Synonym
GW627368X; GW 627368X; GW-627368X; GW627368; GW 627368; GW-627368.
IUPAC/Chemical Name
2-(4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl)-N-(phenylsulfonyl)acetamide
InChi Key
XREWXJVMYAXCJV-UHFFFAOYSA-N
InChi Code
InChI=1S/C30H28N2O6S/c1-3-37-28-23-12-8-9-13-24(23)29(38-4-2)27-25(28)19-32(30(27)34)21-16-14-20(15-17-21)18-26(33)31-39(35,36)22-10-6-5-7-11-22/h5-17H,3-4,18-19H2,1-2H3,(H,31,33)
SMILES Code
O=C(NS(=O)(C1=CC=CC=C1)=O)CC2=CC=C(N(CC3=C4C(OCC)=C(C=CC=C5)C5=C3OCC)C4=O)C=C2
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
GW627368 (GW627368X) is a novel, potent and selective competitive antagonist of prostanoid EP4 receptor with additional human
TP receptor affinity, with pKi values of 7.0 and 6.8 for human prostanoid EP4 and TP receptors respectively.
In vitro activity:
GW627368X inhibits growth in cervical cancer cells by inducing apoptosis was indicated by morphological studies using
DAPI/Rhodamine phalloidin staining (Figure 2a). Typical changes in cell morphology including cell shrinkage, disruption of actin
filaments, nuclear fragmentation and apoptososme formation was observed. Apoptotic cell death was further confirmed by a timedependent increase in terminal deoxynucleotidyl transferase dUTP nick-end labeling (TUNEL)-positive green nuclei (Figure 2b).
Reference: Cell Death Dis. 2016 Mar 24;7(3):e2154. https://pubmed.ncbi.nlm.nih.gov/27010855/
In vivo activity:
To evaluate the effect of GW627368X on signaling within tumor environment, the expression profile of various phosphorylated and
non-phosphorylated proteins were studied by immunohistochemistry and western blotting (Fig. 3). A significant decrease in
phosphorylation level of signaling mediators like EGFR, VEGFR, Akt, MAPK etc was observed with increase in dose of the drug
while the total proteins seemed to remain equal in all the sets (Fig. 3D). In addition, highly significant down regulation of COX-2 and
EP4 was observed (Fig. 3A). The key player of the cascade, Prostaglandin E2 in plasma and tissue was quantified using enzyme
immune assay. The plasma and tissue levels of prostaglandin E-2 drastically reduced from 720.7 ± 11.11pg/ml in control group to 200
± 0.7076 pg/g in high treatment group vs. 248.8 ± 16.40 pg/ml in normal mice (Fig. 3C). The effect was highly significant.
Reference: Cancer Biol Ther. 2015;16(6):922-32. https://pubmed.ncbi.nlm.nih.gov/25894216/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
30.0 |
55.08 |
|
| DMF:PBS (pH 7.2) (1:2) |
0.3 |
0.55 |
|
| DMSO |
54.8 |
100.66 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
544.62
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Parida S, Pal I, Parekh A, Thakur B, Bharti R, Das S, Mandal M. GW627368X inhibits proliferation and induces apoptosis in
cervical cancer by interfering with EP4/EGFR interactive signaling. Cell Death Dis. 2016 Mar 24;7(3):e2154. doi:
10.1038/cddis.2016.61. PMID: 27010855; PMCID: PMC4823960.
2. Wilson RJ, Giblin GM, Roomans S, Rhodes SA, Cartwright KA, Shield VJ, Brown J, Wise A, Chowdhury J, Pritchard S, Coote J,
Noel LS, Kenakin T, Burns-Kurtis CL, Morrison V, Gray DW, Giles H. GW627368X ((N-{2-[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2Hbenzo[f]isoindol-2-yl)phenyl]acetyl} benzene sulphonamide): a novel, potent and selective prostanoid EP4 receptor antagonist. Br J
Pharmacol. 2006 Jun;148(3):326-39. doi: 10.1038/sj.bjp.0706726. PMID: 16604093; PMCID: PMC1751567
3. Parida S, Parekh A, Dey G, Ghosh SC, Mandal M. Molecular inhibition of prostaglandin E2 with GW627368X: Therapeutic
potential and preclinical safety assessment in mouse sarcoma model. Cancer Biol Ther. 2015;16(6):922-32. doi:
10.1080/15384047.2015.1040953. Epub 2015 Apr 20. PMID: 25894216; PMCID: PMC4623220.
In vitro protocol:
1. Parida S, Pal I, Parekh A, Thakur B, Bharti R, Das S, Mandal M. GW627368X inhibits proliferation and induces apoptosis in
cervical cancer by interfering with EP4/EGFR interactive signaling. Cell Death Dis. 2016 Mar 24;7(3):e2154. doi:
10.1038/cddis.2016.61. PMID: 27010855; PMCID: PMC4823960.
2. Wilson RJ, Giblin GM, Roomans S, Rhodes SA, Cartwright KA, Shield VJ, Brown J, Wise A, Chowdhury J, Pritchard S, Coote J,
Noel LS, Kenakin T, Burns-Kurtis CL, Morrison V, Gray DW, Giles H. GW627368X ((N-{2-[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2Hbenzo[f]isoindol-2-yl)phenyl]acetyl} benzene sulphonamide): a novel, potent and selective prostanoid EP4 receptor antagonist. Br J
Pharmacol. 2006 Jun;148(3):326-39. doi: 10.1038/sj.bjp.0706726. PMID: 16604093; PMCID: PMC1751567
In vivo protocol:
1. Parida S, Parekh A, Dey G, Ghosh SC, Mandal M. Molecular inhibition of prostaglandin E2 with GW627368X: Therapeutic
potential and preclinical safety assessment in mouse sarcoma model. Cancer Biol Ther. 2015;16(6):922-32. doi:
10.1080/15384047.2015.1040953. Epub 2015 Apr 20. PMID: 25894216; PMCID: PMC4623220.
Product data sheet
MedKoo Biosciences || http://www.medkoo.com || sales@medkoo.com
2500 Gateway Centre Blvd Suite 400, Morrisville, NC27560, USA. Tel: 919-636-5577, Fax: 919-980-4831
2. Wilson RJ, Giblin GM, Roomans S, Rhodes SA, Cartwright KA, Shield VJ, Brown J, Wise A, Chowdhury J, Pritchard S, Coote J,
Noel LS, Kenakin T, Burns-Kurtis CL, Morrison V, Gray DW, Giles H. GW627368X ((N-{2-[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2Hbenzo[f]isoindol-2-yl)phenyl]acetyl} benzene sulphonamide): a novel, potent and selective prostanoid EP4 receptor antagonist. Br J
Pharmacol. 2006 Jun;148(3):326-39. doi: 10.1038/sj.bjp.0706726. PMID: 16604093; PMCID: PMC1751567
1: Parida S, Parekh A, Dey G, Ghosh SC, Mandal M. Molecular inhibition of
prostaglandin E2 with GW627368X: Therapeutic potential and preclinical safety
assessment in mouse sarcoma model. Cancer Biol Ther. 2015;16(6):922-32. doi:
10.1080/15384047.2015.1040953. Epub 2015 Apr 20. PubMed PMID: 25894216.
2: Wilson RJ, Giblin GM, Roomans S, Rhodes SA, Cartwright KA, Shield VJ, Brown J,
Wise A, Chowdhury J, Pritchard S, Coote J, Noel LS, Kenakin T, Burns-Kurtis CL,
Morrison V, Gray DW, Giles H. GW627368X
((N-{2-[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetyl}
benzene sulphonamide): a novel, potent and selective prostanoid EP4 receptor
antagonist. Br J Pharmacol. 2006 Jun;148(3):326-39. PubMed PMID: 16604093; PubMed
Central PMCID: PMC1751567.
