Transport of the areca nut alkaloid arecaidine by the human proton-coupled amino acid transporter 1 (hPAT1)

Journal of Pharmacy and Pharmacology

Volumn 65, Issue 4, 2013, Pages 582-590

  Voigt, Valerie ^a   Laug, Linda ^a   Zebisch, Katja ^a   Thondorf, Iris ^a   Markwardt, Fritz ^a   Brandsch, Matthias ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

betel nut; Caco 2 cells; HeLa cells; SLC36A1; Xenopus laevis oocytes

Indexed keywords

AMINO ACID TRANSPORTER; ARECAIDINE; ARECOLINE; GUVACINE; PROLINE; PROTON COUPLED AMINO ACID TRANSPORTER 1; UNCLASSIFIED DRUG;

AMINO ACID TRANSPORT; ANIMAL CELL; ARTICLE; CELL MEMBRANE TRANSPORT; CELL STRAIN CACO 2; COMPETITIVE INHIBITION; CONTROLLED STUDY; HELA CELL; HETEROLOGOUS EXPRESSION; MEMBRANE TRANSPORT; NONHUMAN; OOCYTE; XENOPUS LAEVIS;

AMINO ACID TRANSPORT SYSTEMS; ANIMALS; ARECA; ARECOLINE; BINDING, COMPETITIVE; BIOLOGICAL TRANSPORT; CACO-2 CELLS; DRUGS, INVESTIGATIONAL; ENTEROCYTES; FEMALE; GABA AGONISTS; GABA UPTAKE INHIBITORS; HELA CELLS; HUMANS; INTESTINAL ABSORPTION; ISONICOTINIC ACIDS; KINETICS; NICOTINIC ACIDS; NUTS; OOCYTES; RECOMBINANT PROTEINS; SYMPORTERS; XENOPUS LAEVIS;

EID: 84875277344     PISSN: 00223573     EISSN: 20427158     Source Type: Journal    
DOI: 10.1111/jphp.12006     Document Type: Article

References (39)

1. IARC Working. Group on the evaluation of carcinogenic risks to humans. Betel-quid and areca-nut chewing and some areca-nut derived nitrosamines. IARC Monogr Eval Carcinog Risks Hum 2004; 85: 1-334.
2. Wang CK, et al,. Chemical composition and toxicity of Taiwanese betel quid extract. Food Chem Toxicol 1999; 37: 135-144.
3. Yuan J, et al,. Alkaloids from areca (betel) nuts and their effects on human sperm motility in vitro. J Food Sci 2012; 77: T70-T78.
4. Chu NS,. Effects of betel chewing on the central and autonomic nervous systems. J Biomed Sci 2001; 8: 229-236.
5. Nieschulz O,. (Pharmacology of the active substances in betel. 3. Experiments with arecaidine). Arzneimittelforschung 1970; 20: 218-229 (in German).
6. Johnston GA, et al,. Betel nut constituents as inhibitors of γ-aminobutyric acid uptake. Nature 1975; 258: 627-628.
7. Krogsgaard-Larsen P, et al,. A new class of GABA agonist. Nature 1977; 268: 53-55.
8. Nieschulz O, Schmersahl P,. (On the pharmacology of active materials from betel. 2. Transformation of arecoline to arecaidine.). Arzneimittelforschung 1968; 18: 222-225 (in German).
9. Boyland E, Nery R,. Mercapturic acid formation during the metabolism of arecoline and arecaidine in the rat. Biochem J 1969; 113: 123-130.
10. Boll M, et al,. The SLC36 family: proton-coupled transporters for the absorption of selected amino acids from extracellular and intracellular proteolysis. Pflügers Arch 2004; 447: 776-779.
11. Thwaites DT, Anderson CM,. Deciphering the mechanisms of intestinal imino (and amino) acid transport: the redemption of SLC36A1. Biochim Biophys Acta 2007; 1768: 179-197.
12. Thwaites DT, Anderson CM,. The SLC36 family of proton-coupled amino acid transporters and their potential role in drug transport. Br J Pharmacol 2011; 164: 1802-1816.
13. Sagné C, et al,. Identification and characterization of a lysosomal transporter for small neutral amino acids. Proc Natl Acad Sci U S A 2001; 98: 7206-7211.
14. Boll M, et al,. Functional characterization of two novel mammalian electrogenic proton-dependent amino acid cotransporters. J Biol Chem 2002; 277: 22966-22973.
15. Chen Z, et al,. Structure, function and immunolocalization of a proton-coupled amino acid transporter (hPAT1) in the human intestinal cell line Caco-2. J Physiol 2003; 546: 349-361.
16. +-independent) proline transport in human intestinal (Caco-2) epithelial cell monolayers. FEBS Lett 1993; 333: 78-82.
17. Metzner L, et al,. Transport of pharmacologically active proline derivatives by the human proton-coupled amino acid transporter hPAT1. J Pharmacol Exp Ther 2004; 309: 28-35.
18. +/amino acid transporter 1 (PAT1) is the imino acid carrier: an intestinal nutrient/drug transporter in human and rat. Gastroenterology 2004; 127: 1410-1422.
19. Metzner L, et al,. Mutational analysis of histidine residues in the human proton-coupled amino acid transporter PAT1. Biochim Biophys Acta 2008; 1778: 1042-1050.
20. Dorn M, et al,. Identification of a disulfide bridge essential for transport function of the human proton-coupled amino acid transporter hPAT1. J Biol Chem 2009; 284: 22123-22132.
21. Boll M, et al,. Substrate recognition by the mammalian proton-dependent amino acid transporter PAT1. Mol Membr Biol 2003; 20: 261-269.
22. + and substrate transport by the proton-dependent amino acid symporter PAT1. Biochem J 2005; 386: 607-616.
23. Broberg ML, et al,. Function and expression of the proton-coupled amino acid transporter Slc36a1 along the rat gastrointestinal tract: implications for intestinal absorption of gaboxadol. Br J Pharmacol 2012; 167: 654-665.
24. Larsen M, et al,. Intestinal gaboxadol absorption via PAT1 (SLC36A1): modified absorption in vivo following co-administration of L-tryptophan. Br J Pharmacol 2009; 157: 1380-1389.
25. --dependent TauT (SLC6A6). J Physiol 2009; 587: 731-744.
26. Metzner L, et al,. The orally active antihyperglycemic drug β-guanidinopropionic acid is transported by the human proton-coupled amino acid transporter hPAT1. Mol Pharm 2009; 6: 1006-1011.
27. 50 values of the three ionic species of gaboxadol. Eur J Pharm Sci 2011; 42: 192-198.
28. +-coupled amino-acid transporter hPAT1. Br J Pharmacol 2006; 147: 298-306.
29. +-coupled nutrient carriers coexpressed in the small intestine. J Pharmacol Exp Ther 2010; 332: 220-228.
30. Frølund S, et al,. δ-aminolevulinic acid is a substrate for the amino acid transporter SLC36A1 (hPAT1). Br J Pharmacol 2010; 159: 1339-1353.
31. Thondorf I, et al,. Three-dimensional quantitative structure-activity relationship analyses of substrates of the human proton-coupled amino acid transporter 1 (hPAT1). Bioorg Med Chem 2011; 19: 6409-6418.
32. Metzner L, et al,. Serotonin, L-tryptophan and tryptamine are effective inhibitors of the human amino acid transport system PAT1. FASEB J 2005; 19: 1468-1473.
33. Brandsch M,. Transport of drugs by proton-coupled peptide transporters: pearls and pitfalls. Expert Opin Drug Metab Toxicol 2009; 5: 887-905.
34. Geissler S, et al,. Synthesis and intestinal transport of the iron chelator maltosine in free and dipeptide form. Eur J Pharm Biopharm 2011; 78: 75-82.
35. Edwards N, et al,. Amino acid derivatives are substrates or non-transported inhibitors of the amino acid transporter PAT2 (slc36a2). Biochim Biophys Acta 2011; 1808: 260-270.
36. Lee CH, et al,. Population burden of betel quid abuse and its relation to oral premalignant disorders in South, Southeast, and East Asia: an Asian betel-quid consortium study. Am J Public Health 2012; 102: e17-e24.
37. Lin SH, et al,. Hypercalcaemia and metabolic alkalosis with betel nut chewing: emphasis on its integrative pathophysiology. Nephrol Dial Transplant 2002; 17: 708-714.
38. Wu KD, et al,. The milk-alkali syndrome caused by betelnuts in oyster shell paste. J Toxicol Clin Toxicol 1996; 34: 741-745.
39. Nielsen CU, et al,. Carrier-mediated γ-aminobutyric acid transport across the basolateral membrane of human intestinal Caco-2 cell monolayers. Eur J Pharm Biopharm 2012; 81: 458-462.