Name: MC-Val-Cit-PAB-MMAE
Brand: BOC Sciences
Price: 159 USD
Availability: MadeToOrder

Synonyms

VcMMAE; Maleimidocaproyl-valine-citrulline-p-aminobenzoyloxycarbonyl-monomethyl auristatin E; Vedotin

IUPAC Name

[4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methyl N-[(2S)-1-[[(2S)-1-[[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]-N-methylcarbamate

Canonical SMILES

CCC(C)C(C(CC(=O)N1CCCC1C(C(C)C(=O)NC(C)C(C2=CC=CC=C2)O)OC)OC)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)N(C)C(=O)OCC3=CC=C(C=C3)NC(=O)C(CCCNC(=O)N)NC(=O)C(C(C)C)NC(=O)CCCCCN4C(=O)C=CC4=O

InChI

InChI=1S/C68H105N11O15/c1-15-43(8)59(51(92-13)38-55(83)78-37-23-27-50(78)61(93-14)44(9)62(85)71-45(10)60(84)47-24-18-16-19-25-47)76(11)66(89)57(41(4)5)75-65(88)58(42(6)7)77(12)68(91)94-39-46-29-31-48(32-30-46)72-63(86)49(26-22-35-70-67(69)90)73-64(87)56(40(2)3)74-52(80)28-20-17-21-36-79-53(81)33-34-54(79)82/h16,18-19,24-25,29-34,40-45,49-51,56-61,84H,15,17,20-23,26-28,35-39H2,1-14H3,(H,71,85)(H,72,86)(H,73,87)(H,74,80)(H,75,88)(H3,69,70,90)/t43-,44+,45+,49-,50-,51+,56-,57-,58-,59-,60+,61+/m0/s1

InChIKey

NLMBVBUNULOTNS-HOKPPMCLSA-N

Sequence

VXXVV

Density

1.2±0.1 g/cm3

Solubility

Soluble in DMSO, ethanol; insoluble in water

Flash Point

768.8±34.3 °C

Index Of Refraction

1.556

Vapor Pressure

0.0±0.3 mmHg at 25°C

Appearance

Solid Powder

Shipping

Room temperature, or blue ice upon request.

Storage

2 - 8 °C

Pictograms

Irritant; Acute Toxic

Signal Word

Danger

Boiling Point

1347.6±65.0 °C at 760 mmHg

MC-Val-Cit-PAB-MMAE is a highly effective ADC Cytotoxin with Linker widely utilized in the design and development of antibody-drug conjugates (ADCs) for targeted cancer therapy. This potent ADC Cytotoxin combines monomethyl auristatin E (MMAE) with a maleimide-containing MC-Val-Cit-PAB ADC Linker, ensuring efficient and selective delivery of the ADC payload to malignant cells. The stable linker configuration maintains integrity during systemic circulation while enabling controlled intracellular release, which is essential for maximizing therapeutic efficacy and reducing off-target toxicity in ADC applications and oncology research.

The mechanism of MC-Val-Cit-PAB-MMAE involves antibody-mediated recognition and binding to tumor-specific antigens, followed by internalization into the cancer cell. Once inside the lysosome, proteases such as cathepsin B cleave the Val-Cit-PAB linker, releasing the MMAE payload to disrupt microtubule dynamics, ultimately inducing apoptosis in tumor cells. This process highlights the critical role of the ADC payload-linker combination in achieving targeted cytotoxicity. Researchers utilize MC-Val-Cit-PAB-MMAE for assessing ADC efficacy, linker stability, and selective payload delivery, making it a key component for advanced ADC development and translational oncology studies.

MC-Val-Cit-PAB-MMAE also supports versatile ADC bioconjugation strategies thanks to its maleimide functional group, which enables stable coupling with various monoclonal antibodies. The protease-cleavable linker improves intracellular payload release while minimizing systemic exposure, addressing common challenges in ADC design, formulation, and optimization. Its design and functional properties make MC-Val-Cit-PAB-MMAE an indispensable tool for researchers exploring novel ADC payloads, next-generation linker technologies, and tumor-targeted therapeutic strategies.

Applications of MC-Val-Cit-PAB-MMAE include preclinical evaluation of antibody-drug conjugates, ADC linker stability studies, and targeted cytotoxicity assays. It is widely used in research for oncology therapeutics, bioconjugation chemistry, and translational cancer studies, providing a reliable platform to optimize ADC payload delivery, linker cleavage efficiency, and selective cytotoxicity.

1.Cathepsin B Cleavage of vcMMAE-Based Antibody-Drug Conjugate Is Not Drug Location or Monoclonal Antibody Carrier Specific.

Gikanga B1, Adeniji NS1, Patapoff TW1, Chih HW1, Yi L1. Bioconjug Chem. 2016 Apr 20;27(4):1040-9. doi: 10.1021/acs.bioconjchem.6b00055. Epub 2016 Mar 10.

Antibody-drug conjugates (ADCs) require thorough characterization and understanding of product quality attributes. The framework of many ADCs comprises one molecule of antibody that is usually conjugated with multiple drug molecules at various locations. It is unknown whether the drug release rate from the ADC is dependent on drug location, and/or local environment, dictated by the sequence and structure of the antibody carrier. This study addresses these issues with valine-citrulline-monomethylauristatin E (vc-MMAE)-based ADC molecules conjugated at reduced disulfide bonds, by evaluating the cathepsin B catalyzed drug release rate of ADC molecules with different drug distributions or antibody carriers. MMAE drug release rates at different locations on ADC I were compared to evaluate the impact of drug location. No difference in rates was observed for drug released from the VH, VL, or CH2 domains of ADC I. Furthermore, four vc-MMAE ADC molecules were chosen as substrates for cathepsin B for evaluation of Michaelis-Menten parameters.

HPLC

Catalog	Product Name	CAS
BADC-00019	Fmoc-VC-PAB-MMAE	1350456-56-2
BADC-00849	Acetylene-linker-Val-Cit-PABC-MMAE	1411977-95-1
BADC-01448	mDPR-Val-Cit-PAB-MMAE	1491152-26-1
BADC-00958	Amino-PEG4-Val-Cit-PAB-MMAE	1492056-71-9
BADC-01348	Val-Cit-PAB-MMAE TFA salt	1608127-32-7
BADC-01435	N-Ac-Cys-MC-VC-PAB-MMAE	1628933-80-1
BADC-01408	DBM(C6)-VC-PAB-MMAE	1644228-55-6
BADC-01459	MC-betaglucuronide-MMAE-1	1703778-92-0
BADC-01638	OH-Glu-Val-Cit-PAB-MMAE	1895916-23-0
BADC-00855	SuO-Glu-Val-Cit-PAB-MMAE	1895916-24-1

What is MC-Val-Cit-PAB-MMAE?

MC-Val-Cit-PAB-MMAE is a protease-cleavable linker-payload conjugate widely used in antibody-drug conjugates (ADCs). It combines a valine-citrulline dipeptide linker with MMAE, a potent cytotoxin, allowing targeted drug release upon internalization in tumor cells.

10/7/2018

Could you explain how MC-Val-Cit-PAB-MMAE functions in ADCs?

The MC-Val-Cit-PAB-MMAE conjugate remains stable in systemic circulation and releases MMAE selectively in lysosomes after protease cleavage. This mechanism ensures targeted cytotoxicity while minimizing off-target effects.

2/7/2019

Good morning! What are the common applications of MC-Val-Cit-PAB-MMAE in research?

MC-Val-Cit-PAB-MMAE is primarily utilized in the development of ADCs for oncology research, providing a reliable payload for preclinical and clinical studies targeting various tumor antigens.

4/8/2016

May I ask if MC-Val-Cit-PAB-MMAE can be customized for different antibodies?

Yes, MC-Val-Cit-PAB-MMAE can be conjugated to different monoclonal antibodies depending on the desired target antigen, enabling flexibility in ADC design and experimental strategies.

16/6/2021

Dear team, what precautions should we take when handling MC-Val-Cit-PAB-MMAE?

MC-Val-Cit-PAB-MMAE should be handled with standard laboratory safety protocols for cytotoxic compounds, including protective equipment, containment, and proper waste disposal to prevent exposure.

16/9/2018

— Dr. Kevin Wallace, Senior Scientist (USA)

MC-Val-Cit-PAB-MMAE exhibited high purity and stability, critical for reproducible ADC payload attachment.

4/8/2016

— Dr. Emma Collins, ADC Researcher (UK)

Batch uniformity of MC-Val-Cit-PAB-MMAE allowed multiple assay replicates without variation.

16/9/2018

— Dr. Hans Bauer, Medicinal Chemist (Germany)

Fast shipment and well-documented QC for MC-Val-Cit-PAB-MMAE supported efficient lab planning.

16/6/2021

— Dr. Laura King, Biochemist (Canada)

Technical support for MC-Val-Cit-PAB-MMAE helped optimize conjugation efficiency.