Synthesis and cell-selective antitumor properties of amino acid conjugated tumor-associated carbohydrate antigen-coated gold nanoparticles

Carbohydrate Research

Volumn 405, Issue , 2015, Pages 93-101

  Biswas, Souvik ^a   Medina, Scott H ^a   Barchi, Joseph J ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

Cytotoxicity; Friedenreich; Galectin 3; Gold nanoparticles; Thomsen; Tumor associated carbohydrate antigens

Indexed keywords

AMINO ACIDS; ANTIGENS; CARBOHYDRATES; CELL CULTURE; CELLS; CYTOLOGY; CYTOTOXICITY; FIBER OPTIC SENSORS; GOLD; METAL NANOPARTICLES; MOBILE SECURITY; NANOPARTICLES; PROTEINS; TUMORS;

ANTIAPOPTOTIC ACTIVITIES; ANTITUMOR PROPERTY; BIOPHYSICAL TECHNIQUES; FRIEDENREICH; GALECTIN-3; GOLD NANOPARTICLES; HYDROXYL-TERMINATED; THOMSEN;

SYNTHESIS (CHEMICAL);

ALKANE; AMINO ACID DERIVATIVE; ANTINEOPLASTIC AGENT; CARBOHYDRATE; CARBOHYDRATE ANTIGEN; GALECTIN 3; GOLD NANOPARTICLE; HYDROXYL GROUP; MACROGOL; N ALPHA ACETYL O ALPHA (2,3,4,6 TETRA O ACETYL DEXTRO GALACTOPYRANOSYL BETA (1-3) 2 ACETAMIDO 2 DEOXY 3,4,6 TETRA O ACETYL DEXTRO GALACTOPYRANOSYL) LEVO SERINE (9,12,15,18,21,24,27 HEPTAOXA 3 THIOACETYL 30 AZATETRATRIACONTAN 33 YL); N ALPHA ACETYL O ALPHA (2,3,4,6 TETRA O ACETYL DEXTRO GALACTOPYRANOSYL BETA (1-3) 2 ACETAMIDO 2 DEOXY 3,4,6 TETRA O ACETYL DEXTRO GALACTOPYRANOSYL) LEVO THREONINE (9,12,15,18,21,24,27 HEPTAOXA 3 THIOACETYL 30 AZATETRATRIACONTAN 33 YL); N ALPHA ACETYL O ALPHA (DEXTRO GALACTOPYRANOSYL BETA (1-3) 2 ACETAMIDO 2 DEOXY DEXTRO GALACTOPYRANOSYL) LEVO THREONINE (9,12,15,18,21,24,27 HEPTAOXA 3 THIA 30 AZATETRATRIACONTAN 33 YL); N ALPHA FMOC O ALPHA (2,3,4,6 TETRA O ACETYL DEXTRO GALACTOPYRANOSYL BETA (1-3) 2 ACETAMIDO 2 DEOXY 3,4,6 TETRA O ACETYL DEXTRO GALACTOPYRANOSYL) LEVO SERINE (9,12,15,18,21,24,27 HEPTAOXA 3 THIOACETYL 30 AZATETRATRIACONTAN 33 YL); N ALPHA FMOC O ALPHA (2,3,4,6 TETRA O ACETYL DEXTRO GALACTOPYRANOSYL BETA (1-3) 2 ACETAMIDO 2 DEOXY 3,4,6 TETRA O ACETYL DEXTRO GALACTOPYRANOSYL) LEVO THREONINE (9,12,15,18,21,24,27 HEPTAOXA 3 THIOACETYL 30 AZATETRATRIACONTAN 33 YL); SERINE; THOMSEN FRIEDENREICH ANTIGEN; THREONINE; TUMOR ANTIGEN; UNCLASSIFIED DRUG; GOLD; METAL NANOPARTICLE; THOMSEN-FRIEDENREICH ANTIGEN;

ACETYLATION; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL LINE; CANCER INHIBITION; CARBOHYDRATE ANALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; CELL SELECTION; CONTROLLED STUDY; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; PRIORITY JOURNAL; PROTEIN CARBOHYDRATE INTERACTION; PROTEIN EXPRESSION; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; TRANSMISSION ELECTRON MICROSCOPY; ULTRAFILTRATION; CHEMISTRY; DRUG EFFECTS; SYNTHESIS; TUMOR CELL LINE;

ANTIGENS, TUMOR-ASSOCIATED, CARBOHYDRATE; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CHEMISTRY TECHNIQUES, SYNTHETIC; GOLD; HUMANS; METAL NANOPARTICLES; SERINE; THREONINE;

EID: 84924175356     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2014.11.002     Document Type: Article

References (88)

1. S. Hakomori Annu. Rev. Immunol. 2 1984 103
2. S.I. Hakomori Adv. Cancer Res. 52 1989 257
3. G.F. Springer J. Mol. Med. 75 1997 594
4. G.D. Maclean, M.B. Bowenyacyshyn, J. Samuel, A. Meikle, G. Stuart, J. Nation, S. Poppema, M. Jerry, R. Koganty, T. Wong, and B.M. Longenecker J. Immunother. 11 1992 292
5. S. Adluri, F. Helling, S. Ogata, S.L. Zhang, S.H. Itzkowitz, K.O. Lloyd, and P.O. Livingston Cancer Immunol. Immun. 41 1995 185
6. G.F. Springer Crit. Rev. Oncog. 6 1995 57
7. Y. Cao, P. Stosiek, G.F. Springer, and U. Karsten Histochem. Cell Biol. 106 1996 197
8. S.F. Slovin, G. Ragupathi, C. Musselli, C. Fernandez, M. Diani, D. Verbel, S. Danishefsky, P. Livingston, and H.I. Scher Cancer Immunol. Immun. 54 2005 694
9. J. Heimburg-Molinaro, M. Lum, G. Vijay, M.T. Jain, A. Almogren, and K. Rittenhouse-Olson Vaccine 29 2011 8802
10. R. Roy, and T.C. Shiao Chimia 65 2011 24
11. R. Hevey, and C.C. Ling Future Med. Chem. 4 2012 545
12. P. Ulsemer, G. Henderson, K. Toutounian, A. Loffler, J. Schmidt, U. Karsten, M. Blaut, and S. Goletz Cancer Immunol. Immun. 62 2013 875
13. N. Gaidzik, U. Westerlind, and H. Kunz Chem. Soc. Rev. 42 2013 4421
14. S. Ogata, I. Ho, A.L. Chen, D. Dubois, J. Maklansky, A. Singhal, S. Hakomori, and S.H. Itzkowitz Cancer Res. 55 1995 1869
15. W. Bergler, A. Stanek, F. Riedel, G. Petroianu, and K. Horman Eur. Arch. Otorhinolaryngol. 255 1998 414
16. F. Schneider, W. Kemmner, W. Haensch, G. Franke, S. Gretschel, U. Karsten, and P.M. Schlag Cancer Res. 61 2001 4605
17. S. Hakomori Adv. Exp. Med. Biol. 491 2001 369
18. P.H. Wang, Y.F. Li, C.M. Juang, Y.R. Lee, H.T. Chao, H.T. Ng, Y.C. Tsai, and C.C. Yuan Gynecol. Oncol. 86 2002 45
19. M.L. Alpaugh, J.S. Tomlinson, Y. Ye, and S.H. Barsky Am. J. Pathol. 161 2002 619
20. F. Dall'Olio, M. Chiricolo, A. D'Errico, E. Gruppioni, A. Altimari, M. Fiorentino, and W.F. Grigioni Glycobiology 14 2004 39
21. P.A. Videira, M. Correia, N. Malagolini, H.J. Crespo, D. Ligeiro, F.M. Calais, H. Trindade, and F. Dall'Olio BMC Cancer 2009 9
22. M. Perez-Garay, B. Arteta, L. Pages, R. de Llorens, C. de Bolos, F. Vidal-Vanaclocha, and R. Peracaula PLoS ONE 2010 5
23. M.J. Schultz, A.F. Swindall, J.W. Wright, E.S. Sztul, C.N. Landen, and S.L. Bellis J. Ovarian Res. 2013 6
24. Y.F. Zhao, Y.P. Li, H.Y. Ma, W.J. Dong, H.M. Zhou, X.B. Song, J.N. Zhang, and L. Jia Mol. Cell. Proteomics 13 2014 520
25. E. Miyoshi, K. Noda, J.H. Ko, A. Ekuni, T. Kitada, N. Uozumi, Y. Ikeda, N. Matsuura, Y. Sasaki, N. Hayashi, M. Hori, and N. Taniguchi Cancer Res. 59 1999 2237
26. Y.C. Liu, H.Y. Yen, C.Y. Chen, C.H. Chen, P.F. Cheng, Y.H. Juan, C.H. Chen, K.H. Khoo, C.J. Yu, P.C. Yang, T.L. Hsu, and C.H. Wong Proc. Natl. Acad. Sci. U.S.A. 108 2011 11332
27. S. Villar-Portela, L. Muinelo-Romay, E. Cuevas, E. Gil-Martin, and A. Fernandez-Briera Histopathology 63 2013 174
28. S. Kawai, S. Kato, H. Imai, Y. Okada, and C. Ishioka Oncol. Rep. 29 2013 13
29. Y.C. Lu, C.N. Chen, C.Y. Chu, J.H. Lu, B.J. Wang, C.H. Chen, M.C. Huang, T.H. Lin, C.C. Pan, S.S.A. Chen, W.M. Hsu, Y.F. Liao, P.Y. Wu, H.Y. Hsia, C.C. Chang, and H. Lee Biochem. J. 460 2014 69
30. S. Hakomori Curr. Opin. Immunol. 3 1991 646
31. R. Watanabe, C. Ohyama, H. Aoki, T. Takahashi, M. Satoh, S. Saito, S. Hoshi, A. Ishii, M. Saito, and Y. Arai Cancer Res. 62 2002 3850
32. G. Ragupathi, N.X. Liu, C. Musselli, S. Powell, K. Lloyd, and P.O. Livingston J. Immunol. 174 2005 5706
33. A. Cazet, S. Groux-Degroote, B. Teylaert, K.M. Kwon, S. Lehoux, C. Slomianny, C.H. Kim, X. Le Bourhis, and P. Delannoy Biol. Chem. 390 2009 601
34. A. Prinetti, T. Cao, G. Illuzzi, S. Prioni, M. Aureli, N. Gagliano, G. Tredici, V. Rodriguez-Menendez, V. Chigorno, and S. Sonnino J. Biol. Chem. 286 2011 40900
35. C.L. Brooks, A. Schietinger, S.N. Borisova, P. Kufer, M. Okon, T. Hirama, C.R. MacKenzie, L.X. Wang, H. Schreiber, and S.V. Evans Proc. Natl. Acad. Sci. U.S.A. 107 2010 10056
36. J.M. Burchell, A. Mungul, and J. Taylor-Papadimitriou J. Mammary Gland Biol. 6 2001 355
37. F.A. Hanisch Biol. Chem. 382 2001 143
38. J. Taylor-Papadimitriou, J.M. Burchell, T. Plunkett, R. Graham, I. Correa, D. Miles, and M. Smith J. Mammary Gland Biol. 7 2002 209
39. A. Mungul, L. Cooper, I. Brockhausen, K. Ryder, U. Mandel, H. Clausen, A. Rughetti, D.W. Miles, J. Taylor-Papadimitriou, and J.M. Burchell Int. J. Oncol. 25 2004 937
40. D.H. Dube, and C.R. Bertozzi Nat. Rev. Drug Disc. 4 2005 477
41. T. Ninkovic, and F.G. Hanisch J. Immunol. 179 2007 2380
42. S.J. Storr, L. Royle, C.J. Chapman, U.M.A. Hamid, J.F. Robertson, A. Murray, R.A. Dwek, and P.M. Rudd Glycobiology 18 2008 456
43. H.J. An, S.R. Kronewitter, M.L.A. de Leoz, and C.B. Lebrilla Curr. Opin. Chem. Biol. 13 2009 601
44. J.A. Goetz, Y. Mechref, P. Kang, M.H. Jeng, and M.V. Novotny Glycoconjugate J. 26 2009 117
45. C.A. Reis, H. Osorio, L. Silva, C. Gomes, and L. David J. Clin. Pathol. 63 2010 322
46. P.H. Jensen, D. Kolarich, and N.H. Packer FEBS J. 277 2010 81
47. K. Taniuchi, R.L. Cerny, A. Tanouchi, K. Kohno, N. Kotani, K. Honke, T. Saibara, and M.A. Hollingsworth Oncogene 30 2011 4843
48. C.B. Madsen, C. Petersen, K. Lavrsen, M. Harndahl, S. Buus, H. Clausen, A.E. Pedersen, and H.H. Wandall PLoS ONE 2012 7
49. N. Remmers, J.M. Anderson, E.M. Linde, D.J. DiMaio, A.J. Lazenby, H.H. Wandall, U. Mandel, H. Clausen, F. Yu, and M.A. Hollingsworth Clin. Cancer Res. 2013 1981 19
50. S. Kaur, S. Kumar, N. Momi, A.R. Sasson, and S.K. Batra Nat. Rev. Gastroenterol. Hepatol. 10 2013 607
51. C.H. Chiang, C.H. Wang, H.C. Chang, S.V. More, W.S. Li, and W.C. Hung J. Cell. Physiol. 223 2010 492
52. H. Chen, D.Y. Wang, and X.L. Li Chin. J. Org. Chem. 29 2009 703
53. A. Rek, E. Krenn, and A.J. Kungl Br. J. Pharmacol. 157 2009 686
54. A. Almogren, J. Abdullah, K. Ghapure, K. Ferguson, V.V. Glinsky, and K. Rittenhouse-Olson Front. Biosci. 4 2012 840
55. V.V. Glinsky, G.V. Glinsky, K. Rittenhouse-Olson, M.E. Huflejt, O.V. Glinskii, S.L. Deutscher, and T.P. Quinn Cancer Res. 61 2001 4851
56. V.V. Glinsky, G.V. Glinsky, O.V. Glinskii, V.H. Huxley, J.R. Turk, V.V. Mossine, S.L. Deutscher, K.J. Pienta, and T.P. Quinn Cancer Res. 63 2003 3805
57. S.K. Khaldoyanidi, V.V. Glinsky, L. Sikora, A.B. Glinskii, V.V. Mossine, T.P. Quinn, G.V. Glinsky, and P. Sriramarao J. Biol. Chem. 278 2003 4127
58. O.V. Glinskii, S. Sud, V.V. Mossine, T.P. Mawhinney, D.C. Anthony, G.V. Glinsky, K.J. Pienta, and V.V. Glinsky Neoplasia 14 2012 65
59. K. Rittenhouse-Olson Expert Opin. Biol. Ther. 7 2007 923
60. J. Heimburg-Molinaro, A. Almogren, S. Morey, O.V. Glinskii, R. Roy, G.E. Wilding, R.P. Cheng, V.V. Glinsky, and K. Rittenhouse-Olson Neoplasia 11 2009 780
61. V.G. Sendra, N. Zlocowski, G.A. Nores, and F.J. Irazoqui Immunol. Cell Biol. 88 2010 787
62. R. Roy, T.C. Shiao, and K. Rittenhouse-Olson Braz. J. Pharm. Sci. 49 2013 85
63. J. Zou, V.V. Glinsky, L.A. Landon, L. Matthews, and S.L. Deutscher Carcinogenesis 26 2005 309
64. V.V. Glinsky, M.E. Huflejt, G.V. Glinsky, S.L. Deutscher, and T.P. Quinn Cancer Res. 60 2000 2584
65. K.D. Johnson, O.V. Glinskii, V.V. Mossine, J.R. Turk, T.P. Mawhinney, D.C. Anthony, C.J. Henry, V.H. Huxley, G.V. Glinsky, K.J. Pienta, A. Raz, and V.V. Glinsky Neoplasia 9 2007 662
66. J.R. Newton-Northup, M.T. Dickerson, L.X. Ma, C.L. Besch-Williford, and S.L. Deutscher Clin. Exp. Metastasis 30 2013 119
67. M. Mammen, S.K. Choi, and G.M. Whitesides Angew. Chem., Int. Ed. 37 1998 2755
68. S.A. Svarovsky, Z. Szekely, and J.J. Barchi Tetrahedron: Asymmetry 16 2005 587
69. A. Sundgren, and J.J. Barchi Carbohydr. Res. 343 2008 1594
70. R.P. Brinas, A. Sundgren, M. Maetani, O. Abbudayyeh, H.A. Young, M. Sanford, and J.J. Barchi Abstr. Pap. Am. Chem. Soc. 2010 240
71. R.P. Brinas, A. Sundgren, P. Sahoo, S. Morey, K. Rittenhouse-Olson, G.E. Wilding, W. Deng, and J.J. Barchi Bioconjugate Chem. 23 2012 1513
72. E.C. Dreaden, A.M. Alkilany, X.H. Huang, C.J. Murphy, and M.A. El-Sayed Chem. Soc. Rev. 41 2012 2740
73. A. Kumar, X. Zhang, and X.J. Liang Biotechnol. Adv. 31 2013 593
74. A.M. Alkilany, S.E. Lohse, and C.J. Murphy Acc. Chem. Res. 46 2013 650
75. S.K. Libutti, G.F. Paciotti, L. Myer, R. Haynes, W. Gannon, M. Walker, G. Seidel, A. Byrnes, N. Yuldasheva, and L. Tamarkin J. Clin. Oncol. 2009 27
76. S.K. Libutti, G.F. Paciotti, A.A. Byrnes, H.R. Alexander, W.E. Gannon, M. Walker, G.D. Seidel, N. Yuldasheva, and L. Tamarkin Clin. Cancer Res. 16 2010 6139
77. J.M. de la Fuente, A.G. Barrientos, T.C. Rojas, J. Rojo, J. Canada, A. Fernandez, and S. Penades Angew. Chem., Int. Ed. 40 2001 2258
78. C. Tromas, J. Rojo, J.M. de la Fuente, A.G. Barrientos, R. Garcia, and S. Penades Angew. Chem., Int. Ed. 40 2001 3052
79. X.L. Huang, J.J. Barchi, E.D.T. Lung, P.P. Roller, P.L. Nara, J. Muschik, and R.R. Garrity Biochemistry-US 36 1997 10846
80. J.J. Barchi Biopolymers 99 2013 713
81. S.S. Mallajosyula, K.M. Adams, J.J. Barchi, and A.D. MacKerell J. Chem. Inf. Model. 53 2013 1127
82. F. Corzana, J.H. Busto, G. Jimenez-Oses, M.G. de Luis, J.L. Asensio, J. Jimenez-Barbero, J.M. Peregrina, and A. Avenoza J. Am. Chem. Soc. 129 2007 9458
83. G.A. Naganagowda, T.L. Gururaja, J. Satyanarayana, and M.J. Levine J. Pept. Res. 54 1999 290
84. S.A. Svarovsky, and J.J. Barchi Carbohydr. Res. 338 2003 1925
85. Y.L. Zhang, S.M. Muthana, J.J. Barchi, and J.C. Gildersleeve Org. Lett. 14 2012 3958
86. Y.L. Zhang, S.M. Muthana, D. Farnsworth, O. Ludek, K. Adams, J.J. Barchi, and J.C. Gildersleeve J. Am. Chem. Soc. 134 2012 6316
87. V.V. Glinsky, G. Kiriakova, O.V. Glinskii, V.V. Mossine, T.P. Mawhinney, J.R. Turk, A.B. Glinskii, V.H. Huxley, J.E. Price, and G.V. Glinsky Neoplasia 11 2009 901
88. C.F. Bian, Y. Zhang, H. Sun, D.F. Li, and D.C. Wang PLoS ONE 2011 6