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MC-Val-Cit-PAB-NH-C2-NH-Boc

  CAS No.: 1616727-22-0   Cat No.: BADC-01745 4.5  

MC-Val-Cit-PAB-NH-C2-NH-Boc is a cathepsin cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs).

MC-Val-Cit-PAB-NH-C2-NH-Boc

Structure of 1616727-22-0

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ADC Linker
Molecular Formula
C36H54N8O10
Molecular Weight
758.86

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IUPAC Name
tert-butyl N-[2-[[4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methoxycarbonylamino]ethyl]carbamate
Canonical SMILES
CC(C)C(C(=O)NC(CCCNC(=O)N)C(=O)NC1=CC=C(C=C1)COC(=O)NCCNC(=O)OC(C)(C)C)NC(=O)CCCCCN2C(=O)C=CC2=O
InChI
InChI=1S/C36H54N8O10/c1-23(2)30(43-27(45)11-7-6-8-21-44-28(46)16-17-29(44)47)32(49)42-26(10-9-18-38-33(37)50)31(48)41-25-14-12-24(13-15-25)22-53-34(51)39-19-20-40-35(52)54-36(3,4)5/h12-17,23,26,30H,6-11,18-22H2,1-5H3,(H,39,51)(H,40,52)(H,41,48)(H,42,49)(H,43,45)(H3,37,38,50)/t26-,30-/m0/s1
InChIKey
NBIUDKXQNRHCFG-YZNIXAGQSA-N

MC-Val-Cit-PAB-NH-C2-NH-Boc is a versatile chemical conjugate that incorporates a peptide linker system, designed for controlled delivery of bioactive compounds, especially in the context of targeted drug delivery. The conjugate consists of a valine-citrulline peptide linker, which can be cleaved by specific enzymes, such as those overexpressed in certain cancers, allowing the release of the attached active compound. The Boc-protected amine at the end of the linker, NH-C2-NH-Boc, is commonly used for further modifications or as a masking group to ensure stability until activation. This structure enhances the conjugate's ability to target specific tissues or cells while minimizing systemic toxicity.

One of the primary applications of MC-Val-Cit-PAB-NH-C2-NH-Boc is in the development of targeted cancer therapies. The peptide linker is designed to be cleaved by enzymes present in the tumor microenvironment, such as specific proteases or enzymes that are overexpressed in cancerous tissues. By attaching cytotoxic agents or therapeutic molecules to the conjugate, these compounds can be selectively activated and released at the tumor site. This ensures that the therapeutic agent is delivered specifically to the cancer cells, improving the drug's efficacy and reducing its impact on healthy tissues.

MC-Val-Cit-PAB-NH-C2-NH-Boc also shows potential in peptide-based drug delivery systems, where it can be used to improve the stability and solubility of bioactive peptides or proteins. Many therapeutic peptides suffer from poor pharmacokinetics, such as rapid degradation or poor absorption. The incorporation of the MC-Val-Cit-PAB-NH-C2-NH-Boc structure can help protect peptides from enzymatic degradation and improve their stability in circulation, while the peptide linker can allow for targeted release of the therapeutic peptide once it reaches its target tissue. This improves the bioavailability and therapeutic efficacy of peptide-based drugs.

Another key application of MC-Val-Cit-PAB-NH-C2-NH-Boc is in the field of gene therapy, particularly in the targeted delivery of gene-modifying agents or RNA therapeutics. By attaching oligonucleotides, siRNA, or other genetic material to the conjugate, the compound can be directed specifically to target cells or tissues with high expression of the relevant enzyme or receptor. This selective delivery system increases the efficiency of gene therapies by ensuring that the genetic material is delivered directly to the cells requiring treatment, while minimizing off-target effects that could result in unintended genetic alterations.

Finally, MC-Val-Cit-PAB-NH-C2-NH-Boc can be utilized in drug discovery and screening applications. The conjugate's flexibility allows for the attachment of a wide variety of bioactive compounds, making it a useful tool for testing new drugs or for exploring novel therapeutic pathways. Researchers can use this conjugate to develop compounds that are specifically activated by certain enzymes or cellular conditions, aiding in the identification of novel drug candidates with selective therapeutic profiles. This targeted approach can improve the success rate of drug discovery efforts, especially for diseases that are difficult to treat with conventional methods.

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

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Historical Records: PNU-159682 | Mal-Phe-C4-VC-PAB-DMEA-PNU-159682 | DMEA-PNU-159682 | MA-PEG4-VC-PAB-DMEA-PNU159682 | PNU159682-EDA | DBCO-PEG4-VC-PAB-DMEA-PNU159682 | VA-PAB-DMEA-PNU159682 | PNU-159682 carboxylic acid | MC-VC-PAB-DMEA-PNU159682 | Mc-Val-Cit-PABC-PNP | MC-Val-Cit-PAB-NH-C2-NH-Boc
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