PSI (trifluoroacetate salt)
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 464338

CAS#: To be determined

Description: PSI is a synthetic peptide proteasome inhibitor.

Chemical Structure

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PSI (trifluoroacetate salt)
CAS# To be determined
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464338
Name: PSI (trifluoroacetate salt)
CAS#: To be determined
Chemical Formula: C34H51F3N4O10
Exact Mass: 0.00
Molecular Weight: 732.800
Elemental Analysis: C, 55.73; H, 7.02; F, 7.78; N, 7.65; O, 21.83

Price and Availability

Size Price Availability Quantity
10mg USD -2 2 Weeks
25mg USD -2 2 Weeks
50mg USD -2 2 Weeks
100mg USD -2 2 Weeks
200mg USD -2 2 Weeks
500mg USD -2 2 Weeks
2g USD -2 2 Weeks
5g USD -2 2 Weeks
1mg USD 260 2 Weeks
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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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Formic Acid 1.0 1.36

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.

Recalculate based on batch purity %
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: 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.
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.

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