Irreversible SAH hydrolase inhibitor
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(−)-Neplanocin A

Item No. 10584

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5R-(6-amino-9H-purin-9-yl)-3-(hydroxymethyl)-3-cyclopentene-1S,2R-diol
CAS Number
72877-50-0
Molecular Formula
C11H13N5O3
Formula Weight
263.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.2 mg/mlDMSO: 3 mg/mlPBS (pH 7.2): 0.3 mg/ml
λmax
262 nm
SMILES
OCC1=C[C@@H](N2C=NC3=C2N=CN=C3N)[C@H](O)[C@@H]1O
InChi Code
InChI=1S/C11H13N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h1,3-4,6,8-9,17-19H,2H2,(H2,12,13,14)/t6-,8-,9+/m1/s1
InChi Key
XUGWUUDOWNZAGW-VDAHYXPESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $297

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    1 mg

    $561

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    5 mg

    $2,306

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    Cayman Chemical
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    Product Description

    (−)-Neplanocin A potently and irreversibly inactivates SAH hydrolase (Ki = 8.39 nM).1 It has antitumor activity against mouse leukemia L1210 cells and broad-spectrum antiviral activity.2,3,4,1 Neplanocin A is more potent against vesicular stomatitis than the reversible SAH hydrolase inhibitor 3-deazaneplanocin (ID50 = 0.07 and 0.3 μg/ml, respectively).3,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Borchardt, R.T., Keller, B.T., and Patel-Thombre, U. Neplanocin A. A potent inhibitor of S-adenosylhomocysteine hydrolase and of vaccinia virus multiplication in mouse L929 cells. The Journal of Biological Chemisty 259(7), 4353-4358 (1984).

    2. Yaginuma, S., Muto, N., Tsujino, M., et al. Studies on neplanocin A, new antitumor antibiotic. I. Producing organism, isolation and characterization. J. Antibiot. (Tokyo) 34(4), 359-366 (1981).

    3. De Clercq, E. Antiviral and antimetabolic activities of neplanocins. Antimicrob. Agents Chemother. 28(1), 84-89 (1985).

    4. Borcherding, D.R., Narayanan, S., Hasobe, M., et al. Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 11. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase. J. Med. Chem. 31, 1729-1738 (1988).

    5. Tseng, C.K.H., Marquez, V.E., Fuller, R.W., et al. Synthesis of 3-deazaneplanocin A, a powerful inhibitor of S-adenosylhomocysteine hydrolase with potent and selective in vitro and in vivo antiviral activities. J. Med. Chem. 32(7), 1442-1446 (1989).