159858-21-6

Basic information

• Product Name: L-Ornithine, N5-(aMinocarbonyl)-N2-[N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-valyl]-
• Synonyms: L-Ornithine, N5-(aMinocarbonyl)-N2-[N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-valyl]-;(S)-2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid;L-Ornithine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-N5-(aminocarbonyl)-;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl-N5-(aminocarbonyl)-L-ornithine
• CAS NO: 159858-21-6
• Molecular Formula: C₂₆H₃₂N₄O₆
• Molecular Weight: 496.55548
• Product Categories: Linker
• Mol File: 159858-21-6.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 787.1±60.0 °C(Predicted)
• Appearance: /
• Density: 1.269±0.06 g/cm3(Predicted)
• PKA: 3.41±0.10(Predicted)
• CAS DataBase Reference: L-Ornithine, N5-(aMinocarbonyl)-N2-[N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-valyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Ornithine, N5-(aMinocarbonyl)-N2-[N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-valyl]-(159858-21-6)
• EPA Substance Registry System: L-Ornithine, N5-(aMinocarbonyl)-N2-[N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-valyl]-(159858-21-6)

Safety Data

• Hazardous Substances Data: 159858-21-6(Hazardous Substances Data)

Usage

General Description

L-Ornithine, N5-(aminocarbonyl)-N2-[N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl]- is a chemical compound that is a derivative of L-ornithine, an amino acid involved in the urea cycle in humans. L-Ornithine, N5-(aMinocarbonyl)-N2-[N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-valyl]- is a combination of L-ornithine and aminocarbonyl, a functional group containing a carbonyl group attached to an amino group. Additionally, it contains a valyl group and a fluoren-9-ylmethoxy group. This chemical is used in scientific research and may have potential applications in the pharmaceutical industry for its biological and therapeutic properties.

Upstream product

• 72-18-4 L-valine 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 130878-68-1 2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate 
• 372-75-8 Citrulline 
• 68858-20-8 Fmoc-Val-OH 
• 13594-51-9 D-citrulline 

Downstream Products

• 159858-22-7 (9H-fluorenyl)methyl ((S)-1-(((S)-1-(((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidovalerylamido-2-yl)amino))-3-methylbutyramido-2-yl)-carbamate 
• 646502-53-6 4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate 
• 1639351-92-0 N-((S)-1-(((S)-1-((4-(chloromethyl)phenyl)amino)-1-oxo-5-ureidopentan- 2-yl)amino)-3-methyl-1-oxobutan-2-yl)-6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamide 

Relevant articles and documents

Development of bifunctional anti-PD-L1 antibody MMAE conjugate with cytotoxicity and immunostimulation

In recent years, tumor immunotherapy, especially the combination of PD1/PD-L1 inhibitors and chemotherapy, has developed rapidly. However, the systemic side effects induced by chemotherapy remain a crucial problem that needs to be addressed. Antibody drug conjugates (ADCs) are exceptional target-specific prodrugs that greatly improve the therapeutic window of chemotherapy drugs. Therefore, designing PD-L1-targeting ADCs is an interesting research project. In this study, we confirmed for the first time that the commercial anti-PD-L1 antibody Atezolizumab has better endocytosis efficiencies than Avelumab, and was more suitable for ADC design. Then, the most popular cytotoxic payload MMAE was conjugated to Atezolizumab via a classical dipeptide (valine-alanine) linker to generate a bifunctional PD-L1 ADC (ADC 3). An in vitro cytotoxicity test indicated the potent tumor cell inhibitory activity of ADC 3, with EC50 values of 9.75 nM to 11.94 nM. In addition, a co-culture of PBMCs in vitro proved that ADC 3 retained the immune activation effect of the Atezolizumab antibody. Moreover, ADC 3 exhibited a higher tumor inhibition rate and tumor regression rate in humanized immune system mice. To the best of our knowledge, this is the most active PD-L1-ADC reported thus far, which may promote the development of immunotherapy and novel ADCs.

ANTIBODY-DRUG CONJUGATE

Provided herein is an antibody-drug conjugate (ADC) especially a PEGylated mono or bispecific antibody-drug conjugate (BsADC) prepared with site-specific conjugation to provide homogeneous conjugate with high potency and low toxicity. It also relates to a

PARA-AMINO-BENZYL LINKERS, PROCESS FOR THEIR PREPARATION AND THEIR USE IN CONJUGATES

The present invention relates to para-amino-benzyl linker compounds useful for linking drug moieties to antibodies, to linker-drug compounds in which said para-amino-benzyl linker compounds are covalently linked to drug moieties, and to antibody-drug conjugates in which said para-amino-benzyl linker compounds are covalently linked to drug wherein said drug is enzymatically cleaved from the conjugate at a particular cell or tissue type targeted by said antibody.