhawat","year":"2000","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"10.1016\/j.bioorg.2020.104243_b0085","series-title":"World malaria report 2017","author":"WHO","year":"2017"},{"key":"10.1016\/j.bioorg.2020.104243_b0090","doi-asserted-by":"crossref","unstructured":"\u00c9.B.V.S. Cavalcanti, V. de Paulo Emerenciano, L. Scotti, M.T. Scotti, Chapter 7 - Flavonoids from Asteraceae asmultitarget source ofcompounds against protozoal diseases, in: A. Speck-Planche (Ed.), Multi-Scale approaches in drug discovery, Elsevier, 2017: pp. 149\u2013190. https:\/\/doi.org\/10.1016\/B978-0-08-101129-4.00007-2.","DOI":"10.1016\/B978-0-08-101129-4.00007-2"},{"key":"10.1016\/j.bioorg.2020.104243_b0095","doi-asserted-by":"crossref","first-page":"1680","DOI":"10.1126\/science.1175667","article-title":"Chloroquine transport via the malaria parasite\u2019s Chloroquine resistance transporter","volume":"325","author":"Martin","year":"2009","journal-title":"Science"},{"key":"10.1016\/j.bioorg.2020.104243_b0100","doi-asserted-by":"crossref","unstructured":"T.E. Wellems, L.J. Panton, I.Y. Gluzman, V.E. do Rosario, R.W. Gwadz, A. Walker-Jonah, D.J. Krogstad, Chloroquine resistance not linked to mdr -like genes in a Plasmodium falciparum cross, Nature. 345 (1990) 253\u2013255. https:\/\/doi.org\/10.1038\/345253a0.","DOI":"10.1038\/345253a0"},{"key":"10.1016\/j.bioorg.2020.104243_b0105","doi-asserted-by":"crossref","first-page":"3345","DOI":"10.1021\/jm0600545","article-title":"Inhibition of Plasmodium falciparum fatty acid biosynthesis: Evaluation of FabG, FabZ, and FabI as drug targets for flavonoids","volume":"49","author":"Tasdemir","year":"2006","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104243_b0110","doi-asserted-by":"crossref","first-page":"2987","DOI":"10.1016\/0006-2952(88)90286-9","article-title":"Differential effects of flavonoids as inhibitors of tyrosine protein kinases and serine\/threonine protein kinases","volume":"37","author":"Masatoshi","year":"1988","journal-title":"Biochem. Pharmacol."},{"key":"10.1016\/j.bioorg.2020.104243_b0115","doi-asserted-by":"crossref","first-page":"4410","DOI":"10.1158\/0008-5472.CAN-05-3310","article-title":"Inhibition of mammalian Thioredoxin reductase by some flavonoids: Implications for Myricetin and Quercetin anticancer activity","volume":"66","author":"Lu","year":"2006","journal-title":"Cancer Res."},{"key":"10.1016\/j.bioorg.2020.104243_b0120","doi-asserted-by":"crossref","first-page":"25970","DOI":"10.1074\/jbc.M203539200","article-title":"Thioredoxin reductase is essential for the survival of Plasmodium falciparum erythrocytic stages","volume":"277","author":"Krnajski","year":"2002","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.bioorg.2020.104243_b0125","doi-asserted-by":"crossref","first-page":"58","DOI":"10.1016\/j.ijpharm.2008.09.023","article-title":"Studies of intestinal permeability of 36 flavonoids using Caco-2 cell monolayer model","volume":"367","author":"Tian","year":"2009","journal-title":"Int. J. Pharm."},{"key":"10.1016\/j.bioorg.2020.104243_b0130","doi-asserted-by":"crossref","first-page":"1715","DOI":"10.1016\/S0031-9422(00)98561-3","article-title":"Myricetin and quercetin methyl ethers from Haplopappus integerrimus var","volume":"20","author":"Ayanoglu","year":"1981","journal-title":"Punctatus, Phytochemistry."},{"key":"10.1016\/j.bioorg.2020.104243_b0135","doi-asserted-by":"crossref","first-page":"703","DOI":"10.1002\/jhet.5570380327","article-title":"Structure elucidation, conformational analysis and thermal effects on membrane bilayers of an antimicrobial myricetin ether derivative","volume":"38","author":"Demetzos","year":"2001","journal-title":"J. Heterocycl. Chem."},{"key":"10.1016\/j.bioorg.2020.104243_b0140","doi-asserted-by":"crossref","first-page":"1610","DOI":"10.1055\/s-0036-1591773","article-title":"Synthesis of benzopyran-fused flavone derivatives via microwave-assisted intramolecular C-H activation","volume":"50","author":"Sipos","year":"2018","journal-title":"Synthesis."},{"key":"10.1016\/j.bioorg.2020.104243_b0145","doi-asserted-by":"crossref","first-page":"6345","DOI":"10.1016\/j.tetlet.2013.09.051","article-title":"Regioselective iodination of flavonoids by N-iodosuccinimide under neutral conditions","volume":"54","author":"Lu","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/j.bioorg.2020.104243_b0150","doi-asserted-by":"crossref","first-page":"1808","DOI":"10.1021\/acs.jnatprod.6b00274","article-title":"Effects of functional groups and sugar composition of Quercetin derivatives on their radical scavenging properties","volume":"79","author":"Kato","year":"2016","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.bioorg.2020.104243_b0155","doi-asserted-by":"crossref","DOI":"10.1002\/cbdv.201600487","article-title":"Flavonoids from Potentilla parvifolia Fisch. and their neuroprotective effects in human neuroblastoma SH-SY5Y cells in vitro","volume":"14","author":"Yuan","year":"2017","journal-title":"Chem. Biodiver."},{"key":"10.1016\/j.bioorg.2020.104243_b0160","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1016\/j.tiv.2017.06.027","article-title":"Influence of flavonols and quercetin derivative compounds on MA-10 Leydig cells steroidogenic genes expressions","volume":"44","author":"Cormier","year":"2017","journal-title":"Toxicol. in Vitro."},{"key":"10.1016\/j.bioorg.2020.104243_b0165","doi-asserted-by":"crossref","first-page":"3061","DOI":"10.1039\/C5OB02537K","article-title":"Synthesis of rocaglamide derivatives and evaluation of their Wnt signal inhibitory activities","volume":"14","author":"Arai","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"10.1016\/j.bioorg.2020.104243_b0170","doi-asserted-by":"crossref","first-page":"4176","DOI":"10.1021\/jf060234n","article-title":"Hydroxylated polymethoxyflavones and methylated flavonoids in sweet orange (Citrus sinensis) Peel","volume":"54","author":"Li","year":"2006","journal-title":"J. Agric. Food Chem."},{"key":"10.1016\/j.bioorg.2020.104243_b0175","doi-asserted-by":"crossref","first-page":"90","DOI":"10.1016\/j.fitote.2017.07.014","article-title":"5,6,7,3\u2032,4\u2032,5\u2032-Hexamethoxyflavone from the Australian plant Eremophila debilis (Myoporaceae)","volume":"126","author":"Butler","year":"2018","journal-title":"Fitoterapia."},{"key":"10.1016\/j.bioorg.2020.104243_b0180","doi-asserted-by":"crossref","first-page":"4946","DOI":"10.1073\/pnas.1501023112","article-title":"Mechanisms of hematin crystallization and inhibition by the antimalarial drug chloroquine","volume":"112","author":"Olafson","year":"2015","journal-title":"PNAS."},{"key":"10.1016\/j.bioorg.2020.104243_b0185","doi-asserted-by":"crossref","unstructured":"P. V\u00e1squez-Ocm\u00edn, J.-F. Gallard, A.-C.V. Baelen, K. Leblanc, S. Cojean, E. Mouray, P. Grellier, C. Amasifu\u00e9n, G. Bernadat, L. Evanno, B. Figad\u00e8re, A. Maciuk, Antiplasmodial biodereplication based on highly efficient methods, (2020). https:\/\/doi.org\/10.26434\/chemrxiv.11828802.v1.","DOI":"10.26434\/chemrxiv.11828802.v1"},{"key":"10.1016\/j.bioorg.2020.104243_b0190","doi-asserted-by":"crossref","first-page":"3324","DOI":"10.1021\/ac300065t","article-title":"Detection, characterization, and screening of heme-binding molecules by mass spectrometry for malaria drug discovery","volume":"84","author":"Mu\u00f1oz-Durango","year":"2012","journal-title":"Anal. Chem."},{"key":"10.1016\/j.bioorg.2020.104243_b0195","doi-asserted-by":"crossref","unstructured":"P. V\u00e1squez-Ocm\u00edn, S. Cojean, E. Rengifo, S. Suyyagh-Albouz, C.A. Amasifuen Guerra, S. Pomel, B. Cabanillas, K. Mej\u00eda, P.M. Loiseau, B. Figad\u00e8re, A. Maciuk, Antiprotozoal activity of medicinal plants used by Iquitos-Nauta road communities in Loreto (Peru), J. Ethnopharmacol. 210 (2018) 372\u2013385. https:\/\/doi.org\/10.1016\/j.jep.2017.08.039.","DOI":"10.1016\/j.jep.2017.08.039"},{"key":"10.1016\/j.bioorg.2020.104243_b0200","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0022-1759(83)90303-4","article-title":"Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays","volume":"65","author":"Mosmann","year":"1983","journal-title":"J. Immunol. Meth."},{"key":"10.1016\/j.bioorg.2020.104243_b0205","doi-asserted-by":"crossref","first-page":"3658","DOI":"10.1093\/bioinformatics\/btx491","article-title":"FAF-Drugs4: free ADME-tox filtering computations for chemical biology and early stages drug discovery","volume":"33","author":"Lagorce","year":"2017","journal-title":"Bioinformatics"},{"key":"10.1016\/j.bioorg.2020.104243_b0210","doi-asserted-by":"crossref","first-page":"6927","DOI":"10.1021\/acs.biochem.8b00959","article-title":"Quantification of Free Ferriprotoporphyrin IX Heme and Hemozoin for Artemisinin Sensitive versus Delayed Clearance Phenotype Plasmodium falciparum Malarial Parasites","volume":"57","author":"Heller","year":"2018","journal-title":"Biochemistry"}],"container-title":["Bioorganic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0045206820315418?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0045206820315418?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,11,19]],"date-time":"2025-11-19T15:24:59Z","timestamp":1763565899000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0045206820315418"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,11]]},"references-count":42,"alternative-id":["S0045206820315418"],"URL":"https:\/\/doi.org\/10.1016\/j.bioorg.2020.104243","relation":{},"ISSN":["0045-2068"],"issn-type":[{"value":"0045-2068","type":"print"}],"subject":[],"published":{"date-parts":[[2020,11]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Correlation study on methoxylation pattern of flavonoids and their heme-targeted antiplasmodial activity","name":"articletitle","label":"Article Title"},{"value":"Bioorganic Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bioorg.2020.104243","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2020 Elsevier Inc. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"104243"}}