253863-34-2

Basic information

• Product Name: Aloc-D-Ala-Phe-Lys(Aloc)-p-aminobenzyl oxycarbonyl p-nitrophenyl carbonate
• Synonyms: Aloc-D-Ala-Phe-Lys(Aloc)-p-aminobenzyl oxycarbonyl p-nitrophenyl carbonate
• CAS NO: 253863-34-2
• Molecular Weight: 802.838
• Mol File: 253863-34-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Aloc-D-Ala-Phe-Lys(Aloc)-p-aminobenzyl oxycarbonyl p-nitrophenyl carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: Aloc-D-Ala-Phe-Lys(Aloc)-p-aminobenzyl oxycarbonyl p-nitrophenyl carbonate(253863-34-2)
• EPA Substance Registry System: Aloc-D-Ala-Phe-Lys(Aloc)-p-aminobenzyl oxycarbonyl p-nitrophenyl carbonate(253863-34-2)

Safety Data

• Hazardous Substances Data: 253863-34-2(Hazardous Substances Data)

Upstream product

• 146982-27-6 (S)-6-allyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid 
• 253863-21-7 Fmoc-Phe-Lys(Boc)-OBu 
• 253863-23-9 Boc-D-Ala-Phe-Lys(Boc)-OBu 
• 253863-25-1 Aloc-D-Ala-Phe-Lys(Aloc)-OH 
• 101214-43-1 Fmoc-Phe-ONSu 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 253863-26-2 Aloc-D-Ala-Phe-Lys(Aloc)-PAB-OH 
• 623-04-1 4-aminobenzenemethanol 
• 918936-47-7 (R)-2-(((allyloxy)carbonyl)amino)propanoic acid 

Downstream Products

• 949144-97-2 C₆₂H₇₀N₆O₂₀ 
• 220369-59-5 C₆₁H₇₀N₆O₂₀ 
• 393521-96-5 (4-Hydroxymethyl-phenyl)-carbamic acid 4-{(S)-6-allyloxycarbonylamino-2-[(S)-2-((R)-2-allyloxycarbonylamino-propionylamino)-3-phenyl-propionylamino]-hexanoylamino}-benzyl ester 
• 253863-28-4 C₆₁H₇₀N₆O₁₉ 
• 393522-02-6 C₆₉H₇₇N₇O₂₂ 
• 393522-19-5 Carbonic acid 4-[4-(4-{(S)-6-allyloxycarbonylamino-2-[(S)-2-((R)-2-allyloxycarbonylamino-propionylamino)-3-phenyl-propionylamino]-hexanoylamino}-benzyloxycarbonylamino)-benzyloxycarbonylamino]-benzyl ester 4-nitro-phenyl ester 
• 393522-16-2 C₄₉H₅₇N₇O₁₂ 
• 393521-99-8 Carbonic acid 4-(4-{(S)-6-allyloxycarbonylamino-2-[(S)-2-((R)-2-allyloxycarbonylamino-propionylamino)-3-phenyl-propionylamino]-hexanoylamino}-benzyloxycarbonylamino)-benzyl ester 4-nitro-phenyl ester 

Relevant articles and documents

Synthesis and biological characterization of protease-activated prodrugs of doxazolidine

Doxazolidine (doxaz) is a new anthracycline anticancer agent. While structurally similar to doxorubicin (dox), doxaz acts via a distinct mechanism to selectively enhance anticancer activity over cardiotoxicity, the most significant clinical impediment to successful anthracycline treatment. Here, we describe the synthesis and characterization of a prodrug platform designed for doxaz release mediated by secreted proteolytic activity, a common association with invasiveness and poor prognosis in cancer patients. GaFK-Doxaz is hydrolyzable by the proteases plasmin and cathepsin B, both strongly linked with cancer progression, as well as trypsin. We demonstrate that activation of GaFK-Doxaz releases highly potent doxaz that powerfully inhibits the growth of a wide variety of cancer cells (average IC50 of 8 nM). GaFK-Doxaz is stable in human plasma and is poorly membrane permeable, thereby limiting activation to locally secreted proteolytic activity and reducing the likelihood of severe side effects.

Cathepsin B-sensitive dipeptide prodrugs. 1. A model study of structural requirements for efficient release of doxorubicin

A series of lysosomal protease-sensitive peptides attached to doxorubicin (DOX) was prepared as model substrates for internalizing anticancer immunoconjugates and potential antimetastasis prodrugs. Rates of cathepsin B-mediated release of free drug was measured for each, and human plasma stabilities for representative examples.