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
Compound class: Peptide or derivative
Comment: A fluorescent dipeptide.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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. Alghamdi O, King N, Jones GL, Moens PDJ. (2021)
Effect of ageing and hypertension on the expression and activity of PEPT2 in normal and hypertrophic hearts.
Amino Acids, 53 (2): 183-193. [PMID:33404911]
3. Alghamdi OA, King N, Andronicos NM, Jones GL, Chami B, Witting PK, Moens PDJ. (2022)
Hypertension alters the function and expression profile of the peptide cotransporters PEPT1 and PEPT2 in the rodent renal proximal tubule.
Amino Acids, 54 (7): 1001-1011. [PMID:35386060]
4. 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]
5. 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]
6. 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]
7. 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]
8. 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]
9. 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]
10. Takano M, Kuriyama S, Kameda N, Kawami M, Yumoto R. (2022)
Effect of Corticosteroids on Peptide Transporter 2 Function and Induction of Innate Immune Response by Bacterial Peptides in Alveolar Epithelial Cells.
Biol Pharm Bull, 45 (2): 213-219. [PMID:35110509]
11. 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]
12. 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]