{
"METABOLOMICS WORKBENCH":{"STUDY_ID":"ST001033","ANALYSIS_ID":"AN001694","VERSION":"1","CREATED_ON":"August 14, 2018, 12:30 pm"},

"PROJECT":{"PROJECT_TITLE":"A Potent, in vivo Active Antimalarial Series Based on a Triazolopyrazine Core: Open Source Malaria Series 4","PROJECT_SUMMARY":"The mode of action of a representative active compound was investigated using an unbiased metabolomics approach, which has previously been shown to reveal both novel and established modes of action of antimalarials (Creek et al 2016, DOI: 10.1128/AAC.01226-16). The active antimalarial OSM-S-313, and the inactive analogue OSM-S-291, were incubated with trophozoite stage P. falciparum parasites for five hours alongside reference compounds including atovaquone (ATV), chloroquine (CQ), dihydroartemisisin (DHA) and three PfATP4 inhibitors, MMV00073, MMV397264 and MMV390482. Metabolomics analysis of cell pellets and spent media allowed reproducible detection of diverse metabolites from a range of metabolic pathways, with the most significant OSM-S-313-induced perturbations observed within peptide, lipid and energy metabolism, suggesting a specific impact on parasite metabolism.","INSTITUTE":"Monash University","LAST_NAME":"Creek","FIRST_NAME":"Darren","ADDRESS":"Monash Institute of Pharmaceutical Sciences, 381 Royal Parade, Parkville, Melbourne, Victoria, 3052, Australia","EMAIL":"darren.creek@monash.edu","PHONE":"+61 (0) 3 9903 9249"},

"STUDY":{"STUDY_TITLE":"Determination of mode of action of anti-malalrial drugs using untargeted metabolomics","STUDY_SUMMARY":"The mode of action of a representative active compound was investigated using an unbiased metabolomics approach, which has previously been shown to reveal both novel and established modes of action of antimalarials (Creek et al 2016, DOI: 10.1128/AAC.01226-16). The active antimalarial OSM-S-313, and the inactive analogue OSM-S-291, were incubated with trophozoite stage P. falciparum parasites for five hours alongside reference compounds including atovaquone (ATV), chloroquine (CQ), dihydroartemisisin (DHA) and three PfATP4 inhibitors, MMV00073, MMV397264 and MMV390482. Metabolomics analysis of cell pellets and spent media allowed reproducible detection of diverse metabolites from a range of metabolic pathways, with the most significant OSM-S-313-induced perturbations observed within peptide, lipid and energy metabolism, suggesting a specific impact on parasite metabolism.","INSTITUTE":"Monash University","LAST_NAME":"Creek","FIRST_NAME":"Darren","ADDRESS":"Monash Institute of Pharmaceutical Sciences, 381 Royal Parade, Parkville, Melbourne, Victoria, 3052, Australia","EMAIL":"darren.creek@monash.edu","PHONE":"+61 (0) 3 9903 9249"},

"SUBJECT":{"SUBJECT_TYPE":"Cultured cells","SUBJECT_SPECIES":"Plasmodium falciparum","TAXONOMY_ID":"36329","GENOTYPE_STRAIN":"3D7","SUBJECT_COMMENTS":"Malaria parasite"},
"SUBJECT_SAMPLE_FACTORS":[
{
"Subject ID":"P_000073",
"Sample ID":"P_000073_1",
"Factors":{"drug treatment":"MMV00073"}
},
{
"Subject ID":"P_000073",
"Sample ID":"P_000073_2",
"Factors":{"drug treatment":"MMV00073"}
},
{
"Subject ID":"P_000073",
"Sample ID":"P_000073_3",
"Factors":{"drug treatment":"MMV00073"}
},
{
"Subject ID":"P_000073",
"Sample ID":"P_000073_4",
"Factors":{"drug treatment":"MMV00073"}
},
{
"Subject ID":"P_390482",
"Sample ID":"P_390482_1",
"Factors":{"drug treatment":"MMV390482"}
},
{
"Subject ID":"P_390482",
"Sample ID":"P_390482_2",
"Factors":{"drug treatment":"MMV390482"}
},
{
"Subject ID":"P_390482",
"Sample ID":"P_390482_3",
"Factors":{"drug treatment":"MMV390482"}
},
{
"Subject ID":"P_390482",
"Sample ID":"P_390482_4",
"Factors":{"drug treatment":"MMV390482"}
},
{
"Subject ID":"P_397264",
"Sample ID":"P_397264_1",
"Factors":{"drug treatment":"MMV397264"}
},
{
"Subject ID":"P_397264",
"Sample ID":"P_397264_2",
"Factors":{"drug treatment":"MMV397264"}
},
{
"Subject ID":"P_397264",
"Sample ID":"P_397264_3",
"Factors":{"drug treatment":"MMV397264"}
},
{
"Subject ID":"P_397264",
"Sample ID":"P_397264_4",
"Factors":{"drug treatment":"MMV397264"}
},
{
"Subject ID":"P_ATV",
"Sample ID":"P_ATV_1",
"Factors":{"drug treatment":"Atovaquone"}
},
{
"Subject ID":"P_ATV",
"Sample ID":"P_ATV_2",
"Factors":{"drug treatment":"Atovaquone"}
},
{
"Subject ID":"P_ATV",
"Sample ID":"P_ATV_3",
"Factors":{"drug treatment":"Atovaquone"}
},
{
"Subject ID":"P_ATV",
"Sample ID":"P_ATV_4",
"Factors":{"drug treatment":"Atovaquone"}
},
{
"Subject ID":"P_CQ",
"Sample ID":"P_CQ_1",
"Factors":{"drug treatment":"Chloroquine"}
},
{
"Subject ID":"P_CQ",
"Sample ID":"P_CQ_2",
"Factors":{"drug treatment":"Chloroquine"}
},
{
"Subject ID":"P_CQ",
"Sample ID":"P_CQ_3",
"Factors":{"drug treatment":"Chloroquine"}
},
{
"Subject ID":"P_CQ",
"Sample ID":"P_CQ_4",
"Factors":{"drug treatment":"Chloroquine"}
},
{
"Subject ID":"P_DHA",
"Sample ID":"P_DHA_1",
"Factors":{"drug treatment":"Dihydroartemisisin"}
},
{
"Subject ID":"P_DHA",
"Sample ID":"P_DHA_2",
"Factors":{"drug treatment":"Dihydroartemisisin"}
},
{
"Subject ID":"P_DHA",
"Sample ID":"P_DHA_3",
"Factors":{"drug treatment":"Dihydroartemisisin"}
},
{
"Subject ID":"P_DHA",
"Sample ID":"P_DHA_4",
"Factors":{"drug treatment":"Dihydroartemisisin"}
},
{
"Subject ID":"P_DMSO",
"Sample ID":"P_DMSO_1",
"Factors":{"drug treatment":"DMSO"}
},
{
"Subject ID":"P_DMSO",
"Sample ID":"P_DMSO_2",
"Factors":{"drug treatment":"DMSO"}
},
{
"Subject ID":"P_DMSO",
"Sample ID":"P_DMSO_3",
"Factors":{"drug treatment":"DMSO"}
},
{
"Subject ID":"P_DMSO",
"Sample ID":"P_DMSO_4",
"Factors":{"drug treatment":"DMSO"}
},
{
"Subject ID":"P_S291",
"Sample ID":"P_S291_1",
"Factors":{"drug treatment":"OSM-S-291"}
},
{
"Subject ID":"P_S291",
"Sample ID":"P_S291_2",
"Factors":{"drug treatment":"OSM-S-291"}
},
{
"Subject ID":"P_S291",
"Sample ID":"P_S291_3",
"Factors":{"drug treatment":"OSM-S-291"}
},
{
"Subject ID":"P_S291",
"Sample ID":"P_S291_4",
"Factors":{"drug treatment":"OSM-S-291"}
},
{
"Subject ID":"P_S313",
"Sample ID":"P_S313_1",
"Factors":{"drug treatment":"OSM-S-313"}
},
{
"Subject ID":"P_S313",
"Sample ID":"P_S313_2",
"Factors":{"drug treatment":"OSM-S-313"}
},
{
"Subject ID":"P_S313",
"Sample ID":"P_S313_3",
"Factors":{"drug treatment":"OSM-S-313"}
},
{
"Subject ID":"P_S313",
"Sample ID":"P_S313_4",
"Factors":{"drug treatment":"OSM-S-313"}
}
],
"COLLECTION":{"COLLECTION_SUMMARY":"Plasmodium falciparum (3D7 strain) parasites were cultured in vitro according to the established method (Trager and Jensen 1976, DOI: 10.1126/science.781840) with minor modifications and incubated with test compounds as previously described (Creek et al 2016, DOI: 10.1128/AAC.01226-16). Briefly, parasites were brought to a tightly synchronous life stage population (within 4 hours of the 48 hour life cycle) by treating with 5% (w/v) sorbitol twice at an interval of 14 hours, and incubated for a further 58 hours to bring all parasites to mid-trophozoite stage (27-31 hours post infection). These cells were used for drug treatment and further analysis.","SAMPLE_TYPE":"Cultured cells"},

"TREATMENT":{"TREATMENT_SUMMARY":"In 96 well plates, 200 μl cultures at 7% parasitemia and 3% haematocrit were incubated with 1 µM of test compounds for a further 5 hours (32-36 hours post infection). Each compound was incubated in four replicates and untreated controls were treated with DMSO."},

"SAMPLEPREP":{"SAMPLEPREP_SUMMARY":"After incubation with the test compounds for 5 hours, all red blood cells were settled at the bottom of the culture wells. Culture medium was carefully removed and the metabolism of the cells was quenched by placing the plate on ice and adding ice-cold phosphate buffered saline (PBS) to the culture wells. All subsequent extraction steps were performed on ice. Cells were centrifuged for 5 min at 400g in a chilled centrifuge at 4°C. The supernatant was carefully removed and 135 µl of ice-cold methanol (containing internal standards TRIS, CHAPS, CAPS and PIPES) was added followed by rapid mixing of the cell suspension using the pipette three times. Spent media samples were also prepared by adding 10 µl of the culture supernatants to 140 µl of ice-cold methanol (containing internal standards). All samples were agitated on ice for 1 hour and then centrifuged for 10 min at 1000g in a chilled centrifuge at 4°C. The supernatant was transferred to glass vials and stored at -80°C until analysis."},

"CHROMATOGRAPHY":{"CHROMATOGRAPHY_SUMMARY":"Metabolite extracts were analysed using hydrophilic interaction (HILIC) liquid chromatography (LC) and high resolution mass spectrometry on an Orbitrap system.","CHROMATOGRAPHY_TYPE":"HILIC","INSTRUMENT_NAME":"Thermo Q Exactive Orbitrap","COLUMN_NAME":"ZIC-pHILIC (Merck Sequant) column","FLOW_GRADIENT":"linear gradient -time, %B as follows: 0min- 80%, 15min- 50%, 18min- 5%, 21min- 5%, 24min- 80%, 32min- 80%.","FLOW_RATE":"300 μL/min","COLUMN_TEMPERATURE":"25°C","SOLVENT_A":"20 mM ammonium carbonate in water","SOLVENT_B":"100% acetonitrile","INTERNAL_STANDARD":"internal standards (CHAPS, CAPS, PIPES and TRIS; all at 1 µM)","SAMPLE_INJECTION":"10 μL"},

"ANALYSIS":{"ANALYSIS_TYPE":"MS"},

"MS":{"MS_COMMENTS":"-","INSTRUMENT_NAME":"Thermo Q Exactive Orbitrap","INSTRUMENT_TYPE":"Orbitrap","MS_TYPE":"ESI","ION_MODE":"UNSPECIFIED","CAPILLARY_TEMPERATURE":"300°C","CAPILLARY_VOLTAGE":"+50 V","SPRAY_VOLTAGE":"4kV","RESOLUTION_SETTING":"35000","SCAN_RANGE_MOVERZ":"85- 1275 m/z"},

"MS_METABOLITE_DATA":{
"Units":"Peak height",

"Data":[{"Metabolite":"Choline phosphate","P_000073_1":"11493079","P_000073_2":"10790535","P_000073_3":"8861662","P_000073_4":"11812059","P_390482_1":"12141188","P_390482_2":"11851542","P_390482_3":"10276706","P_390482_4":"10616261","P_397264_1":"13893780","P_397264_2":"8962466","P_397264_3":"10670365","P_397264_4":"8869440","P_ATV_1":"14505151","P_ATV_2":"14207368","P_ATV_3":"19686704","P_ATV_4":"18926386","P_CQ_1":"12509494","P_CQ_2":"14373732","P_CQ_3":"13074049","P_CQ_4":"12916272","P_DHA_1":"44163612","P_DHA_2":"42106536","P_DHA_3":"35871380","P_DHA_4":"42207148","P_DMSO_1":"18211904","P_DMSO_2":"18698354","P_DMSO_3":"16020323","P_DMSO_4":"15654699","P_S291_1":"13501043","P_S291_2":"16126070","P_S291_3":"16112257","P_S291_4":"15905515","P_S313_1":"16305161","P_S313_2":"12782953","P_S313_3":"14501632","P_S313_4":"10505726"},{"Metabolite":"Nicotinate","P_000073_1":"66848","P_000073_2":"47654","P_000073_3":"103067","P_000073_4":"66180","P_390482_1":"112911","P_390482_2":"87785","P_390482_3":"123508","P_390482_4":"119650","P_397264_1":"110831","P_397264_2":"117761","P_397264_3":"129709","P_397264_4":"120160","P_ATV_1":"121590","P_ATV_2":"46965","P_ATV_3":"125433","P_ATV_4":"81936","P_CQ_1":"65286","P_CQ_2":"60029","P_CQ_3":"140904.8438","P_CQ_4":"116506.4297","P_DHA_1":"105035.8594","P_DHA_2":"65878.09375","P_DHA_3":"120453.1094","P_DHA_4":"169701.8906","P_DMSO_1":"66322.20313","P_DMSO_2":"61058.19531","P_DMSO_3":"68330.17188","P_DMSO_4":"47608.09766","P_S291_1":"159403.7969","P_S291_2":"48431.76953","P_S291_3":"62227.80469","P_S291_4":"70847.24219","P_S313_1":"114458.1563","P_S313_2":"77696.375","P_S313_3":"107275.9141","P_S313_4":"104783.1797"},{"Metabolite":"CMP","P_000073_1":"42007","P_000073_2":"53946","P_000073_3":"35715","P_000073_4":"39770","P_390482_1":"39854","P_390482_2":"29497","P_390482_3":"33784","P_390482_4":"34493","P_397264_1":"33389","P_397264_2":"30725","P_397264_3":"41626","P_397264_4":"32462","P_ATV_1":"31792","P_ATV_2":"33284","P_ATV_3":"62788","P_ATV_4":"55300","P_CQ_1":"42934","P_CQ_2":"42123","P_CQ_3":"51379.51172","P_CQ_4":"39256.76953","P_DHA_1":"94918.40625","P_DHA_2":"129937.0234","P_DHA_3":"107674.2266","P_DHA_4":"103663.4375","P_DMSO_1":"59371.98047","P_DMSO_2":"60273.22656","P_DMSO_3":"62075.66406","P_DMSO_4":"56060.0625","P_S291_1":"47961.95313","P_S291_2":"43745.84766","P_S291_3":"75940.21094","P_S291_4":"72249.97656","P_S313_1":"38094.87891","P_S313_2":"42345.75781","P_S313_3":"41245.05078","P_S313_4":"35819.61328"},{"Metabolite":"Hercynine","P_000073_1":"8859457","P_000073_2":"10174829","P_000073_3":"10736033","P_000073_4":"13573259","P_390482_1":"11000977","P_390482_2":"9764962","P_390482_3":"10993747","P_390482_4":"13921940","P_397264_1":"7610829","P_397264_2":"6370428","P_397264_3":"11423167","P_397264_4":"10713717","P_ATV_1":"12705864","P_ATV_2":"15440512","P_ATV_3":"10733621","P_ATV_4":"13483216","P_CQ_1":"13595807","P_CQ_2":"14836521","P_CQ_3":"13948139","P_CQ_4":"12514707","P_DHA_1":"10829145","P_DHA_2":"13586833","P_DHA_3":"13351235","P_DHA_4":"16679534","P_DMSO_1":"7382138.5","P_DMSO_2":"6411735","P_DMSO_3":"7754488","P_DMSO_4":"8646674","P_S291_1":"1906394.375","P_S291_2":"9997590","P_S291_3":"9458525","P_S291_4":"11003970","P_S313_1":"11008415","P_S313_2":"7396088","P_S313_3":"15158185","P_S313_4":"9474806"},{"Metabolite":"FA 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(mins)":"11.12550396","Mass":"353.0716076","Formula":"C11H19N3O6S2","Metabolite identification":"Level 2"},{"Metabolite":"L-beta-aspartyl-L-glutamicacid","Retention Time (mins)":"14.02396037","Mass":"262.0801015","Formula":"C9H14N2O7","Metabolite identification":"Level 2"},{"Metabolite":"(-)-Argemonine","Retention Time (mins)":"12.42084607","Mass":"355.1778144","Formula":"C21H25NO4","Metabolite identification":"Level 2"},{"Metabolite":"D-4'-Phosphopantothenate","Retention Time (mins)":"14.93095421","Mass":"299.0766047","Formula":"C9H18NO8P","Metabolite identification":"Level 2"},{"Metabolite":"PS(18:2(9Z,12Z)/0:0)","Retention Time (mins)":"4.351431711","Mass":"521.2745229","Formula":"C24H44NO9P","Metabolite identification":"Level 2"},{"Metabolite":"Asp-Cys-Cys-Ser","Retention Time (mins)":"16.82657171","Mass":"426.088202","Formula":"C13H22N4O8S2","Metabolite identification":"Level 2"},{"Metabolite":"dihydrothymidine","Retention Time (mins)":"14.92830004","Mass":"244.1059006","Formula":"C10H16N2O5","Metabolite identification":"Level 2"},{"Metabolite":"1,2-Dihydroxy-5-(methylthio)pent-1-en-3-one","Retention Time (mins)":"7.917710096","Mass":"162.0350206","Formula":"C6H10O3S","Metabolite identification":"Level 2"},{"Metabolite":"S-Methyl-5-thio-D-ribose 1-phosphate","Retention Time (mins)":"12.72545592","Mass":"260.0118321","Formula":"C6H13O7PS","Metabolite identification":"Level 2"},{"Metabolite":"L-Pipecolate","Retention Time (mins)":"12.35014517","Mass":"129.0789892","Formula":"C6H11NO2","Metabolite identification":"Level 1"},{"Metabolite":"Thr-Pro","Retention Time (mins)":"11.37934046","Mass":"216.1108491","Formula":"C9H16N2O4","Metabolite identification":"Level 2"},{"Metabolite":"Ala-Pro","Retention Time (mins)":"11.32346325","Mass":"186.1006061","Formula":"C8H14N2O3","Metabolite identification":"Level 2"},{"Metabolite":"Aspartyl-L-proline","Retention Time (mins)":"15.2586538","Mass":"230.0904663","Formula":"C9H14N2O5","Metabolite identification":"Level 2"},{"Metabolite":"Asn-Gly-Pro-Pro","Retention Time (mins)":"10.92762413","Mass":"383.1804657","Formula":"C16H25N5O6","Metabolite identification":"Level 2"},{"Metabolite":"Ala-Glu-Glu-His","Retention Time (mins)":"15.27313045","Mass":"484.1924693","Formula":"C19H28N6O9","Metabolite identification":"Level 2"},{"Metabolite":"Glu-Glu-Pro","Retention Time (mins)":"16.63878338","Mass":"373.1488583","Formula":"C15H23N3O8","Metabolite identification":"Level 2"},{"Metabolite":"Ala-Lys-Lys-Asp","Retention Time (mins)":"14.18628684","Mass":"460.2646125","Formula":"C19H36N6O7","Metabolite identification":"Level 2"},{"Metabolite":"Lys-Pro","Retention Time (mins)":"15.17246384","Mass":"243.1583776","Formula":"C11H21N3O3","Metabolite identification":"Level 2"},{"Metabolite":"Asn-Leu-Pro-Pro","Retention Time (mins)":"10.82361996","Mass":"439.2433955","Formula":"C20H33N5O6","Metabolite identification":"Level 2"},{"Metabolite":"Ala-Gly-Ser","Retention Time (mins)":"12.60291301","Mass":"233.101189","Formula":"C8H15N3O5","Metabolite identification":"Level 2"},{"Metabolite":"[PS(18:1)] 1-(9Z-octadecenoyl)-sn-glycero-3-phosphoserine","Retention Time (mins)":"4.31446178","Mass":"523.2917002","Formula":"C24H46NO9P","Metabolite identification":"Level 2"},{"Metabolite":"Glycylproline","Retention Time (mins)":"12.38836948","Mass":"172.0848842","Formula":"C7H12N2O3","Metabolite identification":"Level 2"},{"Metabolite":"N-Acetylmethionine","Retention Time (mins)":"7.809380472","Mass":"191.0616312","Formula":"C7H13NO3S","Metabolite identification":"Level 2"},{"Metabolite":"Thr-Thr-Ser","Retention Time (mins)":"16.41751528","Mass":"307.1384014","Formula":"C11H21N3O7","Metabolite identification":"Level 2"},{"Metabolite":"Ser-Ser-Ser","Retention Time (mins)":"16.40925297","Mass":"279.1070384","Formula":"C9H17N3O7","Metabolite identification":"Level 2"},{"Metabolite":"Pro-Ser","Retention Time (mins)":"12.75553037","Mass":"202.0955136","Formula":"C8H14N2O4","Metabolite identification":"Level 2"},{"Metabolite":"Ala-Gly-Pro","Retention Time (mins)":"12.42465007","Mass":"243.1221379","Formula":"C10H17N3O4","Metabolite identification":"Level 2"},{"Metabolite":"Thr-Ser","Retention Time (mins)":"11.8842334","Mass":"206.0903796","Formula":"C7H14N2O5","Metabolite identification":"Level 2"},{"Metabolite":"Ser-Ser","Retention Time (mins)":"13.07125422","Mass":"192.0747819","Formula":"C6H12N2O5","Metabolite identification":"Level 2"},{"Metabolite":"N2-Succinyl-L-arginine","Retention Time (mins)":"12.81089579","Mass":"274.1280909","Formula":"C10H18N4O5","Metabolite identification":"Level 2"}]
}

}