JPM-OEt | CAS#262381-84-0 | cathepsin inhibitor

MedKoo Cat#: 563498 | Name: JPM-OEt

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

JPM-OEt is a broad spectrum cysteine cathepsin inhibitor.

Chemical Structure

JPM-OEt

CAS#262381-84-0

Theoretical Analysis

MedKoo Cat#: 563498

Name: JPM-OEt

CAS#: 262381-84-0

Chemical Formula: C20H28N2O6

Exact Mass: 392.1947

Molecular Weight: 392.45

Elemental Analysis: C, 61.21; H, 7.19; N, 7.14; O, 24.46

Price and Availability

Size	Price	Availability
5mg	USD 450.00	Inquiry
10mg	USD 750.00	Inquiry
25mg	USD 1,250.00	Inquiry

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

JPM-OEt; JPM OEt; JPMOEt; JPM-565 Ethyl ester;

IUPAC/Chemical Name

ethyl (2S,3S)-3-(((S)-1-((4-hydroxyphenethyl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)oxirane-2-carboxylate

InChi Key

VRFYYTLIPKHELT-ULQDDVLXSA-N

InChi Code

InChI=1S/C20H28N2O6/c1-4-27-20(26)17-16(28-17)19(25)22-15(11-12(2)3)18(24)21-10-9-13-5-7-14(23)8-6-13/h5-8,12,15-17,23H,4,9-11H2,1-3H3,(H,21,24)(H,22,25)/t15-,16-,17-/m0/s1

SMILES Code

O=C([C@H]1O[C@@H]1C(N[C@H](C(NCCC2=CC=C(O)C=C2)=O)CC(C)C)=O)OCC

Appearance

Solid powder

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

Shelf Life

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A24O01B16

View CoA: current batch, Lot# A20O12B22

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

JPM-OEt is a broad spectrum cysteine cathepsin inhibitor.

In vitro activity:

To evaluate the binding specificity of VGT-309 to individual cysteine cathepsins as well as the activity dependence of the probe, this study incubated OE19 cells with 1 μM VGT-309 for 2 hours after pretreatment of cells for 30 minutes with 100 μM JPM-OEt, a pan-cathepsin inhibitor. This study found that VGT-309 labeled all examined cathepsins, and that pretreatment with JPM-OEt blocked labeling of all cathepsins, confirming the high degree of selectivity of the probe (Figure 2(b)). Reference: Mol Imaging. 2022 Jul 14;2022:5447290. https://pubmed.ncbi.nlm.nih.gov/35903245/

In vivo activity:

Visible lung and spine metastatic nodules were observed in vehicle and JPM-OEt treatment groups, whereas tumors were undetectable in the CA-074 group (Figure 4H, 4I). Importantly, measurement of cysteine cathepsin B and L activity in primary tumor tissue lysates derived from mice treated with JPM-OEt and CA-074 revealed that both inhibitors reduced tumor cathepsin B activity significantly (Figure 4G, p<0.005), yet CA-074 was more effective. In contrast, only JPM-OEt inhibited cathepsin L activity (Figure 4G, p<0.05). Reference: Cancer Res. 2012 Mar 1;72(5):1199-209. https://pubmed.ncbi.nlm.nih.gov/22266111/

	Solvent	mg/mL	mM
Solubility
	DMSO	125.0	318.51

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 392.45 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. Kennedy GT, Azari FS, Nadeem B, Chang A, Segil A, Bernstein E, Desphande C, Kucharczuk JC, Delikatny EJ, Singhal S. Preclinical Evaluation of an Activity-Based Probe for Intraoperative Imaging of Esophageal Cancer. Mol Imaging. 2022 Jul 14;2022:5447290. doi: 10.1155/2022/5447290. PMID: 35903245; PMCID: PMC9328188. 2. Schurigt U, Sevenich L, Vannier C, Gajda M, Schwinde A, Werner F, Stahl A, von Elverfeldt D, Becker AK, Bogyo M, Peters C, Reinheckel T. Trial of the cysteine cathepsin inhibitor JPM-OEt on early and advanced mammary cancer stages in the MMTV-PyMT-transgenic mouse model. Biol Chem. 2008 Aug;389(8):1067-74. doi: 10.1515/BC.2008.115. PMID: 18710344. 3. Withana NP, Blum G, Sameni M, Slaney C, Anbalagan A, Olive MB, Bidwell BN, Edgington L, Wang L, Moin K, Sloane BF, Anderson RL, Bogyo MS, Parker BS. Cathepsin B inhibition limits bone metastasis in breast cancer. Cancer Res. 2012 Mar 1;72(5):1199-209. doi: 10.1158/0008-5472.CAN-11-2759. Epub 2012 Jan 19. PMID: 22266111; PMCID: PMC3538126. 4. Bell-McGuinn KM, Garfall AL, Bogyo M, Hanahan D, Joyce JA. Inhibition of cysteine cathepsin protease activity enhances chemotherapy regimens by decreasing tumor growth and invasiveness in a mouse model of multistage cancer. Cancer Res. 2007 Aug 1;67(15):7378-85. doi: 10.1158/0008-5472.CAN-07-0602. PMID: 17671208.

In vitro protocol:

In vivo protocol:

1. Withana NP, Blum G, Sameni M, Slaney C, Anbalagan A, Olive MB, Bidwell BN, Edgington L, Wang L, Moin K, Sloane BF, Anderson RL, Bogyo MS, Parker BS. Cathepsin B inhibition limits bone metastasis in breast cancer. Cancer Res. 2012 Mar 1;72(5):1199-209. doi: 10.1158/0008-5472.CAN-11-2759. Epub 2012 Jan 19. PMID: 22266111; PMCID: PMC3538126. 2. Bell-McGuinn KM, Garfall AL, Bogyo M, Hanahan D, Joyce JA. Inhibition of cysteine cathepsin protease activity enhances chemotherapy regimens by decreasing tumor growth and invasiveness in a mouse model of multistage cancer. Cancer Res. 2007 Aug 1;67(15):7378-85. doi: 10.1158/0008-5472.CAN-07-0602. PMID: 17671208.

1: Withana NP, Blum G, Sameni M, Slaney C, Anbalagan A, Olive MB, Bidwell BN, Edgington L, Wang L, Moin K, Sloane BF, Anderson RL, Bogyo MS, Parker BS. Cathepsin B inhibition limits bone metastasis in breast cancer. Cancer Res. 2012 Mar 1;72(5):1199-209. doi: 10.1158/0008-5472.CAN-11-2759. Epub 2012 Jan 19. PubMed PMID: 22266111; PubMed Central PMCID: PMC3538126. 2: Elie BT, Gocheva V, Shree T, Dalrymple SA, Holsinger LJ, Joyce JA. Identification and pre-clinical testing of a reversible cathepsin protease inhibitor reveals anti-tumor efficacy in a pancreatic cancer model. Biochimie. 2010 Nov;92(11):1618-24. doi: 10.1016/j.biochi.2010.04.023. Epub 2010 May 4. PubMed PMID: 20447439; PubMed Central PMCID: PMC3814225. 3: Schurigt U, Sevenich L, Vannier C, Gajda M, Schwinde A, Werner F, Stahl A, von Elverfeldt D, Becker AK, Bogyo M, Peters C, Reinheckel T. Trial of the cysteine cathepsin inhibitor JPM-OEt on early and advanced mammary cancer stages in the MMTV-PyMT-transgenic mouse model. Biol Chem. 2008 Aug;389(8):1067-74. doi: 10.1515/BC.2008.115. PubMed PMID: 18710344. 4: Bell-McGuinn KM, Garfall AL, Bogyo M, Hanahan D, Joyce JA. Inhibition of cysteine cathepsin protease activity enhances chemotherapy regimens by decreasing tumor growth and invasiveness in a mouse model of multistage cancer. Cancer Res. 2007 Aug 1;67(15):7378-85. PubMed PMID: 17671208. 5: Greenbaum D, Medzihradszky KF, Burlingame A, Bogyo M. Epoxide electrophiles as activity-dependent cysteine protease profiling and discovery tools. Chem Biol. 2000 Aug;7(8):569-81. PubMed PMID: 11048948. 6: Shi GP, Bryant RA, Riese R, Verhelst S, Driessen C, Li Z, Bromme D, Ploegh HL, Chapman HA. Role for cathepsin F in invariant chain processing and major histocompatibility complex class II peptide loading by macrophages. J Exp Med. 2000 Apr 3;191(7):1177-86. PubMed PMID: 10748235; PubMed Central PMCID: PMC2193169. 7: Bogyo M, Verhelst S, Bellingard-Dubouchaud V, Toba S, Greenbaum D. Selective targeting of lysosomal cysteine proteases with radiolabeled electrophilic substrate analogs. Chem Biol. 2000 Jan;7(1):27-38. PubMed PMID: 10662686.