Synthesis and 124I-labeling of m-iodophenylpyrrolomorphinan as a potential PET imaging agent for delta opioid (DOP) receptors

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 50, Issue 3, 2007, Pages 165-170

  Akgün, Eyup ^a   Portoghese, Philip S ^a   Sajjad, Munawwar ^b   Nabi, Hani A ^b  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY AT BUFFALO   (United States)

Author keywords

DOP receptor agonist; Iodine 124; m IPPM; Positron emission tomography

Indexed keywords

POSITRON EMISSION TOMOGRAPHY; POSITRONS; ZINC COMPOUNDS;

DELTA OPIOID RECEPTOR AGONIST; DELTA-OPIOID RECEPTOR; IMAGING AGENT; IODINE-124; KETOAMIDES; LABELINGS; M-IODOPHENYLPYRROLOMORPHINAN; OPIOID RECEPTORS; PET IMAGING; SODIUM-ACETATE BUFFER;

IODINE;

3 IODOPHENYLPYRROLOMORPHINAN; 3 IODOPHENYLPYRROLOMORPHINAN I 124; 7,10 DIMETHYL 5,6,7,8,12,12B HEXAHYDRO 4,8 METHANOBENZOFURO[3,2-E]PYRROLO[2,3Q]ISOQUINOLINE 1,8 A DIHYDROXY 11 (3 IODOPHENYL)CARBOXAMIDE; 7,10 DIMETHYL 5,6,7,8,12,12B HEXAHYDRO 4,8 METHANOBENZOFURO[3,2-E]PYRROLO[2,3Q]ISOQUINOLINE 1,8 A DIHYDROXY 11 (3 TRIMETHYLISTANNYLPHENYL)CARBOXAMIDE; ACETIC ACID; AMIDE; BUFFER; CONTRAST MEDIUM; DELTA OPIATE RECEPTOR; PHENYLAZO BETA KETOAMIDE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; LABELING INDEX; POSITRON EMISSION TOMOGRAPHY;

EID: 34248598915     PISSN: 03624803     EISSN: 10991344     Source Type: Journal    
DOI: 10.1002/jlcr.1216     Document Type: Article

References (34)

1. Dhawan BN, Cesselin F, Raghubir R, Reisine T, Bradley PB, Portoghese PS, Hamon M. Pharmacol Rev 1996; 48: 567-592.
2. Gutstein HB, Akil H. In Goodman and Gilman's The Pharmacologic Basis of Therapeutics (11th edn), Brunten LL (ed.). McGraw-Hill: New York, 2006; 547-590.
3. Waldhoer M, Bartlett SE, Whistler JL. Annu Rev Biochem 2004; 73: 953-990.
4. Scherrer G, Befort K, Contet C, Becker J, Matifas A, Kieffer BL. Eur J Neurosci 2004; 19: 2239-2248.
5. Dionne RA, Dobbins KR, Hargreaves KN. Clin Pharmacol Ther 1991; 49: 183.
6. Peters GR, Gaylor S. Clin Pharmacol Ther 1989; 45: 130.
7. Wei Z-Y, Brown W, Takasaki B, Plobeck N, Delorme D, Zhou F, Yang H, Jones P, Gawell L, Gagnon H, Schmidt R, Yue S-Y, Walpole C, Payza K, St-Onge S, Labarre M, Godbout C, Jakob A, Butterworth J, Kamassah A, Morin P-E, Projean D, Ducharme J, Roberts E. J Med Chem 2000; 43: 3895-3905.
8. Rapaka RS, Porreca F. Pharmaceut Res 1991; 8: 1-8.
9. Petrillo P, Angelici O, Bingham S, Ficalora G, Garnier M, Zaratin PF, Petrone G, Pozzi O, Sbacchi M, Stean TO, Upton N, Dondio GM, Scheideler MA. J Pharmacol Exp Ther 2003; 307: 1079-1089.
10. Mansour A, Khachaturian H, Lewis ME, Akil H, Watson SJ. Trends Neurosci 1988; 11: 308-314.
11. Gavériaux C, Pelluso J, Simonin F, Kieffer BL. FEBS Lett 1995; 369: 272-276.
12. Kieffer BL, Befort K, Gaveriaux-Ruff C, Hirth CG. Proc Nat Acad Sci USA 1992; 89: 12048-12052.
13. Evans CJ, Keith DE, Morrison H, Magendzo K, Edwards RH. Science 1992; 18: 1952-1955.
14. Milligan G. Mol Pharmacol 2004; 66: 1-7.
15. Jordan BA, Devi LA. Nature 1999; 399: 697-700.
16. Gomes I, Jordan BA, Gupta A, Trapaidze N, Nagy V, Devi LA. J Neurosci 2000; RC110-1-Rc110/5.
17. Xie Z, Gupta RB, Daniels DJ, Portoghese PS. J Pharmacol Exp Ther 2005; 68: 1079-1086.
18. Bhushan RG, Sharma SK, Xie Z, Daniels DJ, Portoghese PS. J Med Chem 2004; 47: 2969-2972.
19. Waldhoer M, Fong J, Jones RM, Lunzer MM, Sharma SK, Kostenis E, Portoghese PS, Whistler JL. Proc Nat Acad Sci USA 2005; 102: 9050-9055.
20. Gupta A, Décaillot FM, Devi LA. AAPS J 2006; 8: E153-E159.
21. Pascal G, Milligan G. Mol Pharmacol 2005; 68: 905-915.
22. Burns HD, Hamill TG, Eng W-S, Francis B, Fioravanti C, Gibson RE. Curr Opin Chem Biol 1999; 3: 388-394.
23. Dondio G, Ronzonie S, Farina C, Graziani D, Parini C, Petrillo P, Giardina GAM. Il Farmaco 2001; 56: 117-119.
24. Dondio G, Ronzonie S, Petrillo P. Exp Opin Ther Patents 1997; 7: 1075-1098.
25. Dondio G, Ronzonie S, Petrillo P. Exp Opin Ther Patents (part II) 1999; 9: 353-374.
26. Giulio D, Silvano R, Andrea PG, Divide G. Patent WO9725331; 1997.
27. Lever JR, Scheffel U, Kinter CM, Ravert HT, Dannale RF, Wagner Jr HN, Frost JJ. Eur J Pharmacol 1992; 216: 459-460.
28. Lever JR, Kinter CM, Ravert HT, Musachio JL, Mathews WB, Dannals RF. J Label Compd Radiopharm 1995; 36: 137-146.
29. Mathews WB, Kinter CM, Palma J, Daniels RV, Ravert HT, Dannals RF, Lever JR. J Label Compd Radiopharm 1999; 42: 43-54.
30. Sajjad M, Bars E, Nabi HA. Appl Radiat Isot 2006; 64: 965-970.
31. Beholz LG, Benovsky P, Ward DL, Barta NS, Stille JR. J Org Chem 1997; 62: 1033-1042.
32. Sandler SR, Karo W. Organic Functional Group Preparations (vol. 12-II). Academic Press: San Diago 1986; 367.
33. Koziorowski J, Henssen C, Weinreich R. App Radiat Isot 1998; 49: 955-959.
34. Akgün E, Sajjad M, Portoghese PS. J Label Compd Radiopharm 2006; 49: 857-866.