Synthesis and in vitro evaluation of novel lipophilic monophosphorylated gemcitabine derivatives and their nanoparticles

International Journal of Pharmaceutics

Volumn 429, Issue 1-2, 2012, Pages 123-134

  Lansakara P , Dharmika S P ^a   Rodriguez, B Leticia ^a   Cui, Zhengrong ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Cancer cells; Gemcitabine resistance; In vitro cytotoxicity; Nanoparticles

Indexed keywords

2' 2' DIFLUORO 5'MONOPHOSPHATE(1 STEARATE 2 CHLOROPROPYL)CYTOSINE; 2' 2' DIFLUORO CYTOSINE 5' OCTADECYLPHOSPHATE; 4 N ACETYL 2' 2 DIFLUORO CYTOSINE 5' OCTADECYLPHOSPHATE; 4 N HEPTADECYLCARBONYL 2' 2' DIFLUORO CYTOSINE 5' SODIUMMONOPHOSPHATE; 4 N STEAROYL GEMCITABINE; ANTINEOPLASTIC AGENT; DEOXYCYTIDINE KINASE; EQUILIBRATIVE NUCLEOSIDE TRANSPORTER 1; GEMCITABINE; GLYCEROL STEARATE; RIBONUCLEOTIDE REDUCTASE; SOLID LIPID NANOPARTICLE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CANCER CELL; CONTROLLED STUDY; CYTOTOXICITY; DEAMINATION; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; LIPOPHILICITY; MOUSE; NONHUMAN; PHOSPHORYLATION; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANIMALS; ANTIMETABOLITES, ANTINEOPLASTIC; CELL LINE, TUMOR; DEOXYCYTIDINE; DEOXYCYTIDINE KINASE; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; EQUILIBRATIVE NUCLEOSIDE TRANSPORTER 1; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; LIPIDS; MICE; NANOPARTICLES; NEOPLASMS; RIBONUCLEOSIDE DIPHOSPHATE REDUCTASE; TUMOR SUPPRESSOR PROTEINS;

EID: 84859595895     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2012.03.014     Document Type: Article

References (51)

1. R.L. Alexander, B.T. Greene, S.V. Torti, and G.L. Kucera A novel phospholipid gemcitabine conjugate is able to bypass three drug-resistance mechanisms Cancer Chemother. Pharmacol. 56 2005 15 21 (Pubitemid 41201751)
2. R.L. Alexander, and G.L. Kucera Lipid nucleoside conjugates for the treatment of cancer Curr. Pharm. Des. 11 2005 1079 1089 (Pubitemid 40403369)
3. R.L. Alexander, S.L. Morris-Natschke, K.S. Ishaq, R.A. Fleming, and G.L. Kucera Synthesis and cytotoxic activity of two novel 1-dodecylthio-2- decyloxypropyl-3-phosphatidic acid conjugates with gemcitabine and cytosine arabinoside J. Med. Chem. 46 2003 4205 4208 (Pubitemid 37122463)
4. R. Andersson, U. Aho, B.I. Nilsson, G.J. Peters, M. Pastor-Anglada, W. Rasch, and M.L. Sandvold Gemcitabine chemoresistance in pancreatic cancer: molecular mechanisms and potential solutions Scand. J. Gastroenterol. 44 2009 782 786
5. M. Barton-Burke Gemcitabine: a pharmacologic and clinical overview Cancer Nurs. 22 1999 176 183 (Pubitemid 29352696)
6. A.M. Bergman, P.P. Eijk, V.W.T. Ruiz van Haperen, K. Smid, G. Veerman, I. Hubeek, P. van den IJssel, B. Ylstra, and G.J. Peters In vivo induction of resistance to gemcitabine results in increased expression of ribonucleotide reductase subunit M1 as the major determinant Cancer Res. 65 2005 9510 9516 (Pubitemid 41508021)
7. A.M. Bergman, C.M. Kuiper, D.A. Voorn, E.M. Comijn, F. Myhren, M.L. Sandvold, H.R. Hendriks, and G.J. Peters Antiproliferative activity and mechanism of action of fatty acid derivatives of arabinofuranosylcytosine in leukemia and solid tumor cell lines Biochem. Pharmacol. 67 2004 503 511 (Pubitemid 38232890)
8. A.M. Bergman, H.M. Pinedo, and G.J. Peters Determinants of resistance to 2′,2′-difluorodeoxycytidine (gemcitabine) Drug Resist. Updat. 5 2002 19 33
9. E.G. Bligh, and W.J. Dyer Lipid extraction of C. elegans Can. J. Biochem. Physiol. 37 1959 911 917
10. D.Y. Bouffard, J. Laliberté, and R.L. Momparler Kinetic studies on 2′,2′-difluorodeoxycytidine (gemcitabine) with purified human deoxycytidine kinase and cytidine deaminase Biochem. Pharmacol. 45 1993 1857 1861 (Pubitemid 23150977)
11. I. Boukovinas, C. Papadaki, P. Mendez, M. Taron, D. Mavroudis, A. Koutsopoulos, M. Sanchez-Ronco, J.J. Sanchez, M. Trypaki, E. Staphopoulos, V. Georgoulias, R. Rosell, and J. Souglakos Tumor BRCA1, RRM1 and RRM2 mRNA expression levels and clinical response to first-line gemcitabine plus docetaxel in non-small-cell lung cancer patients PLoS ONE 3 2008 e3695
12. M. Candelaria, L. Cetina, J. de la Garza, and A. Dueñas- Gonzálz Clinical implications of gemcitabine in the treatment of cervical cancer Eur. J. Cancer Suppl. 5 2007 37 43 (Pubitemid 46754969)
13. M. Candelaria, E. de la Cruz-Hernández, E. Pérez- Cárdenas, C. Trejo-Becerril, O. Gutiérrez-Hernández, and A. Dueñas-González Pharmacogenetics and pharmacoepigenetics of gemcitabine Med. Oncol. 27 2010 1133 1143
14. P. Ceppi, M. Volante, S. Novello, I. Rapa, K. Danenberg, P. Danenberg, A. Cambieri, G. Selvaggi, S. Saviozzi, R. Calogero, M. Papotti, and G. Scagliotti ERCC1 and RRM1 gene expressions but not EGFR are predictive of shorter survival in advanced non-small-cell lung cancer treated with cisplatin and gemcitabine Ann. Oncol. 17 2006 1818 1825 (Pubitemid 44884058)
15. L. Cetina, L. Rivera, M. Candelaria, J. de la Garza, and A. Dueñas-González Chemoradiation with gemcitabine for cervical cancer in patients with renal failure Anticancer Drugs 15 2004 761 766 (Pubitemid 39281299)
16. T.C. Chou, and P. Talalay Quantitative analysis of dose-effect relationships: the combined effects of multiple drugs or enzyme inhibitors Adv. Enzyme Regul. 22 1984 27 55
17. W.-G. Chung, B.R. Sloat, M.A. Sandoval, D.S.P. Lansakara-P, and Z. Cui Stearoyl gemcitabine nanoparticles overcome resistance related to the over-expression of ribonucleotide reductase subunit M1 J. Control. Release 157 2012 132 140
18. V.L. Damaraju, S. Damaraju, J.D. Young, S.A. Baldwin, J. Mackey, M.B. Sawyer, and C.E. Cass Nucleoside anticancer drugs: the role of nucleoside transporters in resistance to cancer chemotherapy Oncogene 22 2003 7524 7536 (Pubitemid 37487174)
19. J.D. Davidson, L. Ma, M. Flagella, S. Geeganage, L.M. Gelbert, and C.A. Slapak An Increase in the expression of ribonucleotide reductase large subunit 1 is associated with gemcitabine resistance in non-small cell lung cancer cell lines Cancer Res. 64 2004 3761 3766 (Pubitemid 38697284)
20. M.S. Duxbury, H. Ito, M.J. Zinner, S.W. Ashley, and E.E. Whang RNA interference targeting the M2 subunit of ribonucleotide reductase enhances pancreatic adenocarcinoma chemosensitivity to gemcitabine Oncogene 23 2003 1539 1548
21. E. Giovannetti, M. Del Tacca, V. Mey, N. Funel, S. Nannizzi, S. Ricci, C. Orlandini, U. Boggi, D. Campani, M. Del Chiaro, M. Iannopollo, G. Bevilacqua, F. Mosca, and R. Danesi Transcription analysis of human equilibrative nucleoside transporter-1 predicts survival in pancreas cancer patients treated with gemcitabine Cancer Res. 66 2006 3928 3935
22. Y.-G. Goan, B. Zhou, E. Hu, S. Mi, and Y. Yen Overexpression of ribonucleotide reductase as a mechanism of resistance to 2,2- difluorodeoxycytidine in the human KB cancer cell line Cancer Res. 59 1999 4204 4207 (Pubitemid 29418726)
23. V. Gregoire, J.F. Rosier, M. De Bast, M. Bruniaux, B. De Coster, M. Octave-Prignot, and P. Scalliet Role of deoxycytidine kinase (dCK) activity in gemcitabine's radioenhancement in mice and human cell lines in vitro Radiother. Oncol. 63 2002 329 338 (Pubitemid 34874561)
24. Z.-w. Guo, and J.M. Gallo Selective protection of 2′,2′- difluorodeoxycytidine (gemcitabine) J. Org. Chem. 64 1999 8319 8322
25. V. Heinemann, L. Schulz, R.D. Issels, and P. W. Gemcitabine: a modulator of intracellular nucleotide and deoxynucleotide metabolism Semin. Oncol. 22 1995 11 18
26. V. Heinemann, Y.-Z. Xu, S. Chubb, A. Sen, L.W. Hertel, G.B. Grindey, and W. Plunkett Cellular elimination of 2′,2′-difluorodeoxycytidine 5′-triphosphate: a mechanism of self-potentiation Cancer Res. 52 1992 533 539
27. P. Huang, and W. Plunkett Induction of apoptosis by gemcitabine Semin. Oncol. 4 1995 19 25
28. M.L. Immordino, P. Brusa, F. Rocco, S. Arpicco, M. Ceruti, and L. Cattel Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing lipophilic gemcitabine prodrugs J. Control. Release 100 2004 331 346 (Pubitemid 39572916)
29. L.P. Jordheim, O. Guittet, M. Lepoivre, C.M. Galmarini, and C. Dumontet Increased expression of the large subunit of ribonucleotide reductase is involved in resistance to gemcitabine in human mammary adenocarcinoma cells Mol. Cancer Ther. 4 2005 1268 1276 (Pubitemid 41149575)
30. A. Kalykaki, P. Papakotoulas, S. Tsousis, I. Boukovinas, K. Kalbakis, L. Vamvakas, A. Kotsakis, N. Vardakis, P. Papadopoulou, V. Georgoulias, and D. Mavroudis Gemcitabine plus oxaliplatin (GEMOX) in pretreated patients with advanced ovarian cancer: a multicenter Phase II Study of the Hellenic Oncology Research Group (HORG) Anticancer Res. 28 2008 495 500 (Pubitemid 351362859)
31. J.R. Kroep, W.J.P. Loves, C.L. van der Wilt, E. Alvarez, I. Talianidis, E. Boven, B.J.M. Braakhuis, C.J. van Groeningen, H.M. Pinedo, and G.J. Peters Pretreatment deoxycytidine kinase levels predict in vivo gemcitabine sensitivity. Supported by Eli Lilly & Co., International, The Netherlands Mol. Cancer Ther. 1 2002 371 376
32. J. Laliberté, and R.L. Momparler Human cytidine deaminase: purification of enzyme, cloning, and expression of its complementary DNA Cancer Res. 54 1994 5401 5407 (Pubitemid 24336032)
33. R. Maréchal, J.R. Mackey, R. Lai, P. Demetter, M. Peeters, M. Polus, C.E. Cass, I. Salmon, J. Devire, and J.-L. Van Laethem Deoxycitidine kinase is associated with prolonged survival after adjuvant gemcitabine for resected pancreatic adenocarcinoma Cancer 116 2010 5200 5206
34. V. Mey, E. Giovannetti, F.D. Braud, S. Nannizzi, G. Curigliano, F. Verweij, O.D. Cobelli, S. Pece, M.D. Tacca, and R. Danesi In vitro synergistic cytotoxicity of gemcitabine and pemetrexed and pharmacogenetic evaluation of response to gemcitabine in bladder cancer patients Br. J. Cancer 95 2006 289 297 (Pubitemid 44187589)
35. E. Mini, S. Nobili, B. Caciagli, I.I. Landin, and T. Mazzei Cellular pharmacology of gemcitabine Ann. Oncol. 17 2006 v7 v12
36. K. Ohtaka, N. Kohya, K. Sato, Y. Kitajima, T. Ide, M. Mitsuno, and K. Miyazaki Ribonucleotide reductase subunit M1 is a possible chemoresistance marker to gemcitabine in biliary tract carcinoma Oncol. Rep. 20 2008 279 286
37. Perie, J., Monsan, P.F., Willson, M.J., Klaebe, A., Lauth, N.J., Thibault, P.A., 1990. Process for the preparation of lysophosphatidic acids and of salts of the latter FR. Patent 2636331.
38. C.R. Raetz, M.Y. Chu, S. Srivastava, and J.G. Turcotte A phospholipid derivative of cytosine arabinoside and its conversion to phosphatidylinositol by animal tissue Science 196 1977 303 305 (Pubitemid 8076955)
39. R. Rosell, K.D. Danenberg, V. Alberola, G. Bepler, J.J. Sanchez, C. Camps, M. Provencio, D. Isla, M. Taron, P. Diz, and A. Artal Ribonucleotide reductase messenger RNA expression and survival in gemcitabine/cisplatin-treated advanced non-small cell lung cancer patients Clin. Cancer Res 10 2004 1318 1325 (Pubitemid 38365223)
40. V.W. Ruiz van Haperen, G. Veerman, B.J. Braakhuis, J.B. Vermorken, E. Boven, A. Leyva, and G.J. Peters Deoxycytidine kinase and deoxycytidine deaminase activities in human tumour xenografts Eur. J. Cancer 29A 1993 2132 2137 (Pubitemid 23348130)
41. A.B. Sandler, J. Nemunaitis, C. Denham, J. von Pawel, Y. Cormier, U. Gatzemeier, K. Mattson, C. Manegold, M.C. Palmer, A. Gregor, B. Nguyen, C. Niyikiza, and L.H. Einhorn Phase III trial of gemcitabine plus cisplatin versus cisplatin alone in patients with locally advanced or metastatic non-small-cell lung cancer J. Clin. Oncol. 18 2000 122
42. C. Sezgin, B. Karabulut, R. Uslu, U.A. Sanli, G. Goksel, Y. Yuzer, and E. Goker Gemcitabine treatment in patients with inoperable locally advanced/metastatic pancreatic cancer and prognostic factors Scand. J. Gastroenterol. 40 2005 1486 1492 (Pubitemid 43028211)
43. B.R. Sloat, M.A. Sandoval, A.M. Hau, Y. He, and Z. Cui Strong antibody responses induced by protein antigens conjugated onto the surface of lecithin-based nanoparticles J. Control. Release 141 2010 93 100
44. B.R. Sloat, M.A. Sandoval, D. Li, W.-G. Chung, D.S.P. Lansakara-P, P.J. Proteau, K. Kiguchi, J. DiGiovanni, and Z. Cui In vitro and in vivo anti-tumor activities of a gemcitabine derivative carried by nanoparticles Int. J. Pharm. 409 2011 278 288
45. X. Song, P.L. Lorenzi, C.P. Landowski, B.S. Vig, J.M. Hilfinger, and G.L. Amidon Amino acid ester prodrugs of the anticancer agent gemcitabine: synthesis, bioconversion, metabolic bioevasion, and hPEPT1-mediated transport Mol. Pharm. 2 2005 157 167 (Pubitemid 41295363)
46. J. Spratlin, R. Sangha, D. Glubrecht, L. Dabbagh, J.D. Young, C. Dumontet, C. Cass, R. Lai, and J.R. Mackey The absence of human equilibrative nucleoside transporter 1 is associated with reduced survival in patients with gemcitabine-treated pancreas adenocarcinoma Clin. Cancer Res. 10 2004 6956 6961 (Pubitemid 39383046)
47. H. Ueno, K. Kiyosawa, and N. Kaniwa Pharmacogenomics of gemcitabine: can genetic studies lead to tailor-made therapy? Br. J. Cancer 97 2007 145 151 (Pubitemid 47057479)
48. K.A. Watanabe, and J.J. Fo A simple method for selective acylation of cytidine of the 4-amino group J. Angew. Chem. Int. Ed. 5 1966 579 580
49. W. Wu, J. Sigmond, G.J. Peters, and R.F. Borch Synthesis and biological activity of a gemcitabine phosphoramidate prodrug J. Med. Chem. 50 2007 3743 3746 (Pubitemid 47195480)
50. Y. Yen Ribonucleotide reductase subunit one as gene therapy target Clin. Cancer Res. 9 2003 4304 4308 (Pubitemid 37248384)
51. P.A. Zucali, G.L. Ceresoli, I. Garassino, F. De Vincenzo, R. Cavina, E. Campagnoli, F. Cappuzzo, S. Salamina, H.J. Soto Parra, and A. Santoro Gemcitabine and vinorelbine in pemetrexed-pretreated patients with malignant pleural mesothelioma Cancer 112 2008 1555 1561 (Pubitemid 351441168)