Synthesis of hybrid distamycin-cysteine labeled with 99mTc: A model for a novel class of cancer imaging agents

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 12, 2000, Pages 1397-1400

  Baraldi, Pier Giovanni ^a   Romagnoli, Romeo ^a   Duatti, Adriano ^a   Bolzati, Cristina ^a   Piffanelli, Adriano ^a   Bianchi, Nicoletta ^a   Mischiati, Carlo ^a   Gambari, Roberto ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; DISTAMYCIN A; RADIOPHARMACEUTICAL AGENT; TECHNETIUM 99M;

ARTICLE; CHEMICAL MODIFICATION; DIAGNOSTIC IMAGING; DRUG SYNTHESIS; MOLECULAR HYBRIDIZATION; REACTION ANALYSIS; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; TUMOR DIAGNOSIS;

CYSTEINE; DISTAMYCINS; HUMANS; NEOPLASMS; ORGANOTECHNETIUM COMPOUNDS; RADIOPHARMACEUTICALS;

EID: 0034686494     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00250-X     Document Type: Article

References (25)

1. (a) Arcamone, F.; Orezzi, P. G.; Barbieri, W.; Nicolella, V.; Penco, S. Gazz. Chim. Ital. 1967, 97, 1097.
2. (b) Arcamone, F.; Penco, S.; Orezzi, P. G.; Nicolella, V.; Pirelli, A. Nature 1964, 203, 1064.
3. For the biological activities of distamycin A see: (c) Hahn, F.E. in Antibiotics III: Mechanism of action of antimicrobial and antitumor agents; Corcoran, J. W.; Hahn, F. E. Eds.; Springer Verlag: New York, 1975, 79.
4. (d) Bialer, M. In Antiviral Drugs and Interferon; The molecular basis of their activity, Becker, T., Ed.; Martinus Nijoff: Boston, 1984; p 143.
5. Chen X., Ramakrishnan B., Sundaralingam M. J. Mol. Biol. 267:1997;1157.
6. Pelton J.G., Wemmer D.E. J. Am. Chem. Soc. 112:1990;1393.
7. (a) Cozzi, P.; Mongelli, N. Curr. Pharm. Des. 1998, 4, 181.
8. (b) Baraldi, P. G.; Cacciari, B.; Guiotto, A.; Romagnoli, R.; Zaid, A. N.; Spalluto, G. Curr. Pharm. Des. 1998, 4, 249.
9. (c) Zunino, F., Animati, F.; Capranico, G. Curr. Pharm. Des. 1995, 1, 83.
10. Gansow, O. A.; Brechbiel, M. W.; Mirzadeh, S.; Colcher, D.; Roselli, M. Cancer Imagining with Radiolabeled Antibodies, Goldenberg, D. M., Ed.; Kluwer Academic Publishers, 1990, Chapter 7; p 153.
11. For recent reviews related to radiopharmaceuticals containing technetium: (a) Liu, S.; Edwards, D. S. Chem. Rev. 1999, 99, 2235.
12. (b) Jurisson, S. S.; Lyndon, J. D. Chem. Rev. 1999, 99, 2205.
13. (a) Duatti, A. In Technetium and Rhenium in Chemistry and Nuclear Medicine 5, Nicolini, M.; Mazzi, U., Eds.; SG Editoriali: Padova, Italy, 1999; pp 3-17;
14. (b) Bolzati, C.; Boschi, A.; Duatti, A.; Prakash, S.; Uccelli, L.; Tisato, F.; Refosco, F.; Bandoli, G. J. Am. Chem. Soc. in press.
15. Pasqualini, L.; Duatti, A. J. Chem. Soc., Chem. Commun. 1992, 1354.
16. (a) Woodward, R.; Heusler, K.; Gosteli, J.; Naegeli, P. Oppolzer, W.; Ramage, R.; Ranganathan, S. Vorbruggen, H. J. Am. Chem. Soc. 1966, 88, 852.
17. (b) Kemp, D. S.; Carey, R. I. J. Org. Chem. 1989, 54, 3640.
18. 4S; (calcd): C, 45.79; H, 5.44; Cl, 11.26; N, 22.25; S, 5.09; (found): C, 45.67; H, 5.21; Cl, 11.10; N, 22.02; S, 4.86. Mass (Maldi-Tof): 558.0 (M).
19. +].
20. The cytotoxicity was evaluated following the procedure reported in the article: Geroni, C.; Pesenti, E.; Tagliabue, G.; Ballinari, D.; Mongelli, N.; Broggini, M.; Erba, E.; D'Incalci, M.; Spreafico, F.; Grandi, M. Int. J. Canc. 1993, 68, 916.
21. 14,15 Conditions of PCRs were: denaturation, 92 °C, 1 min; annealing, 55 °C, 1 min; elongation, 72 °C, 1 min (20 cycles). The effects of DNA-binding drugs were analysed after incubating target DNA at room temperature, for 5 min, with increasing amounts of the compounds, as reported in the text, followed by polymerase chain reaction. Amplified DNA was analysed by electrophoresis on 2.5% agarose, in TAE (0.04 M Tris-acetate, 0.001 EDTA), 0.5 μg/mL ethidium bromide.
22. Bianchi N., Passadore M., Feriotto G., Mischiati C., Gambari R., Piva R. J. Ster. Biochem and Mol. Biol. 54:1995;211.
23. Passadore M., Feriotto G., Bianchi N., Aguiari G.L., Mischiati C., Piva R., Gambari R. J. Biochem. Biophys. Methods. 29:1994;307.
24. Passadore M., Bianchi N., Feriotto G., Mischiati C., Giacomini P., Piva R., Gambari R. Biochem. J. 308:1995;513.
25. For a recent review see: Volkert, W. A.; Hoffman, T. J. Chem. Rev. 1999, 99, 2269.