New molecular markers for prostate tumor imaging: A study on 2-methylene substituted fatty acids as new AMACR inhibitors

Chemistry - A European Journal

Volumn 17, Issue 36, 2011, Pages 10144-10150

  Morgenroth, Agnieszka ^a,b   Urusova, Elizaveta A ^b   Dinger, Cornelia ^b   Al Momani, Ehab ^b   Kull, Thomas ^b   Glatting, Gerhard ^b   Frauendorf, Holm ^c   Jahn, Olaf ^d   Mottaghy, Felix M ^a   Reske, Sven N ^b   Zlatopolskiy, Boris D ^a,b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b UNIVERSITY OF ULM   (Germany)

^c UNIVERSITY OF GÖTTINGEN   (Germany)

^d MAX PLANCK INSTITUTE OF EXPERIMENTAL MEDICINE   (Germany)

Author keywords

antitumor agents; fatty acids; imaging agents; inhibitors; metabolism; radiopharmaceuticals

Indexed keywords

2-METHYLENE; ANTI-TUMOR AGENTS; BILE ACID; BINDING LIGANDS; BREAST CANCER; EPIMERIZATION; FATTY ACID METABOLISM; IMAGING AGENTS; INTERCONVERSIONS; METHYLACYL-COA RACEMASE; MITOCHONDRIAL ENZYMES; MOLECULAR IMAGING; MOLECULAR MARKER; NEW STRATEGY; PROSTATE CARCINOMA; PROSTATE CELLS; PROSTATE TUMOR; RADIOPHARMACEUTICALS; THIOESTERS; WT CELLS;

CELL CULTURE; DISEASES; ISOMERS; METABOLISM; PHYSIOLOGY; PLANTS (BOTANY); REACTION INTERMEDIATES; TUMORS;

FATTY ACIDS;

2 METHYLACYL COENZYME A RACEMASE; ALPHA-METHYLACYL-COA RACEMASE; DIAGNOSTIC AGENT; ENZYME INHIBITOR; FATTY ACID; ISOMERASE;

ARTICLE; CARCINOMA; CELL TRACKING; CHEMISTRY; DRUG ANTAGONISM; ENZYMOLOGY; HUMAN; MALE; METHODOLOGY; PROSTATE TUMOR; SYNTHESIS; TUMOR CELL LINE;

CARCINOMA; CELL LINE, TUMOR; CELL TRACKING; ENZYME INHIBITORS; FATTY ACIDS; HUMANS; MALE; PROSTATIC NEOPLASMS; RACEMASES AND EPIMERASES;

EID: 80052002152     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201003176     Document Type: Article

References (44)

1. A. Jemal, R. Siegel, E. Ward, Y. Hao, J. Xu, J. Thun, CA Cancer J. Clin. 2009, 59, 225-249.
2. P. J. Effert, R. Bares, S. Handt, J. M. Wolff, U. G. Büll, J. Urol. 1996, 155, 994-998.
3. S. N. Reske, N. M. Blumstein, B. Neumaier, H.-W. Gottfried, F. Finsterbusch, D. Kocot, P. Möller, G. Glatting, S. Perner, J. Nucl. Med. 2006, 47, 1249-1254.
4. S. N. Reske, N. M. Blumstein, G. Glatting, Urologia 2006, 45, 707-714.
5. O. Schillaci, F. Calabria, M. Tavolozza, C. Cicciò, M. Carlani, C. R. Caracciolo, R. Daniely, A. Orlacchio, G. Simonetti, Nucl. Med. Commun. 2010, 31, 39-45
6. M. Farsad, R. Schiavina, P. Castellucci, C. Nanni, B. Corti, G. Martorana, R. Canini, W. Grigioni, S. Boschi, M. Marengo, C. Pettinato, E. Salizzoni, N. Monetti, R. Franchi, S. Fanti, J. Nucl. Med. 2005, 46, 1642-1649.
7. M. D. Lloyd, D. J. Darley, A. S. Wierzbicki, M. D. Threadgill, FEBS J. 2008, 275, 1089-1102.
8. W. Schmitz, C. Albers, R. Fingerhut, E. Conzelmann, Eur. J. Biochem. 1995, 231, 815-822.
9. P. T. Went, G. Sauter, M. Oberholzer, L. Bubendorf, Pathology 2006, 38, 426-432.
10. K. Shilo, T. Dracheva, H. Mani, J. Fukuoka, I. A. Sesterhenn, W.-S. Chu, J. H. Shih, J. Jen, W. D. Travis, T. J. Franks, Arch. Pathol. Lab. Med. 2007, 131, 1555-1560.
11. W. A. Lee, Oncology 2006, 71, 246-250.
12. J. Luo, J. Hicks, W. R. Gage, R. J. Wanders, W. B. Isaacs, A. M. De Marzo, J. Urol. 2002, 167, 57-58.
13. J. Luo, S. Zha, W. R. Gage, T. A. Dunn, J. L. Hicks, C. J. Bennett, C. M. Ewing, E. A. Platz, S. Ferdinandusse, R. J. Wanders, J. M. Trent, W. B. Isaacs, A. M. De Marzo, Cancer Res. 2002, 62, 2220-2226.
14. M. A. Rubin, M. Zhou, S. M. Dhanasekaran, S. Varambally, T. R. Barrette, M. G. Sanda, K. J. Pienta, D. Ghosh, A. Chinnaiyan, J. Am. Med. Assoc. 2002, 287, 1662-1670.
15. K. Takahara, H. Azuma, T. Sakamoto, S. Kiyama, T. Inamoto, N. Ibuki, T. Nishida, H. Nomi, T. Ubai, N. Segawa, Y. Katsuoka, Anticancer Res. 2009, 29, 2497-2505.
16. To date the only published work in this area is:, A. J. Carnell, I. Hale, S. Denis, R. J. A. Wanders, W. B. Isaacs, B. A. Wilson, S. Ferdinandusse, J. Med. Chem. 2007, 50, 2700-2707.
17. B. Bhaumik, W. Schmitz, A. Hassinen, J. K. Hiltunen, E. Conzelmann, R. K. Wierenga, J. Mol. Biol. 2007, 367, 1145-1161.
18. D. J. Darley, D. S. Butler, S. J. Prideaux, T. W. Thornton, A. D. Wilson, T. J. Woodman, M. D. Threadgill, M. D. Lloyd, Org. Biomol. Chem. 2009, 7, 543-552.
19. M. Smrcina, P. Majer, E. Majerova, T. A. Guerassina, M. A. Eissenstat, Tetrahedron 1997, 53, 12867-12874.
20. B. Hin, P. Majer, T. Tsukamoto, J. Org. Chem. 2002, 67, 7365-7368.
21. P. E. Pfeffer, E. Kinsel, L. Silbert, J. Org. Chem. 1972, 37, 1256-1258.
22. H. X. Zhang, F. Guibe, G. Balavoine, J. Org. Chem. 1990, 55, 1857-1867.
23. 2R has been observed, see:, T. Yokozawa, T. Nakai, N. Ishikawa, Tetrahedron Lett. 1984, 25, 3987-3990, as well as hydrolysis of 3,3,3-trifluoro-2-methylpropionic acid into methylmalonic acid (2 n NaOH, 100 °C, 3 h, 85 %)
24. M. W. Buxton, M. Stacey, J. C. Tatlow, J. Chem. Soc. 1954, 366-373.
25. P. Baumhof, R. Mazitschek, A. Giantis, Angew. Chem. 2001, 113, 3784-3786
26. Angew. Chem. Int. Ed. 2001, 40, 3672-3674.
27. Dodecylmalonyl-CoA (20) could be obtained by reaction of dodecylmalonyl mono-thiophenolate with coenzyme A.
28. S. Ferdinandusse, S. Denis, P. T. Clayton, A. Graham, J. E. Rees, J. T. Allen, B. N. McLean, A. Y. Brown, P. Vreken, H. R. Waterham, R. J. A. Wanders, Nat. Genet. 2000, 24, 188-191.
29. See the Supporting Information for details of the synthesis.
30. Version 5.02 for Windows; GraphPad Software, San Diego, California, USA.
31. G. Glatting, P. Kletting, S. N. Reske, K. Hohl, C. Ring, Med. Phys. 2007, 34, 4285-4292.
32. B. M. Gallagher, J. S. Fowler, N. I. Gutterson, R. R. MacGregor, C.-N. Wan, A. P. Wolf, J. Nucl. Med. 1978, 19, 1154-1161.
33. See, for example:, L. Aloj, C. Caracõ, E. Jagoda, W. C. Eckelman, R. D. Neumann, Cancer Res. 1999, 59, 4709-4714 and
34. W. Eckelman, Nucl. Med. Biol. 1994, 21, 759-769.
35. R. J. A. Wanders, S. Ferdinandusse, G. A. Jansen, P. Vreken, H. R. Waterham, C. W. T. van Roermund, E. G. van Grunsven, Biochem. Soc. Trans. 2001, 29, 250-267.
36. K. M. Knights, C. J. Drogemuller, Curr. Drug Metab. 2000, 1, 49-66.
37. 131I- 7 c).
38. 131I- 7 c could not be detected after the hydrolysis step, even in the crude reaction mixture. According to our observations, 1′-trialkyltinvinyl substituted compounds are generally less reactive to an electrophilic radioiodine species compared with the corresponding 2′-isomers. Furthermore, 1′-radioiodovinyl substituted compounds are much more sensitive to the base-induced dehydrohalogenation than their 2′-substituted counterparts.
39. 11C-choline in the same panel of malign and benign cell lines showed no statistically significant differences in accumulation of radioactivity.
40. K. Savolainen, P. Bhaumik, W. Schmitz, T. J. Kotti, E. Conzelmann, R. K. Wierenga, J. K. Hiltunen, J. Biol. Chem. 2004, 280, 12611-12620.
41. J. N. Mubiru, G. L. Shen-Ong, A. J. Valente, D. A. Troyer, Gene 2004, 327, 89-98.
42. See, for example:, M. P. Grillo, G. Chiellini, M. Tonelli, L. Z. Benet, Drug Metab. Dispos. 2001, 29, 1210-1215 for a study of the differences in CoA-thioesterification of valproic and 2-fluorovalproic acids.
43. High-level expression of long-chain fatty acyl-CoA synthetase 4 (ACSL4) was detected in DU145 cell line. In contrast, the LNCaP cell line did not express this protein at all, and LNCaP AI cells expressed ACSL4 at low level. For further details, see:, M. E. Monaco, C. J. Creighton, P. Lee, X. Zou, M. K. Topham, D. M. Stafforini, Transl. Oncol. 2010, 3, 91-98.
44. M. Zhou, A. M. Chinnaiyan, C. G. Kleer, P. C. Lucas, M. A. Rubin, Am. J. Surg. Pathol. 2002, 26, 926-931.