SangivamycinA cytotoxic purine nucleoside

Sangivamycin (CAS 18417-89-5)

Sangivamycin | CAS 18417-89-5 is rated 5.0 out of 5 by 1.
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Synonym: 7-Deaza-7-carbamoyladenosine
Application: A cytotoxic purine nucleoside
CAS Number: 18417-89-5
Molecular Weight: 309.3
Molecular Formula: C12H15N5O5
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* Refer to Certificate of Analysis for lot specific data (including water content).
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Sangivamycin is a cytotoxic purine nucleoside active against human cytomegalovirus (HCMV). Sangivamycin is also a selective and potent PKC (protein kinase C) inhibitor (IC50 = 10μM). The inhibition is competitive with respect to ATP and non-competitive with respect to histone and lipid cofactors. The phosphorylation of histone H1 protein is a mechanism by which Sangivamycin prevents the cell growth and acts as cytotoxic agent against a variety of human cancers.


References

1. Turk, S R., et al., 1987. Pyrrolo[2,3-d]pyrimidine nucleosides as inhibitors of human cytomegalovirus. Antimicrobial agents and chemotherapy. 31(4): 544-50. PMID: 3037998
2. Loomis, C R., et al., 1988. Sangivamycin, a nucleoside analogue, is a potent inhibitor of protein kinase C. The Journal of biological chemistry. 263(4): 1682-92. PMID: 3338987
3. Greene, N M., et al., 1995. Kinetics and localization of the phosphorylation of rhodopsin by protein kinase C. The Journal of biological chemistry. 270(12): 6710-7. PMID: 7896814

Physical State :
Solid
Solubility :
Soluble in cold water, and 0.1 M KOH.
Storage :
Store at 4° C
Boiling Point :
880.6° C at 760 mmHg (Predicted)
Refractive Index :
n20D 1.89 (Predicted)
IC50 :
HFF: IC50 = 10 nM (human); L1210: IC50 = 3 nM (mouse); Human herpesvirus 5: IC50 = 30 nM; KB: IC50 = 80 nM (human); PKC: IC50 = 10 µM
Ki Data :
GRK 1: Ki= 180 nM (human); GRK 2: Ki= 67 µM (human)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
UY9355000
PubChem CID :
14978
MDL Number :
MFCD00214391
SMILES :
O.NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(N)=NC=N2

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Certificate of Analysis

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Rated 5 out of 5 by from Greene et al Greene et al. (PubMed ID 7896814) found that sangivamycin inhibited the phosphorylation of rhodopsin via protein kinase C inactivation. -SCBT Publication Review
Date published: 2015-06-24
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