MC-Val-Cit-PAB-carfilzomib - CAS 2055896-83-6

MC-Val-Cit-PAB-carfilzomib - CAS 2055896-83-6 Catalog number: BADC-00630

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MC-Val-Cit-PAB-carfilzomib is a drug-linker conjugate for ADC with potent antitumor activity by using carfilzomib (an irreversible proteasome inhibitor), linked via the ADC linker MC-Val-Cit-PAB.

General Information

Category
ADCs Cytotoxin with Linkers
Product Name
MC-Val-Cit-PAB-carfilzomib
CAS
2055896-83-6
Catalog Number
BADC-00630
Molecular Formula
C68H96N11O13
Molecular Weight
1275.56

Chemical Structure

  • MC-Val-Cit-PAB-carfilzomib
Synonyms
MC Val Cit PAB carfilzomib
Canonical SMILES
O=C([C@]1(CO1)C)[C@H](CC(C)C)NC([C@H](CC2=CC=CC=C2)NC([C@H](CC(C)C)NC([C@H](CCC3=CC=CC=C3)NC(C[N+]4(CCOCC4)CC5=CC=C(NC([C@H](CCCNC(N)=O)NC([C@H](C(C)C)NC(CCCCCN6C(C=CC6=O)=O)=O)=O)=O)C=C5)=O)=O)=O)=O
1.Targeted drug delivery through the traceless release of tertiary and heteroaryl amines from antibody-drug conjugates
Staben LR, et al.
The reversible attachment of a small-molecule drug to a carrier for targeted delivery can improve pharmacokinetics and the therapeutic index. Previous studies have reported the delivery of molecules that contain primary and secondary amines via an amide or carbamate bond; however, the ability to employ tertiary-amine-containing bioactive molecules has been elusive. Here we describe a bioreversible linkage based on a quaternary ammonium that can be used to connect a broad array of tertiary and heteroaryl amines to a carrier protein. Using a concise, protecting-group-free synthesis we demonstrate the chemoselective modification of 12 complex molecules that contain a range of reactive functional groups. We also show the utility of this connection with both protease-cleavable and reductively cleavable antibody-drug conjugates that were effective and stable in vitro and in vivo. Studies with a tertiary-amine-containing antibiotic show that the resulting antibody-antibiotic conjugate provided appropriate stability and release characteristics and led to an unexpected improvement in activity over the conjugates previously connected via a carbamate.

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