Addition of amino acid moieties to lapatinib increases the anti-cancer effect via amino acid transporters

Biopharmaceutics and Drug Disposition

Volumn 35, Issue 1, 2014, Pages 60-69

  Maeng, Han Joo ^a   Kim, Eun Seo ^b   Chough, Chieyeon ^c   Joung, Misuk ^c   Lim, Jee Woong ^c   Shim, Chang Koo ^b   Shim, Won Sik ^d  

^a Inje University   (South Korea)

^b Seoul National University   (South Korea)

^c Yangji Chemical Co Ltd   (South Korea)

^d Gachon University   (South Korea)

Author keywords

amino acid transporters; cancer cells; lapatinib; multi drug resistance (MDR); tyr lapatinib; val lapatinib

Indexed keywords

ANTINEOPLASTIC AGENT; GLUTAMINE; LAPATINIB; TYROSINE; VALINE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL; CANCER CELL CULTURE; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG CONJUGATION; HUMAN; HUMAN CELL; LUNG CANCER; PROTEIN INTERACTION;

AMINO ACID TRANSPORTERS; CANCER CELLS; LAPATINIB; MULTI-DRUG RESISTANCE (MDR); TYR-LAPATINIB; VAL-LAPATINIB;

AMINO ACID TRANSPORT SYSTEMS; ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; DOGS; GLUTAMINE; HUMANS; MADIN DARBY CANINE KIDNEY CELLS; PROTEIN KINASE INHIBITORS; QUINAZOLINES; TYROSINE; VALINE;

EID: 84892188813     PISSN: 01422782     EISSN: 1099081X     Source Type: Journal    
DOI: 10.1002/bdd.1872     Document Type: Article

References (34)

1. Sharom FJ,. ABC multidrug transporters: structure, function and role in chemoresistance. Pharmacogenomics 2008; 9: 105-127.
2. Medina MA, Sanchez-Jimenez F, Marquez J,. Rodriguez Qusada A, Nunez de Castro I. Relevance of glutamine metabolism to tumor cell growth. Mol Cell Biochem 1992; 113: 1-15.
3. Fuchs BC, Bode BP,. Amino acid transporters ASCT2 and LAT1 in cancer: partners in crime? Semin Cancer Biol 2005; 15: 254-266.
4. Song X, Lorenzi PL, Landowski CP, Vig BS, Hilfinger JM, Amidon GL,. Amino acid ester prodrugs of the anticancer agent gemcitabine: synthesis, bioconversion, metabolic bioevasion, and hPEPT1-mediated transport. Mol Pharm 2005; 2: 157-167.
5. Landwoski CP, Song X, Lorenzi PL, Hilfinger JM, Amidon GL,. Floxuridine amino acid ester prodrugs: enhancing Caco-2 permeability and resistance to glycosidic bond metabolism. Pharm Res 2005; 22: 1510-1518.
6. Landwoski CP, Vig BS, Song X, Amidon GL,. Targeted delivery to PEPT1-overexpressing cells: acidic, basic, and secondary floxuridine amino acid ester prodrugs. Mol Cancer Ther 2005; 4: 659-667.
7. Tsume Y, Hilfinger JM, Amidon GL,. Enhanced cancer cell growth inhibition by dipeptide prodrugs of floxuridine: increased transporter affinity and metabolic stability. Mol Pharm 2008; 5: 717-727.
8. Tsume Y, Vig BS, Sun J, et al,. Enhanced absorption and growth inhibition with amino acid monoester prodrugs of floxuridine by targeting hPEPT1 transporters. Molecules 2008; 13: 1441-1454.
9. Kwak EY, Shim WS, Chang JE, et al,. Enhanced intracellular accumulation of a non-nucleoside anti-cancer agent via increased uptake of its valine ester prodrug through amino acid transporters. Xenobiotica 2012; 42: 603-613.
10. Bence AK, Anderson EB, Halepota MA, et al,. Phase I pharmacokinetic studies evaluating single and multiple doses of oral GW572016, a dual EGFR-ErbB2 inhibitor, in healthy subjects. Invest New Drugs 2005; 23: 39-49.
11. Geyer CE, Forster J, Lindquist D, et al,. Lapatinib plus capecitabine for HER2-positive advanced breast cancer. N Engl J Med 2006; 355: 2733-2743.
12. Polli JW, Humphreys JE, Harmon KA, et al,. The role of efflux and uptake transporters in N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2- (methylsulfonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamine (GW572016, Lapatinib) disposition and drug interactions. Drug Metab Dispos 2008; 36: 695-701.
13. Choi HK, Choi S, Lee Y, et al,. Non-vanilyl resiniferatoxin analogues as potent and metabolically stable transient receptor portential vanilloid 1 agonists. Bioorg Med Chem 2009; 17: 690-698.
14. Takabatake D, Fujita T, Shien T, et al,. Tumor inhibitory effect of gefitib (ZD1839, Iressa) and taxane combination therapy in EGFR-overexpressing breast cancer cell lines (MCF7/ADR, MDA-MB-231). Int J Cancer 2007; 120: 181-188.
15. Zhang Y, Qin K, Wang J, Hung T, Zhao RY,. Dividing roles of prion protein in staurosporine-mediated apotosis. Biochem Biophys Res Commun 2006; 349: 759-768.
16. Umapathy NS, Dun Y, Martin PM, et al,. Expression and function of system N glutamine transporters (SN1/SN2 or SNAT3/SNAT5) in retinal ganglion cells. Invest Ophthalmol Vis Sci 2008; 49: 5151-5160.
17. Yanagida O, Kanai Y, Chairoungdua A, et al,. Human l -type amino acid transporter 1 (LAT1): characterization of function and expression in tumor cell lines. Biochim Biophys Acta 2001; 1514: 291-302.
18. Endo M, Miwa M, Ura M, et al,. A water soluble prodrug of a novle camptothecin analog is efficacious against breast cancer resistance protein-expressing tumor xenografts. Cancer Chemother Pharmacol 2010; 65: 363-371.
19. Adams DJ, Waud WR, Wani MC, et al,. BACPTDP: a water-soluble camptothecin pro-drug with enhanced activity in hypoxia/acidic tumors. Cancer Chemother Pharmacol 2011; 67: 855-865.
20. Ferquson MJ, Ahmed FY, Cassidy J,. The role of pro-drug therapy in the treatment of cancer. Drug Resist Update 2001; 4: 225-232.
21. Diez-Torrubia A, Garcia-Aparico C, Cabrera S, et al,. Application of dipeptidyl peptidase IV (DPPIV/CD26) based prodrug approach to different amine-containing drugs. J Med Chem 2010; 53: 559-572.
22. Johnson SRD, Leary A,. Lapatinib: a novel EGFR/HER2 tyrosine kinase inhibitor for cancer. Drugs Today 2006; 42: 441-453.
23. Bhat HK, Vadqama JV,. Role of estrogen receptor in the regulation of estrogen induced amino acid transport of system A in breast cancer and other receptor positive tumor cells. Int J Mol Med 2002; 9: 271-279.
24. Shennan DB, Thomson J, Barber MC, Travers MT,. Functional and molecular characteristics of system L in human breast cancer cells. Biochim Biophys Acta 2003; 1611: 81-90.
25. Shennan DB, Thomson J, Gow IF, Travers MT, Barber MC,. l-L eucine transport in human breast cancer cells (MCF-7 and MDA-MB-231): kinetics, regulation by estrogen and molecular identity of the transporter. Biochim Biophys Acta 2004; 1664: 206-216.
26. Shennan DB, Thomson J,. Inhibition of system L (LAT1/CD98hc) reduces the growth of cultured human breast cancer cells. Oncol Rep 2008; 20: 885-889.
27. Quan Y, Jin Y, Faria TN, et al,. Expression profile of drug and nutrient absorption related genes in Madin-Darby canine kidney (MDCK) cells grown under differentiation conditions. Pharmaceutics 2012; 4: 314-333.
28. Ganapathy ME, Huang W, Wang H, Ganapathy V, Leibach FH,. Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2. Biochem Biophys Res Commun 1998; 246: 470-475.
29. Balimane PV, Tamai I, Guo A, et al,. Direct evidence for peptide transporter(PepT1)-mediated uptake of a nonpeptide prodrug, valacyclovir. Biochem Biophys Res Commun 1998; 250: 246-251.
30. Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ,. Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in mammalian cell line. J Pharmacol Exp Ther 1999; 289: 448-454.
31. Sugawara M, Huang W, Fei YJ, Leibach FH, Ganapathy V, Ganapathy ME,. Transport of valganciclovir, a ganciciclovir prodrug, via peptide transporters PEPT1 and PEPT2. J Pharm Sci 2000; 89: 781-789.
32. Sun Y, Sun J, Shi S, et al,. Synthesis, transport and pharmacokinetics of 5′-amino acid ester prodrugs of 1-β- d -arabinofuranosylcytosine. Mol Pharm 2008; 6: 315-325.
33. Bailey PD, Boyd CA, Bronk JR, et al,. How to make drugs orally active: a substrate template for peptide transporter PepT1. Angew Chem Int Ed 2000; 39: 505-508.
34. Wood ER, Trusdale AT, McDonald OB, et al,. A unique structure for epidermal growth factor receptor bound to GW572016 (Lapatinib): relationships among protein conformation, inhibitor off-rate, and receptor activity in tumor cells. Cancer Res 2004; 64: 6652-6659.