イソブチルメチルキサンチン
- 関
- IBMX
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/05/09 23:07:08」(JST)
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| IBMX |
|
IUPAC name
1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
|
Other names
3-Isobutyl-1-methylxanthine
|
| Identifiers |
| CAS number |
28822-58-4 Y |
| PubChem |
3758 |
| ChemSpider |
3627 Y |
| UNII |
TBT296U68M Y |
| DrugBank |
DB07954 |
| KEGG |
C13708 Y |
| ChEBI |
CHEBI:34795 Y |
| ChEMBL |
CHEMBL275084 Y |
| IUPHAR ligand |
388 |
| Jmol-3D images |
Image 1 |
-
O=C2N(c1ncnc1C(=O)N2C)CC(C)C
|
-
InChI=1S/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) Y
Key: APIXJSLKIYYUKG-UHFFFAOYSA-N Y
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)
Key: APIXJSLKIYYUKG-UHFFFAOYAL
|
| Properties |
| Molecular formula |
C10H14N4O2 |
| Molar mass |
222.3 g/mol |
| Appearance |
White solid |
| Melting point |
199-201 °C |
| Solubility |
Soluble in ethanol, DMSO, and methanol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| Y (verify) (what is: Y/N?) |
| Infobox references |
|
|
IBMX, 3-isobutyl-1-methylxanthine, like other methylated xanthine derivatives, is both a
- competitive nonselective phosphodiesterase inhibitor [1] which raises intracellular cAMP, activates PKA, inhibits TNF-alpha [2][3] and leukotriene [4] synthesis, and reduces inflammation and innate immunity [4] and
- nonselective adenosine receptor antagonist.[5]
As a phosphodiesterase inhibitor, IBMX has IC50 = 2-50 μM [6] and does not inhibit PDE8 or PDE9.[7]
References
- ^ Essayan DM. (2001). "Cyclic nucleotide phosphodiesterases.". J Allergy Clin Immunol. 108 (5): 671–80. doi:10.1067/mai.2001.119555. PMID 11692087.
- ^ Deree J, Martins JO, Melbostad H, Loomis WH, Coimbra R. (2008). "Insights into the regulation of TNF-alpha production in human mononuclear cells: the effects of non-specific phosphodiesterase inhibition.". Clinics (Sao Paulo). 63 (3): 321–8. doi:10.1590/S1807-59322008000300006. PMC 2664230. PMID 18568240.
- ^ Marques LJ, Zheng L, Poulakis N, Guzman J, Costabel U (February 1999). "Pentoxifylline inhibits TNF-alpha production from human alveolar macrophages". Am. J. Respir. Crit. Care Med. 159 (2): 508–11. doi:10.1164/ajrccm.159.2.9804085. PMID 9927365.
- ^ a b Peters-Golden M, Canetti C, Mancuso P, Coffey MJ. (2005). "Leukotrienes: underappreciated mediators of innate immune responses.". J Immunol. 174 (2): 589–94. PMID 15634873.
- ^ Daly JW, Jacobson KA, Ukena D. (1987). "Adenosine receptors: development of selective agonists and antagonists.". Prog Clin Biol Res. 230 (1): 41–63. PMID 3588607.
- ^ Mol. Pharmacol 6: 597. 1970.
- ^ Soderling and Beavo Current Opinion in Cell Biol. 2000 12 174
|
Phosphodiesterase inhibitors
|
|
| PDE1 |
- MMPX
- SCH-51866
- Vinpocetine
|
|
| PDE2 |
|
|
| PDE3 |
- Amrinone
- Anagrelide
- Bucladesine
- Cilostamide
- Cilostazol
- Enoximone
- KMUP-1
- Milrinone
- Quazinone
- RPL-554
- Siguazodan
- Trequinsin
- Vesnarinone
- Zardaverine
|
|
| PDE4 |
- Arofylline
- Atizoram
- Cilomilast
- Denbutylline
- Drotaverine
- Etazolate
- Filaminast
- Glaucine
- HT-0712
- Ibudilast
- ICI-63197
- Irsogladine
- Luteolin
- Mesembrine
- Piclamilast
- Roflumilast
- Rolipram
- Ro20-1724
- RPL-554
- YM-976
|
|
| PDE5 |
- Acetildenafil
- Aildenafil
- Avanafil
- Dipyridamole
- Icariin
- Lodenafil
- Mirodenafil
- MY-5445
- Nitrosoprodenafil
- Sildenafil
- Sulfoaildenafil
- T-0156
- Tadalafil
- Udenafil
- Vardenafil
|
|
| PDE6 |
|
|
| PDE7 |
|
|
| PDE9 |
|
|
| PDE10 |
- Papaverine
- PF-2545920
- Tofisopam
|
|
| Nonselective |
- Caffeine
- Doxofylline
- IBMX
- Pentoxifylline
- Propentofylline
- Theophylline
|
|
English Journal
- Evidence for inhibitory autocrine effects of proinsulin C-peptide on pancreatic β-cell function and insulin secretion.
- McKillop AM1, Ng MT, Abdel-Wahab YH, Flatt PR.
- Diabetes, obesity & metabolism.Diabetes Obes Metab.2014 Oct;16(10):937-46. doi: 10.1111/dom.12300. Epub 2014 Apr 27.
- AIMS: Autocrine and paracrine regulatory mechanisms ensure integrated secretion of islet hormones that respond efficiently to changes in metabolic need. As proinsulin C-peptide exerts various biological effects and binds to cell membranes including insulin-secreting β cells, its physiological role
- PMID 24702738
- Polyomavirus small T antigen interacts with yes-associated protein to regulate cell survival and differentiation.
- Hwang JH1, Pores Fernando AT2, Faure N3, Andrabi S4, Hahn WC5, Schaffhausen BS6, Roberts TM7.
- Journal of virology.J Virol.2014 Oct;88(20):12055-64. doi: 10.1128/JVI.01399-14. Epub 2014 Aug 13.
- Murine polyomavirus small t antigen (PyST) regulates cell cycle, cell survival, apoptosis, and differentiation and cooperates with middle T antigen (MT) to transform primary cells in vitro and in vivo. Like all polyomavirus T antigens, PyST functions largely via its interactions with host cell prote
- PMID 25122798
- MicroRNA-378 controls classical brown fat expansion to counteract obesity.
- Pan D1, Mao C1, Quattrochi B1, Friedline RH2, Zhu LJ1, Jung DY2, Kim JK2, Lewis B1, Wang YX1.
- Nature communications.Nat Commun.2014 Aug 22;5:4725. doi: 10.1038/ncomms5725.
- Both classical brown adipocytes and brown-like beige adipocytes are considered as promising therapeutic targets for obesity; however, their development, relative importance and functional coordination are not well understood. Here we show that a modest expression of miR-378/378* in adipose tissue sp
- PMID 25145289
Japanese Journal
- Caffeic Acid Phenethyl Ester Inhibits Differentiation to Adipocytes in 3T3-L1 Mouse Fibroblasts
- Juman Sachiko,Yasui Naomi,Okuda Hiroto,Ueda Ai,Negishi Hiroko,Miki Tomohiro,Ikeda Katsumi
- Biological and Pharmaceutical Bulletin 33(9), 2010
- … 3T3-L1 cells were differentiated for adipocytes given high glucose Dulbecco's modified Eagle's medium (DMEM) supplemented with 10% fetal bovine serum (FBS), 1 μM dexamethasone (DEX), 500 μM isobutylmethylxanthine (IBMX), and 5 μg/ml insulin for 7 days. …
- NAID 130000322343
- Inverse regulation of leptin mRNA expression by short- and long-chain fatty acids in cultured bovine adipocytes
- Soliman Mohamed,Kimura Kazuhiro,Ahmed Mohamed,Yamaji Daisuke,Matsushita Yukiko,Okamatsu-Ogura Yuko,Makondo Kennedy,Saito Masayuki
- Domestic Animal Endocrinology 33(4), 400-409, 2007
- … Bovine stromal vascular cells isolated from subcutaneous adipose tissue of Holstein cows were cultured to confluence and treated sequentially with dexamethasone and isobutylmethylxanthine for 2 days and insulin and troglitazone for 12 days to achieve full differentiation to adipocytes. …
- NAID 120000949896
★リンクテーブル★
[★]
- 関
- 1-methyl-3-isobutylxanthine、isobutylmethylxanthine
[★]
- 英
- isobutylmethylxanthine、IBMX
- 関
- 1-メチル-3-イソブチルキサンチン