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(−)-Neplanocin A

Item № 10584
CAS № 72877-50-0
Purity ≥98%
product image
                (CAS 72877-50-0)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     500 µg $221.00 0.00
     1 mg $420.00 0.00
     5 mg $1,728.00 0.00

Pricing updated 2019-03-21. Prices are subject to change without notice.

Description

S-Adenosylhomocysteine (SAH) hydrolase catalyzes the reversible hydrolysis of SAH to adenosine and homocysteine. The inhibition of SAH hydrolase causes the intracellular accumulation of SAH, elevating the ratio of SAH to S-adenosylmethionine (SAM) and inhibiting SAM-dependent methyltransferase. (−)-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

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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
A crystalline solid
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

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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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 Journal of Antibiotics 34(4), 359-366 (1981).

3. De Clercq, E. Antiviral and antimetabolic activities of neplanocins Antimicrobial Agents and Chemotherapy 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 Journal of Medicinal Chemistry 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 Journal of Medicinal Chemistry 32, 1442-1446 (1989).

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