β-Ala-Lys-AMCA   Click here for help

GtoPdb Ligand ID: 9501

Synonyms: β-alanyl-lysyl-N-7-amino-4-methylcoumarin-3-acetic acid | Beta-Ala-Lys-N(epsilon)-AMCA
 Ligand is labelled
Comment: A fluorescent dipeptide.
2D Structure
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SMILES / InChI / InChIKey
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Canonical SMILES NCCC(=O)NC(C(=O)O)CCCCNC(=O)Cc1c(=O)oc2c(c1C)ccc(c2)N
Isomeric SMILES NCCC(=O)N[C@H](C(=O)O)CCCCNC(=O)Cc1c(=O)oc2c(c1C)ccc(c2)N
InChI InChI=1S/C21H28N4O6/c1-12-14-6-5-13(23)10-17(14)31-21(30)15(12)11-19(27)24-9-3-2-4-16(20(28)29)25-18(26)7-8-22/h5-6,10,16H,2-4,7-9,11,22-23H2,1H3,(H,24,27)(H,25,26)(H,28,29)/t16-/m0/s1
InChI Key BXZFTTVQAOLWHY-INIZCTEOSA-N
References
1. Agu R, Cowley E, Shao D, Macdonald C, Kirkpatrick D, Renton K, Massoud E. (2011)
Proton-coupled oligopeptide transporter (POT) family expression in human nasal epithelium and their drug transport potential.
Mol Pharm, 8 (3): 664-72. [PMID:21366347]
2. Dieck ST, Heuer H, Ehrchen J, Otto C, Bauer K. (1999)
The peptide transporter PepT2 is expressed in rat brain and mediates the accumulation of the fluorescent dipeptide derivative beta-Ala-Lys-Nepsilon-AMCA in astrocytes.
Glia, 25 (1): 10-20. [PMID:9888294]
3. Iwao T, Toyota M, Miyagawa Y, Okita H, Kiyokawa N, Akutsu H, Umezawa A, Nagata K, Matsunaga T. (2014)
Differentiation of human induced pluripotent stem cells into functional enterocyte-like cells using a simple method.
Drug Metab Pharmacokinet, 29 (1): 44-51. [PMID:23822979]
4. Kottra G, Spanier B, Verri T, Daniel H. (2013)
Peptide transporter isoforms are discriminated by the fluorophore-conjugated dipeptides β-Ala- and d-Ala-Lys-N-7-amino-4-methylcoumarin-3-acetic acid.
Physiol Rep, 1 (7): e00165. [PMID:24744852]
5. Romano A, Barca A, Kottra G, Daniel H, Storelli C, Verri T. (2010)
Functional expression of SLC15 peptide transporters in rat thyroid follicular cells.
Mol Cell Endocrinol, 315 (1-2): 174-81. [PMID:19913073]
6. Rühl A, Hoppe S, Frey I, Daniel H, Schemann M. (2005)
Functional expression of the peptide transporter PEPT2 in the mammalian enteric nervous system.
J Comp Neurol, 490 (1): 1-11. [PMID:16041713]
7. Sun D, Wang Y, Tan F, Fang D, Hu Y, Smith DE, Jiang H. (2013)
Functional and molecular expression of the proton-coupled oligopeptide transporters in spleen and macrophages from mouse and human.
Mol Pharm, 10 (4): 1409-16. [PMID:23442152]
8. Zimmermann M, Kappert K, Stan AC. (2010)
U373-MG cells express PepT2 and accumulate the fluorescently tagged dipeptide-derivative β-Ala-Lys-N(ε)-AMCA.
Neurosci Lett, 486 (3): 174-8. [PMID:20868728]
9. Zimmermann M, Stan AC. (2010)
PepT2 transporter protein expression in human neoplastic glial cells and mediation of fluorescently tagged dipeptide derivative beta-Ala-Lys-Nepsilon-7-amino-4-methyl-coumarin-3-acetic acid accumulation.
J Neurosurg, 112 (5): 1005-14. [PMID:19612975]