Synonym
Thioinosinic-acid; Thio-IMP; ThioIMP; Thio IMP; NSC 520722; NSC520722; NSC-520722;
IUPAC/Chemical Name
((2R,3S,4R,5R)-3,4-dihydroxy-5-(6-mercapto-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate
InChi Key
ZKRFOXLVOKTUTA-KQYNXXCUSA-N
InChi Code
InChI=1S/C10H13N4O7PS/c15-6-4(1-20-22(17,18)19)21-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)23/h2-4,6-7,10,15-16H,1H2,(H,11,12,23)(H2,17,18,19)/t4-,6-,7-,10-/m1/s1
SMILES Code
O[C@H]1[C@H]([C@H](n(cn2)c3c2c(S)ncn3)O[C@@H]1COP(O)(O)=O)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
364.27
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Aboul-Fadl T, Agrawal VK, Buckheit RW Jr, Broom AD. An unusual "senseless" 2',5'-oligoribonucleotide with potent anti-HIV activity. Nucleosides Nucleotides Nucleic Acids. 2004;23(3):545-54. doi: 10.1081/NCN-120030713. PMID: 15113022.
2: Hyde RM, Broom AD, Buckheit RW Jr. Antiviral amphipathic oligo- and polyribonucleotides: analogue development and biological studies. J Med Chem. 2003 May 8;46(10):1878-85. doi: 10.1021/jm0203276. PMID: 12723951.
3: Buckheit RW Jr, Lackman-Smith C, Snow MJ, Halliday SM, White EL, Ross LJ, Agrawal VK, Broom AD. PMTI, a broadly active unusual single-stranded polyribonucleotide, inhibits human immunodeficiency virus replication by multiple mechanisms. Antivir Chem Chemother. 1999 Jan;10(1):23-32. doi: 10.1177/095632029901000103. PMID: 10079876.
4: Lennard L, Hale JP, Lilleyman JS. Red blood cell hypoxanthine phosphoribosyltransferase activity measured using 6-mercaptopurine as a substrate: a population study in children with acute lymphoblastic leukaemia. Br J Clin Pharmacol. 1993 Oct;36(4):277-84. doi: 10.1111/j.1365-2125.1993.tb00365.x. PMID: 12959304; PMCID: PMC1364679.
5: Lennard L, Singleton HJ. High-performance liquid chromatographic assay of the methyl and nucleotide metabolites of 6-mercaptopurine: quantitation of red blood cell 6-thioguanine nucleotide, 6-thioinosinic acid and 6-methylmercaptopurine metabolites in a single sample. J Chromatogr. 1992 Nov 27;583(1):83-90. doi: 10.1016/0378-4347(92)80347-s. PMID: 1484095.
6: Ha T, Morgan SL, Vaughn WH, Eto I, Baggott JE. Detection of inhibition of 5-aminoimidazole-4-carboxamide ribotide transformylase by thioinosinic acid and azathioprine by a new colorimetric assay. Biochem J. 1990 Dec 1;272(2):339-42. doi: 10.1042/bj2720339. PMID: 2268263; PMCID: PMC1149705.
7: Bishop GA, Hall BM. Effects of immunosuppressive drugs on functions of activated T lymphocytes. Cyclosporine inhibition of gamma interferon production in the presence of interleukin. Transplantation. 1988 May;45(5):967-72. doi: 10.1097/00007890-198805000-00026. PMID: 3130699.
8: Lennard L. Assay of 6-thioinosinic acid and 6-thioguanine nucleotides, active metabolites of 6-mercaptopurine, in human red blood cells. J Chromatogr. 1987 Dec 25;423:169-78. doi: 10.1016/0378-4347(87)80340-7. PMID: 3443647.
9: Tomasovic SP, Higashikubo R, Cohen AM, Broom AD. Comparative kinetics of poly(6-thioinosinic acid) and 6-mercaptopurine treated L1210 cells. Cytometry. 1982 Jul;3(1):48-54. doi: 10.1002/cyto.990030111. PMID: 6889485.
