UP202-56 - CAS 163838-04-8
Category: Inhibitor
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Molecular Formula:
C33H37N7O4
Molecular Weight:
595.69
COA:
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Targets:
Adenosine Receptor
Description:
UP202-56, an adenosine analogue, selectively acts via A1 receptors to significantly decrease noxiously-evoked spinal c-Fos protein expression.
Synonyms:
2-cyclopropyl-1-[(2S,3S,4R,5R)-5-[6-[2-[1-[(2,5-dimethylphenyl)methyl]-5-methylindol-3-yl]ethylamino]purin-9-yl]-3,4-dihydroxyoxolan-2-yl]ethanone
Storage:
Store in a cool and dry place (or refer to the Certificate of Analysis).
MSDS:
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Density:
1.47±0.1 g/cm3
InChIKey:
JULMZFRVKFLKMZ-IMNMKIORSA-N
InChI:
1S/C34H38N6O4/c1-19-4-6-21(3)24(12-19)16-39-15-23(25-13-20(2)5-9-26(25)39)10-11-35-32-28-33(37-17-36-32)40(18-38-28)34-30(43)29(42)31(44-34)27(41)14-22-7-8-22/h4-6,9,12-13,15,17-18,22,29-31,34,42-43H,7-8,10-11,14,16H2,1-3H3,(H,35,36,37)/t29-,30+,31+,34+/m0/s1
Canonical SMILES:
CC1=CC(=C(C=C1)C)CN2C=C(C3=C2C=CC(=C3)C)CCNC4=NC=NC5=C4N=CN5C6C(C(C(O6)C(=O)CC7CC7)O)O
1.The heme environment of mouse neuroglobin: histidine imidazole plane orientations obtained from solution NMR and EPR spectroscopy as compared with X-ray crystallography.
Walker FA J Biol Inorg Chem. 2006 Jun;11(4):391-7. Epub 2006 Apr 4.
The 1H NMR chemical shifts of the heme methyl groups of the ferriheme complex of metneuroglobin (Du et al. in J. Am. Chem. Soc. 125:8080-8081, 2003) predict orientations of the axial histidine ligands (Shokhirev and Walker in J. Biol. Inorg. Chem. 3:581-594, 1998) that are not consistent with the X-ray data (Vallone et al. in Proteins Struct. Funct. Bioinf. 56:85-94, 2004), and the EPR spectrum (Vinck et al. in J. Am. Chem. Soc. 126:4516-4517, 2004) is only marginally consistent with these data. The reasons for these inconsistencies appear to be rooted in the high degree of aqueous solution exposure of the heme group and the fact that there are no strong hydrogen-bond acceptors for the histidine imidazole N-H protons provided by the protein. Similar inconsistencies may exist for other water-soluble heme proteins, and 1H NMR spectroscopy provides a simple means to verify whether the solution structure of the heme center is the same as or different from that in the crystalline state.
2.Stabilization of cytochrome b
Hu S;He B;Wang XJ;Gao SQ;Wen GB;Lin YW Spectrochim Acta A Mol Biomol Spectrosc. 2017 Mar 5;174:118-123. doi: 10.1016/j.saa.2016.11.032. Epub 2016 Nov 20.
Heme proteins perform a large array of biological functions, with the heme group bound non-covalently or covalently. To probe the stabilization role of conserved tyrosine residue in the secondary sphere of heme site in heme proteins, we herein used cytochrome b;5; (Cyt b;5;) as a model protein, and mutated Tyr30 to Phe or His by removal of Tyr30 associated H-bond network and hydrophobic interaction. We performed thermal-induced unfolding studies for the two mutants, Y30F Cyt b;5; and Y30H Cyt b;5;, as monitored by both UV-Vis and CD spectroscopy, as well as heme transfer studies from these proteins to apo-myoglobin, with wild-type Cyt b;5; under the same conditions for comparison. The reduced stability of both mutants indicates that both the H-bonding and hydrophobic interactions associated with Tyr30 contribute to the protein stability. Moreover, we performed molecular modeling studies, which revealed that the hydrophobic interaction in the local region of Y30F Cyt b;5; was well-remained, whereas Y30H Cyt b;5; formed an H-bond network. These observations suggest that the conserved Tyr30 in Cyt b;5; is not replaceable due to the presence of both the H-bond network and hydrophobic interaction in the secondary sphere of the heme active site.
3.Carbon monoxide inhibits hemotoxic activity of Elapidae venoms: potential role of heme.
Nielsen VG;Frank N;Matika RW Biometals. 2018 Feb;31(1):51-59. doi: 10.1007/s10534-017-0066-2. Epub 2017 Nov 23.
Envenomation by hemotoxic enzymes continues to be a major cause of morbidity and mortality throughout the world. With regard to treatment, the gold standard to abrogate coagulopathy caused by these venoms is still the administration of antivenom; however, despite antivenom therapy, coagulopathy still occurs and recurs. Of interest, this laboratory has demonstrated in vitro and in vivo that coagulopathy inducing venom derived from snakes of the family Viperidae exposed to carbon monoxide (CO) is inhibited, potentially by an attached heme. The present investigation sought to determine if venoms derived from snakes of the Elapidae family (taipans and cobras) could also be inhibited with CO or with the metheme inducing agent, O-phenylhydroxylamine (PHA). Assessing changes in coagulation kinetics of human plasma with thrombelastography, venoms from Elapidae snakes were exposed in isolation to CO (five species) or PHA (one specie) and placed in human plasma to assess changes in procoagulant or anticoagulant activity. The procoagulant activity of two taipan venoms and anticoagulant activity of three cobra venoms were significantly inhibited by CO. The venom of the inland taipan was also inhibited by PHA.
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CAS 163838-04-8 UP202-56

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