238750-77-1

Basic information

• Product Name: Tosedostat
• Synonyms: tosedostat;alpha-[[(2R)-2-[(1S)-1-Hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methyl-1-oxopentyl]amino]benzeneacetic acid cyclopentyl ester;Benzeneacetic acid, alpha-(((2R)-2-((1S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl)-4-methyl-1-oxopentyl)amino)-, cyclopentyl ester, (alphas)-;Chr-2797;α-[[(2R)-2-[(1S)-1-Hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methyl-1-oxopentyl]amino]-benzeneaceticacidcyclopentlyester;Tosedostat (CHR2797);CHR2797 (Tosedostat);BB-76163
• CAS NO: 238750-77-1
• Molecular Formula: C21H30N2O6
• Molecular Weight: 406.47
• EINECS: 200-258-5
• Product Categories: Amines;Aromatics;Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labelled Compounds;Inhibitor
• Mol File: 238750-77-1.mol
• Article Data: 0

Chemical Properties

• Appearance: /
• Density: 1.24
• Refractive Index: 1.566
• Storage Temp.: Store at -20°C
• Solubility: ≥40.6 mg/mL in DMSO; insoluble in H2O; ≥15.07 mg/mL in EtOH with ultrasonic
• PKA: 9.44±0.40(Predicted)
• CAS DataBase Reference: Tosedostat(CAS DataBase Reference)
• NIST Chemistry Reference: Tosedostat(238750-77-1)
• EPA Substance Registry System: Tosedostat(238750-77-1)

Safety Data

• Hazardous Substances Data: 238750-77-1(Hazardous Substances Data)

Usage

Description

Tosedostat is an inhibitor of aminopeptidases, which has demonstrated the ability to inhibit the proliferation of human leukemia cell lines in vitro, irrespective of p53, PTEN, or K-RAS mutational status. It also induces the up-regulation of genes in amino acid transport and metabolic pathways and inhibits the phosphorylation of mammalian target of rapamycin (mTOR) substrates in HL-60 cells, which are markers of amino acid depletion. In vivo, tosedostat has been shown to reduce total tumor burden and the number of spontaneous metastases in a mouse MDA-MB-435 xenograft model. Formulations containing tosedostat are currently under clinical investigation for the treatment of myeloid leukemia.

Uses

Used in Anticancer Applications:
Tosedostat is used as an anticancer agent for its potent antiproliferative effects against a range of tumor cell lines in vitro and in vivo. It shows selectivity for transformed over nontransformed cells and is at least 300 times more potent than the prototypical aminopeptidase inhibitor, Bestatin.
Used in Drug Development:
Tosedostat is used as a pharmacological active acid product (CHR-79888) inside cells, which is derived from the novel metalloenzyme inhibitor CHR-2797. This conversion enhances its antiproliferative effects and contributes to its potential as a therapeutic agent in the treatment of myeloid leukemia.
Used in Clinical Research:
Tosedostat is used in clinical investigations for the development of formulations targeting myeloid leukemia, leveraging its ability to inhibit aminopeptidases and reduce tumor burden in preclinical models.

Biological Activity

Aminopeptidase inhibitor (IC 50 values are 100, 150, 220, > 1000, > 5000, > 10000 and > 30000 nM for LAP, PuSA, aminopeptidase N, aminopeptidase B, PILSAP, LTA 4 hydrolase and MetAP2 respectively). Potently inhibits tumor cell proliferation in a variety of tumor cell lines in vitro and in vivo .

InChI:InChI=1/C21H30N2O6/c1-13(2)12-16(18(24)20(26)23-28)19(25)22-17(14-8-4-3-5-9-14)21(27)29-15-10-6-7-11-15/h3-5,8-9,13,15-18,24,28H,6-7,10-12H2,1-2H3,(H,22,25)(H,23,26)/t16-,17+,18+/m1/s1