Val-cit-PAB-OH is a peptide prodrug linker used for the synthesis of ADC durgs such as MC-Val-Cit-PAB (MC-Val-Cit-PAB-OH).MC-Val-Cit-PAB is a novel cathepsin cleavable ADC linker that is utilized for the synthesis of antibody-drug conjugate (ADC) such as some of the FDA approved ADC drugs including brentuximab vedotin. The mechanism is like this: the Val-Cit will specifically be cleaved by catepsin B as this enzyme is only present in the lysosome, the ADC warhead/payload (the drug) will be released in the cell. The Azido group will react with DBCO, BCN or other Alkyne groups through click chemistry. The hydrophilic PEG spacer increases solubility in aqueous media.
Physicochemical Properties
| Molecular Formula | C18H29N5O4 |
| Molecular Weight | 379.45396 |
| Exact Mass | 379.22 |
| Elemental Analysis | C, 56.98; H, 7.70; N, 18.46; O, 16.86 |
| CAS # | 159857-79-1 |
| Related CAS # | Val-cit-PAB-OH;159857-79-1 |
| PubChem CID | 54387473 |
| Appearance | White to off-white solid powder |
| LogP | -0.5 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 10 |
| Heavy Atom Count | 27 |
| Complexity | 492 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | CC(C)[C@@H](C(=O)N[C@@H](CCCNC(=O)N)C(=O)NC1=CC=C(C=C1)CO)N |
| InChi Key | VEGGTWZUZGZKHY-GJZGRUSLSA-N |
| InChi Code | InChI=1S/C18H29N5O4/c1-11(2)15(19)17(26)23-14(4-3-9-21-18(20)27)16(25)22-13-7-5-12(10-24)6-8-13/h5-8,11,14-15,24H,3-4,9-10,19H2,1-2H3,(H,22,25)(H,23,26)(H3,20,21,27)/t14-,15-/m0/s1 |
| Chemical Name | (S)-2-((S)-2-amino-3-methylbutanamido)-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide |
| Synonyms | Val-cit-PAB-OH; Val-Cit-PAB |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets |
Protease Cleavable Linker Cleavable Linker |
| References | Adv Protein Chem Struct Biol. 2015;98:1-55. |
Solubility Data
| Solubility (In Vitro) | DMSO : ≥ 100 mg/mL (~263.54 mM) |
| Solubility (In Vivo) | 10% DMSO+ 40% PEG300+ 5% Tween-80+ 45% Saline: ≥ 2.08 mg/mL (5.48 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6354 mL | 13.1770 mL | 26.3539 mL | |
| 5 mM | 0.5271 mL | 2.6354 mL | 5.2708 mL | |
| 10 mM | 0.2635 mL | 1.3177 mL | 2.6354 mL |