6-THIOGUANOSINE Chemical Properties

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

pka

13.21±0.70(Predicted)

form 

Solid

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)

Safety Information

Safety Statements 

24/25

RTECS 

UP0200000

HS Code 

29349990

Toxicity

LD50 intraperitoneal in mouse: 156mg/kg

6-THIOGUANOSINE Usage And Synthesis

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

6-THIOGUANOSINE(85-31-4)Related Product Information

• 6-THIOGUANOSINE
• 6-Thioguanosine hydrate
• 6-MERCAPTOPURINE RIBOSIDE
• Purine
• 2-Aminopurine
• Guanine
• 2-Aminopurine riboside
• 6-thioguanosine 5'-triphosphate
• 1-METHYL-6-THIOGUANOSINE
• 8-(2-AMINOETHYL) THIOGUANOSINE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, SP-ISOMER, IMMOBILIZED ON AGAROSE GEL
• sulfinosine
• 2-AMINO-6-MERCAPTO-9-(2',3',5'-TRI-O-ACETYL-B-RIBOFURANOSYL)PURINE
• 2-AMINO-6-CHLORO-[(4-METHYLPHENYL)THIO]-9-(2',3',5'-TRI-O-ACETYL-BETA-D-RIBOFURANOSYL)PURINE
• 7-METHYL-6-THIOGUANOSINE
• S-(2-HYDROXY-5-NITROBENZYL)-6-THIOGUANOSINE
• S-(4-NITROBENZYL)-6-THIOGUANOSINE (NBTG) POTENT ADENOSINE TRAN,S-(4-NITROBENZYL)-6-THIOGUANOSINE,S-(P-NITROBENZYL)-6-THIOGUANOSINE
• 8-(2-AMINOETHYL) THIOGUANOSINE-3',5'-CYCLIC MONOPHOSPHATE, IMMOBILIZED ON AGAROSE GEL
• 2'-deoxy-6-thioguanosine 5'-triphosphate