Pteroyl-γ-glutamate-cysteine synthesis and its application in folate receptor-mediated cancer cell targeting using folate-tethered liposomes

Analytical Biochemistry

Volumn 332, Issue 1, 2004, Pages 168-177

  Zhang, Yonghua ^a,b   Guo, Lili ^a   Roeske, Roger W ^a   Antony, Aśok C ^a,b   Jayaram, Hiremagalur N ^a,b  

^a INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b Richard L Roudeboush Vet Aff M   (United States)

Author keywords

Cancer cell targeting; Cytotoxicity; Doxorubicin; Folate receptors; Liposomes; Peptide synthesis

Indexed keywords

AMINO ACIDS; CELLS; CONTROLLED DRUG DELIVERY; CYTOLOGY; CYTOTOXICITY; DISEASES; GENE TRANSFER; LIPOSOMES;

CANCER CELL TARGETING; CHEMOTHERAPEUTIC AGENTS; DOXORUBICIN; FOLATE RECEPTOR; HUMAN COLON CANCER; PEPTIDE SYNTHESIS; SYNTHETIC METHODS; TARGETING LIGANDS;

TARGETED DRUG DELIVERY;

ACETIC ACID DERIVATIVE; CALCEIN; CYSTEINE; DOXORUBICIN; FOLIC ACID; LIPOSOME; RECEPTOR;

ARTICLE; CANCER CELL; CELL STRAIN CACO 2; CONTROLLED STUDY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG EFFECT; FEMALE; GENE OVEREXPRESSION; HELA CELL; HUMAN; HUMAN CELL; PRIORITY JOURNAL; RELIABILITY; REPRODUCIBILITY; SYNTHESIS;

EID: 4143081572     PISSN: 00032697     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ab.2004.05.034     Document Type: Article

References (39)

1. Antony A.C. Megaloblastic anemias. Hoffman R. Hematology: Basic Principles and Practice. 2000;446-485 Churchill-Livingstone, New York
2. Weitman S., Anderson R.G.W., Kamen B.A. Folate binding proteins. Dakshinamurti K. Vitamin Receptors: Vitamins as Ligands in Cell Communication. 1994;107-136 Cambridge University Press, Cambridge, UK
3. Kamen B.A. Folate receptor-α Massaro E.J., Rogers J.M. Folate and Human Development. 2002;117-135 Humana Press, Totowa, NJ
4. Antony A.C. The biological chemistry of folate receptors. Blood. 79:1992;2807-2820
5. Matherly L.H., Goldman D.I. Membrane transport of folates. Vitam. Horm. 66:2003;403-456
6. Antony A.C. Folate receptors. Annu. Rev. Nutr. 16:1996;501-521
7. Sirotnak F.M., Tolner B. Carrier-mediated membrane transport of folates in mammalian cells. Annu. Rev. Nutr. 19:1999;91-122
8. Rothberg K.G., Ying Y.S., Kolhouse J.F., Kamen B.A., Anderson R.G. The glycophospholipid-linked folate receptor internalizes folate without entering the clathrin-coated pit endocytic pathway. J. Cell Biol. 110:1990;637-649
9. Antony A.C., Utley C., Van Horne K.C., Kolhouse J.F. Isolation and characterization of a folate receptor from human placenta. J. Biol. Chem. 256:1981;9684-9692
10. Verma R.S., Antony A.C. Immunoreactive folate-binding proteins from human saliva: Isolation and comparison of two distinct species. Biochem.J. 286:1992;707-715. Erratum in Biochem. J. 289 (1993) 927
11. Selhub J., Franklin W.A. The folate-binding protein of rat kidney, purification, properties, and cellular distribution. J. Biol. Chem. 259:1984;6601-6606
12. Ross J.F., Chaudhuri P.K., Ratnam M. Differential regulation of folate receptor isoforms in normal and malignant tissues in vivo and in established cell lines: physiologic and clinical implications. Cancer. 73:1994;2432-2443
13. Weitman S.D., Weinberg A.G., Coney L.R., Zurawski V.R., Jennings D.S., Kamen B.A. Cellular localization of the folate receptor: potential role in drug toxicity and folate homeostasis. Cancer Res. 52:1992;6708-6711
14. Pillai M.R., Chacko P., Kesari L.A., Jayaprakash P.G., Jayaram H.N., Antony A.C. Expression of folate receptors and heterogeneous nuclear ribonucleoprotein E1 in women with human papillomavirus mediated transformation of cervical tissue to cancer. J. Clin. Pathol. 56:2003;569-574
15. Mathias C.J., Green M.A. A kit formulation for preparation of [(111)In]In-DTPA-folate, a folate-receptor-targeted radiopharmaceutical. Nucl. Med. Biol. 25:1998;585-587
16. Mathias C.J., Wang S., Waters D.J., Turek J.J., Low P.S., Green M.A. Indium-111-DTPA-folate as a potential folate-receptor-targeted radiopharmaceutical. J. Nucl. Med. 39:1998;1579-1585
17. Schuber F. Chemistry of ligand-coupling to liposomes. Philippot J.R., Schuber F. Liposomes as Tools in Basic Research and Industry. 1995;21-41 CRC Press, Boca Raton, FL
18. Lee R.J., Low P.S. Delivery of liposomes into cultured KB cells via folate receptor-mediated endocytosis. J. Biol. Chem. 269:1994;3198-3204
19. Leamon C.P., DePrince R.B., Hendren R.W. Folate-mediated drug delivery: effect of alternative conjugation chemistry. J. Drug Targeting. 7:1999;157-169
20. Reddy J.A., Abburi C., Hofland H., Howard S.J., Vlahov I., Wils P., Leamon C.P. Folate-targeted, cationic liposome-mediated gene transfer into disseminated peritoneal tumors. Gene Ther. 9:2002;1542-1550
21. Sun X.L., Murphy B.R., Li Q.J., Gullapalli S., Mackins J., Jayaram H.N., Srivastava A., Antony A.C. Transduction of folate receptor cDNA into cervical carcinoma cells using recombinant adeno-associated virions delays cell proliferation in vitro and in vivo. J. Clin. Invest. 96:1995;1535-1547
22. Antony A., Tang Y.S., Khan R.A., Biju M.P., Xiao X., Li Q.J., Sun X.L., Jayaram H.N., Stabler S.P. Translational upregulation of folate receptors is mediated by homocysteine via RNA-heterogeneous nuclear ribonucleoprotein E1 interactions. J. Clin. Invest. 113:2004;285-301
23. Lee R.J., Low P.S. Folate-mediated tumor cell targeting of liposome-entrapped doxorubicin in vitro. Biochim. Biophys. Acta. 1233:1995;134-144
24. Antony A.C., Kane M.A., Portillo R.M., Elwood P.C., Kolhouse J.F. Studies of the role of a particulate folate-binding protein in the uptake of 5-methyltetrahydrofolate by cultured human KB cells. J. Biol. Chem. 260:1985;14911-14917
25. Cory A.H., Owen T.C., Barltrop J.A., Cory J.G. Use of an aqueous soluble tetrazolium/formazan assay for cell growth assays in culture. Cancer Commun. 3:1991;207-212
26. McHugh M., Cheng Y.C. Demonstration of a high affinity folate binder in human cell membranes and its characterization in cultured human KB cells. J. Biol. Chem. 254:1979;11312-11318
27. Kane M.A., Elwood P.C., Portillo R.M., Antony A.C., Najfeld V., Finley A., Waxman S., Kolhouse J.F. Influence on immunoreactive folate-binding proteins of extracellular folate concentration in cultured human cells. J. Clin. Invest. 81:1988;1398-1406
28. Henderson G.B., Tsuji J.M., Kumar H.P. Mediated uptake of folate by a high-affinity binding protein in sublines of L1210 cells adapted to nanomolar concentrations of folate. J. Membr. Biol. 101:1988;247-258
29. Jansen G., Kathmann I., Rademaker B.C., Braakhuis B.J., Westerhof G.R., Rijksen G., Schornagel J.H. Expression of a folate binding protein in L1210 cells grown in low folate medium. Cancer Res. 49:1989;1959-1963
30. Sadasivan E., Rothenberg S.P. The complete amino acid sequence of a human folate binding protein from KB cells determined from the cDNA. J. Biol. Chem. 264:1989;5806-5811
31. Hsueh C.T., Dolnick B.J. Altered folate-binding protein mRNA stability in KB cells grown in folate-deficient medium. Biochem. Pharmacol. 45:1993;2537-2545
32. Zhu W.Y., Alliegro M.A., Melera P.W. The rate of folate receptor alpha (FR alpha) synthesis in folate depleted CHL cells is regulated by a translational mechanism sensitive to media folate levels, while stable overexpression of its mRNA is mediated by gene amplification and an increase in transcript half-life. J. Cell. Biochem. 81:2001;205-219
33. Sadasivan E., Regec A., Rothenberg S.P. The half-life of the transcript encoding the folate receptor alpha in KB cells is reduced by cytosolic proteins expressed in folate-replete and not in folate-depleted cells. Gene. 291:2002;149-158
34. Chan W.C., White P.D. Fmoc Solid Phase Peptide Synthesis: A Practical Approach. 2000;Oxford University Press, New York
35. Leamon C.P., Weigl D., Hendren R.W. Folate copolymer-mediated transfection of cultured cells. Bioconjug. Chem. 10:1999;947-957
36. Speth P.A., van Hoesel Q.G., Haanen C. Clinical pharmacokinetics of doxorubicin. Clin. Pharmacokinet. 15:1988;15-31
37. Siegal T., Horowitz A., Gabizon A. Doxorubicin encapsulated in sterically stabilized liposomes for the treatment of a brain tumor model: Biodistribution and therapeutic efficacy. J. Neurosurg. 83:1995;1029-1037
38. Gabizon A.A. Pegylated liposomal doxorubicin: metamorphosis of an old drug into a new form of chemotherapy. Cancer Invest. 19:2001;424-436
39. Low P.S., Antony A.C. Folate receptor-targeted drugs for cancer and inflammatory diseases. Adv. Drug Deliv. Rev. 56:2004;1055-1058