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call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js Jmol JavaScript applet jmolApplet0_object__595009435690574__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__595009435690574__) call loadScript javascripts\jsmol\core\corestate.z.js viewerOptions: { "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:49929","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__595009435690574__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"595009435690574","bgcolor":"#000" } (C) 2012 Jmol Development Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $ java.vendor: j2s java.version: 0.0 os.name: j2s Access: ALL memory: 0.0/0.0 processors available: 1 useCommandThread: false appletId:jmolApplet0_object (signed) starting HoverWatcher_1 getValue emulate = null defaults = "Jmol" getValue boxbgcolor = null getValue bgcolor = #000 backgroundColor = "#000" getValue ANIMFRAMECallback = null getValue APPLETREADYCallback = Jmol._readyCallback APPLETREADYCallback = "Jmol._readyCallback" getValue ATOMMOVEDCallback = null getValue CLICKCallback = null getValue ECHOCallback = null getValue ERRORCallback = null getValue EVALCallback = null getValue HOVERCallback = null getValue LOADSTRUCTCallback = null getValue MEASURECallback = null getValue MESSAGECallback = null getValue MINIMIZATIONCallback = null getValue PICKCallback = null getValue RESIZECallback = null getValue SCRIPTCallback = null getValue SYNCCallback = null getValue STRUCTUREMODIFIEDCallback = null getValue doTranslate = null language=en_US getValue popupMenu = null getValue script = null Jmol applet jmolApplet0_object__595009435690574__ ready call loadScript javascripts\jsmol\core\corescript.z.js call loadScript javascripts\jsmol\J\script\FileLoadThread.js starting QueueThread0_2 script 1 started starting HoverWatcher_3 starting HoverWatcher_4 The Resolver thinks Mol Marvin 05160816383D starting HoverWatcher_5 Time for openFile( Marvin 05160816383D 10 9 0 0 0 0 999 V2000 -0.0530 -0.1900 -0.0070 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2450 -1.5040 -0.0170 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9370 0.7250 -0.0140 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2410 0.3210 -0.0310 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6880 0.3170 0.0090 S 0 0 0 0 0 0 0 0 0 0 0 0 1.1720 -1.7910 -0.0300 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4670 -2.1630 -0.0120 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7220 1.6710 -0.0060 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8660 1.1140 -0.0350 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4400 -0.2930 0.7440 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 1 5 2 0 0 0 0 2 6 1 0 0 0 0 2 7 1 0 0 0 0 3 4 1 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 4 10 1 0 0 0 0 M END): 15 ms reading 10 atoms ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false 1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. Default Van der Waals type for model set to Babel 10 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
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| InChI=1S/CH5N3S/c2-1(5)4-3/h3H2,(H3,2,4,5) |
| BRWIZMBXBAOCCF-UHFFFAOYSA-N |
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1-amino-2-thiourea
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ChemIDplus
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1-aminothiourea
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ChemIDplus
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2-thiosemicarbazide
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ChemIDplus
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aminothio-urea
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ChemIDplus
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aminothiourea
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ChEBI
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isothiosemicarbazide
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ChemIDplus
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N-aminothiourea
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ChemIDplus
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thiocarbamoyl hydrazide
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ChEBI
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thiocarbamoylhydrazine
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ChemIDplus
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thiocarbamylhydrazine
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ChemIDplus
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thiosemicarbazide
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ChemIDplus
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506320
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Reaxys Registry Number
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Reaxys
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79-19-6
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CAS Registry Number
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NIST Chemistry WebBook
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79-19-6
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CAS Registry Number
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ChemIDplus
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Araújo DE, de Oliveira AA, Cabral MDS, Costa AF, Silva BC, do Carmo Silva L, de Menezes LB, de Almeida Soares CM, Amaral AC, Pereira M (2020)
Investigation of thiosemicarbazide free or within chitosan nanoparticles in a murine model of vulvovaginal candidiasis.
Brazilian journal of microbiology : [publication of the Brazilian Society for Microbiology] 51, 1465-1473 [PubMed:32638273]
[show Abstract]
Vulvovaginal candidiasis is a serious health problem affecting numerous women around the world. Its treatment is based on antifungals which may not provide an effective cure because of the resistance presented by its etiological pathogens Candida spp. Candida albicans is the most prevalent species related to vulvovaginal candidiasis. Here, we evaluated the in vivo antifungal potential of thiosemicarbazide and thiosemicarbazide encapsulated within chitosan nanoparticles in a murine model of vulvovaginal candidiasis. The results demonstrated the antifungal capacity of free or nanoencapsulated thiosemicarbazide within chitosan to reduce the fungal load in the vaginal tissue of infected mice. In addition, histological analyses indicated the absence or a mild to moderate infection in thiosemicarbazide-treated groups. Statistical tests confirmed the existence of significant differences between the treated and the control groups. Therefore, our results suggest a potential application of thiosemicarbazide and encapsulated thiosemicarbazide as an alternative vulvovaginal candidiasis therapy. | Moharana AK, Dash RN, Subudhi BB (2020)
Thiosemicarbazides: Updates on Antivirals Strategy.
Mini reviews in medicinal chemistry 20, 2135-2152 [PubMed:32811412]
[show Abstract]
The challenges of viral infection have increased in recent decades due to the emergence of resistance, cross-resistance and drying up of antiviral drug discovery. Many neglected tropical viruses including the chikungunya virus, dengue virus & Japanese encephalitis virus have gradually become global pathogens. This has further increased the burden of viral infection which necessitates the continuous development of antiviral therapy. The antiviral chemistry began with the development of thiosemicarbazide derived thiosemicarbazones as antiviral. Although very few thiosemicarbazides have progressed into clinical application, it still inspires antiviral development. During last 3 decades (1990- 2020), several efforts have been made to develop suitable antiviral by using thiosemicarbazide scaffold. Its hybridization with other pharmacophores has been used as a strategy to enhance safety and efficacy. Cyclization and substitution of thiosemicarbazides have also been used to develop potent antiviral. With the ability to form coordinate bonds, thiosemicarbazides have been used either as metal complex or chelator against viruses. This work is an attempt to systematically review the research on the use of thiosemicarbazides as an antiviral scaffold. It also reviews the structure-activity relationship and translational suitability of thiosemicarbazide derived compounds. | Namiecińska E, Sobiesiak M, Małecka M, Guga P, Rozalska B, Budzisz E (2019)
Antimicrobial and Structural Properties of Metal Ions Complexes with Thiosemicarbazide Motif and Related Heterocyclic Compounds.
Current medicinal chemistry 26, 664-693 [PubMed:29493443]
[show Abstract]
Antibiotic resistance acquired by various bacterial fungal and viral pathogens poses therapeutic problems of increasing severity. Among the infections that are very difficult to treat, biofilm-associated cases are one of the most hazardous. Complex structure of a biofilm and unique physiology of the biofilm cells contribute to their extremely high resistance to environmental conditions, antimicrobial agents and the mechanisms of host immune response. Therefore, the biofilm formation, especially by multidrugresistant pathogens, is a serious medical problem, playing a pivotal role in the development of chronic and recurrent infections. These factors create a limitation for using traditional chemiotherapeutics and contribute to a request for development of new approaches for treatment of infectious diseases. Therefore, early reports on antimicrobial activity of several complexes of metal ions, bearing thiosemicarbazide or thiosemicarbazones as the ligands, gave a boost to worldwide search for new, more efficient compounds of this class, to be used as alternatives to commonly known drugs. In general, depending on the presence of other heteroatoms, these ligands may function in a di-, tri- or tetradentate forms (e.g., of N,S,-, N,N,S-, N,N,N,S-, N,N,S,S-, or N,S,O-type), which impose different coordination geometries to the resultant complexes. In the first part of this review, we describe the ways of synthesis and the structures of the ligands based on the thiosemicarbazone motif, while the second part deals with the antimicrobial activity of their complexes with selected metal ions. | Gera A, Mohan C, Madan J, Arora S (2019)
Molecular Hybrids of N-Phthaloylglycyl Hydrazide and Hydrazinecarbothioamide with Anti-inflammatory and Anti-oxidant Activities.
Current organic synthesis 16, 1055-1066 [PubMed:31984886]
[show Abstract]
BackgroundOxidative stress due to high levels of reactive organic species is the cause of the progression of inflammation in various diseases. The molecules possessing both anti-inflammatory and antioxidant activity can be the promising key to treat inflammatory diseases. Phthalimide and hydrazinecarbothioamide are anti-inflammatory and anti-oxidant pharmacophores.ObjectiveMolecular hybrids possessing above two pharmacophores were designed. A series of N-phenyl substituted 2-(2-(1,3-dioxoisoindolin-2-yl)acetyl)-N-phenylhydrazine-1-carbothioamide (CGS compounds) was synthesized and evaluated for biological activities.MethodsN-phthaloylglycyl hydrazide was reacted with unsubstituted/substituted phenyl isothiocyanates to yield CGS compounds. Synthesized compounds were evaluated for in vivo anti-inflammatory activity in carrageenan rat paw edema model, and in vitro anti-oxidant activity by DPPH assay. Levels of TNF-α and oxidative stress at the site of inflammation were measured. The genetic algorithm-PLS regression based QSAR model correlating the effect of N-phenyl substituent on the anti-inflammatory activity was developed. Further, the interaction of the active compound in the TNF-α binding pocket was studied by in silico docking.ResultsCompound containing the 2-OCH3, 4-NO2 (CGS-5); 4-CF3 (CGS-9); 4-NO2 (CGS-3) showed significant anti-inflammatory activity (percentage inhibition of paw edema after 3 hour = 58.24, 50.38, 40.05, respectively) and potent anti-oxidant activity (IC50 =0.045, 0.998, 0.285 μg/ml, respectively). Reduced levels of TNF- α and increased levels of GSH were observed for the above three compounds. Descriptors for QSAR model identified by GA-PLS were WPSA1, Weta1unity, WDunity, SC3, VC5, MlogP, and WTPT3. The identified model was highly predictive, and value of root mean square error of prediction for internal (leave one out) and external validation was: 1.579, 1.325.ConclusionMolecular hybrids of phthalimide and hydrazinecarbothioamide were synthesized. Some of the compounds possessed promising anti-inflammatory and anti-oxidant activities. | Salazar P, Tapia R (2015)
Epilepsy and hippocampal neurodegeneration induced by glutamate decarboxylase inhibitors in awake rats.
Epilepsy research 116, 27-33 [PubMed:26354164]
[show Abstract]
Glutamic acid decarboxylase (GAD), the enzyme responsible for GABA synthesis, requires pyridoxal phosphate (PLP) as a cofactor. Thiosemicarbazide (TSC) and γ-glutamyl-hydrazone (PLPGH) inhibit the free PLP-dependent isoform (GAD65) activity after systemic administration, leading to epilepsy in mice and in young, but not in adult rats. However, the competitive GAD inhibitor 3-mercaptopropionic acid (MPA) induces convulsions in both immature and adult rats. In the present study we tested comparatively the epileptogenic and neurotoxic effects of PLPGH, TSC and MPA, administered by microdialysis in the hippocampus of adult awake rats. Cortical EEG and motor behavior were analyzed during the next 2h, and aspartate, glutamate and GABA were measured by HPLC in the microdialysis-collected fractions. Twenty-four hours after drug administration rats were fixed for histological analysis of the hippocampus. PLPGH or TSC did not affect the motor behavior, EEG or cellular morphology, although the extracellular concentration of GABA was decreased. In contrast, MPA produced intense wet-dog shakes, EEG epileptiform discharges, a >75% reduction of extracellular GABA levels and remarkable neurodegeneration of the CA1 region, with >80% neuronal loss. The systemic administration of the NMDA glutamate receptor antagonist MK-801 30 min before MPA did not prevent the MPA-induced epilepsy but significantly protected against its neurotoxic effect, reducing neuronal loss to <30%. We conclude that in adult awake rats, drugs acting on PLP availability have only a weak effect on GABA neurotransmission, whereas direct GAD inhibition produced by MPA induces hyperexcitation leading to epilepsy and hippocampal neurodegeneration. Because this degeneration was prevented by the blockade of NMDA receptors, we conclude that it is due to glutamate-mediated excitotoxicity consequent to disinhibition of the hippocampal excitatory circuits. | Di Costanzo L, Pique ME, Christianson DW (2007)
Crystal structure of human arginase I complexed with thiosemicarbazide reveals an unusual thiocarbonyl mu-sulfide ligand in the binuclear manganese cluster.
Journal of the American Chemical Society 129, 6388-6389 [PubMed:17469833] | Schultka R, Cech S (1990)
[Application of "mild" periodic acid oxidation to the ultrahistochemical detection of sialic acid-containing compounds in human fallopian tube epithelium].
Acta histochemica 88, 65-69 [PubMed:2162618]
[show Abstract]
2 histochemical methods were used to analyse the carbohydrates in the human oviductal epithelium, namely the periodic acid-semicarbazide-silver proteinate and the 'mild' periodic acid-thiosemicarbazide-silver proteinate technique. It was possible to detect periodate reactive substances and sialic acid-containing compounds, namely separately. The 'mild' periodic acid oxidation is a selective technique for the histochemical demonstration of the existence of unsubstituted acylneuraminic acids. The ultrahistochemical results show that, firstly, periodate reactive particles are located in the cytoplasm of ciliated and nonciliated cells. The material appears in form of beta-granula (glycogen). Secondly, we could observe fine granular reactive products in the lysosomal-like and lipid droplet-like structures. In these subjects the positive granula encircling ring-like the homogeneous matrix occur in the peripheral zone of the morphological substrate investigated. By the way, these granula situated in the periphery of organelles are alone reacting after staining with 'mild' periodic acid-thiosemicarbazide-silver proteinate; this means, the glycogen particles are unstained. Thus the findings indicate that, in the cells of the human oviductal epithelium, sialic acid-containing compounds are ultrahistochemically visualized by 'mild' periodic acid oxidation in combination with thiosemicarbazide and silver proteinate. | Nanchahal J, Tidman MJ (1985)
A study of the dermo-epidermal junction in dystrophic epidermolysis bullosa using the periodic acid-thiosemicarbazide-silver proteinate technique.
The British journal of dermatology 113, 397-404 [PubMed:2415149]
[show Abstract]
Dermo-epidermal separation in dystrophic epidermolysis bullosa (DEB) is thought to results from an abnormality of anchoring fibrils which, in normal skin, are stained selectively by the periodic acid-thiosemicarbazide-silver proteinate technique. This method was applied to non-lesional skin from four patients with generalized recessive DEB, five with localized recessive DEB and one with dominant DEB. No anchoring fibrils were present in the subjects with generalized recessive DEB, but they were morphologically normal in the case of dominant DEB and in three patients with mild localized recessive DEB. Two patients with a more severe form of localized recessive DEB possessed attenuated anchoring fibrils which lacked the normal banding of the mid-portion. The lamina densa, normally unlabelled, was consistently stained in patients with generalized recessive DEB, suggesting a biochemical abnormality of this structure. |
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