PSI TFA | CAS# | proteasome inhibitor

MedKoo Cat#: 464338 | Name: PSI TFA

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Description:

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

PSI is a synthetic peptide proteasome inhibitor. PSI enhanced apoptotic activity of TRAIL. PSI dramatically inhibited cell proliferation and induced apoptosis of PEL cells through the accumulation of p21.

Chemical Structure

PSI TFA

CAS#To be determined

Theoretical Analysis

MedKoo Cat#: 464338

Name: PSI TFA

CAS#: To be determined

Chemical Formula: C34H51F3N4O10

Exact Mass: 0.0000

Molecular Weight: 732.80

Elemental Analysis: C, 55.73; H, 7.02; F, 7.78; N, 7.65; O, 21.83

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00	2 Weeks

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Related CAS #

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Synonym

PSI TFA salt; Proteasome Inhibitor I; Z-Ile-Glu(OtBu)-Ala-Leu-aldehyde; Z-Ile-Glu(OtBu)-Ala-Leu-CHO; PSI (trifluoroacetate salt); PSI trifluoroacetate salt

IUPAC/Chemical Name

tert-butyl (S)-4-((2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-methylpentanamido)-5-(((S)-1-(((S)-4-methyl-1-oxopentan-2-yl)amino)-1-oxopropan-2-yl)amino)-5-oxopentanoate 2,2,2-trifluoroacetate

InChi Key

DCCRGIXOEPOQJI-BGGSUVIVSA-N

InChi Code

InChI=1S/C32H50N4O8.C2HF3O2/c1-9-21(4)27(36-31(42)43-19-23-13-11-10-12-14-23)30(41)35-25(15-16-26(38)44-32(6,7)8)29(40)33-22(5)28(39)34-24(18-37)17-20(2)3;3-2(4,5)1(6)7/h10-14,18,20-22,24-25,27H,9,15-17,19H2,1-8H3,(H,33,40)(H,34,39)(H,35,41)(H,36,42);(H,6,7)/t21-,22-,24-,25-,27-;/m0./s1

SMILES Code

O=C(OCC1=CC=CC=C1)N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H](CC(C)C)C=O)=O)C)=O)CCC(OC(C)(C)C)=O)=O)[C@H](CC)C.OC(C(F)(F)F)=O

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 formic acid

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

PSI inhibits proteasome activities (IC50s = 0.25 and 6.5 µM), is cytotoxic to various human leukemia cells (IC50s = 4.9 to 17.5 nM), and selectively induces apoptosis in endothelial cells (EC50s = 7 to 24 nM) over confluent cells (EC50s = 7,830 to 8,150 nM). PSI also causes ubiquitin-protein conjugate accumulation in neuronal cells.

In vitro activity:

PSI induced apoptosis in HL-60 leukemia cells by activating caspases, modulating Bcl-2 family proteins, and stimulating stress pathways. It also triggered changes in protein expression. Multidrug-resistant HL-60 variants showed resistance to PSI, which is not solely due to drug efflux protein overexpression but is linked to factors like low Bax levels and impaired JNK activation. Reference: Biochem Pharmacol. 2008 Jun 15;75(12):2276-88. https://pubmed.ncbi.nlm.nih.gov/18468579/

In vivo activity:

In a rat model of Parkinson's disease, the in vivo effects of PSI were examined. Rats receiving PSI showed reduced volume in the substantia nigra, changes in brain metabolites, motor dysfunction, and decreased dopamine levels in the striatum. This suggests that PSI treatment leads to significant alterations in the nigro-striatal pathway and motor impairment, as confirmed by MRI and spectroscopy. Reference: PLoS One. 2013;8(2):e56501. https://pubmed.ncbi.nlm.nih.gov/23431380/

	Solvent	mg/mL	mM
Solubility
	Formic Acid	1.0	1.36

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 732.80 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. Huong PT, Moon DO, Kim SO, Kim KE, Jeong SJ, Lee KW, Lee KS, Jang JH, Erikson RL, Ahn JS, Kim BY. Proteasome inhibitor-I enhances tunicamycin-induced chemosensitization of prostate cancer cells through regulation of NF-κB and CHOP expression. Cell Signal. 2011 May;23(5):857-65. doi: 10.1016/j.cellsig.2011.01.010. Epub 2011 Jan 27. PMID: 21276850. 2. Choi MR, Najafi F, Safa AR, Drexler HC. Analysis of changes in the proteome of HL-60 promyeloid leukemia cells induced by the proteasome inhibitor PSI. Biochem Pharmacol. 2008 Jun 15;75(12):2276-88. doi: 10.1016/j.bcp.2008.03.017. Epub 2008 Apr 7. PMID: 18468579; PMCID: PMC2494601. 3. Delli Pizzi S, Rossi C, Di Matteo V, Esposito E, Guarnieri S, Mariggiò MA, Franciotti R, Caulo M, Thomas A, Onofrj M, Tartaro A, Bonanni L. Morphological and metabolic changes in the nigro-striatal pathway of synthetic proteasome inhibitor (PSI)-treated rats: a MRI and MRS study. PLoS One. 2013;8(2):e56501. doi: 10.1371/journal.pone.0056501. Epub 2013 Feb 19. PMID: 23431380; PMCID: PMC3576393. 4. Khonsari B, Klassen R. Impact of Pus1 Pseudouridine Synthase on Specific Decoding Events in Saccharomyces cerevisiae. Biomolecules. 2020 May 7;10(5):729. doi: 10.3390/biom10050729. PMID: 32392804; PMCID: PMC7277083.

In vitro protocol:

In vivo protocol:

1. Delli Pizzi S, Rossi C, Di Matteo V, Esposito E, Guarnieri S, Mariggiò MA, Franciotti R, Caulo M, Thomas A, Onofrj M, Tartaro A, Bonanni L. Morphological and metabolic changes in the nigro-striatal pathway of synthetic proteasome inhibitor (PSI)-treated rats: a MRI and MRS study. PLoS One. 2013;8(2):e56501. doi: 10.1371/journal.pone.0056501. Epub 2013 Feb 19. PMID: 23431380; PMCID: PMC3576393. 2. Khonsari B, Klassen R. Impact of Pus1 Pseudouridine Synthase on Specific Decoding Events in Saccharomyces cerevisiae. Biomolecules. 2020 May 7;10(5):729. doi: 10.3390/biom10050729. PMID: 32392804; PMCID: PMC7277083.

This message contains search results from the National Center for Biotechnology Information (NCBI) at the U.S. National Library of Medicine (NLM). Do not reply directly to this message Sent On: Wed Sep 04 13:02:58 2024 Search: Proteasome Inhibitor I From: evan.izzo@medkoo.com 20 selected items PubMed Results Items 1-20 of 20 (Display the 20 citations in PubMed) 1: Bu Z, Yang J, Zhang Y, Luo T, Fang C, Liang X, Peng Q, Wang D, Lin N, Zhang K, Tang W. Sequential Ubiquitination and Phosphorylation Epigenetics Reshaping by MG132-Loaded Fe-MOF Disarms Treatment Resistance to Repulse Metastatic Colorectal Cancer. Adv Sci (Weinh). 2023 Aug;10(23):e2301638. doi: 10.1002/advs.202301638. Epub 2023 Jun 11. PMID: 37303273; PMCID: PMC10427397. 2: Huynh TK, Ho CY, Tsai CH, Wang CK, Chen YJ, Bau DT, Tu CY, Li TS, Huang WC. Proteasome Inhibitors Suppress ErbB Family Expression through HSP90-Mediated Lysosomal Degradation. Int J Mol Sci. 2019 Sep 27;20(19):4812. doi: 10.3390/ijms20194812. PMID: 31569723; PMCID: PMC6801459. 3: Capretti MG, Marsico C, Conti M, Corvaglia LT, Arcuri S, Faldella G, Re MC. Nevirapine prophylaxis to prevent HIV-1 mother-to-child transmission: pharmacokinetic considerations in preterm infants. New Microbiol. 2016 Oct;39(4):314-316. Epub 2016 Jun 10. PMID: 27284987. 4: Al-Mansour Z, Ramanathan M. Post-Autologous (ASCT) Stem Cell Transplant Therapy in Multiple Myeloma. Adv Hematol. 2014;2014:652395. doi: 10.1155/2014/652395. Epub 2014 Nov 24. PMID: 25525435; PMCID: PMC4265378. 5: Kang CH, Choi YH, Moon SK, Kim WJ, Kim GY. Quercetin inhibits lipopolysaccharide-induced nitric oxide production in BV2 microglial cells by suppressing the NF-κB pathway and activating the Nrf2-dependent HO-1 pathway. Int Immunopharmacol. 2013 Nov;17(3):808-13. doi: 10.1016/j.intimp.2013.09.009. Epub 2013 Sep 25. PMID: 24076371. 6: Delli Pizzi S, Rossi C, Di Matteo V, Esposito E, Guarnieri S, Mariggiò MA, Franciotti R, Caulo M, Thomas A, Onofrj M, Tartaro A, Bonanni L. Morphological and metabolic changes in the nigro-striatal pathway of synthetic proteasome inhibitor (PSI)-treated rats: a MRI and MRS study. PLoS One. 2013;8(2):e56501. doi: 10.1371/journal.pone.0056501. Epub 2013 Feb 19. PMID: 23431380; PMCID: PMC3576393. 7: Walker JA, Rossini G, Thompson MW, Wenke JC, Baer D. Effect of proteasome inhibitor 1 on wound healing: a potential scar prevention therapy. Wounds. 2013 Feb;25(2):28-33. PMID: 25867804. 8: Nayak MK, Kulkarni PP, Dash D. Regulatory role of proteasome in determination of platelet life span. J Biol Chem. 2013 Mar 8;288(10):6826-34. doi: 10.1074/jbc.M112.403154. Epub 2013 Jan 17. PMID: 23329846; PMCID: PMC3591593. 9: Katsnelson A. Next-generation proteasome inhibitor approved in multiple myeloma. Nat Biotechnol. 2012 Nov;30(11):1011-2. doi: 10.1038/nbt1112-1011. PMID: 23138275. 10: Stefanova N, Kaufmann WA, Humpel C, Poewe W, Wenning GK. Systemic proteasome inhibition triggers neurodegeneration in a transgenic mouse model expressing human α-synuclein under oligodendrocyte promoter: implications for multiple system atrophy. Acta Neuropathol. 2012 Jul;124(1):51-65. doi: 10.1007/s00401-012-0977-5. Epub 2012 Apr 11. PMID: 22491959; PMCID: PMC3377902. 11: Seol DW. p53-Independent up-regulation of a TRAIL receptor DR5 by proteasome inhibitors: a mechanism for proteasome inhibitor-enhanced TRAIL-induced apoptosis. Biochem Biophys Res Commun. 2011 Dec 9;416(1-2):222-5. doi: 10.1016/j.bbrc.2011.11.053. Epub 2011 Nov 19. PMID: 22120628. 12: Barboza NR, Cardoso J, de Paula Lima CV, Soares MJ, Gradia DF, Hangai NS, Bahia MT, de Lana M, Krieger MA, Guerra de Sá R. Expression profile and subcellular localization of HslV, the proteasome related protease from Trypanosoma cruzi. Exp Parasitol. 2012 Feb;130(2):171-7. doi: 10.1016/j.exppara.2011.10.011. Epub 2011 Nov 9. PMID: 22085770. 13: Saji C, Higashi C, Niinaka Y, Yamada K, Noguchi K, Fujimuro M. Proteasome inhibitors induce apoptosis and reduce viral replication in primary effusion lymphoma cells. Biochem Biophys Res Commun. 2011 Dec 2;415(4):573-8. doi: 10.1016/j.bbrc.2011.10.107. Epub 2011 Oct 31. PMID: 22074820. 14: Huong PT, Moon DO, Kim SO, Kim KE, Jeong SJ, Lee KW, Lee KS, Jang JH, Erikson RL, Ahn JS, Kim BY. Proteasome inhibitor-I enhances tunicamycin-induced chemosensitization of prostate cancer cells through regulation of NF-κB and CHOP expression. Cell Signal. 2011 May;23(5):857-65. doi: 10.1016/j.cellsig.2011.01.010. Epub 2011 Jan 27. PMID: 21276850. 15: Koyama Y, Tanaka K. Intracerebroventricular administration of an endothelin ET(B)-receptor agonist increases expression of matrix metalloproteinase-2 and -9 in rat brain. J Pharmacol Sci. 2010;114(4):433-43. doi: 10.1254/jphs.10195fp. Epub 2010 Nov 26. PMID: 21127388. 16: Bukhatwa S, Zeng BY, Rose S, Jenner P. The effects of dose and route of administration of PSI on behavioural and biochemical indices of neuronal degeneration in the rat brain. Brain Res. 2010 Oct 1;1354:236-42. doi: 10.1016/j.brainres.2010.07.060. Epub 2010 Aug 3. PMID: 20678493. 17: Suh J, Im DS, Moon GJ, Ryu KS, de Silva R, Choi IS, Lees AJ, Guénette SY, Tanzi RE, Gwag BJ. Hypoxic ischemia and proteasome dysfunction alter tau isoform ratio by inhibiting exon 10 splicing. J Neurochem. 2010 Jul;114(1):160-70. doi: 10.1111/j.1471-4159.2010.06732.x. Epub 2010 Apr 3. PMID: 20374429. 18: Lomako J, Lomako WM, Carothers Carraway CA, Carraway KL. Regulation of the membrane mucin Muc4 in corneal epithelial cells by proteosomal degradation and TGF-beta. J Cell Physiol. 2010 Apr;223(1):209-14. doi: 10.1002/jcp.22028. PMID: 20054827; PMCID: PMC2873043. 19: Shin M, Jan C, Jacquard C, Jarraya B, Callebert J, Launay JM, Hantraye P, Remy P, Palfi S, Brouillet E. Chronic systemic treatment with a high-dose proteasome inhibitor in mice produces akinesia unrelated to nigrostriatal degeneration. Neurobiol Aging. 2011 Nov;32(11):2100-2. doi: 10.1016/j.neurobiolaging.2009.11.015. Epub 2009 Dec 16. PMID: 20018410. 20: Kawahata I, Tokuoka H, Parvez H, Ichinose H. Accumulation of phosphorylated tyrosine hydroxylase into insoluble protein aggregates by inhibition of an ubiquitin-proteasome system in PC12D cells. J Neural Transm (Vienna). 2009 Dec;116(12):1571-8. doi: 10.1007/s00702-009-0304-z. Epub 2009 Sep 12. PMID: 19756365.