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Mc-Val-Cit-PABC-PNP

  CAS No.: 159857-81-5   Cat No.: BADC-00501   Purity: >98% 4.5  

Mc-Val-Cit-PABC-PNP is a cleavable ADC linker designed for targeted drug release in tumor microenvironments. Featuring a para-aminobenzyl carbamate (PABC) spacer and PNP leaving group, this valine-citrulline linker is ideal for protease-sensitive antibody-drug conjugates, enabling efficient payload delivery in lysosomal conditions.

Mc-Val-Cit-PABC-PNP

Structure of 159857-81-5

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Category
ADC Linker
Molecular Formula
C35H43N7O11
Molecular Weight
737.76
Shipping
Room temperature
Shipping
Store in a cool and dry place and at 0 - 4°C for short term (days to weeks) or -20°C for long term (months to years).

* For research and manufacturing use only. We do not sell to patients.

Size Price Stock Quantity
25 mg $298 In stock
50 mg $523 In stock

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Popular Publications Citing BOC Sciences Products
Synonyms
[4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methyl (4-nitrophenyl) carbonateMc-Val-Cit-PABC-PNP159857-81-5MC-Val-Cit-PAB-PNPSCHEMBL3205376HYSPJPGXSALJRR-DHIFEGFHSA-NC3
IUPAC Name
Canonical SMILES
CC(C)C(C(=O)NC(CCCNC(=O)N)C(=O)NC1=CC=C(C=C1)COC(=O)OC2=CC=C(C=C2)[N+](=O)[O-])NC(=O)CCCCCN3C(=O)C=CC3=O
InChI
1S/C35H43N7O11/c1-22(2)31(40-28(43)8-4-3-5-20-41-29(44)17-18-30(41)45)33(47)39-27(7-6-19-37-34(36)48)32(46)38-24-11-9-23(10-12-24)21-52-35(49)53-26-15-13-25(14-16-26)42(50)51/h9-18,22,27,31H,3-8,19-21H2,1-2H3,(H,38,46)(H,39,47)(H,40,43)(H3,36,37,48)/t27-,
InChIKey
HYSPJPGXSALJRR-DHIFEGFHSA-N
Density
1.338±0.06 g/cm3
Solubility
Soluble in DMSO, not soluble in water
Flash Point
579.4±34.3 °C
Index Of Refraction
1.599
PSA
261.15000
Vapor Pressure
0.0±0.3 mmHg at 25°C
Appearance
Solid powder
Quantity
Grams-Kilos
Shelf Life
2 years
Shipping
Room temperature
Storage
Store in a cool and dry place and at 0 - 4°C for short term (days to weeks) or -20°C for long term (months to years).
Boiling Point
1034.5±65.0 °C | Condition: Press: 760 Torr
1. EGFR Targeted Cetuximab-Valine-Citrulline (vc)-Doxorubicin Immunoconjugates- Loaded Bovine Serum Albumin (BSA) Nanoparticles for Colorectal Tumor Therapy
Yanyan Liu, Yuanfen Liu, Yue Zhang, Jiasheng Tu, Zixuan Ye, Yan Shen Int J Nanomedicine . 2021 Mar 26;16:2443-2459. doi: 10.2147/IJN.S289228.
Background:Specific modifications to carriers to achieve targeted delivery of chemotherapeutics into malignant tissues are a critical point for efficient diagnosis and therapy. In this case, bovine serum albumin (BSA) was conjugated with cetuximab-valine-citrulline (vc)-doxorubicin (DOX) to target epidermal growth factor receptor (EGFR) and enable the release of drug in EGFR-overexpressed tumor cells.Methods:Maleimidocaproyl-valine-citrulline-p-aminobenzylcarbonyl-p-nitrophenol (MC-Val-Cit-PAB-PNP) and DOX were used to synthesize MC-Val-Cit-PAB-DOX, which was further linked with cetuximab to prepare antibody-drug conjugates (ADCs). Then, the ADCs were adsorbed to the surface of the BSA nanoparticles (NPs), which were prepared by a desolvation method to obtain cetuximab-vc-DOX-BSA-NPs. The cetuximab-vc-DOX conjugates adsorbed on the surface of the BSA nanoparticles were determined and optimized by size exclusion chromatography. An in vitro cytotoxicity study was conducted using a colon carcinoma cell line with different EGFR-expression levels to test the selectivity of cetuximab-vc-DOX-NPs.Results:The vc-DOX and cetuximab-vc-DOX conjugates were both synthesized successfully and their structural characteristics confirmed by1H-NMR and SDS-PAGE. The MTT assay showed stronger cytotoxicity of cetuximab-vc-DOX-NPs versus control IgG-vc-DOX-NPs in EGFR-overexpressing RKO cells. Cellular binding and intracellular accumulation determined by flow cytometry and confocal laser scanning microscopy revealed the strong binding ability of cetuximab-vc-DOX-NPs to RKO cells. The in vivo imaging study demonstrated that cetuximab-vc-DOX-NPs exhibited higher fluorescent intensity in tumor tissues than non-decorated nanoparticles (IgG-vc-DOX-NPs). In vivo tumor inhibition and survival tests showed that cetuximab-vc-DOX-NPs revealed higher tumor inhibition efficacy and lower systemic toxicity than control IgG-vc-DOX- NPs.Conclusion:The obtained results emphasize that cetuximab-vc-DOX-NPs, with good tumor-targeting ability and low systemic toxicity, are a promising targeting system for drug delivery.
2. Cryptophycin-55/52 based antibody-drug conjugates: Synthesis, efficacy, and mode of action studies
Weirong Lai, Mengdan Wu, Jinliang Yang, Lantu Gou, Hao Chen, Yuxi Wang, Yiwen Zhang, Ruixue Wang, Yujia Peng, Cuiyu Guo, Ruirui Zhang, Ying Lu, Yuyin Fu, Wei Liao, Qinhuai Lai, Yuqin Yao, Xiaohua Jiang, Lin Yu, Xin Wang, Tairan Kang, Zhixiong Zhang, Yiran Tao Eur J Med Chem . 2020 Aug 1;199:112364. doi: 10.1016/j.ejmech.2020.112364.
Cryptophycin-52 (CR52), a tubulin inhibitor, exhibits promising antitumor activity in vitro (picomolar level) and in mouse xenograft models. However, the narrow therapeutic window in clinical trials limits its further development. Antibody-drug conjugate (ADC), formed by coupling cytotoxic compound (payload) to an antibody via a linker, can deliver drug to tumor locations in a targeted manner by antibody, enhancing the therapeutic effects and reducing toxic and side effects. In this study, we aim to explore the possibility of CR52-based ADC for tumor targeted therapy. Due to the lack of a coupling site in CR52, its prodrug cryptophycin-55 (CR55) containing a free hydroxyl was synthesized and conjugated to the model antibody trastuzumab (anti-HER2 antibody drug approved by FDA for breast cancer therapy) via the linkers based on Mc-NHS and Mc-Val-Cit-PAB-PNP. The average drug-to-antibody ratios (DARs) of trastuzumab-CR55 conjugates (named T-L1-CR55, T-L2-CR55, and T-L3-CR55) were 3.50, 3.29, and 3.35, respectively. These conjugates exhibited potent cytotoxicity in HER2-positive tumor cell lines with IC50values at low nanomolar levels (0.58-1.19 nM). Further, they displayed significant antitumor activities at the doses of 10 mg/kg in established ovarian cancer (SKOV3) and gastric cancer (NCI-N87) xenograft models without overt toxicities. Finally, the drug releases were analyzed and the results indicated that T-L3-CR55 was able to effectively release CR55 and further epoxidized to CR52, which may be responsible for its best performance in antitumor activities. In conclusion, our results demonstrated that these conjugates have the potential for tumor targeted therapy, which provides insights to further research the CR55/CR52-based ADC for tumor therapy.

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: MMAE-SMCC | 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
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