| Identification | More | [Name]
6-THIOGUANOSINE | [CAS]
85-31-4 | [Synonyms]
2-AMINO-6-MERCAPTOPURINE RIBOSIDE
6-MERCAPTO-2-AMINOPURINE RIBOSIDE
6-MERCAPTOGUANOSINE
6-THIOGUANOSINE
2-amino-1,9-dihydro-9-beta-d-ribofuranosyl-6h-purine-6-thion
2-amino-6-mercapto-9(beta-d-ribofuranosyl)purine
2-amino-6-mercaptopurineribonucleoside
2-amino-9-(beta-d-ribofuranosyl)purine-6-thiol
2-amino-9-beta-d-ribofuranosyl-9h-purine-6-thio
2-amino-9-beta-d-ribofuranosyl-9h-purine-6-thiol
6-thiodeoxyguanosine
6-thioguanineribonucleoside
6-thioguanineriboside
6-thio-guanosin
nsc-29422
ribosylthioguanine
sk18615
sri759
thioguanineriboside
thioguanosine | [EINECS(EC#)]
201-597-2 | [Molecular Formula]
C10H13N5O4S | [MDL Number]
MFCD00005736 | [Molecular Weight]
299.31 | [MOL File]
85-31-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Tan Powder | [Melting point ]
230-231°C | [Boiling point ]
756.9±70.0 °C(Predicted) | [density ]
2.18 | [refractive index ]
1.6460 (estimate) | [storage temp. ]
Keep in dark place,Sealed in dry,Store in freezer, under -20°C | [solubility ]
DMF: 2 mg/ml
DMSO: 5 mg/ml | [form ]
Solid | [pka]
13.21±0.70(Predicted) | [color ]
Off-white to light yellow | [InChI]
InChI=1S/C10H13N5O4S/c11-10-13-7-4(8(20)14-10)12-2-15(7)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,20)/t3-,5-,6-,9-/m1/s1 | [InChIKey]
OTDJAMXESTUWLO-UUOKFMHZSA-N | [SMILES]
OC[C@H]1O[C@@H](N2C3=C(C(NC(=N3)N)=S)N=C2)[C@H](O)[C@@H]1O | [CAS DataBase Reference]
85-31-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Tan Powder | [Uses]
antineoplastic | [Definition]
ChEBI: 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-oxolanyl]-3H-purine-6-thione is a purine nucleoside. | [Purification Methods]
Thioguanosine is crystallised (as hemihydrate) from hot H2O (charcoal) and cooled slowly to give tapered prisms. It also crystallises by dissolving in dilute NH3 and acidifying with acetic acid, and then recrystallising from H2O. UV: (pH 4-6) max at 257nm ( 8,820) and 342nm ( 24,800), and (pH 10.4-12.0) max at 252nm ( 14,700) and 319.5nm ( 21,000). [Fox et al. J Am Chem Soc 80 1667 1958, Beilstein 26 III/IV 3927.] | [References]
[1] J W WEISS H C P. Inhibition of ribosomal RNA maturation in Novikoff hepatoma cells by toyocamycin, tubercidin, and 6-thioguanosine.[J]. Cancer research, 1974, 34 3: 581-587.
[2] MONIQUE AKOACHERE. Identification of an in vivo inhibitor of Bacillus anthracis spore germination.[J]. The Journal of Biological Chemistry, 2007, 282 16: 12112-12118. DOI: 10.1074/jbc.m611432200
[3] D L HILL R F P. Use of Escherichia coli mutants to evaluate purines, purine nucleosides, and analogues.[J]. Antimicrobial Agents and Chemotherapy, 1973, 4 2: 125-132. DOI: 10.1128/aac.4.2.125
[4] N T VETHE S B S Bremer. IMP dehydrogenase basal activity in MOLT-4 human leukaemia cells is altered by mycophenolic acid and 6-thioguanosine.[J]. Scandinavian Journal of Clinical & Laboratory Investigation, 2008, 68 4: 277-285. DOI: 10.1080/00365510701724871 |
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