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제품정보 (DICE 배송 시 비용 별도)
실험식(Hill 표기법):
C10H14N4O2
CAS 번호:
Molecular Weight:
222.24
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
249-259-3
MDL number:
Beilstein/REAXYS Number:
247859
제품 이름
3-Isobutyl-1-methylxanthine, ≥99% (HPLC), powder
Quality Level
assay
≥99% (HPLC)
form
powder
color
white to off-white
mp
200-201 °C (lit.)
solubility
DMSO: 1 M (with gentle warming), ethanol: 10 mg/mL
storage temp.
−20°C
SMILES string
CC(C)CN1C(=O)N(C)C(=O)c2[nH]cnc12
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)
InChI key
APIXJSLKIYYUKG-UHFFFAOYSA-N
Gene Information
human ... PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)
rat ... Adora1(29290), Adora2a(25369)
General description
3-isobutyl-1-methylxanthine/IBMX is a non-selective, non-specific inhibitor of cAMP and cGMP phosphodiesterases. IBMX can induce melanogenesis, and can be used as a positive control in melanogenesis research. In oocyte research, IBMX assists in maintaining the germinal vesicle (GV) arrest of prophase I oocytes.
Application
3-Isobutyl-1-methylxanthine has been used:
- in the differentiation of mesenchymal stem cells (MSC)
- as a culture medium supplement for inducing adipogenic differentiation
- as a supplement in Krebs-Ringer buffer with HEPES (KRBH) solution for inducing glucose-stimulated insulin secretion (GSIS)
- in the characterization of adipose-derived mesenchymal stem cells
- in cyclic adenosine monophosphate (cAMP) assay
- in phosphodiesterase (PDE) inhibition
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.
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.
저장 등급
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
프로토콜
TrueGel3D® Hydrogel Plate protocol guides high-throughput culture of human adipose MSCs for screening applications.
A conserved aromatic lock for the tryptophan rotameric switch in TM-VI of seven-transmembrane receptors
Holst B, et al.
The Journal of Biological Chemistry, 285(6), 3973-3985 (2010)
ZebraBeat: a flexible platform for the analysis of the cardiac rate in zebrafish embryos
De L, et al.
Scientific reports, 4, 4898-4898 (2014)
Crystal structures of phosphodiesterases 4 and 5 in complex with inhibitor 3-isobutyl-1-methylxanthine suggest a conformation determinant of inhibitor selectivity
Huai Q, et al.
The Journal of Biological Sciences, 279(13), 13095-13101 (2004)