Synonym
Carbocyclic inosine; NSC103529; NSC-103529; NSC 103529
IUPAC/Chemical Name
6H-Purin-6-one, 9-(2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl)-1,9-dihydro-, (1S-(1alpha,2beta,3beta,4alpha))-
InChi Key
WJJOLBUDGLOYDT-UXXCCHNYSA-N
InChi Code
InChI=1S/C11H14N4O4/c16-2-5-1-6(9(18)8(5)17)15-4-14-7-10(15)12-3-13-11(7)19/h3-6,8-9,16-18H,1-2H2,(H,12,13,19)/t5-,6-,8-,9+/m0/s1
SMILES Code
O=C1NC=NC2=C1N=CN2[C@@H]3[C@@H](O)[C@@H](O)[C@H](CO)C3
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
>3 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
266.26
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: Hiraoka O, Satake H, Iguchi S, Matsuda A, Ueda T, Wataya Y. Carbocyclic inosine as a potent anti-leishmanial agent: the metabolism and selective cytotoxic effects of carbocyclic inosine in promastigotes of Leishmania tropica and Leishmania donovani. Biochem Biophys Res Commun. 1986 Feb 13;134(3):1114-21. doi: 10.1016/0006-291x(86)90366-9. PMID: 3753868.
2: Wataya Y, Satake H, Hiraoka O, Aji T, Morishige K, Kimura JY, Ishii A, Matsuda A, Ueda T, Fukukawa K. Anti-parasite activity of nucleoside analogues: the metabolism of carbocyclic inosine in promastigotes of Leishmania tropica and Leishmania donovani and its activity against amastigotes of Leishmania donovani in vitro. Nucleic Acids Symp Ser. 1986;(17):149-51. PMID: 3562260.
3: Bennett LL Jr, Brockman RW, Rose LM, Allan PW, Shaddix SC, Shealy YF, Clayton JD. Inhibition of utilization of hypoxanthine and guanine in cells treated with the carbocyclic analog of adenosine. Phosphates of carbocyclic nucleoside analogs as inhibitors of hypoxanthine (guanine) phosphoribosyltransferase. Mol Pharmacol. 1985 Jun;27(6):666-75. PMID: 2987661.
4: Morishige K, Aji T, Ishii A, Yasuda T, Wataya Y. Leishmania donovani: pilot study for evaluation of therapeutic effects of inosine analogs against amastigotes in vitro and in vivo. Exp Parasitol. 1995 Jun;80(4):665-71. doi: 10.1006/expr.1995.1082. PMID: 7758547.
5: Secrist JA 3rd, Montgomery JA, Shealy YF, O'Dell CA, Clayton SJ. Resolution of racemic carbocyclic analogues of purine nucleosides through the action of adenosine deaminase. Antiviral activity of the carbocyclic 2'-deoxyguanosine enantiomers. J Med Chem. 1987 Apr;30(4):746-9. doi: 10.1021/jm00387a032. PMID: 3031295.
6: Isaac BG, Ayer SW, Letendre LJ, Stonard RJ. Herbicidal nucleosides from microbial sources. J Antibiot (Tokyo). 1991 Jul;44(7):729-32. doi: 10.7164/antibiotics.44.729. PMID: 1880062.
7: Chun BK, Song GY, Chu CK. Stereocontrolled syntheses of carbocyclic C-nucleosides and related compounds. J Org Chem. 2001 Jul 13;66(14):4852-8. doi: 10.1021/jo010224f. PMID: 11442416.
