The first design and synthesis of [11C]MKC-1 ([11C]Ro 31-7453), a new potential PET cancer imaging agent

Nuclear Medicine and Biology

Volumn 37, Issue 7, 2010, Pages 763-775

  Wang, Min ^a   Gao, Mingzhang ^a   Miller, Kathy D ^a   Sledge, George W ^a   Hutchins, Gary D ^a   Zheng, Qi Huang ^a  

^a INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

11C MKC 1 ( 11C Ro 31 7453); Cancer imaging; Positron emission tomography; Radiosynthesis

Indexed keywords

2 (2,4 DICHLOROPHENYL) 3 (1 METHYL 3 INDOLYL)MALEIMIDE; 3 INDOLEGLYOXYLIC ACID; ACETAMIDE DERIVATIVE; ACID ANHYDRIDE; BISINDOLYLMALEIC ANHYDRIDE; BISINDOLYLMALEIMIDE; CARBON 11; ENZASTAURIN; GLYOXYLIC ACID DERIVATIVE; INDOLEACETAMIDE; MALEIMIDE; MKC 1; RO 31 7453; UNCLASSIFIED DRUG;

ARTICLE; CANCER SCINTISCANNING; CHEMICAL MODIFICATION; DRUG ACTIVITY; DRUG DESIGN; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; ISOTOPE LABELING; POSITRON EMISSION TOMOGRAPHY; RADIOCHEMISTRY;

CARBON RADIOISOTOPES; HUMANS; INDOLES; MOLECULAR STRUCTURE; NEOPLASMS; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS;

EID: 77956995416     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2010.04.186     Document Type: Article

References (28)

1. Davis P.D., Hill C.H., Lawton G., Nixon J.S., Wilkinson S.E., Hurst S.A., et al. Inhibitors of protein kinase C. 1. 2,3-bisarylmaleimides. J Med Chem 1992, 35:177-184.
2. Zhang H.C., Bonaga L.V.R., Ye H., Derian C.K., Damiano B.P., Maryanoff B.E. Novel bis(indolyl)maleimide pyridinophanes that are potent, selective inhibitors of glycogen synthase kinase-3. Bioorg Med Chem Lett 2007, 17:2863-2868.
3. Ilovich O., Billauer H., Dotan S., Mishani E. Labeled 3-aryl-4-indolylmaleimide derivatives and their potential as angiogenic PET biomarkers. Bioorg Med Chem 2010, 18:612-620.
4. EntreMed. MKC-1 for oncology. http://www.entremed.com/science/mkc-1/.
5. Wheeler W.J., Clodfelter D.K. Synthesis of the tritiated isotopomers of enzastaurin and its N-des-pyridylmethyl metabolite for use in ADME studies. J Labelled Compd Radiopharm 2008, 51:175-181.
6. Cross D.A.E., Culbert A.A., Chalmers K.A., Facci L., Skaper S.D., Reith A.D. Selective small-molecule inhibitors of glycogen synthase kinase-3 activity protect primary neurons from death. J Neurochem 2001, 77:94-102.
7. Coghlan M.P., Culbert A.A., Cross D.A.E., Corcoran S.L., Yates J.W., Pearce N.J., et al. Selective small molecule inhibitors of glycogen synthase kinase-3 modulate glycogen metabolism and gene transcription. Chem Biol 2000, 7:793-803.
8. Salazar R., Bissett D., Twelves C., Breimer L., DeMario M., Campbell S., et al. A phase I clinical and pharmacokinetic study of Ro 31-7453 given as a 7- or 14-day oral twice daily schedule every 4 weeks in patients with solid tumors. Clin Cancer Res 2004, 10:4374-4382.
9. Dupont J., Bienvenu B., Aghajanian C., Pezzulli S., Sabbatini P., Vongphrachanh P., et al. A phase I clinical and pharmacokinetic study of Ro 31-7453 given as a 7- or 14-day oral twice daily schedule every 4 weeks in patients with solid tumors. J Clin Oncol 2004, 22:3366-3374.
10. Worker C. AACR-91st meeting. Interview with Dr Lars Breimer. IDrugs 2000, 3:723-725.
11. 11C]methyl triflate. Int J Rad Appl Instrum A 1992, 43:1383-1385.
12. 11C]methyl triflate. Nucl Med Biol 1999, 26:467-471.
13. Davis P.D., Bit R.A. A mild conversion of maleic anhydrides into maleimides. Trtrahedron Lett 1990, 31:5201-5204.
14. Dhingra UH, Huryn DM, Ke J, Weber GF. Substituted bisindolymaleimides for the inhibition of cell proliferation. WO Patent No. 9947518, 1999.
15. Roy S., Gribble G.W. Synthesis of a novel N-nitroalkyl bisindolylmaleimide. Synth Commun 2007, 37:1879-1886.
16. Gribble G.W., Saulnier M.G., Obaza-Nutaitis J.A., Ketcha D.M. A versatile and efficient construction of the 6H-pyrido[4,3-b]carbazole ring system. Syntheses of the antitumor alkaloids ellipticine, 9-methoxyellipticine, and olivacine, and their analogs. J Org Chem 1992, 57:5891-5899.
17. 18F]hemicholinium-3. Bioorg Med Chem Lett 2007, 17:2220-2224.
18. 11C-radio-synthesis system. J Labelled Compd Radiopharm 2005, 48:S225.
19. Mock B.H., Glick-Wilson B.E., Zheng Q.H., DeGrado T.R. Automated measurement of specific activity of radiolabeled ligands during synthesis. J Labelled Compd Radiopharm 2005, 48:S224.
20. Zheng Q.H., Mock B.H. Purification of carbon-11 PET radiotracers from unlabeled precursors by preparative HPLC and SPE. Biomed Chromatogr 2005, 19:671-676.
21. Faul M.M., Winneroski L.L., Krumrich C.A. A new, efficient method for the synthesis of bisindolylmaleimides. J Org Chem 1998, 63:6053-6058.
22. Faul M.M., Engler T.A., Sullivan K.A., Grutsch J.L., Clayton M.T., Martinelli M.J., et al. Synthetic approaches to indolo[6,7-a]pyrrolo[3,4-c]carbazoles: potent cyclin D1/CDK4 inhibitors. J Org Chem 2004, 69:2967-2975.
23. Brown R.K., Garrison R.A. Derivatives of indole, 6-amino-3-indoleacetic acid. J Am Chem Soc 1955, 77:3839-3842.
24. Bergman J., Sand P. Synthesis of indoles via ring closure of 2-alkyintroaniline derivatives. Tetrahedron 1990, 46:6085-6112.
25. Roy S., Roy S., Gribble G.W. A practical method for the synthesis of indolylaryl- and bisindolylmaleimides. Org Lett 2006, 8:4975-4977.
26. Knor S., Khrenov A.V., Laufer B., Saenko E.L., Hauser C.A.E., Kessler H. Development of a peptidomimetic ligand for efficient isolation and purification of factor VIII via affinity chromatography. J Med Chem 2007, 50:4329-4339.
27. Pour M., Spulak M., Balsanek V., Kunes J., Kubanova P., Buchta V. Synthesis and structure-antifungal activity relationships of 3-aryl-5-alkyl-2,5-dihydrofuran-2-ones and their carbanalogues: further refinement of tentative pharmacophore group. Bioorg Med Chem 2003, 11:2843-2866.
28. Roy S., Eastman A., Gribble G.W. Synthesis of bisindolylmaleimides related to GF109203x and their efficient conversion to the bioactive indolocarbazoles. Org Biomol Chem 2006, 4:3228-3234.