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PMC:7696151 / 1312-5131 JSONTXT

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LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
48 20-54 Chemical denotes 4-aminoquinolonehydroxychloroquine
49 56-59 Chemical denotes HCQ MESH:D006886
50 265-272 Chemical denotes quinine MESH:D011803
51 277-287 Chemical denotes cinchonine MESH:C010086
52 504-511 Chemical denotes quinine MESH:D011803
53 560-588 Disease denotes systemic lupus erythematosus MESH:D008180
58 622-629 Chemical denotes quinine MESH:D011803
59 858-869 Chemical denotes chloroquine MESH:D002738
60 871-873 Chemical denotes CQ MESH:D002738
61 638-645 Disease denotes malaria MESH:D008288
68 973-980 Chemical denotes quinine MESH:D011803
69 1154-1161 Chemical denotes quinine MESH:D011803
70 1199-1201 Chemical denotes CQ MESH:D002738
71 1206-1209 Chemical denotes HCQ MESH:D006886
72 1341-1343 Chemical denotes CQ MESH:D002738
73 1404-1407 Chemical denotes HCQ MESH:D006886
84 1748-1752 Gene denotes ClN3 Gene:1201
85 1544-1559 Species denotes new coronavirus Tax:2697049
86 1561-1570 Species denotes 2019-nCoV Tax:2697049
87 1631-1674 Species denotes severe acute respiratory syndrome (SARS-CoV Tax:694009
88 1844-1852 Species denotes patients Tax:9606
89 1738-1740 Chemical denotes CQ MESH:D002738
90 1787-1790 Chemical denotes HCQ MESH:D006886
91 1792-1803 Chemical denotes C18H26ClN3O
92 1575-1583 Disease denotes COVID-19 MESH:C000657245
93 1835-1843 Disease denotes COVID-19 MESH:C000657245
97 1862-1864 Chemical denotes CQ MESH:D002738
98 1869-1872 Chemical denotes HCQ MESH:D006886
99 1939-1955 Chemical denotes 4-aminoquinoline MESH:C001920
106 2218-2223 Chemical denotes water MESH:D014867
107 2354-2357 Chemical denotes HCQ MESH:D006886
108 2433-2435 Chemical denotes CQ MESH:D002738
109 2440-2443 Chemical denotes HCQ MESH:D006886
110 2594-2599 Chemical denotes R-HCQ
111 2654-2659 Chemical denotes S-HCQ
116 2860-2888 Chemical denotes 4-aminoquinolinesderivatives
117 3190-3197 Chemical denotes carbons MESH:D002244
118 2901-2909 Disease denotes toxicity MESH:D064420
119 3115-3123 Disease denotes toxicity MESH:D064420
138 3669-3677 Species denotes patients Tax:9606
139 3215-3217 Chemical denotes CQ MESH:D002738
140 3222-3225 Chemical denotes HCQ MESH:D006886
141 3246-3255 Chemical denotes phosphate MESH:D010710
142 3260-3268 Chemical denotes sulphate MESH:D013431
143 3370-3373 Chemical denotes HCQ MESH:D006886
144 3403-3405 Chemical denotes CQ MESH:D002738
145 3421-3429 Disease denotes toxicity MESH:D064420
146 3461-3467 Disease denotes nausea MESH:D009325
147 3469-3483 Disease denotes stomach cramps MESH:D009120
148 3518-3527 Disease denotes diarrhoea MESH:D003967
149 3614-3625 Disease denotes retinopathy MESH:D012164
150 3661-3668 Disease denotes malaria MESH:D008288
151 3693-3714 Disease denotes inflammatory diseases MESH:D007249
152 3720-3740 Disease denotes rheumatoid arthritis MESH:D001172
153 3742-3758 Disease denotes Sjögren syndrome MESH:D012859
154 3760-3775 Disease denotes dermatomyositis MESH:D003882
155 3781-3809 Disease denotes systemic lupus erythematosus MESH:D008180

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T3 560-588 Phenotype denotes systemic lupus erythematosus http://purl.obolibrary.org/obo/HP_0002725
T4 3461-3467 Phenotype denotes nausea http://purl.obolibrary.org/obo/HP_0002018
T5 3518-3527 Phenotype denotes diarrhoea http://purl.obolibrary.org/obo/HP_0002014
T6 3614-3625 Phenotype denotes retinopathy http://purl.obolibrary.org/obo/HP_0000488
T7 3720-3740 Phenotype denotes rheumatoid arthritis http://purl.obolibrary.org/obo/HP_0001370
T8 3781-3809 Phenotype denotes systemic lupus erythematosus http://purl.obolibrary.org/obo/HP_0002725

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T12 0-2 Sentence denotes 1.
T13 3-15 Sentence denotes Introduction
T14 16-181 Sentence denotes The 4-aminoquinolonehydroxychloroquine (HCQ) was synthesized for the first time in 1946, but its history began as far back as the 1600s thanks to the Incas in Chile.
T15 182-404 Sentence denotes They introduced the special properties of cinchona bark to the Jesuits and in 1820 quinine and cinchonine were isolated and identified as the main alkaloids responsible for the antimalarial activity attributed to the bark.
T16 405-499 Sentence denotes For these reasons, in 1900, the Dutch and British transplanted this “miraculous tree” to Java.
T17 500-597 Sentence denotes The quinine soon began to be also used for the treatment of systemic lupus erythematosus [1,2,3].
T18 598-729 Sentence denotes The increasing need for quinine, due to malaria diffusion, led the pharmaceutical industry to the creation of a synthetic molecule.
T19 730-793 Sentence denotes In 1934 Johann (Hans) Andersag and co-workers at the Bayer I.G.
T20 794-937 Sentence denotes Farbenindustrie in Elberfeld laboratories, Germany, synthesized chloroquine (CQ) for the first time, judged by the Germans to be too toxic [4].
T21 938-1063 Sentence denotes However, the production of natural quinine was blocked by the Japanese army’s occupation of Java during the Second World War.
T22 1064-1162 Sentence denotes Therefore, it was necessary to deepen the studies on molecules that could replace natural quinine.
T23 1163-1344 Sentence denotes The Americans soon synthesized from CQ the HCQ, which resulted in it being less toxic than its ancestor so that in 1955 the scientific community proposed it as an alternative to CQ.
T24 1345-1422 Sentence denotes Figure 1 represents the historical development that led to HCQ synthesis [5].
T25 1423-1678 Sentence denotes This molecule, which has always been known as antimalarial, has come back into vogue in recent months due to the ongoing new coronavirus (2019-nCoV, or COVID-19 or 2019-nCo) worldwide pandemic, that causes a severe acute respiratory syndrome (SARS-CoV-2).
T26 1679-1861 Sentence denotes In fact, several research groups have evaluated the use of CQ (C18H26ClN3) and in particular its derivative HCQ (C18H26ClN3O), as a promising treatment for COVID-19 patients [6,7,8].
T27 1862-2070 Sentence denotes CQ and HCQ have a core structure consisting of two aromatic rings fused, the 4-aminoquinoline nucleus, and an amphiphilic weak basic side chain (represented in green and red colors in Figure 1, respectively).
T28 2071-2207 Sentence denotes The two chemical structures differ only for the hydroxyl group at the end of N-ethyl side chain (represented in blue color in Figure 1).
T29 2208-2402 Sentence denotes These are water-soluble molecules and, for their chemical nature, can pass the cell membranes; however, the presence of the hydroxyl group in the HCQ makes it more polar and less lipophilic [8].
T30 2403-2555 Sentence denotes Moreover, the accumulation of CQ and HCQ in intracellular compartments is due principally to the side chain and both have enantiomers (R and S isomers).
T31 2556-2660 Sentence denotes Researches also demonstrated that the R-HCQ is present in the blood at higher concentrations than S-HCQ.
T32 2661-2753 Sentence denotes These results suggested the stereoselective processes in the metabolism of the molecule [9].
T33 2754-2960 Sentence denotes Studies of structure-activity relationships have demonstrated that the halogen substitutions of different 4-aminoquinolinesderivatives reduced the toxicity, but it also reduced the pharmacological activity.
T34 2961-3064 Sentence denotes Instead, the therapeutic ratio is decreased by substitution of the alkyl side chain with an aryl chain.
T35 3065-3205 Sentence denotes Nevertheless, the therapeutic ratio decreases and toxicity increases with an increase of the alkyl side-chain length above 5 carbons [7,10].
T36 3206-3348 Sentence denotes Usually, CQ and HCQ are administered as phosphate and sulphate salts, respectively, and both drugs are absorbed in the upper intestinal tract.
T37 3349-3435 Sentence denotes However, clinically, HCQ is more frequently used than CQ for its lesser toxicity [11].
T38 3436-3626 Sentence denotes Both molecules give mild nausea, stomach cramps, gastrointestinal upset, and mild diarrhoea as adverse effects and long-term usage determines loss of retinal function and severe retinopathy.
T39 3627-3819 Sentence denotes These drugs are used, to date, in malaria patients and in several inflammatory diseases like rheumatoid arthritis, Sjögren syndrome, dermatomyositis, and systemic lupus erythematosus [7,8,10].