870487-08-4

Basic information

• Product Name: (6S,9S)-1-amino-9-isopropyl-13,13-dimethyl-1,8,11-trioxo-12-oxa-2,7,10-triazatetradecane-6-carboxylic acid
• Synonyms: (6S,9S)-1-amino-9-isopropyl-13,13-dimethyl-1,8,11-trioxo-12-oxa-2,7,10-triazatetradecane-6-carboxylic acid
• CAS NO: 870487-08-4
• Molecular Weight: 374.437
• Mol File: 870487-08-4.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 624.8±55.0 °C(Predicted)
• Density: 1.183±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (6S,9S)-1-amino-9-isopropyl-13,13-dimethyl-1,8,11-trioxo-12-oxa-2,7,10-triazatetradecane-6-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (6S,9S)-1-amino-9-isopropyl-13,13-dimethyl-1,8,11-trioxo-12-oxa-2,7,10-triazatetradecane-6-carboxylic acid(870487-08-4)
• EPA Substance Registry System: (6S,9S)-1-amino-9-isopropyl-13,13-dimethyl-1,8,11-trioxo-12-oxa-2,7,10-triazatetradecane-6-carboxylic acid(870487-08-4)

Safety Data

• Hazardous Substances Data: 870487-08-4(Hazardous Substances Data)

Usage

Description

(6S,9S)-1-amino-9-isopropyl-13,13-dimethyl-1,8,11-trioxo-12-oxa-2,7,10-triazatetradecane-6-carboxylic acid, also known as Boc-Val-Cit, is a cleavable ADC linker with a unique structure. It consists of an amino group, isopropyl and dimethyl groups, and a carboxylic acid group. The Val-Cit part of the molecule can be specifically cleaved by Cathepsin B, while the Boc group can be removed under acidic conditions.

Uses

Used in Pharmaceutical Industry:
Boc-Val-Cit is used as a cleavable ADC linker for targeted cancer therapy. Its unique structure allows for the specific cleavage of the Val-Cit part by Cathepsin B, an enzyme overexpressed in various cancer cells. This selective cleavage enables the release of the drug payload in the tumor microenvironment, increasing the therapeutic efficacy and reducing side effects.
Used in Drug Delivery Systems:
Boc-Val-Cit is also used in the development of drug delivery systems for improved cancer treatment. Its ability to be cleaved under specific conditions allows for the controlled release of the drug payload, enhancing the bioavailability and therapeutic outcomes. Additionally, the Boc group can be removed under acidic conditions, further enhancing the drug's activity in the tumor microenvironment.

Upstream product

• 13734-41-3 t-Boc-L-valine 
• 133174-15-9 (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid 
• 3392-12-9 Boc-Val-ONSu 
• 93964-78-4 methyl (S)-2-amino-5-ureidopentanoate hydrochloride 
• 372-75-8 Citrulline 
• 60-29-7 diethyl ether 
• 77-92-9 citric acid 

Downstream Products

• 1013922-08-1 Boc-Val-Cit-PABE-SN₃₈ 
• 870487-09-5 tert-butyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentane-2-yl)amino)-3-methyl-1-oxobutane-2-yl)carbamate 
• 870487-10-8 tert-butyl ((5)-3-methyl-1-(((5)-1-((4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-1-oxobutan-2-yl)carbamate 
• 1615234-88-2 C₂₉H₄₇N₇O₇ 
• 1615234-91-7 C₃₆H₅₀N₈O₁₁ 

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As a versatile reaction for bioconjugation, Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC) has enormous potential in the synthesis of antibody-drug conjugates (ADCs). In order to optimize CuAAC-based ADC synthesis, we characterized kinetically different formulation processes by mimicking ADC synthesis using small molecules and subsequently revealed unique kinetic behaviors of different combinations of alkyne and azide conditions. Our results indicate that under ADC synthesis conditions, for an alkyne-containing drug, its concentration has minimal impact on the reaction rate when an antibody has a non-metal-chelating azide but is proportional to concentration when an antibody contains a metal-chelating azide; however, for an alkyne-containing antibody, the ADC synthesis rate is proportional to the concentration of a drug with a non-metal-chelating azide but displays almost no dependence on drug concentration with a metal-chelating azide. Based on our results, we designed and tested an optimal “click” formulation strategy that allowed rapid and cost-effective synthesis of a new ADC.