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PMC:7128678 / 11096-14484 JSONTXT

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LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
324 54-57 Gene denotes CLQ
325 30-42 Chemical denotes gangliosides MESH:D005732
349 3253-3266 Gene denotes CLQ-OH/CLQ-OH
350 2236-2247 Chemical denotes chloroquine MESH:D002738
351 2258-2276 Chemical denotes hydroxychloroquine MESH:D006886
352 2278-2284 Chemical denotes CLQ-OH
353 2297-2308 Chemical denotes ganglioside MESH:D005732
354 2309-2312 Chemical denotes GM1 MESH:D005677
355 2353-2356 Chemical denotes GM1 MESH:D005677
356 2420-2428 Chemical denotes ceramide MESH:D002518
357 2522-2533 Chemical denotes sialic-acid MESH:D019158
358 2545-2555 Chemical denotes saccharide MESH:D002241
359 2606-2618 Chemical denotes carbohydrate MESH:D002241
360 2629-2632 Chemical denotes GM1 MESH:D005677
361 2661-2676 Chemical denotes CLQ–ganglioside
362 2828-2836 Chemical denotes ceramide MESH:D002518
363 2837-2842 Chemical denotes sugar MESH:D000073893
364 2865-2873 Chemical denotes nitrogen MESH:D009584
365 2917-2928 Chemical denotes ganglioside MESH:D005732
366 2971-2974 Chemical denotes GM1 MESH:D005677
367 3085-3088 Chemical denotes GM1 MESH:D005677
368 3116-3119 Chemical denotes GM1 MESH:D005677
369 3163-3169 Chemical denotes CLQ-OH
370 3301-3307 Chemical denotes CLQ-OH
371 3327-3330 Chemical denotes GM1 MESH:D005677
410 378-383 Species denotes human Tax:9606
411 87-99 Chemical denotes sialic acids MESH:D012794
412 138-150 Chemical denotes gangliosides MESH:D005732
413 219-225 Chemical denotes CLQ-OH
414 240-251 Chemical denotes sialic acid MESH:D019158
415 320-335 Chemical denotes ganglioside GM1 MESH:D005677
416 400-412 Chemical denotes gangliosides MESH:D005732
417 489-500 Chemical denotes ganglioside MESH:D005732
418 564-574 Chemical denotes saccharide MESH:D002241
419 583-586 Chemical denotes GM1 MESH:D005677
420 633-643 Chemical denotes saccharide MESH:D002241
421 658-669 Chemical denotes ganglioside MESH:D005732
422 794-799 Chemical denotes water MESH:D014867
423 836-848 Chemical denotes sialic acids MESH:D012794
424 917-928 Chemical denotes carboxylate
425 942-953 Chemical denotes sialic acid MESH:D019158
426 957-960 Chemical denotes GM1 MESH:D005677
427 1037-1058 Chemical denotes N-acetylgalactosamine MESH:D000116
428 1060-1066 Chemical denotes GalNAc
429 1079-1082 Chemical denotes GM1 MESH:D005677
430 1123-1131 Chemical denotes hydrogen MESH:D006859
431 1206-1214 Chemical denotes ceramide MESH:D002518
432 1215-1220 Chemical denotes sugar MESH:D000073893
433 1238-1248 Chemical denotes saccharide MESH:D002241
434 1271-1279 Chemical denotes chlorine MESH:D002713
435 1317-1325 Chemical denotes ceramide MESH:D002518
436 1345-1353 Chemical denotes nitrogen MESH:D009584
437 1396-1402 Chemical denotes pyrane
438 1421-1426 Chemical denotes sugar MESH:D000073893
439 1441-1448 Chemical denotes glucose MESH:D005947
440 1450-1453 Chemical denotes Glc MESH:D005947
441 1685-1688 Chemical denotes GM1 MESH:D005677
442 1697-1708 Chemical denotes ganglioside MESH:D005732
443 1852-1858 Chemical denotes CLQ-OH
444 2029-2035 Chemical denotes CLQ-OH
445 2111-2117 Chemical denotes CLQ-OH
446 2138-2150 Chemical denotes sialic acids MESH:D012794
447 2180-2192 Chemical denotes gangliosides MESH:D005732

LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T243 30-42 CHEBI:28892;CHEBI:28892 denotes gangliosides
T244 68-79 GO:0045333;UBERON:0000065 denotes respiratory
T245 80-85 UBERON:0000065 denotes tract
T246 87-99 CHEBI:26667;CHEBI:26667 denotes sialic acids
T247 120-133 CHEBI:17089;CHEBI:17089;BV_11 denotes glycoproteins
T248 138-150 CHEBI:28892;CHEBI:28892 denotes gangliosides
T249 240-251 CHEBI:26667;CHEBI:26667 denotes sialic acid
T250 320-331 CHEBI:5386;CHEBI:5386 denotes ganglioside
T251 378-383 SP_6;NCBITaxon:9606 denotes human
T252 384-399 GO:0005886 denotes plasma membrane
T253 400-412 CHEBI:28892;CHEBI:28892 denotes gangliosides
T254 489-500 CHEBI:28892;CHEBI:28892 denotes ganglioside
T255 523-536 SO:0000409 denotes binding sites
T256 564-574 CHEBI:32111;CHEBI:32111 denotes saccharide
T257 633-643 CHEBI:32111;CHEBI:32111 denotes saccharide
T258 658-669 CHEBI:28892;CHEBI:28892 denotes ganglioside
T259 794-799 CHEBI:15377;CHEBI:15377 denotes water
T260 836-842 CHEBI:30563;CHEBI:30563 denotes sialic
T261 843-848 CHEBI:41865;CHEBI:41865 denotes acids
T262 929-934 CHEBI:24433;CHEBI:24433 denotes group
T263 942-953 CHEBI:26667;CHEBI:26667 denotes sialic acid
T264 986-1001 CHEBI:64766;CHEBI:64766 denotes cationic groups
T265 1206-1214 CHEBI:17761;CHEBI:17761 denotes ceramide
T266 1238-1248 CHEBI:32111;CHEBI:32111 denotes saccharide
T267 1271-1279 CHEBI:33910;CHEBI:33910 denotes chlorine
T268 1280-1284 CHEBI:33250;CHEBI:33250 denotes atom
T269 1317-1325 CHEBI:17761;CHEBI:17761 denotes ceramide
T270 1441-1448 CHEBI:17234;CHEBI:17234 denotes glucose
T271 1668-1681 SO:0000409 denotes binding sites
T272 1697-1708 CHEBI:28892;CHEBI:28892 denotes ganglioside
T273 1735-1744 CHEBI:36357;CHEBI:36357 denotes molecules
T274 1884-1896 SO:0000409 denotes binding site
T275 2036-2045 CHEBI:36357;CHEBI:36357 denotes molecules
T276 2138-2150 CHEBI:26667;CHEBI:26667 denotes sialic acids
T277 2180-2192 CHEBI:16856;CHEBI:16856 denotes gangliosides
T278 2236-2247 CHEBI:3638;DG_10;CHEBI:3638 denotes chloroquine
T279 2258-2276 CHEBI:5801;DG_20;CHEBI:5801 denotes hydroxychloroquine
T280 2297-2308 CHEBI:16856;CHEBI:16856 denotes ganglioside
T281 2380-2388 GO:0016020 denotes membrane
T282 2420-2428 CHEBI:17761;CHEBI:17761 denotes ceramide
T283 2451-2457 CHEBI:37527;CHEBI:37527 denotes acidic
T284 2481-2500 GO:0005615 denotes extracellular space
T285 2522-2533 CHEBI:26667;CHEBI:26667 denotes sialic-acid
T286 2545-2555 CHEBI:32111;CHEBI:32111 denotes saccharide
T287 2606-2618 CHEBI:16646;CHEBI:16646 denotes carbohydrate
T288 2665-2676 CHEBI:5386;CHEBI:5386 denotes ganglioside
T289 2828-2836 CHEBI:17761;CHEBI:17761 denotes ceramide
T290 2874-2879 CHEBI:33250;CHEBI:33250 denotes atoms
T291 2898-2904 CHEBI:37527;CHEBI:37527 denotes acidic
T292 2917-2928 CHEBI:5386;CHEBI:5386 denotes ganglioside
T293 2975-2984 GO:0032991 denotes complexed
T294 3013-3022 CHEBI:36357;CHEBI:36357 denotes molecules
T295 3097-3106 CHEBI:36357;CHEBI:36357 denotes molecules
T296 3120-3128 CHEBI:36357;CHEBI:36357 denotes molecule
T297 3170-3179 CHEBI:36357;CHEBI:36357 denotes molecules
T298 3308-3317 CHEBI:36357;CHEBI:36357 denotes molecules

LitCovid-PD-FMA-UBERON

Id Subject Object Predicate Lexical cue fma_id
T42 30-42 Body_part denotes gangliosides http://purl.org/sig/ont/fma/fma82816
T43 68-85 Body_part denotes respiratory tract http://purl.org/sig/ont/fma/fma265130
T44 120-133 Body_part denotes glycoproteins http://purl.org/sig/ont/fma/fma62925
T45 138-150 Body_part denotes gangliosides http://purl.org/sig/ont/fma/fma82816
T46 320-331 Body_part denotes ganglioside http://purl.org/sig/ont/fma/fma82816
T47 384-399 Body_part denotes plasma membrane http://purl.org/sig/ont/fma/fma63841
T48 400-412 Body_part denotes gangliosides http://purl.org/sig/ont/fma/fma82816
T49 489-500 Body_part denotes ganglioside http://purl.org/sig/ont/fma/fma82816
T50 658-669 Body_part denotes ganglioside http://purl.org/sig/ont/fma/fma82816
T51 1037-1058 Body_part denotes N-acetylgalactosamine http://purl.org/sig/ont/fma/fma82786
T52 1215-1220 Body_part denotes sugar http://purl.org/sig/ont/fma/fma82737
T53 1326-1330 Body_part denotes axis http://purl.org/sig/ont/fma/fma12520
T54 1421-1426 Body_part denotes sugar http://purl.org/sig/ont/fma/fma82737
T55 1441-1448 Body_part denotes glucose http://purl.org/sig/ont/fma/fma82743
T56 1450-1453 Body_part denotes Glc http://purl.org/sig/ont/fma/fma82743
T57 1697-1708 Body_part denotes ganglioside http://purl.org/sig/ont/fma/fma82816
T58 2180-2192 Body_part denotes gangliosides http://purl.org/sig/ont/fma/fma82816
T59 2297-2308 Body_part denotes ganglioside http://purl.org/sig/ont/fma/fma82816
T60 2481-2500 Body_part denotes extracellular space http://purl.org/sig/ont/fma/fma70022
T61 2606-2618 Body_part denotes carbohydrate http://purl.org/sig/ont/fma/fma82737
T62 2665-2676 Body_part denotes ganglioside http://purl.org/sig/ont/fma/fma82816
T63 2837-2842 Body_part denotes sugar http://purl.org/sig/ont/fma/fma82737
T64 2917-2928 Body_part denotes ganglioside http://purl.org/sig/ont/fma/fma82816

LitCovid-PD-UBERON

Id Subject Object Predicate Lexical cue uberon_id
T4 68-85 Body_part denotes respiratory tract http://purl.obolibrary.org/obo/UBERON_0000065
T5 622-625 Body_part denotes tip http://purl.obolibrary.org/obo/UBERON_2001840
T6 2595-2598 Body_part denotes tip http://purl.obolibrary.org/obo/UBERON_2001840

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T71 350-351 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T72 378-383 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T73 384-390 http://purl.obolibrary.org/obo/UBERON_0001969 denotes plasma
T74 391-399 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membrane
T75 414-415 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T76 678-679 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T77 680-681 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T78 874-875 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T79 884-885 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T80 1027-1036 http://purl.obolibrary.org/obo/UBERON_0001456 denotes faced the
T81 1147-1148 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T82 1174-1175 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T83 1221-1229 http://purl.obolibrary.org/obo/UBERON_0007651 denotes junction
T84 1261-1265 http://purl.obolibrary.org/obo/CLO_0001387 denotes 4(c)
T85 1541-1542 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T86 1765-1766 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T87 1814-1815 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T88 2123-2124 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T89 2367-2368 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T90 2380-2388 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membrane
T91 2575-2576 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T92 2635-2636 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T93 2735-2736 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T94 2843-2851 http://purl.obolibrary.org/obo/UBERON_0007651 denotes junction

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T180 30-42 Chemical denotes gangliosides http://purl.obolibrary.org/obo/CHEBI_28892
T181 87-99 Chemical denotes sialic acids http://purl.obolibrary.org/obo/CHEBI_26667
T182 94-99 Chemical denotes acids http://purl.obolibrary.org/obo/CHEBI_37527
T183 120-133 Chemical denotes glycoproteins http://purl.obolibrary.org/obo/CHEBI_17089
T184 138-150 Chemical denotes gangliosides http://purl.obolibrary.org/obo/CHEBI_28892
T185 240-251 Chemical denotes sialic acid http://purl.obolibrary.org/obo/CHEBI_26667
T186 247-251 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T187 320-335 Chemical denotes ganglioside GM1 http://purl.obolibrary.org/obo/CHEBI_18216|http://purl.obolibrary.org/obo/CHEBI_61048
T189 320-331 Chemical denotes ganglioside http://purl.obolibrary.org/obo/CHEBI_28892
T190 332-335 Chemical denotes GM1 http://purl.obolibrary.org/obo/CHEBI_73110
T191 400-412 Chemical denotes gangliosides http://purl.obolibrary.org/obo/CHEBI_28892
T192 489-500 Chemical denotes ganglioside http://purl.obolibrary.org/obo/CHEBI_28892
T193 564-574 Chemical denotes saccharide http://purl.obolibrary.org/obo/CHEBI_16646
T194 583-586 Chemical denotes GM1 http://purl.obolibrary.org/obo/CHEBI_18216|http://purl.obolibrary.org/obo/CHEBI_61048|http://purl.obolibrary.org/obo/CHEBI_73110
T197 633-643 Chemical denotes saccharide http://purl.obolibrary.org/obo/CHEBI_16646
T198 658-669 Chemical denotes ganglioside http://purl.obolibrary.org/obo/CHEBI_28892
T199 794-799 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T200 836-848 Chemical denotes sialic acids http://purl.obolibrary.org/obo/CHEBI_26667
T201 843-848 Chemical denotes acids http://purl.obolibrary.org/obo/CHEBI_37527
T202 929-934 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T203 942-953 Chemical denotes sialic acid http://purl.obolibrary.org/obo/CHEBI_26667
T204 949-953 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T205 957-960 Chemical denotes GM1 http://purl.obolibrary.org/obo/CHEBI_18216|http://purl.obolibrary.org/obo/CHEBI_61048|http://purl.obolibrary.org/obo/CHEBI_73110
T208 986-1001 Chemical denotes cationic groups http://purl.obolibrary.org/obo/CHEBI_64766
T209 1037-1058 Chemical denotes N-acetylgalactosamine http://purl.obolibrary.org/obo/CHEBI_28800
T210 1060-1066 Chemical denotes GalNAc http://purl.obolibrary.org/obo/CHEBI_28037|http://purl.obolibrary.org/obo/CHEBI_28800
T212 1079-1082 Chemical denotes GM1 http://purl.obolibrary.org/obo/CHEBI_18216|http://purl.obolibrary.org/obo/CHEBI_61048|http://purl.obolibrary.org/obo/CHEBI_73110
T215 1123-1131 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T216 1206-1214 Chemical denotes ceramide http://purl.obolibrary.org/obo/CHEBI_17761|http://purl.obolibrary.org/obo/CHEBI_52639
T218 1238-1248 Chemical denotes saccharide http://purl.obolibrary.org/obo/CHEBI_16646
T219 1271-1284 Chemical denotes chlorine atom http://purl.obolibrary.org/obo/CHEBI_23116
T220 1271-1279 Chemical denotes chlorine http://purl.obolibrary.org/obo/CHEBI_29310
T221 1280-1284 Chemical denotes atom http://purl.obolibrary.org/obo/CHEBI_33250
T222 1317-1325 Chemical denotes ceramide http://purl.obolibrary.org/obo/CHEBI_17761|http://purl.obolibrary.org/obo/CHEBI_52639
T224 1345-1353 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T225 1441-1448 Chemical denotes glucose http://purl.obolibrary.org/obo/CHEBI_17234|http://purl.obolibrary.org/obo/CHEBI_4167
T227 1450-1453 Chemical denotes Glc http://purl.obolibrary.org/obo/CHEBI_17234
T228 1685-1688 Chemical denotes GM1 http://purl.obolibrary.org/obo/CHEBI_18216|http://purl.obolibrary.org/obo/CHEBI_61048|http://purl.obolibrary.org/obo/CHEBI_73110
T231 1697-1708 Chemical denotes ganglioside http://purl.obolibrary.org/obo/CHEBI_28892
T232 1735-1744 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T233 2036-2045 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T234 2138-2150 Chemical denotes sialic acids http://purl.obolibrary.org/obo/CHEBI_26667
T235 2145-2150 Chemical denotes acids http://purl.obolibrary.org/obo/CHEBI_37527
T236 2180-2192 Chemical denotes gangliosides http://purl.obolibrary.org/obo/CHEBI_28892
T237 2236-2247 Chemical denotes chloroquine http://purl.obolibrary.org/obo/CHEBI_3638
T238 2258-2276 Chemical denotes hydroxychloroquine http://purl.obolibrary.org/obo/CHEBI_5801
T239 2297-2312 Chemical denotes ganglioside GM1 http://purl.obolibrary.org/obo/CHEBI_18216|http://purl.obolibrary.org/obo/CHEBI_61048
T241 2297-2308 Chemical denotes ganglioside http://purl.obolibrary.org/obo/CHEBI_28892
T242 2309-2312 Chemical denotes GM1 http://purl.obolibrary.org/obo/CHEBI_73110
T243 2353-2356 Chemical denotes GM1 http://purl.obolibrary.org/obo/CHEBI_18216|http://purl.obolibrary.org/obo/CHEBI_61048|http://purl.obolibrary.org/obo/CHEBI_73110
T246 2420-2428 Chemical denotes ceramide http://purl.obolibrary.org/obo/CHEBI_17761|http://purl.obolibrary.org/obo/CHEBI_52639
T248 2529-2533 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T249 2545-2555 Chemical denotes saccharide http://purl.obolibrary.org/obo/CHEBI_16646
T250 2606-2618 Chemical denotes carbohydrate http://purl.obolibrary.org/obo/CHEBI_16646
T251 2629-2632 Chemical denotes GM1 http://purl.obolibrary.org/obo/CHEBI_18216|http://purl.obolibrary.org/obo/CHEBI_61048|http://purl.obolibrary.org/obo/CHEBI_73110
T254 2665-2676 Chemical denotes ganglioside http://purl.obolibrary.org/obo/CHEBI_28892
T255 2828-2836 Chemical denotes ceramide http://purl.obolibrary.org/obo/CHEBI_17761|http://purl.obolibrary.org/obo/CHEBI_52639
T257 2865-2873 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T258 2874-2879 Chemical denotes atoms http://purl.obolibrary.org/obo/CHEBI_33250
T259 2917-2928 Chemical denotes ganglioside http://purl.obolibrary.org/obo/CHEBI_28892
T260 2971-2974 Chemical denotes GM1 http://purl.obolibrary.org/obo/CHEBI_18216|http://purl.obolibrary.org/obo/CHEBI_61048|http://purl.obolibrary.org/obo/CHEBI_73110
T263 3013-3022 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T264 3085-3088 Chemical denotes GM1 http://purl.obolibrary.org/obo/CHEBI_18216|http://purl.obolibrary.org/obo/CHEBI_61048|http://purl.obolibrary.org/obo/CHEBI_73110
T267 3097-3106 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T268 3116-3119 Chemical denotes GM1 http://purl.obolibrary.org/obo/CHEBI_18216|http://purl.obolibrary.org/obo/CHEBI_61048|http://purl.obolibrary.org/obo/CHEBI_73110
T271 3120-3128 Chemical denotes molecule http://purl.obolibrary.org/obo/CHEBI_25367
T272 3170-3179 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T273 3308-3317 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T274 3327-3330 Chemical denotes GM1 http://purl.obolibrary.org/obo/CHEBI_18216|http://purl.obolibrary.org/obo/CHEBI_61048|http://purl.obolibrary.org/obo/CHEBI_73110

LitCovid-PD-GlycoEpitope

Id Subject Object Predicate Lexical cue glyco_epitope_db_id
T3 332-335 GlycoEpitope denotes GM1 http://www.glycoepitope.jp/epitopes/EP0050
T4 583-586 GlycoEpitope denotes GM1 http://www.glycoepitope.jp/epitopes/EP0050
T5 957-960 GlycoEpitope denotes GM1 http://www.glycoepitope.jp/epitopes/EP0050
T6 1079-1082 GlycoEpitope denotes GM1 http://www.glycoepitope.jp/epitopes/EP0050
T7 1685-1688 GlycoEpitope denotes GM1 http://www.glycoepitope.jp/epitopes/EP0050
T8 2309-2312 GlycoEpitope denotes GM1 http://www.glycoepitope.jp/epitopes/EP0050
T9 2353-2356 GlycoEpitope denotes GM1 http://www.glycoepitope.jp/epitopes/EP0050
T10 2629-2632 GlycoEpitope denotes GM1 http://www.glycoepitope.jp/epitopes/EP0050
T11 2971-2974 GlycoEpitope denotes GM1 http://www.glycoepitope.jp/epitopes/EP0050
T12 3085-3088 GlycoEpitope denotes GM1 http://www.glycoepitope.jp/epitopes/EP0050
T13 3116-3119 GlycoEpitope denotes GM1 http://www.glycoepitope.jp/epitopes/EP0050
T14 3327-3330 GlycoEpitope denotes GM1 http://www.glycoepitope.jp/epitopes/EP0050

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T83 0-60 Sentence denotes 3.3 Molecular recognition of gangliosides by CLQ and CLQ-OH
T84 61-151 Sentence denotes In the respiratory tract, sialic acids are usually part of glycoproteins and gangliosides.
T85 152-297 Sentence denotes Molecular modelling approaches were used to assess whether CLQ and CLQ-OH can recognize sialic acid units in their natural molecular environment.
T86 298-413 Sentence denotes In these simulations, ganglioside GM1 was chosen as a representative example of human plasma membrane gangliosides.
T87 414-467 Sentence denotes A first series of simulations was performed with CLQ.
T88 468-587 Sentence denotes When merged with the ganglioside, CLQ had two distinct binding sites, both located in the polar saccharide part of GM1.
T89 588-683 Sentence denotes The first site was located at the tip of the saccharide moiety of the ganglioside Fig. 4 (a,b).
T90 684-743 Sentence denotes The energy of interaction was estimated to be -47 kJ.mol−1.
T91 744-878 Sentence denotes CLQ retained the typical L-shape structure of the water-soluble conformer bound to isolated sialic acids [compare Figs 2(c) and 4(a)].
T92 879-1009 Sentence denotes From a mechanistic point of view, the carboxylate group of the sialic acid of GM1 was oriented towards the cationic groups of CLQ.
T93 1010-1150 Sentence denotes The rings of CLQ faced the N-acetylgalactosamine (GalNAc) residue of GM1, establishing both OH-π interaction and hydrogen bonding Fig. 4(b).
T94 1151-1266 Sentence denotes The second site was in a large area including both the ceramide–sugar junction and the saccharide moiety Fig. 4(c).
T95 1267-1456 Sentence denotes The chlorine atom of CLQ was oriented towards the ceramide axis, allowing the nitrogen-containing ring of CLQ to stack on to the pyrane ring of the first sugar residue [i.e. glucose (Glc)].
T96 1457-1611 Sentence denotes The perfect geometric complementarity of the two partners Fig. 4(c,d) accounted for a particularly high energy of interaction in this case (-61 kJ.mol−1).
T97 1612-1813 Sentence denotes Interestingly, there was no overlap between the two CLQ-binding sites on GM1, so the ganglioside could accommodate two CLQ molecules Fig. 4(e), reaching a global energy of interaction of -108 kJ.mol−1.
T98 1814-1914 Sentence denotes A similar situation was observed with CLQ-OH, which occupies the same binding site as CLQ Fig. 4(f).
T99 1915-2070 Sentence denotes In this case, the energy of interaction was further increased by stabilizing contacts established between the two CLQ-OH molecules, reaching -120 kJ.mol−1.
T100 2071-2193 Sentence denotes Overall, these data showed that CLQ and CLQ-OH have a good fit for sialic acids, either isolated or bound to gangliosides.
T101 2194-2313 Sentence denotes Fig. 4 Molecular modelling simulations of chloroquine (CLQ) and hydroxychloroquine (CLQ-OH) binding to ganglioside GM1.
T102 2314-2764 Sentence denotes The surface electrostatic potential of GM1 indicates a non-polar, membrane-embedded part corresponding to ceramide (white areas), and an acidic part protruding in the extracellular space corresponding to the sialic-acid-containing saccharide part (red areas). (a) CLQ bound to the tip of the carbohydrate moiety of GM1. (b) Molecular mechanism of CLQ–ganglioside interactions. (c) Molecular dynamics simulations revealed a second site of interaction.
T103 2765-3280 Sentence denotes In this case, the aromatic cycles of CLQ are positioned at the ceramide–sugar junction, whereas the nitrogen atoms interact with the acidic part of the ganglioside (not illustrated). (d,e) Surface views of GM1 complexed with one (d) or two (e) CLQ molecules (both in blue), illustrating the geometric complementarity of GM1 and CLQ molecules. (f) One GM1 molecule can also accommodate two distinct CLQ-OH molecules simultaneously, after slight rearrangement allowing increased fit due to CLQ-OH/CLQ-OH interactions.
T104 3281-3388 Sentence denotes To improve clarity, CLQ-OH molecules bound to GM1 are represented in two distinct colours (blue and green).