Abstract
New conjugated arylidine, enamine, and annelated pyrido derivatives of quinoxaline 1,4-dioxide were synthesized via utilization of an active allylic methyl group. Biodistribution studies were carried out by injecting a solution of an 125I derivative of an enamine-substituted quinoxaline 1,4-dioxide in normal and tumor-bearing mice. The uptake in solid tumor was over 6% of the injected dose per gram tissue body weight at 4 h post injection. These data revealed localization of the tracer in the tumor tissues with a high percentage sufficient to show a radiotherapeutic effect and showed that this is a promising tool for diagnosis. Also the radiotoxicity of the 125I-substituted compound on Ehrlich ascites carcinoma cells may encourage this behavior.
Graphical Abstract
Similar content being viewed by others
References
Zarranz B, Jaso A, Aldana I, Monge A (2004) Bioorg Med Chem 12:3711
Denny WA, Wilson WR (1986) J Med Chem 29:879
Overgaad J (1992) Radiother Oncol 24:564
Fuchs T, Chowdhury G, Barnes CL, Gates KS (2001) J Org Chem 66:107
Villa MA (2001) Radiobiologia 1:7
Brown JM, Koong AJ (1999) J Natl Cancer Inst 83:178
Ibrahim IT, Wally MA (2009) J Radioanal Nucl Chem. doi:101007/s10967-009-0039-1
Benson AB III, Trump DL, Cummings KB, Fischer PH (1985) Biochem Pharmacol 34:3925
Mester J, DeGoeij K, Sluyser M (1996) Eur J Cancer 32A:1603
Unak T (2000) Curr Pharm 11:1127
Walicka MA, Adelstein SJ, Kassis AI (1998) Radiat Res 149:134
Monge A, Palop JA, López de Cerain A, Senador V, Martinez-Crespo FJ, Sainz Y, Narro S, Garcia E, de Miguel C, Gonzalez M, Hamilton E, Barker AJ, Clarke ED, Greenhow DT (1995) J Med Chem 38:1786
Chowdhury G, Kotandeniya D, Daniels JS, Barnes CL, Gates KS (2004) Chem Res Toxicol 17:1399
Fuchs T, Gates KS, Hwang J-T, Greenberg MM (1999) Chem Res Toxicol 12:1190
Sternberg ED, Dolphin D, Bruckner C (1998) Tetrahedron 54:4151
Dolphin D (1994) Cancer J Chem 72:1005
Rouhl AM (1998) Chem Eng News 76:22
Doughery TJ (1987) Photochem Photobiol 45:879
Miller J (1999) J Chem Ed 76:592
Issidorides CH, Haddadin MJ (1966) J Org Chem 31:4067
Haddadin MJ, Issidorides CH (1993) Heterocycles 35:1503
Lyubchanskaya VM, Alekseeva LM, Granik VG (1992) Chem Heterocycl Comp 28:34
Chi KH, Wang HE, Chen FD (2001) J Nucl Med 42:345
Kassis AI, Sastry KSR, Adelestein SJ (1987) Radiat Res 109:78
Montgomery J (1970) Med Chem 3:680
Harrison KA, Dalrymple GV, Baranowska-Kortylewicz J (1996) J Nucl Med 37:13S
Kassis AI, Tumeh SS, Wen PY (1996) J Nucl Med 37:19S
Hofer KG, Van Loon N, Schnederman MH, Charlton DE (1992) Radiat Res 130:121
Klecker RW Jr, Jenkins JF, Kinsella TJ, Fine RL, Strong JM, Clin JM (1985) Pharmacol Ther 38:45
El-Ghany EA, Mahdy MA, Attallah K, Ghazy FS (2002) J Radioanal Nucl Chem 1:156
El-Ghany EA, Mahdy MA, Attallah K, Ghazy FS (2004) Arab J Nucl Sci Appl 37:1
Desombre ER (1992) Cancer Res 52:5752
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
El-Gogary, S.R., Waly, M.A., Ibrahim, I.T. et al. Synthesis and UV absorption of new conjugated quinoxaline 1,4-dioxide derivatives anticipated as tumor imaging and cytotoxic agents. Monatsh Chem 141, 1253–1262 (2010). https://doi.org/10.1007/s00706-010-0386-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-010-0386-1