MedKoo Cat#: 581616 | Name: 7-Deazainosine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

7-Deazainosine is a biochemical. 7-deazainosine can be synthesized from 7-deazaadenosine (tubercidin) in one step. Differences were found between the toxicologic effects of tubercidin (7-deazaadenosine) (I) and those of 7-deazainosine (II) which were consistent with the idea that II requires conversion into anabolites of I in order to exert biol. effects. In rodents treated parenterally, and in dogs treated orally, I was 6-to 20-fold more toxic than II. Severe local reactions occurred only in rats treated with I. In view of the lack of local and renal toxicity, 7-Deazainosine may offer therapeutic advantages over I provided that hepatotoxicity is not a limiting factor.

Chemical Structure

7-Deazainosine
7-Deazainosine
CAS#2862-16-0

Theoretical Analysis

MedKoo Cat#: 581616

Name: 7-Deazainosine

CAS#: 2862-16-0

Chemical Formula: C11H13N3O5

Exact Mass: 267.0855

Molecular Weight: 267.24

Elemental Analysis: C, 49.44; H, 4.90; N, 15.72; O, 29.93

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
Antibiotics XK-101-2; 7-Deazainosine ;
Synonym
7-Deazainosine; Deaminohydroxytubercindin; 7 Deazainosine; 7Deazainosine.
IUPAC/Chemical Name
4H-Pyrrolo(2,3-d)pyrimidin-4-one, 1,7-dihydro-7-beta-D-ribofuranosyl- (8CI)(9CI)
InChi Key
DPRSKJHWKNHBOW-KCGFPETGSA-N
InChi Code
InChI=1S/C11H13N3O5/c15-3-6-7(16)8(17)11(19-6)14-2-1-5-9(14)12-4-13-10(5)18/h1-2,4,6-8,11,15-17H,3H2,(H,12,13,18)/t6-,7-,8-,11-/m1/s1
SMILES Code
O=C1C2=C(N([C@H]3[C@@H]([C@@H]([C@@H](CO)O3)O)O)C=C2)NC=N1
Appearance
Solid powder
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 267.24 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.

Recalculate based on batch purity %
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: Leonard P, Ingale SA, Ding P, Ming X, Seela F. Studies on the glycosylation of pyrrolo[2,3-d] pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose: the formation of regioisomers during toyocamycin and 7-deazainosine syntheses. Nucleosides Nucleotides Nucleic Acids. 2009 May;28(5):678-94. doi: 10.1080/15257770903091953. PubMed PMID: 20183609. 2: Al Safarjalani ON, Rais RH, Kim YA, Chu CK, Naguib FN, el Kouni MH. 7-Deaza-6-benzylthioinosine analogues as subversive substrate of Toxoplasma gondii adenosine kinase: activities and selective toxicities. Biochem Pharmacol. 2008 Oct 15;76(8):958-66. doi: 10.1016/j.bcp.2008.07.035. Epub 2008 Aug 7. PubMed PMID: 18755159; PubMed Central PMCID: PMC2581922. 3: Ciliberti N, Durini E, Manfredini S, Vertuani S. 7-deazainosine derivatives: synthesis and characterization of 7- and 7,8-substituted pyrrolo [2,3-d]pyrimidine ribonucleosides. Nucleosides Nucleotides Nucleic Acids. 2008 May;27(5):525-33. doi: 10.1080/15257770802089009. PubMed PMID: 18569790. 4: Moreau C, Wagner GK, Weber K, Guse AH, Potter BV. Structural determinants for N1/N7 cyclization of nicotinamide hypoxanthine 5'-dinucleotide (NHD+) derivatives by ADP-ribosyl cyclase from aplysia californica: Ca2+-mobilizing activity of 8-substituted cyclic inosine 5'-diphosphoribose analogues in T-lymphocytes. J Med Chem. 2006 Aug 24;49(17):5162-76. PubMed PMID: 16913705. 5: Mao C, Cook WJ, Zhou M, Federov AA, Almo SC, Ealick SE. Calf spleen purine nucleoside phosphorylase complexed with substrates and substrate analogues. Biochemistry. 1998 May 19;37(20):7135-46. PubMed PMID: 9585525. 6: Hirota K, Monguchi Y, Sako M, Kitade Y. Substitution effect of purine nucleosides on diisobutylaluminum hybride reduction. Nucleic Acids Symp Ser. 1995;(34):15-6. PubMed PMID: 8841529. 7: Kim J, Pordesimo EO, Toth SI, Schmitz FJ, Van Altena I. Pantherinine, a cytotoxic aromatic alkaloid, and 7-deazainosine from the ascidian Aplidium pantherinum. J Nat Prod. 1993 Oct;56(10):1813-6. PubMed PMID: 8277319. 8: Kim SH, Okazaki K, Okabe T, Nishimura T, Kondo T, Tanaka N, Suzuki H. Structure-activity relationships of cadeguomycin analogs. J Antibiot (Tokyo). 1991 Jun;44(6):659-64. PubMed PMID: 2071491. 9: Bzowska A, Kulikowska E, Shugar D. Properties of purine nucleoside phosphorylase (PNP) of mammalian and bacterial origin. Z Naturforsch C. 1990 Jan-Feb;45(1-2):59-70. PubMed PMID: 2109978. 10: Wood SG, Ubasawa A, Martin D, Jiricny J. Guanine and adenine analogues as tools in the investigation of the mechanisms of mismatch repair in E. coli. Nucleic Acids Res. 1986 Aug 26;14(16):6591-602. PubMed PMID: 3529037; PubMed Central PMCID: PMC311666. 11: Jiricny J, Wood SG, Martin D, Ubasawa A. Oligonucleotide duplexes containing inosine, 7-deazainosine, tubercidin, nebularine and 7-deazanebularine as substrates for restriction endonucleases HindII, SalI and TaqI. Nucleic Acids Res. 1986 Aug 26;14(16):6579-90. PubMed PMID: 3018674; PubMed Central PMCID: PMC311665. 12: Dixon L, Jiricny J, Hohn T. Oligonucleotide directed mutagenesis of cauliflower mosaic virus DNA using a repair-resistant nucleoside analogue: identification of an agnogene initiation codon. Gene. 1986;41(2-3):225-31. PubMed PMID: 3519365. 13: Rainey P, Nolan PA, Townsend LB, Robins RK, Fox JJ, Secrist Iii JA, Santi DV. Inosine analogs as anti-leishmanial agents. Pharm Res. 1985 Sep;2(5):217-20. doi: 10.1023/A:1016360710842. PubMed PMID: 24272839. 14: LaFon SW, Nelson DJ, Berens RL, Marr JJ. Inosine analogs. Their metabolism in mouse L cells and in Leishmania donovani. J Biol Chem. 1985 Aug 15;260(17):9660-5. PubMed PMID: 4019491. 15: Seela F, Ott J, Franzen D. Poly(2-methylthio-7-deazainosinic acid)--hydrophobic stabilization of polynucleotide secondary structure by the 2-methylthio group. Nucleic Acids Res. 1983 Sep 10;11(17):6107-20. PubMed PMID: 6889137; PubMed Central PMCID: PMC326338. 16: Berman JD, Lee LS, Robins RK, Revankar GR. Activity of purine analogs against Leishmania tropica within human macrophages in vitro. Antimicrob Agents Chemother. 1983 Aug;24(2):233-6. PubMed PMID: 6638989; PubMed Central PMCID: PMC185143. 17: Miles DL, Miles DW, Eyring H. Interferon induction: a conformational hypothesis. Proc Natl Acad Sci U S A. 1979 Mar;76(3):1018-21. PubMed PMID: 286290; PubMed Central PMCID: PMC383178. 18: Maskos K. Interaction of metal ions with nucleic acids. Interaction of copper(II) with inosine and its derivatives. Acta Biochim Pol. 1978;25(2):113-27. PubMed PMID: 726790. 19: Mihich E, Simpson CL, Mulhern AI. Comparative study of the toxicologic effects of 7-deazaadenosine (tubercidin) and 7-deazainosine. Cancer Res. 1969 Jan;29(1):116-23. PubMed PMID: 5763972. 20: Bloch A, Mihich E, Leonard RJ, Nichol CA. Studies on the biologic activity and mode of action of 7-deazainosine. Cancer Res. 1969 Jan;29(1):110-5. PubMed PMID: 4974300.