- 関
- 1-methyl-3-isobutylxanthine、isobutylmethylxanthine
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/05/22 14:29:02」(JST)
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IBMX
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Names |
IUPAC name
1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
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Other names
3-Isobutyl-1-methylxanthine
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Identifiers |
CAS Registry Number
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28822-58-4 Y |
ChEBI |
CHEBI:34795 Y |
ChEMBL |
ChEMBL275084 Y |
ChemSpider |
3627 Y |
DrugBank |
DB07954 Y |
InChI
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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
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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
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IUPHAR ligand |
388 |
Jmol-3D images |
Image |
KEGG |
C13708 Y |
PubChem |
3758 |
SMILES
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O=C2N(c1ncnc1C(=O)N2C)CC(C)C
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UNII |
TBT296U68M Y |
Properties |
Chemical formula
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C10H14N4O2 |
Molar mass |
222.3 g/mol |
Appearance |
White solid |
Melting point |
199 to 201 °C (390 to 394 °F; 472 to 474 K) |
Solubility |
Soluble in ethanol, DMSO, and methanol |
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Y verify (what is: Y/N?) |
Infobox references |
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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. doi:10.4049/jimmunol.174.2.589. 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
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PDE1 |
- MMPX
- SCH-51866
- Vinpocetine
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PDE2 |
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PDE3 |
- Amrinone
- Anagrelide
- Bucladesine
- Cilostamide
- Cilostazol
- Enoximone
- KMUP-1
- Milrinone
- Quazinone
- RPL-554
- Siguazodan
- Trequinsin
- Vesnarinone
- Zardaverine
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PDE4 |
- Apremilast
- Arofylline
- Atizoram
- Cilomilast
- Denbutylline
- Drotaverine
- Etazolate
- Filaminast
- Glaucine
- HT-0712
- Ibudilast
- ICI-63197
- Irsogladine
- Luteolin
- Mesembrine
- Piclamilast
- Roflumilast
- Rolipram
- RPL-554
- YM-976
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PDE5 |
- Acetildenafil
- Aildenafil
- Avanafil
- Dipyridamole
- Icariin
- Lodenafil
- Mirodenafil
- MY-5445
- Nitrosoprodenafil
- Sildenafil
- Sulfoaildenafil
- T-0156
- Tadalafil
- Udenafil
- Vardenafil
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PDE6 |
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PDE7 |
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PDE9 |
|
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PDE10 |
- Papaverine
- PF-2545920
- Tofisopam
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PDE11 |
BC11-38
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Nonselective |
- Caffeine
- Doxofylline
- IBMX
- Pentoxifylline
- Propentofylline
- Theophylline
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Adenosinergics
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Receptor
(ligands) |
AR
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- Agonists: 2-(1-Hexynyl)-N-methyladenosine
- 2-Cl-IB-MECA
- 2'-MeCCPA
- 4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil
- 5'-N-ethylcarboxamidoadenosine
- Adenosine
- Apadenoson
- ATL-146e
- BAY 60–6583
- Binodenoson
- Capadenoson
- CCPA
- CGS-21680
- CP-532,903
- Evodenoson
- GR 79236
- LUF-5835
- LUF-5845
- N6-Cyclopentyladenosine
- Neladenoson dalanate
- Regadenoson
- SDZ WAG 994
- Selodenoson
- Sonedenoson
- Tecadenoson
- UK-432,097
- Antagonists: 8-Chlorotheophylline
- 8-Phenyl-1,3-dipropylxanthine
- 8-Phenyltheophylline
- Acefylline
- Aminophylline
- ATL-444
- Bamifylline
- Cafedrine
- Caffeine
- Caffeine citrate
- Cartazolate
- CF-101
- CGS-15943
- Choline theophyllinate
- CPX
- CVT-6883
- Dimethazan
- DMPX
- DPCPX
- Dyphylline
- Enprofylline
- Etazolate
- Fenethylline
- IBMX
- Isovaleric acid
- Istradefylline
- KF-26777
- MRE3008F20
- MRS-1220
- MRS-1334
- MRS-1706
- MRS-1754
- MRS-3777
- Paraxanthine
- Pentoxifylline
- Preladenant
- Propentofylline
- Proxyphylline
- PSB-10
- PSB-11
- PSB 36
- PSB-603
- PSB-788
- PSB-1115
- Rolofylline
- SCH-442,416
- SCH-58261
- Theobromine
- Theodrenaline
- Theophylline
- Tozadenant
- Tracazolate
- VUF-5574
- ZM-241,385
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Transporter
(blockers) |
ENTs
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- Barbiturates
- Benzodiazepines
- Cilostazol
- Dilazep
- Dipyridamole
- Ethanol
- Hexobendine
- NBMPR
- Pentoxifylline
- Propentofylline
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PMAT
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English Journal
- In vitro effects of 2-hydroxyestradiol-17β on ovarian follicular steroid secretion in the catfish Heteropneustes fossilis and identification of the receptor and signaling mechanisms.
- Chourasia TK, Joy KP.SourceDepartment of Zoology, Centre of Advanced Study, Banaras Hindu University, Varanasi 221 005, India.
- General and comparative endocrinology.Gen Comp Endocrinol.2012 Feb 1;175(3):500-13. Epub 2011 Dec 19.
- Ovarian pieces containing postvitellogenic follicles were incubated in vitro with different concentrations of the catecholestrogen 2-hydroxyestradiol-17β (2-OHE(2)) to evaluate its effects on steroid production and germinal vesicle breakdown (GVBD) in the catfish Heteropneustes fossilis. The incuba
- PMID 22202599
- A calmodulin inhibitor, W-7 influences the effect of cyclic adenosine 3', 5'-monophosphate signaling on ligninolytic enzyme gene expression in Phanerochaete chrysosporium.
- Sakamoto T, Yao Y, Hida Y, Honda Y, Watanabe T, Hashigaya W, Suzuki K, Irie T.AbstractABSTRACT: The capacity of white-rot fungi to degrade wood lignin may be highly applicable to the development of novel bioreactor systems, but the mechanisms underlying this function are not yet fully understood. Lignin peroxidase (LiP) and manganese peroxidase (MnP) , which are thought to be very important for the ligninolytic property, demonstrated increased activity in Phanerochaete chrysosporium RP-78 (FGSC #9002, ATCC MYA-4764TM) cultures following exposure to 5 mM cyclic adenosine 3', 5'-monophosphate (cAMP) and 500 micro Molar 3'-isobutyl-1-methylxanthine (IBMX), a phosphodiesterase inhibitor. Real-time reverse transcription polymerase chain reaction (RT-PCR) analysis revealed that transcription of most LiP and MnP isozyme genes was statistically significantly upregulated in the presence of the cAMP and IBMX compared to the untreated condition. However, 100 micro Molar calmodulin (CaM) inhibitor N-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide (W-7), which had insignificant effects on fungal growth and intracellular cAMP concentration, not only offset the increased activity and transcription induced by the drugs, but also decreased them to below basal levels. Like the isozyme genes, transcription of the CaM gene (cam) was also upregulated by cAMP and IBMX. These results suggest that cAMP signaling functions to increase the transcription of LiP and MnP through the induction of cam transcription.
- AMB Express.AMB Express.2012 Jan 24;2(1):7. [Epub ahead of print]
- ABSTRACT: The capacity of white-rot fungi to degrade wood lignin may be highly applicable to the development of novel bioreactor systems, but the mechanisms underlying this function are not yet fully understood. Lignin peroxidase (LiP) and manganese peroxidase (MnP) , which are thought to be very im
- PMID 22273182
- Olfactory responses to explosives associated odorants are enhanced by zinc nanoparticles.
- Moore CH, Pustovyy O, Dennis JC, Moore T, Morrison EE, Vodyanoy VJ.SourceDepartment of Anatomy, Physiology and Pharmacology, Auburn University, Auburn, AL 36849, USA.
- Talanta.Talanta.2012 Jan 15;88:730-3. Epub 2011 Nov 12.
- Many odorants related to manufactured explosives have low volatilities and are barely detectable as odors. We previously reported that zinc metal nanoparticles increased rat olfactory epithelium responses, measured by electroolfactogram (EOG), to several odorants. Here, we report that nanomolar conc
- PMID 22265566
Japanese Journal
- Effects of Nicorandil on the cAMP-Dependent Cl^- Current in Guinea-Pig Ventricular Cells
- NISHIMURA Nami,REIEN Yoshie,MATSUMOTO Akio,OGURA Takehiko,MIYATA Yuuichi,SUZUKI Kazumasa,NAKAZATO Yuji,DAIDA Hiroyuki,NAKAYA Haruaki
- Journal of pharmacological sciences 112(4), 415-423, 2010-04-20
- … When the ICl,cAMP was activated by 3-isobutyl-1-methylxanthine (IBMX, 30 μM), either nicorandil or SNAP failed to enhance the isoproterenol-induced ICl,cAMP. …
- NAID 10027908999
- 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 & Pharmaceutical Bulletin 33(9), 1484-1488, 2010
- … 3T3-L1 cells were differentiated for adipocytes given high glucose Dulbeccos modified Eagles 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
Related Links
- Buy IBMX (CAS 28822-58-4), a potent inhibitor of phosphodiesterases, from Santa Cruz Biotechnology. MW: 222.24, MF: C10H14N4O2, Purity ≥99% ... IBMX is one of the most potent and nonspecific inhibitors of cyclic nucleotide ...
- 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 ...
Related Pictures
★リンクテーブル★
[★]
- 英
- isobutylmethylxanthine、IBMX
- 関
- 1-メチル-3-イソブチルキサンチン
[★]
1-メチル-3-イソブチルキサンチン
- 関
- IBMX
[★]
イソブチルメチルキサンチン
- 関
- IBMX
[★]
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- inclusion body myositis