3-(1-Naphthyl)-D-alanine (BAT-007797)

Category
D-Amino Acids
Catalog number
BAT-007797
CAS number
78306-92-0
Molecular Formula
C13H13NO2
Molecular Weight
215.25
3-(1-Naphthyl)-D-alanine
Synonyms
D-3-Ala(1-naphthyl)-OH; (R)-2-Amino-3-(naphthalen-1-yl)propanoic acid; D-1-Naphthylalanine; (R)-2-AMINO-3-(NAPHTHALEN-1-YL)PROPANOIC ACID; H-D-1-Nal-OH; 3-(1-NAPHTHYL)-D-ALA; (2R)-2-amino-3-(naphthalen-1-yl)propanoic acid
Related CAS
122745-09-9 (hydrochloride)
Appearance
Off-white powder
Purity
≥ 98% (HPLC)
Density
1.254±0.06 g/cm3 (Predicted)
Melting Point
215-219 °C
Boiling Point
412.3±33.0 °C (Predicted)
Storage
Store at 2-8 °C
1.[D-1-Nal4]endomorphin-2 is a potent micro-opioid receptor antagonist in the aequorin luminescence-based calcium assay.
Fichna J1, Piestrzeniewicz M, Gach K, Poels J, Burgeon E, Vanden Broeck J, Janecka A. Life Sci. 2006 Aug 8;79(11):1094-9. Epub 2006 Mar 21.
A functional assay, based on aequorin-derived luminescence triggered by receptor-mediated changes in Ca(2+) levels, was used to examine relative potency and efficacy of the micro-opioid receptor antagonists. A series of position 3- and 4-substituted endomorphin-2 (Tyr-Pro-Phe-Phe-NH(2)) analogues containing D-3-(1-naphthyl)-alanine (D-1-Nal) or D-3-(2-naphthyl)-alanine (D-2-Nal), which were previously shown to reverse antinociception induced by endomorphin-2 in the in vivo hot-plate test in mice, was tested in the aequorin luminescence-based calcium assay to examine their micro-opioid antagonist potency in vitro. A recombinant mammalian cell line expressing the micro-opioid receptor together with a luminescent reporter protein, apoaequorin, was used in the study. The results obtained in this functional assay indicated that analogues with D-1-Nal or D-2-Nal substitutions in position 4 of endomorphin-2 are strong micro-opioid receptor antagonists, while those substituted in position 3 are partial agonists.
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