Synthesis and characterization of mono-, Di-, and tri-poly(ethylene glycol) chlorin e6 conjugates for the photokilling of human ovarian cancer cells

Journal of Organic Chemistry

Volumn 77, Issue 23, 2012, Pages 10638-10647

  Kimani, Stanley ^a,b   Ghosh, Goutam ^a   Ghogare, Ashwini ^a   Rudshteyn, Benjamin ^a   Bartusik, Dorota ^a   Hasan, Tayyaba ^b   Greer, Alexander ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b MASSACHUSETTS GENERAL HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE ION; CANCER CELLS; CHLORINS; D-MANNITOL; DEUTERATIONS; ESTER BONDS; HYDROLYTIC STABILITY; MITROCHONDRIA; OVARIAN CANCER CELLS; PHOTO-TOXICITY; RADICAL IONS; SINGLET OXYGEN; WATER SOLUBILITIES;

CYTOLOGY; DEUTERIUM; ETHYLENE GLYCOL; OXYGEN; PHOTOSENSITIZERS; POLYETHYLENE GLYCOLS; SOLUBILITY;

CELLS;

17 3 CHLORIN E6 METHOXY TRI(ETHYLENE GLYCOL)ESTER; 17 3,15 2 CHLORIN E6 METHOXY TRI(ETHYLENE GLYCOL)DIESTER; 17 3,15 2,13 1 CHLORIN E6 METHOXY TRI(ETHYLENE GLYCOL)TRIESTER; MANNITOL; OXYGEN; PHOTOSENSITIZING AGENT; TRIETHYLENE GLYCOL; UNCLASSIFIED DRUG; WATER;

ARTICLE; CANCER CELL; CELL SURVIVAL; CELLULAR DISTRIBUTION; CONFORMATIONAL TRANSITION; CYTOPLASM; CYTOTOXICITY; DRUG CONFORMATION; DRUG CONJUGATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROLYSIS; LYSOSOME; MITOCHONDRION; OVARY CANCER; PARTITION COEFFICIENT; PHOTOSENSITIZATION; PHOTOTOXICITY;

FEMALE; HUMANS; OVARIAN NEOPLASMS; PHOTOCHEMOTHERAPY; POLYETHYLENE GLYCOLS; PORPHYRINS; RADIATION-SENSITIZING AGENTS;

EID: 84870927098     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301889s     Document Type: Article

References (44)

1. Roberts, W. G.; Shiau, F.-Y.; Nelson, J. S.; Smith, K. M.; Berns, M. W. J. Nat. Cancer Inst. 1988, 80, 330-336
2. Hamblin, M. R.; Miller, J. L.; Rizvi, I.; Ortel, B.; Maytin, E. V.; Hasan, T. Cancer Res. 2001, 61, 7155-7162
3. OShea, D. F.; Miller, M. A.; Matsueda, H.; Lindsey, J. S. Inorg. Chem. 1996, 35, 7325-7338
4. Hamblin, M. R.; Miller, J. L.; Ortel, B. Photochem. Photobiol. 2000, 72, 533-540
5. Tijerina, M.; KopecÌková, P.; KopecÌek, J. J. Controlled Release 2001, 74, 269-273
6. Kozyrev, A. N.; Chen, Y.; Goswami, L. N.; Tabaczynski, W. A.; Pandey, R. K. J. Org. Chem. 2006, 71, 1949-1960
7. Hargus, J. A.; Fronczek, F. R.; Graca, M.; Vicente, H.; Smith, K. M. Photochem. Photobiol. 2007, 83, 1006-1015
8. Aksenova, A. A.; L, Sebyakin, Yu. L.; Mironov, A. F. Russ. J. Bioorg. Chem. 2001, 27, 124-129
9. Kim, H.-K.; Van den Bossche, J.; Hyun, S.-H.; Thompson, D. H. Bioconjugate Chem. 2012, 23, 2071-2077
10. Xu, H.; Deng, Y.; Chen, D.; Hong, W.; Lu, Y.; Dong, X. J. Controlled Release 2008, 130, 238-245
11. Nakamura, H.; Fang, J.; Gahininath, B.; Tsukigawa, K.; Maeda, H. J. Controlled Release 2011, 155, 367-375
12. Zalipsky, S; Lee, C. Use of functionalized polyethylene glycols for modification of polypeptides. In Poly(ethylene glycol) Chemistry. Biotechnological and Biomedical Applications; Harris, M. J., Ed.; Plenum Press, New York, 1992; pp 347-370.
13. Lavis, L. D. ACS Chem. Biol. 2008, 3, 203-206
14. Fleming, A. B.; Haverstick, K.; Saltzman, W. M. Bioconjugate Chem. 2004, 15, 1364-1375
15. Marcus, Y.; Sasson, K.; Fridkin, M.; Shechter, Y. J. Med. Chem. 2008, 51, 4300-4305
16. Tetko, I. V.; Poda, G. I. J. Med. Chem. 2004, 47, 5601-5604
17. McGill, N. W.; Williams, S. J. J. Org. Chem. 2009, 74, 9388-9398
18. Zhu, J.; Deur, C.; Hegedus, L. S. J. Org. Chem. 1997, 62, 7704-7710
19. ACD Program; Advanced Chemistry Development Inc.: Toronto, ON, Canada.
20. Hirohara, S.; Obata, M.; Ogata, S. I.; Kajiwara, K.; Ohtsuki, C.; Tanihara, M.; Yano, S. J. Photochem Photobiol. B: Biol. 2006, 84, 56-63
21. Hyperchem 8.0; Hypercube, Inc.: Gainesville, Fl.
22. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.1; Gaussian Inc.: Wallingford, CT, 2009.
23. Li, Y.-C.; Rissanen, S.; Stepniewski, M.; Cramariuc, O.; Róg, T.; Mirza, S.; Xhaard, H.; Wytrwal, M.; Kepczynski, M.; Bunker, A. J. Phys. Chem. B 2012, 116, 7334-7341
24. Chefurka, W.; Chatelier, R. C.; Sawyer, W. H. Biochim. Biophys. Acta 1987, 896, 181-186
25. Arun, K. T.; Epe, B.; Ramaiah, D. J. Phys. Chem. B 2002, 106, 11622-11627
26. Dsouza, R. N.; Pischel, U.; Nau, W. M. Chem. Rev. 2011, 111, 7941-7980
27. Laville, I.; Figueiredo, T.; Loock, B.; Pigaglio, S.; Maillard, P.; Grierson, D. S.; Carrez, D.; Croisy, A.; Blais, A. Bioorg. Med. Chem. 2003, 11, 1643-1652
28. Roberts, W. G.; Berns, M. W. Lasers Surg. Med. 1989, 9, 90-101
29. Mojzisova, H.; Bonneau, S.; Vever-Bizet, C.; Brault, D. Biochim. Biophys. Acta, Biomembr. 2007, 1768, 2748-2756
30. Ogilby, P. R.; Foote, C. S. J. Am. Chem. Soc. 1982, 104, 2069-2070
31. Rancan, F.; Maeda, H.; Böhm, F.; Röder, B. Bioconjugate Chem. 2007, 18, 494-499
32. Jensen, R. L.; Arnbjerg, J.; Ogilby, P. R. J. Am. Chem. Soc. 2010, 132, 8098-8105
33. Skovsen, E.; Snyder, J. W.; Lambert, J. D. C.; Ogilby, P. R. J. Phys. Chem. B 2005, 109, 8570-8573
34. Jensen, R. L.; Arnbjerg, J.; Ogilby, P. R. J. Am. Chem. Soc. 2012, 134, 9820-9826
35. Redmond, R. W.; Kochevar, I. E. Photochem. Photobiol. 2006, 82, 1178-1186
36. Engst, P.; Kubat, P.; Jirsa, M. J. Photochem. Photobiol. A: Chem. 1994, 78, 215-219
37. Rodgers, M. A. J.; Snowden, P. T. J. Am. Chem. Soc. 1982, 104, 5541-5543
38. Davidson, R. S.; Trethewey, K. R. J. Am. Chem. Soc. 1976, 98, 4008-4009
39. Huang, L.; St. Denis, T. G.; Xuan, Y.; Huang, Y. Y.; Tanaka, M.; Zadio, A.; Sarna, T.; Hamblin, M. R. Free Radic. Biol. Med. 2012, 10.1016/j. freeradbiomed.2012.09.006
40. Bartusik, D.; Aebisher, D.; Ghosh, G.; Minnis, M.; Greer, A. J. Org. Chem. 2012, 77, 4557-4565
41. Mahendran, A.; Vuong, A.; Aebisher, D.; Gong, Y.; Bittman, R.; Arthur, G.; Kawamura, A.; Greer, A. J. Org. Chem. 2010, 75, 5549-5557
42. ChemBio3D Ultra 12.0; CambridgeSoft Corporation: Cambridge, U.K.
43. Dennington, R.; Keith, T.; Millam, J. GaussView, Version 5; Semichem Inc.: Shawnee Mission, KS, 2009
44. Celli, J. P.; Solban, N.; Liang, A.; Pereira, S. P.; Hasan, T. Lasers Surg. Med. 2011, 43, 565-574