MC-Val-Cit-PAB-Retapamulin - CAS 1639793-15-9

MC-Val-Cit-PAB-Retapamulin - CAS 1639793-15-9 Catalog number: BADC-00612

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MC-Val-Cit-PAB-retapamulin has a bioreversible linkage based on a quaternary ammonium for targeted delivery and it can improve pharmacokinetics and the therapeutic index. MC-Val-Cit-PAB-retapamulin is used for the antibody-drug conjugates (ADC) that are effective and stable in vitro and in vivo to treat various diseases or disorders.

Category
ADCs Cytotoxin with Linkers
Product Name
MC-Val-Cit-PAB-Retapamulin
CAS
1639793-15-9
Catalog Number
BADC-00612
Molecular Formula
C58H86N7O10S
Molecular Weight
1073.41
MC-Val-Cit-PAB-Retapamulin

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BADC-00612 -- $--
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Description
MC-Val-Cit-PAB-retapamulin has a bioreversible linkage based on a quaternary ammonium for targeted delivery and it can improve pharmacokinetics and the therapeutic index. MC-Val-Cit-PAB-retapamulin is used for the antibody-drug conjugates (ADC) that are effective and stable in vitro and in vivo to treat various diseases or disorders.
IUPAC Name
[(2R,3S,4S,6R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[[(1R,5S)-8-[[4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methyl]-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl]sulfanyl]acetate
Canonical SMILES
C[C@@H]1C23[C@](C(CC3)=O)([H])C([C@H](OC(CS[C@@H]4C[C@@H]5[N@+](CC6=CC=C(NC([C@H](CCCNC(N)=O)NC([C@H](C(C)C)NC(CCCCCN7C(C=CC7=O)=O)=O)=O)=O)C=C6)(C)[C@@H](CC5)C4)=O)C[C@](C=C)(C)[C@H]1O)([C@H](C)CC2)C
InChI
InChI=1S/C58H85N7O10S/c1-9-56(6)32-45(57(7)36(4)24-26-58(37(5)52(56)71)27-25-44(66)51(57)58)75-49(70)34-76-42-30-40-20-21-41(31-42)65(40,8)33-38-16-18-39(19-17-38)61-53(72)43(14-13-28-60-55(59)74)62-54(73)50(35(2)3)63-46(67)15-11-10-12-29-64-47(68)22-23-48(64)69/h9,16-19,22-23,35-37,40-43,45,50-52,71H,1,10-15,20-21,24-34H2,2-8H3,(H5-,59,60,61,62,63,67,72,73,74)/p+1/t36-,37+,40-,41+,42?,43+,45-,50+,51+,52+,56-,57?,58?,65?/m1/s1
Shipping
Room temperature
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.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Historical Records: MC-Val-Cit-PAB-Retapamulin
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