PZ-128 - ≥99% , Proteinase-activated receptor 1 inhibitor, CAS No.371131-16-7, Proteinase-activated receptor 1 inhibitor

CAS: 371131-16-7 Cat. No.: P651809 Molecular Weight: 1086.46 PubChem CID: 72187679

GRADE & PURITY ≥99%

Synonyms

MS-31946 | UNII-IYT6MP4NS9 | PZ 128 | L-Phenylalaninamide, N2-(1-oxohexadecyl)-L-lysyl-L-lysyl-L-seryl-L-arginyl-L-alanyl-L-leucyl- | N-[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-

Storage

Desiccated,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

PZ-128 (P1pal-7), a cell-penetrating lipopeptide pepducin, is a first-in-class, specific and reversible protease-activated receptor-1 (PAR1) antagonist. PZ-128 targets the cytoplasmic surface of PAR1 and interrupts signaling to internally-located G (PAR1-G) proteins. PZ-128 has antiplatelet, anti-metastatic, anti-angiogenic and anticancer effects

In Vitro

PZ-128 (P1pal-7; 3 μM) blocks 90-94% of OVCAR-4 migration toward human ovarian ascites and fibroblast conditioned media. The OVCAR4-treated peritoneal fibroblast conditioned media elicits a 2.2-fold increase in endothelial barrier permeability which could be nearly completely inhibited by PZ-128. PZ-128 is a lipidated ‘pepducin’ which targets the cytoplasmic surface of PAR1 and interrupts signaling to internally-located G proteins. The structure of PZ-128 is found to mimic the off-state of the corresponding intracellular region of PAR1 which is critical for coupling to G proteins. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

PZ-128 (P1pal-7; 10 mg/kg; intraperitoneal injection; every other day; for 6 weeks) treatment significantly reduces mean ascites fluid volume by 60%. PZ-128 treatment also causes a highly significant 84-96% reduction in blood vessel density in both the center and edge of the OVCAR-4 tumors . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Female NCR Nu/Nu mice (5-7 weeks) injected with OVCAR-4 or SKOV-3 cells Dosage: 10 mg/kg Administration: Intraperitoneal injection; every other day; for 6 weeks Result: Significantly reduced mean ascites fluid volume by 60%.

Form:Solid

IC50& Target:PAR1

Specifications

Synonyms

MS-31946 | UNII-IYT6MP4NS9 | PZ 128 | L-Phenylalaninamide, N2-(1-oxohexadecyl)-L-lysyl-L-lysyl-L-seryl-L-arginyl-L-alanyl-L-leucyl- | N-[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

PZ-128 (P1pal-7), a cell-penetrating lipopeptide pepducin, is a first-in-class, specific and reversible protease-activated receptor-1 (PAR1) antagonist. PZ-128 targets the cytoplasmic surface of PAR1 and interrupts signaling to internally-located G (PAR1-

Storage

Desiccated, Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Mechanism of action

Proteinase-activated receptor 1 inhibitor

Purity

≥99%

Product Properties

• ALogP: 4.9

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCCCC(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CO)C(=O)NC(CCCN=C(N)N)C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(CC1=CC=CC=C1)C(=O)N
• IUPAC Name: N-[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]hexadecanamide
• InChIKey: VZRIKWNVDCTBTF-BKGFHLQYSA-N
• INCHI: 1S/C55H99N13O9/c1-5-6-7-8-9-10-11-12-13-14-15-16-20-31-47(70)63-41(28-21-23-32-56)51(74)64-42(29-22-24-33-57)52(75)68-46(37-69)54(77)65-43(30-25-34-61-55(59)60)50(73)62-39(4)49(72)67-45(35-38(2)3)53(76)66-44(48(58)71)36-40-26-18-17-19-27-40/h17-19,26-27,38-39,41-46,69H,5-16,20-25,28-37,56-57H2,1-4H3,(H2,58,71)(H,62,73)(H,63,70)(H,64,74)(H,65,77)(H,66,76)(H,67,72)(H,68,75)(H4,59,60,61)/t39-,41-,42-,43-,44-,45-,46-/m0/s1
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N
• Alternate CAS: 371131-16-7
• PubChem CID: 72187679
• MeSH Entry Terms: P1pal-7;PZ-128 peptide
• Molecular Weight: 1086.46

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Oligopeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Oligopeptides
• Alternative Parents: Phenylalanine and derivatives Leucine and derivatives N-acyl-alpha amino acids and derivatives Serine and derivatives Alpha amino acid amides Alanine and derivatives Amphetamines and derivatives N-acyl amines Secondary carboxylic acid amides Guanidines Primary carboxylic acid amides Carboximidamides Propargyl-type 1,3-dipolar organic compounds Organopnictogen compounds Monoalkylamines Primary alcohols Hydrocarbon derivatives Carbonyl compounds Organic oxides
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alpha-oligopeptide - Phenylalanine or derivatives - Leucine or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Serine or derivatives - Alanine or derivatives - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Amphetamine or derivatives - N-acyl-amine - Fatty amide - Monocyclic benzene moiety - Benzenoid - Fatty acyl - Secondary carboxylic acid amide - Primary carboxylic acid amide - Guanidine - Amino acid or derivatives - Carboxamide group - Carboximidamide - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Alcohol - Primary aliphatic amine - Organonitrogen compound - Organooxygen compound - Primary alcohol - Carbonyl group - Primary amine - Hydrocarbon derivative - Organic oxide - Amine - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (92.04 mM; Need ultrasonic)
• Molecular Weight: 1086.500 g/mol
• XLogP3: 4.900
• Hydrogen Bond Donor Count: 13
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 45
• Exact Mass: 1085.77 Da
• Monoisotopic Mass: 1085.77 Da
• Topological Polar Surface Area: 383.000 Ų
• Heavy Atom Count: 77
• Formal Charge: 0
• Complexity: 1750.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1