28822-58-4 Usage
Description
3-Isobutyl-1-methylxanthine (IBMX) is a non-selective, non-specific inhibitor of cAMP and cGMP phosphodiesterases. It is a white crystalline substance with a yellowish cast, known for its ability to induce melanogenesis and maintain the germinal vesicle arrest of prophase I oocytes. IBMX is also a weak adenosine receptor antagonist and does not inhibit PDE8 or PDE9.
Uses
Used in Pharmaceutical and Research Applications:
3-Isobutyl-1-methylxanthine is used as a phosphodiesterase inhibitor for increasing the intracellular concentration of cAMP, which in turn activates protein kinase A (PKA). This makes it a valuable tool in various research and pharmaceutical applications, including the study of signal transduction pathways and the development of drugs targeting these pathways.
Used in Melanogenesis Research:
IBMX is used as a positive control in melanogenesis research, as it can induce the production of melanin, the pigment responsible for skin, hair, and eye color. This application is particularly relevant in the study of skin pigmentation disorders and the development of treatments for conditions such as vitiligo.
Used in Oocyte Research:
In oocyte research, 3-Isobutyl-1-methylxanthine is used to maintain the germinal vesicle (GV) arrest of prophase I oocytes. This application is crucial for the study of oocyte maturation and development, as well as for assisted reproductive technologies.
Used in Inhibition of Phenylephrine-Induced Release of 5-Hydroxytryptamine:
IBMX is used in the inhibition of phenylephrine-induced release of 5-hydroxytryptamine from neuroendocrine epithelial cells of the airway mucosa, with an IC50 of 1.3 μM. This application is important in the study of airway inflammation and the development of treatments for respiratory disorders.
Used in Inhibition of Ion Channels:
3-Isobutyl-1-methylxanthine also inhibits ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. This makes it a useful tool in the study of ion channel function and the development of treatments for neurological and cardiovascular disorders.
Used in Anticancer Applications:
IBMX is used to inhibit the growth of carcinoma cells both in vivo and in vitro in mice. Its ability to inhibit cancer cell growth makes it a potential candidate for the development of anticancer drugs and therapies.
Biological Activity
Phosphodiesterase inhibitor (IC 50 values are 13, 18, 19, 32 and 50 μ M for PDE4, PDE3, PDE1, PDE5 and PDE2 respectively). Suppresses α -adrenoceptor-mediated 5-HT release from neuroendocrine epithelial cells (IC 50 = 1.3 μ M).
Biochem/physiol Actions
The increase in cAMP level as a result of phosphodiesterase inhibition by IBMX activates PKA, leading to decreased proliferation, increased differentiation, and induction of apoptosis. IBMX inhibits phenylephrine-induced release of 5-hydroxytryptamine from neuroendocrine epithelial cells of the airway mucosa (IC50: 1.3 μM). IBMX also serves as an adenosine receptor antagonist. IBMX has been shown to inhibit ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. IBMX induces calcium release from intracellular stores in sensory neurons.
Purification Methods
Recrystallise it from aqueous EtOH. [Beilstein 26
References
1) Beavo et al. (1970), Effects of xanthine derivatives on lipolysis and on adenosine 3′,5′-monophosphate phosphodiesterase activity; Mol. Pharmacol., 6 597
2) Tomes et al. (1993), Isobutylmethylxanthine and other classical cyclic nucleotide phosphodiesterase inhibitors affect cAMP-dependent protein kinase activity; Cell Signal., 5 615
3) Soderling et al. (2000), Regulation of cAMP and cGMP signaling: new phosphodiesterases and new functions; Curr. Opin. Cell Biol., 12 174
4) Daly et al. (1987), Adenosine receptors: development of selective agonists and antagonists; Prog. Clin. Biol. Res., 230 41
Check Digit Verification of cas no
The CAS Registry Mumber 28822-58-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,8,8,2 and 2 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 28822-58:
(7*2)+(6*8)+(5*8)+(4*2)+(3*2)+(2*5)+(1*8)=134
134 % 10 = 4
So 28822-58-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12)
28822-58-4Relevant articles and documents
Use of (Pivaloyloxy)methyl as a Protecting Group in the Synthesis of Antigenic Theophylline (1,3-Dimethylxanthine) Derivatives
Hu, Mae W.,Singh, Prithipal,Ullman, Edwin F.
, p. 1711 - 1713 (1980)
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Design and synthesis of xanthine analogues as potent and selective PDE5 inhibitors
Wang, Yuguang,Chackalamannil, Samuel,Hu, Zhiyong,Boyle, Craig D.,Lankin, Claire M.,Xia, Yan,Xu, Ruo,Asberom, Theodros,Pissarnitski, Dmitri,Stamford, Andrew W.,Greenlee, William J.,Skell, Jeffrey,Kurowski, Stanley,Vemulapalli, Subbarao,Palamanda, Jairam,Chintala, Madhu,Wu, Ping,Myers, Joyce,Wang, Peng
, p. 3149 - 3152 (2007/10/03)
We have discovered potent and selective xanthine PDE5 inhibitors. Compound 25 (PDE5 IC50=0.6 nM, PDE6/PDE5=101) demonstrated similar functional efficacy and PK profile to Sildenafil (PDE5 IC50=3.5 nM, PDE6/PDE5=7).