Phe-Leu-OH (BAT-006530)
* For research use only

Category
Others
Catalog number
BAT-006530
CAS number
3303-55-7
Molecular Formula
C15H22N2O3
Molecular Weight
278.35
Phe-Leu-OH
Synonyms
L-Phenylalanyl-L-leucine; 2-(2-Amino-3-phenyl-propionylamino)-4-methyl-pentanoic acid; (S)-2-((S)-2-amino-3-phenylpropanamido)-4-methylpentanoic acid; (2S)-2-((2S)-2-amino-3-phenylpropanoylamino)-4-methylpentanoic acid; Phe Leu OH
Appearance
White to off-white powder
Purity
≥ 95% (HPLC)
Density
1.144 g/cm3
Melting Point
258-260 °C
Boiling Point
516.2°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C15H22N2O3/c1-10(2)8-13(15(19)20)17-14(18)12(16)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9,16H2,1-2H3,(H,17,18)(H,19,20)/t12-,13-/m0/s1
InChI Key
RFCVXVPWSPOMFJ-STQMWFEESA-N
Canonical SMILES
CC(C)CC(C(=O)O)NC(=O)C(CC1=CC=CC=C1)N
1.Enzyme-triggered delivery of chlorambucil from conjugates based on the cell-penetrating peptide BP16.
Soler M1, González-Bártulos M, Figueras E, Ribas X, Costas M, Massaguer A, Planas M, Feliu L. Org Biomol Chem. 2015 Feb 7;13(5):1470-80. doi: 10.1039/c4ob01875c.
The undecapeptide KKLFKKILKKL-NH2 (BP16) is a non-toxic cell-penetrating peptide (CPP) that is mainly internalized into cancer cells through a clathrin dependent endocytic mechanism and localizes in late endosomes. Moreover, this CPP is able to enhance the cellular uptake of chlorambucil (CLB) improving its cytotoxicity. In this work, we further explored the cell-penetrating properties of BP16 and those of its arginine analogue BP308. We investigated the influence on the cytotoxicity and on the cellular uptake of conjugating CLB at the N- or the C-terminal end of these undecapeptides. The effect of incorporating the cathepsin B-cleavable sequence Gly-Phe-Leu-Gly in CLB-BP16 and CLB-BP308 conjugates was also evaluated. The activity of CLB was significantly improved when conjugated at the N- or the C-terminus of BP16, or at the N-terminus of BP308. While CLB alone was not active (IC50 of 73.7 to >100 μM), the resulting conjugates displayed cytotoxic activity against CAPAN-1, MCF-7, PC-3, 1BR3G and SKMEL-28 cell lines with IC50 values ranging from 8.
2.Micro-opioid receptor activation in the basolateral amygdala mediates the learning of increases but not decreases in the incentive value of a food reward.
Wassum KM1, Cely IC, Balleine BW, Maidment NT. J Neurosci. 2011 Feb 2;31(5):1591-9. doi: 10.1523/JNEUROSCI.3102-10.2011.
The decision to perform, or not perform, actions known to lead to a rewarding outcome is strongly influenced by the current incentive value of the reward. Incentive value is largely determined by the affective experience derived during previous consumption of the reward-the process of incentive learning. We trained rats on a two-lever, seeking-taking chain paradigm for sucrose reward, in which responding on the initial seeking lever of the chain was demonstrably controlled by the incentive value of the reward. We found that infusion of the μ-opioid receptor antagonist, CTOP (d-Phe-Cys-Tyr-d-Trp-Orn-Thr-Pen-Thr-NH(2)), into the basolateral amygdala (BLA) during posttraining, noncontingent consumption of sucrose in a novel elevated-hunger state (a positive incentive learning opportunity) blocked the encoding of incentive value information normally used to increase subsequent sucrose-seeking responses. Similar treatment with δ [N, N-diallyl-Tyr-Aib-Aib-Phe-Leu-OH (ICI 174,864)] or κ [5'-guanidinonaltrindole (GNTI)] antagonists was without effect.
3.Enzyme-responsive doxorubicin release from dendrimer nanoparticles for anticancer drug delivery.
Lee SJ1, Jeong YI2, Park HK3, Kang DH4, Oh JS3, Lee SG5, Lee HC3. Int J Nanomedicine. 2015 Aug 28;10:5489-503. doi: 10.2147/IJN.S87145. eCollection 2015.
BACKGROUND: Since cancer cells are normally over-expressed cathepsin B, we synthesized dendrimer-methoxy poly(ethylene glycol) (MPEG)-doxorubicin (DOX) conjugates using a cathepsin B-cleavable peptide for anticancer drug targeting.
4.Discovery of mitocryptide-1, a neutrophil-activating cryptide from healthy porcine heart.
Mukai H1, Hokari Y, Seki T, Takao T, Kubota M, Matsuo Y, Tsukagoshi H, Kato M, Kimura H, Shimonishi Y, Kiso Y, Nishi Y, Wakamatsu K, Munekata E. J Biol Chem. 2008 Nov 7;283(45):30596-605. doi: 10.1074/jbc.M803913200. Epub 2008 Sep 3.
Although neutrophils are known to migrate in response to various chemokines and complement factors, the substances involved in the early stages of their transmigration and activation have been poorly characterized to date. Here we report the discovery of a peptide isolated from healthy porcine hearts that activated neutrophils. Its primary structure is H-Leu-Ser-Phe-Leu-Ile-Pro-Ala-Gly-Trp-Val-Leu-Ser-His-Leu-Asp-His-Tyr-Lys-Arg-Ser-Ser-Ala-Ala-OH, and it was indicated to originate from mitochondrial cytochrome c oxidase subunit VIII. This peptide caused chemotaxis at concentrations lower than that inducing beta-hexosaminidase release. Such responses were observed in neutrophilic/granulocytic differentiated HL-60 cells but not in undifferentiated cells, and G(i2)-type G proteins were suggested to be involved in the peptide signaling. Moreover the peptide activated human neutrophils to induce beta-hexosaminidase secretion. A number of other amphipathic neutrophil-activating peptides presumably originating from mitochondrial proteins were also found.
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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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