16,16-Dimethyl Prostaglandin E2 - CAS 39746-25-3
Category: Inhibitor
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Molecular Formula:
C22H36O5
Molecular Weight:
380.52
COA:
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Targets:
Prostaglandin Receptor
Description:
16,16-Dimethyl Prostaglandin E2, a prostaglandin E2 derivative, could induce an increase in hematopoietic stem cell (HSC) numbers in mouse model.
Purity:
≥98% by HPLC
Appearance:
Colourless Liquid
Synonyms:
(5Z,11α,13E,15R)-11,15-Dihydroxy-16,16-dimethyl-9-oxo-prosta-5,13-dien-1oic acid
MSDS:
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InChIKey:
QAOBBBBDJSWHMU-DEXKTNGXSA-N
InChI:
InChI=1S/C22H36O5/c1-4-5-14-22(2,3)20(25)13-12-17-16(18(23)15-19(17)24)10-8-6-7-9-11-21(26)27/h6,8,12-13,16-17,19-20,24-25H,4-5,7,9-11,14-15H2,1-3H3,(H,26,27)/b8-6-,13-12+/t16-,17-,19+,20+/m1/s1
Canonical SMILES:
CCCCC(C)(C)C(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
1.Peripheral prostaglandin E2 prolongs the sensitization of nociceptive dorsal root ganglion neurons possibly by facilitating the synthesis and anterograde axonal trafficking of EP4 receptors.
St-Jacques B1, Ma W2. Exp Neurol. 2014 Nov;261:354-66. doi: 10.1016/j.expneurol.2014.05.028. Epub 2014 Jun 5.
Prostaglandin E2 (PGE2), a well-known pain mediator enriched in inflamed tissues, plays a pivotal role in the genesis of chronic pain conditions such as inflammatory and neuropathic pain. PGE2-prolonged sensitization of nociceptive dorsal root ganglion (DRG) neurons (nociceptors) may contribute to the transition from acute to chronic pain. However, the underlying cellular mechanisms are poorly understood. In this study, we tested the hypothesis that facilitating synthesis and anterograde axonal trafficking of EP receptors contribute to PGE2-prolonged nociceptor sensitization. Intraplantar (i.pl.) injection of a stabilized PGE2 analog, 16,16 dimethyl PGE2 (dmPGE2), in a dose- and time-dependent manner, not only elicited primary tactile allodynia which lasted for 1d, but also prolonged tactile allodynia evoked by a subsequent i.pl. injection of dmPGE2 from 1d to 4d. Moreover, the duration of tactile allodynia was progressively prolonged following multiple sequential i.
2.Chronic prostaglandin E2 treatment induces the synthesis of the pain-related peptide substance P and calcitonin gene-related peptide in cultured sensory ganglion explants.
Ma W1. J Neurochem. 2010 Oct;115(2):363-72. doi: 10.1111/j.1471-4159.2010.06927.x. Epub 2010 Aug 25.
Prostaglandin E2 (PGE2) is a well known pain and pro-inflammatory mediator abundantly produced in inflamed tissue. It causes pain by directly exciting nociceptive primary sensory neurons (nociceptors) and indirectly stimulating the release of pain-related peptide substance P (SP) and calcitonin gene-related peptide (CGRP). In an ex vivo culture of sensory ganglion explants, we tested the hypothesis that PGE2 could induce the synthesis of SP and CGRP in nociceptors. A stabilized PGE2 analog, 16,16-dimethyl PGE2, in a concentration- and time-dependent manner, significantly increased mRNA and peptide levels of SP and CGRP. The agonists of EP1 and EP4 receptors also significantly increased SP and CGRP levels. Moreover, 16,16-dimethyl PGE2-induced SP and CGRP were blocked by EP1 and EP4 antagonists as well as the inhibitors of both protein kinase A and protein kinase C. Nerve growth factor was partially involved in PGE2-induced SP and CGRP synthesis.
3.Endogenous prostaglandin E2 accelerates healing of indomethacin-induced small intestinal lesions through upregulation of vascular endothelial growth factor expression by activation of EP4 receptors.
Takeuchi K1, Tanigami M, Amagase K, Ochi A, Okuda S, Hatazawa R. J Gastroenterol Hepatol. 2010 May;25 Suppl 1:S67-74. doi: 10.1111/j.1440-1746.2010.06222.x.
BACKGROUND AND AIMS: The effects of an EP4 agonist/antagonist on the healing of lesions produced by indomethacin in the small intestine were examined in rats, especially in relation to the expression of vascular endothelial growth factor (VEGF) and angiogenesis.
4.Autocrine prostaglandin E2 signaling promotes tumor cell survival and proliferation in childhood neuroblastoma.
Rasmuson A1, Kock A, Fuskevåg OM, Kruspig B, Simón-Santamaría J, Gogvadze V, Johnsen JI, Kogner P, Sveinbjörnsson B. PLoS One. 2012;7(1):e29331. doi: 10.1371/journal.pone.0029331. Epub 2012 Jan 19.
BACKGROUND: Prostaglandin E(2) (PGE(2)) is an important mediator in tumor-promoting inflammation. High expression of cyclooxygenase-2 (COX-2) has been detected in the embryonic childhood tumor neuroblastoma, and treatment with COX inhibitors significantly reduces tumor growth. Here, we have investigated the significance of a high COX-2 expression in neuroblastoma by analysis of PGE(2) production, the expression pattern and localization of PGE(2) receptors and intracellular signal transduction pathways activated by PGE(2).
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CAS 39746-25-3 16,16-Dimethyl Prostaglandin E2

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