A nucleoside analog with diverse biological activities
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Tubercidin

Item No. 35834

Technical Information
Formal Name
7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
CAS Number
69-33-0
Synonyms
  • 7-Deazaadenosine
  • 7-DZA
  • NSC 56408
Molecular Formula
C11H14N4O4
Formula Weight
Purity
≥98%
A solid
DMF: Slightly solubleDMSO: 2 mg/mlPBS (pH 7.2): 0.25 mg/ml
SMILES
O[C@H]1[C@](O[C@@H]([C@H]1O)CO)([H])N2C3=NC=NC(N)=C3C=C2
InChi Code
InChI=1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1
InChi Key
HDZZVAMISRMYHH-KCGFPETGSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

    Add

    Add

    Add

    Add

    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Tubercidin is a nucleoside analog that has been found in S. tubercidicus and has diverse biological activities.1,2,3,4 It is active against S. faecalis (IC50 = 0.02 µM) and cytotoxic to P388 murine leukemia and A549 human lung adenocarcinoma cells (IC50s = 0.008 and 0.019 µg/ml, respectively).1,2 Tubercidin reduces infection of Calu-3 cells by severe acute respiratory coronavirus 2 (SARS-CoV-2; EC50 = 0.05 µM) but is toxic to A549 cells expressing human ACE2 (A549-ACE2) and Vero cells.3 Tubercidin (5 mg/kg per day), in combination with the nucleoside transport inhibitor prodrug NBMPR-P, increases survival in a mouse model of schistosomiasis but is hepato- and nephrotoxic and induces mortality when administered alone at the same dose for four days.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bloch, A., Leonard, R.J., and Nichol, C.A. On the mode of action of 7-deaza-adenosine (tubercidin). Biochim. Biophys. Acta 138(1), 10-25 (1967).

    2. Biabani, M.F., Gunasekera, S.P., Longley, R.E., et alTubercidin, a cytotoxic agent from the marine sponge Caulospongia biflabellata. Pharm. Biol. 40(4), 302-303 (2002).

    3. Schultz, D.C., Johnson, R.M., Ayyanathan, K., et alPyrimidine inhibitors synergize with nucleoside analogues to block SARS-CoV-2. Nature 604(7904), 134-140 (2022).

    4. el Kouni, M.H., Diop, D., O'Shea, P., et alPrevention of tubercidin host toxicity by nitrobenzylthioinosine 5'-monophosphate for the treatment of schistosomiasis. Antimicrob. Agents Chemother. 33(6), 824-827 (1989).