Leucyl-threonine
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| Category | Others |
| Catalog number | BBF-05165 |
| CAS | 38062-82-7 |
| Molecular Weight | 232.28 |
| Molecular Formula | C10H20N2O4 |
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Specification
| Synonyms | L-leucyl-L-threonine |
| IUPAC Name | 2-[(2-amino-4-methylpentanoyl)amino]-3-hydroxybutanoic acid |
| Canonical SMILES | CC(C)CC(C(=O)NC(C(C)O)C(=O)O)N |
| InChI | InChI=1S/C10H20N2O4/c1-5(2)4-7(11)9(14)12-8(6(3)13)10(15)16/h5-8,13H,4,11H2,1-3H3,(H,12,14)(H,15,16) |
| InChI Key | LRKCBIUDWAXNEG-UHFFFAOYSA-N |
Properties
| Boiling Point | 471.6±45.0°C |
| Density | 1.179±0.06 g/cm3 |
Reference Reading
1. Amphiphilic drug-peptide-polymer conjugates based on poly(ethylene glycol) and hyperbranched polyglycerol for epidermal growth factor receptor targeting: the effect of conjugate aggregation on in vitro activity
Lilla Pethő, György Kasza, Eszter Lajkó, Orsolya Láng, László Kőhidai, Béla Iván, Gábor Mező Soft Matter. 2020 Jun 24;16(24):5759-5769. doi: 10.1039/d0sm00428f.
Numerous peptide-drug conjugates have been developed over the years to enhance the specificity and selectivity of chemotherapeutic agents for tumour cells. In our present work, epidermal growth factor receptor targeting drug-peptide conjugates were prepared using GE11 and D4 peptides. To ensure the drug release, the cathepsin B labile GFLG spacer was incorporated between the targeting peptide and the drug molecule (daunomycin), which significantly increased the hydrophobicity and thereby decreased the water solubility of the conjugates. To overcome the solubility problem, drug-peptide-polymer conjugates with systematic structural variations were prepared, by linking poly(ethylene glycol) (PEG) or a well-defined amino-monofunctional hyperbranched polyglycerol (HbPG) directly or via a pentaglycine spacer to the targeting peptides. All the drug-peptide-polymer conjugates were water-soluble as confirmed by turbidimetric measurements. The results of the in vitro cell viability and cellular uptake measurements on HT-29 human colon adenocarcinoma cells proved that the HbPG and the PEG highly influenced the biological activity. The conjugation of the hydrophilic polymer resulted in the amphiphilic character of the conjugates, which led to self-aggregation and nanoparticle formation that decreased the cellular uptake above a specific aggregation concentration. On the other hand, the hydrodynamic volume and the different polymer chain topology of the linear PEG and the compact hyperbranched HbPG also played an important role in the biological activity. Therefore, in similar systems, the investigation of the colloidal properties is inevitable for the better understanding of the biological activity, which can reveal the structure-activity relationship of amphiphilic drug-peptide-polymer conjugates for efficient tumour targeting.
2. Synthesis, Characterization, and Evaluation of Near-IR Boron Dipyrromethene Bioconjugates for Labeling of Adenocarcinomas by Selectively Targeting the Epidermal Growth Factor Receptor
Nichole E M Kaufman, Qianli Meng, Kaitlin E Griffin, Sitanshu S Singh, Achyut Dahal, Zehua Zhou, Frank R Fronczek, J Michael Mathis, Seetharama D Jois, M Graça H Vicente J Med Chem. 2019 Apr 11;62(7):3323-3335. doi: 10.1021/acs.jmedchem.8b01746. Epub 2019 Mar 25.
A series of five boron dipyrromethene (BODIPY) bioconjugates containing an epidermal growth factor receptor (EGFR)-targeted pegylated LARLLT peptide and/or a glucose or biotin ethylene diamine group were synthesized, and the binding capability of the new conjugates to the extracellular domain of EGFR was investigated using molecular modeling, surface plasmon resonance, fluorescence microscopy, competitive binding assays, and animal studies. The BODIPY conjugates with a LARLLT peptide were found to bind specifically to EGFR, whereas those lacking the peptide bound weakly and nonspecifically. All BODIPY conjugates showed low cytotoxicity (IC50 > 94 μM) in HT-29 cells, both in the dark and upon light activation (1.5 J/cm2). Studies of nude mice bearing subcutaneous human HT-29 xenografts revealed that only BODIPY conjugates bearing the LARLLT peptide showed tumor localization 24 h after intravenous administration. The results of our studies demonstrate that BODIPY bioconjugates bearing the EGFR-targeting peptide 3PEG-LARLLT show promise as near-IR fluorescent imaging agents for colon cancers overexpressing EGFR.
3. Peptide ligands for targeting the extracellular domain of EGFR: Comparison between linear and cyclic peptides
Tyrslai M Williams, Rushikesh Sable, Sitanshu Singh, Maria Graca H Vicente, Seetharama D Jois Chem Biol Drug Des. 2018 Feb;91(2):605-619. doi: 10.1111/cbdd.13125. Epub 2017 Nov 16.
Colorectal cancer (CRC) is the third most common solid internal malignancy among cancers. Early detection of cancer is key to increasing the survival rate of colorectal cancer patients. Overexpression of the EGFR protein is associated with CRC. We have designed a series of peptides that are highly specific for the extracellular domain of EGFR, based on our earlier studies on linear peptides. The previously reported linear peptide LARLLT, known to bind to EGFR, was modified with the goals of increasing its stability and its specificity toward EGFR. Peptide modifications, including D-amino acid substitution, cyclization, and chain reversal, were investigated. In addition, to facilitate labeling of the peptide with a fluorescent dye, an additional lysine residue was introduced onto the linear (KLARLLT) and cyclic peptides cyclo(KLARLLT) (Cyclo.L1). The lysine residue was also converted into an azide group in both a linear and reversed cyclic peptide sequences cyclo(K(N3)larllt) (Cyclo.L1.1) to allow for subsequent "click" conjugation. The cyclic peptides showed enhanced binding to EGFR by SPR. NMR and molecular modeling studies suggest that the peptides acquire a β-turn structure in solution. In vitro stability studies in human serum show that the cyclic peptide is more stable than the linear peptide.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
