2004-03-7 Usage
Description
6-Methylpurine (MeP) is a toxic adenine analog characterized by a methyl substituent at the 6th position on the purine ring. It is a light yellow powder and is known for its inhibitory effects on enzymes that bind adenosyl moieties and can become phosphorylated, leading to the inhibition of RNA and protein synthesis.
Uses
Used in Pharmaceutical Industry:
6-Methylpurine is used as a bisubstrate inhibitor for enzymes that bind adenosyl moieties, making it a valuable compound in the development of pharmaceuticals targeting specific enzyme pathways. Its ability to inhibit RNA and protein synthesis at high phosphorylation levels also contributes to its potential applications in drug discovery and therapeutics.
Used in Biochemical Research:
6-Methylpurine serves as a useful tool in biochemical research, particularly in studying the mechanisms of enzyme inhibition and the role of adenosyl moieties in various biological processes. Its properties as a toxic adenine analog allow researchers to investigate the effects of such modifications on enzyme function and cellular metabolism.
Used in Drug Development:
Due to its inhibitory effects on RNA and protein synthesis, 6-Methylpurine can be utilized in the development of drugs targeting specific diseases and conditions. Its potential as a bisubstrate inhibitor makes it a candidate for the creation of novel therapeutic agents that can modulate enzyme activity and impact cellular processes.
Synthesis Reference(s)
Journal of the American Chemical Society, 95, p. 6407, 1973 DOI: 10.1021/ja00800a042
Check Digit Verification of cas no
The CAS Registry Mumber 2004-03-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,0 and 4 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2004-03:
(6*2)+(5*0)+(4*0)+(3*4)+(2*0)+(1*3)=27
27 % 10 = 7
So 2004-03-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H6N4/c1-4-5-6(9-2-7-4)10-3-8-5/h2-3H,1H3,(H,7,8,9,10)
2004-03-7Relevant articles and documents
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Lettre et al.
, p. 224 (1963)
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Improved synthesis of β-D-6-methylpurine riboside and antitumor effects of the β-D- and α-D-anomers
Marasco Jr., Canio J.,Pera, Paula J.,Spiess, Arthur J.,Bernacki, Ralph,Sufrin, Janice R.
, p. 1015 - 1020 (2007/10/03)
6-Methylpurine-β-D-riboside (β-D-MPR) has been synthesized by coupling 6-methylpurine and 1-O-acety1-2,3,5-tri-O-benzoyl-D-ribose using conditions that produce the β-D-anomer exclusively. The in vitro antitumor effects of β-D-MPR and 6-methyl-purine-α-D-riboside (α-D-MPR) in five human tumor cell lines showed that β-D-MPR was highly active (IC50 values ranging from 6 to 34 nM). a-D-MPR, although less active than β-D-MPR, also exhibited significant antitumor effects (IC50 values ranging from 1.47 to 4.83 μM).
Gene therapy of cancer: activation of nucleoside prodrugs with e. colipurine nucleoside phosphorylase
Secrist III, John A.
, p. 745 - 757 (2007/10/03)
During the last few years, many gene therapy strategies have been developed for various disease targets. The development of anticancer gene therapy strategies to selectively generate cytotoxic nucleoside or nucleotide analogs is an attractive goal. One such approach involves the delivery of herpes simplex virus thymidine kinase followed by the acyclic nucleoside analog ganciclovir. We have developed another gene therapy methodology for the treatment of cancer that has several significant attributes. Specifically, our approach involves the delivery of E. coli purine nucleoside phosphorylase, followed by treatment with a relatively non-toxic nucleoside prodrug that is cleaved by the enzyme to a toxic compound. .This presentation describes the concept, details our search for suitable prodrugs, and summarizes the current biological data. Copyright
