159857-81-5

Basic information

• Product Name: L-OrnithinaMide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aMinocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]Methyl]phenyl]-
• Synonyms: L-OrnithinaMide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aMinocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]Methyl]phenyl]-;Mc-Val-Cit-PABC-PNP;MC-VC-PAB-PNP;MC-VAL-CIT-PAB-PNB;MC-Val-Cit-PAB-PNP;Maleimidocaproyl-L-valine-L-citrulline-p-aminobenzyl alcohol p-nitrophenyl carbonate;L-Ornithinamide;Maleimidocaproyl-L-valine-L-citrulline-p-aminobenzyl alcohol p-nitrophenyl carbonate Mc-Val-Cit-PABC-PNP
• CAS NO: 159857-81-5
• Molecular Formula: C₃₅H₄₃N₇O₁₁
• Molecular Weight: 737.75622
• Product Categories: ADCs Linkers
• Mol File: 159857-81-5.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 1034.5±65.0 °C(Predicted)
• Appearance: /
• Density: 1.338±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 13.24±0.70(Predicted)
• CAS DataBase Reference: L-OrnithinaMide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aMinocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]Methyl]phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: L-OrnithinaMide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aMinocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]Methyl]phenyl]-(159857-81-5)
• EPA Substance Registry System: L-OrnithinaMide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aMinocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]Methyl]phenyl]-(159857-81-5)

Safety Data

• Hazardous Substances Data: 159857-81-5(Hazardous Substances Data)

Usage

Description

L-Ornithinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl]is a complex peptide linker molecule used in the synthesis of antibody-drug conjugates (ADCs). It features a unique structure that includes an L-ornithine amide, a hexyl chain with a pyrrol-1-yl group, a valine residue, and a phenyl group with a nitrophenoxycarbonyloxy side chain. This molecule is designed to facilitate the attachment of anticancer drugs to antibodies, enabling targeted delivery to specific cell populations.

Uses

Used in Pharmaceutical Industry:
L-Ornithinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl]is used as a cathepsin-cleavable ADC linker for the synthesis of antibody-drug conjugates. Its application is to enable the targeted delivery of anticancer compounds to specific cell populations, such as cancer cells, to induce a selective response, such as cell death.
Used in Cancer Treatment:
L-Ornithinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl]is used as a component in the development of antibody-drug conjugates for cancer treatment. The reason for its use is to provide a stable and cleavable linker that can release the attached anticancer drug upon internalization by the target cells, allowing for a more effective and targeted therapeutic approach.

Upstream product

• 159857-80-4 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 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 
• 159857-79-1 (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide 
• 623-04-1 4-aminobenzenemethanol 
• 916746-27-5 N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N⁵-carbamoyl-L-ornithine 
• 692739-25-6 pentafluorophenyl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate 
• 60-32-2 6-aminohexanoic acid 
• 870487-04-0 (S)-(9H-fluoren-9-yl)methyl (1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate 
• 133174-15-9 (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 1037794-22-1 (S)-2-amino-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide 
• 372-75-8 Citrulline 
• 159858-21-6 (S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid 

Downstream Products

• 919995-57-6 maleimidocaproyl-Val-Cit-PAB-MeVal-Val-Dil-Dap-2-chloro-Phe-OH 
• 920017-31-8 maleimidocaproyl-val-Cit-p-aminobenzoyl-NMeVal-Val-Dil-Dap-phosphonophenylalanine 
• 920017-30-7 maleimidocaproyl-Val-Cit-p-aminobenzoyl-NMeVal-Val-Dil-Dap-phosphonophenylalanine 
• 920017-40-9 MC-Val-Cit-PAB-MeVal-Val-Dil-ODMB 
• 945864-36-8 C₆₁H₇₆ClN₁₁O₁₂ 
• 889880-95-9 MC-vc-PAB-(N,N'-2-acetamido-1,3-propanediamine-ethyl)-bis-4-amino-1,8-naphthalimide 
• 889881-02-1 MC-vc-PAB-( N,N'-(2-ethoxy-N-ethylethanamine)-bis-3-nitro-1,8-naphthalimide) 
• 889880-96-0 MC-vc-PAB-(N,N'-2-acetamido-1,3-ethanediamine-propyl)-bis-4-morpholino-1,8-naphthalimide 
• 889880-97-1 MC-vc-PAB-(N,N'-2-acetamido-1,2-propanediamine-ethyl)-bis-4-morpholino-1,8-naphthalimide 
• 889880-98-2 MC-vc-PAB-(N,N'-2-acetamido-1,3-ethanediamine-propyl)-bis-4-amino-1,8-naphthalimide 
• 889880-99-3 MC-vc-PAB-(N,N'-2-acetamido-1,2-propanediamine-ethyl)-bis-3-nitro-1,8-naphthalimide 
• 889881-00-9 MC-vc-PAB-(N,N'-2-acetamido-1,3-ethanediamine-propyl)-bis-3-nitro-1,8-naphthalimide 
• 889881-01-0 MC-vc-PAB-(N,N'-(4-aza-octanyl)-bis-3-nitro-1,8-naphthalimide) 
• 889881-05-4 MC-vc-PAB-(N,N'-(bis-aminoethyl-1,3-propanediamine)-bis-(4-N-methylpiperidine)-1,8 naphthalimide) 

Relevant articles and documents

Novel PIKK inhibitor antibody-drug conjugates: Synthesis and anti-tumor activity

Novel neolymphostin-based antibody-drug conjugate (ADC) precursors were synthesized either through amide couplings between both cleavable and non-cleavable linkers and neolymphostin derivatives, or through Cu(I)-catalyzed acetylene-azide click cycloaddito

DRUG ANTIBODY CONJUGATES

Drug conjugates having formula [D-(X)b-(AA)w-(T)g-(L)-]n-Ab wherein: D is a drug moiety having the following formula (I) or a pharmaceutically acceptable salt or ester thereof, wherein D is covalently attached via a hydroxy group at OR1, OR3 or ZH, or a thiol group at ZH to (X)b if any, or (AA)w if any, or to (T)g if any, or (L); that are useful in the treatment of cancer.

Synthesis, characterization, and targeted chemotherapy of SCT200-linker-monomethyl auristatin E conjugates

Antibody-drug conjugates (ADCs) are currently among the most successful and important strategies for treating patients with solid tumors. ADCs are composed of a monoclonal antibody and warhead, which are conjugated via a linker. Currently, monomethyl auristatin E (MMAE) is the most widely applied warhead in the development of ADCs. However, MMAE-based ADCs are generally constructed using the MC-VC-PABC linker, and this design has limited structural diversity and some disadvantages. Accordingly, in this study, we generated three types of novel linker-MMAE (with alterations in the spacer, catabolizing area, and self-immolative compared with MC-VC-PABC-MMAE) in ADCs, termed SCT200-linker-MMAE conjugates, and then evaluated the linker-drug plasma stability and the rate of drug release by cathepsin B. The binding ability, internalization rates, and efficacy of all SCT200-linker-MMAE ADCs were systematically studied, and the expression of apoptosis-associated proteins and the therapeutic efficacies of SCT200-M-2, -C-2, and -C-4 were evaluated. The results showed that the activities of some of these ADCs were increased for epidermal growth factor receptor-positive tumors. Moreover, the novel linkers designed in this study can be linked with other antibodies to treat other types of cancer. Overall, these findings provide important insights into the application of SCT200-based linkers in ADCs.

ONE-POT PROCESS FOR PREPARING INTERMEDIATE OF ANTIBODY-DRUG CONJUGATE

The present invention relates to a “one-pot process” for preparing intermediate of antibody-drug conjugate. The preparation process provided by the present invention is simple in operation, and needs no such steps like concentration, washing and filtratio