A guanosine analog with diverse biological activities
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Crotonoside

Item No. 28219

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3-dihydro-2-oxo-adenosine
CAS Number
1818-71-9
Synonyms
  • 2-Hydroxyadenosine
  • Isoguanine riboside
  • Isoguanosine
  • NSC 12161
Molecular Formula
C10H13N5O5
Formula Weight
283.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
λmax
249, 300 nm
SMILES
OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=NC(C2=N3)=C(N)NC3=O)O1
InChi Code
InChI=1S/C10H13N5O5/c11-7-4-8(14-10(19)13-7)15(2-12-4)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1
InChi Key
MIKUYHXYGGJMLM-UUOKFMHZSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $72

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    10 mg

    $101

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    25 mg

    $233

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    50 mg

    $394

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    Cayman Chemical
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    Product Description

    Crotonoside is a guanosine analog originally isolated from C. tiglium that has diverse biological activities.1,2,3 It is cytotoxic to P338, L5178Y, Sp2/O, HL-60, and Raji cells in vitro (EC50s = 21, 370, 120, 70, and 400 μM, respectively).1 Crotonoside (48 mg/kg per day for 12 days) reduces tumor growth by 60% in S-180 sarcoma and Ehrlich carcinoma solid tumor mouse models. It has been used as an internal standard for the semi-quantitative analysis and comparison of RNA metabolites in MCF-7 breast cancer cells and MCF-10A mammary epithelial cells.4 Crotonoside decreases the force and rate of contraction in isolated guinea pig atria (EC50s = 2.8 and 17.8 μM, respectively) and reduces carotid blood pressure in anesthetized cats when administered intravenously at a dose of 0.5 μmol/kg.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kim, J.H., Lee, S.J., Han, Y.B., et al. Isolation of isoguanosine from Croton tiglium and its antitumor activity. Arch. Pharm. Res. 17(2), 115-118 (1994).

    2. Fuhrman, F.A., and Fuhrman, G.J. Effects of some naturally-occurring purine ribosides on purinergic receptors in cardiac and smooth muscle. Comp. Biochem. Physiol. C 72(2), 203-210 (1982).

    3. Ewing, P.L., Schlenk, F., and Emerson, G.A. Comparison of smooth muscle effects of crotonoside (isoguanosine) and adenosine. J. Pharmacol. Exp. Ther. 97(3), 379-383 (1949).

    4. Bullinger, D., Neubauer, H., Fehm, T., et al. Metabolic signature of breast cancer cell line MCF-7: Profiling of modified nucleosides via LC-IT MS coupling. BMC Biochem. 8, 25 (2007).