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Key Documents

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C277

Sigma-Aldrich

Chloro-IB-MECA

solid, ≥98% (HPLC)

Sinónimos:

Cl-IB-MECA

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About This Item

Fórmula empírica (notación de Hill):
C18H18ClIN6O4
Número de CAS:
163042-96-4
Peso molecular:
544.73
MDL number:
MFCD01861178
UNSPSC Code:
12352200
PubChem Substance ID:
24278354
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >20 mg/mL

SMILES string

CNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NCc4cccc(I)c4)nc(Cl)nc23

InChI

1S/C18H18ClIN6O4/c1-21-16(29)13-11(27)12(28)17(30-13)26-7-23-10-14(24-18(19)25-15(10)26)22-6-8-3-2-4-9(20)5-8/h2-5,7,11-13,17,27-28H,6H2,1H3,(H,21,29)(H,22,24,25)/t11-,12+,13-,17+/m0/s1

InChI key

IPSYPUKKXMNCNQ-PFHKOEEOSA-N

Gene Information

human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

Biochem/physiol Actions

2-chloro-N(6)-(3-iodobenzyl)adenosine-5′-N-methylcarboxamide (Cl-IB-MECA) is a adenosine receptor. It protects against myocardial ischemia/reperfusion injury in mice.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Y Yao et al.
Biochemical and biophysical research communications, 232(2), 317-322 (1997-03-17)
The effects of novel, selective adenosine (ADO) A3 receptor antagonists of diverse structure on cells of the human HL-60 leukemia and U-937 lymphoma cell lines were examined. Both 3-ethyl 5-benzyl 2-methyl-6-phenyl-4-phenylethynyl-1,4-(+/-)-dihydropyridine-3, 5-dicarboxylate (MRS 1191, 0.5 microM) and 6-carboxy-methyl-5, 9-dihydro-9-methyl-2-phenyl-[1,2,4]-triazolo [5,1-a][2,7]naphthyridine
Cl-IB-MECA [2-Chloro-N6-(3-iodobenzyl) adenosine-5?-N-methylcarboxamide] Reduces Ischemia/Reperfusion Injury in Mice by Activating the A Adenosine Receptor
Ge ZD, et al.
Journal of Pharmacology and Experimental Therapeutics, 319(3), 1200-1210 (2006)
The A3 adenosine receptor agonist 2-Cl-IB-MECA facilitates epileptiform discharges in the CA3 area of immature rat hippocampal slices
Laudadio MA, et al.
Epilepsy Research, 59(2), 83-94 (2004)
K Stambaugh et al.
The American journal of physiology, 273(1 Pt 2), H501-H505 (1997-07-01)
The possible cardioprotective roles of adenosine A1 and A3 receptors were investigated in a cardiac myocyte model of injury. The adenosine A3 receptor is a novel cardiac receptor capable of mediating potentially important cardioprotective functions. Prolonged hypoxia with glucose deprivation
Melanie Wurm et al.
Molecular cancer therapeutics, 20(11), 2250-2261 (2021-09-06)
Despite some impressive clinical results with immune checkpoint inhibitors, the majority of patients with cancer do not respond to these agents, in part due to immunosuppressive mechanisms in the tumor microenvironment. High levels of adenosine in tumors can suppress immune
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