8-Chloroadenosine 3prime,5prime-Cyclic Monophosphate sodium saltA cAMP analog with high selectivity for PKA I

8-Chloroadenosine 3′,5′-Cyclic Monophosphate sodium salt (CAS 41941-56-4)

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Application: A cAMP analog with high selectivity for PKA I
CAS Number: 41941-56-4
Molecular Weight: 385.6
Molecular Formula: C10H10ClN5O6P•Na
* Refer to Certificate of Analysis for lot specific data (including water content).
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8-Chloroadenosine 3',5'-Cyclic Monophosphate sodium salt is a site-selective cAMP analog that inhibits various cancer cell lines such as HT29 colorectal cells and ZR-75-1 breast carcinoma, which is due to selective activation of PKA (protein kinase A) isoenzymes. Studies show that 8-Chloroadenosine 3',5'-Cyclic Monophosphate down-regulates the RI α subunit and up-regulates the RII β subunit of cAMP-dependent protein kinases leading to type II holoenzyme-dependent growth inhibition of caner cells such as HL-60. In addition, it is suggested that 8-Chloroadenosine 3',5'-Cyclic Monophosphate can possibly stimulate the antitumor effect of taxanes at micromolar concentrations. Further studies show that mdr-1 mRNA expression is reduced greatly in the presence of 8-Chloroadenosine 3',5'-Cyclic Monophosphate.


References

1. Rohlff, C., et al. 1993. J. Biol. Chem. 268: 5774-5782. PMID: 8449943
2. Ramage, A.D., et al. 1995. Eur. J. Cancer. 31A: 969-973. PMID: 7646930
3. Scala, S., et al. 1995. J. Clin. Invest. 96: 1026-1034. PMID: 7543490
4. Noguchi, K., et al. 1998. Eur. J. Cancer. 34: 1260-1267. PMID: 9849489
5. McDaid, H.M. and Johnston, P.G. 1999. Clin. Cancer Res. 5: 215-220. PMID: 9918222

Physical State :
Solid
Solubility :
Soluble in water (≥ 200 mM), methanol (≥ 200 mM), DMSO (≥ 200 mM), DMF (≥ 200 mM), and 100% ethanol (13 mM).
Storage :
Store at -20° C
Refractive Index :
n20D 2.01 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
23686913
MDL Number :
MFCD01076560
SMILES :
C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C4=C(C(=NC=N4)N)N=C3Cl)O)OP(=O)(O1)[O-].[Na+]

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Certificate of Analysis

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