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Synthesis, 99mTc-radiolabeling and in vivo evaluation of a new sulphonamide derivative for solid tumor imaging

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Abstract

A novel sulphonamide derivative (EPBS) was prepared at high yield and characterized by 1H NMR and infrared radiation spectroscopy. Its cytotoxic activity was examined in breast carcinoma (MCF-7) cells at a dose of 25 μg/mL. Approximately 68 percent effective inhibition has been achieved. Furthermore, the synthesized ligand was directly radiolabeled with technetium-99m using sodium borohydride. High radiochemical purities (95.5%) were determined using radio-paper chromatography and electrophoresis. Its in vivo evaluation in tumor bearing mice demonstrated a high tumor uptake of the 99mTc-EPBS complex at 30 min post injection (6.74%) and tumor/muscle (T/NT) ratio equal to 5.04 ± 0.05. In conclusion, 99mTc-EPBS agent showed favorable characteristics for the radio-diagnosis of solid tumors.

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References

  1. Chapman JD, Engelhardt EL, Stobbe CC, Schneider RF, Hanks GE (1998) Measuring hypoxia and predicting tumor radioresistance with nuclear medicine assays. Radiother Oncol 46(3):229–237

    Article  CAS  PubMed  Google Scholar 

  2. Harrison L, Blackwell K (2004) Hypoxia and anemia: factors in decreased sensitivity to radiation therapy and chemotherapy? Oncol 9(suppl_5):31–40

    Article  Google Scholar 

  3. Drews J (2000) Drug discovery: a historical perspective. Science 287(5460):1960–1964

    Article  CAS  PubMed  Google Scholar 

  4. Abbate F, Casini A, Owa T, Scozzafava A, Supuran CT (2004) Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorg Med Chem Lett 14(1):217–223

    Article  CAS  PubMed  Google Scholar 

  5. Supuran CT, Casini A, Mastrolorenzo A, Scozzafava A (2004) COX-2 selective inhibitors, carbonic anhydrase inhibition and anticancer properties of sulfonamides belonging to this class of pharmacological agents. Mini Rev Med Chem 4(6):625–632

    Article  CAS  PubMed  Google Scholar 

  6. Ghorab MM, Alsaid MS, Al-Dosari MS, El-Gazzar MG, Parvez MK (2016) Design, synthesis and anticancer evaluation of novel quinazoline-sulfonamide hybrids. Molecules 21(2):189

    Article  PubMed Central  CAS  Google Scholar 

  7. Han T, Goralski M, Gaskill N, Capota E, Kim J, Ting TC, Xie Y, Williams NS, Nijhawan D (2017) Anticancer sulfonamides target splicing by inducing RBM39 degradation via recruitment to DCAF15. Science 356(6336):eaal3755

    Article  PubMed  CAS  Google Scholar 

  8. Santos-Cuevas CL, Ferro-Flores G, de Murphy CA, Ramírez FdM, Luna-Gutiérrez MA, Pedraza-López M, García-Becerra R, Ordaz-Rosado D (2009) Design, preparation, in vitro and in vivo evaluation of99 mTc-N2S2-Tat (49–57)-bombesin: a target-specific hybrid radiopharmaceutical. Int J Pharm 375(1–2):75–83

    Article  CAS  PubMed  Google Scholar 

  9. Schottelius M, Wester H-J (2009) Molecular imaging targeting peptide receptors. Methods 48(2):161–177

    Article  CAS  PubMed  Google Scholar 

  10. de Barros ALB, das Graças Mota L, de Aguiar Ferreira C, de Oliveira MC, de Góes AM, Cardoso VN (2010) Bombesin derivative radiolabeled with technetium-99 m as agent for tumor identification. Bioorg Med Chem Lett 20(21):6182–6184

    Article  PubMed  CAS  Google Scholar 

  11. Kothari K, Prasad S, Korde A, Mukherjee A, Mathur A, Jaggi M, Venkatesh M, Pillai AM, Mukherjee R, Ramamoorthy N (2007) 99 mTc (CO) 3-VIP analogues: preparation and evaluation as tumor imaging agent. Appl Radiat Isot 65(4):382–386

    Article  CAS  PubMed  Google Scholar 

  12. de Barros ALB, Cardoso VN, das Graças Mota L, Leite EA, de Oliveira MC, Alves RJ (2010) A novel d-glucose derivative radiolabeled with technetium-99 m: synthesis, biodistribution studies and scintigraphic images in an experimental model of Ehrlich tumor. Bioorg Med Chem Lett 20(8):2478–2480

    Article  PubMed  CAS  Google Scholar 

  13. Wx Wan, Yang M, Pan Sr Yu, Nj Cj, Wu (2008) [99mTc] polyamine analogs as potential tumor imaging agent. Drug Dev Res 69(8):520–525

    Article  CAS  Google Scholar 

  14. Altiparmak B, Lambrecht FY, Bayrak E, Durkan K (2010) Design and synthesis of 99mTc-citro-folate for use as a tumor-targeted radiopharmaceutical. Int J Pharm 400(1–2):8–14

    Article  CAS  PubMed  Google Scholar 

  15. Mallia MB, Subramanian S, Mathur A, Sarma H, Venkatesh M, Banerjee S (2010) Synthesis and evaluation of 2-, 4-, 5-substituted nitroimidazole-iminodiacetic acid-99mTc (CO) 3 complexes to target hypoxic tumors. J Label Compd Radiopharm 53(8):535–542

    Article  CAS  Google Scholar 

  16. Hsia C-C, Huang F-L, Hung G-U, Shen L-H, Chen C-L, Wang H-E (2011) The biological characterization of99mTc-BnAO-NI as a SPECT probe for imaging hypoxia in a sarcoma-bearing mouse model. Appl Radiat Isot 69(4):649–655

    Article  CAS  PubMed  Google Scholar 

  17. Wang J, Yang J, Yan Z, Duan X, Tan C, Shen Y, Wu W (2011) Synthesis and preliminary biological evaluation of [99mTc (CO) 3 (IDA–PEG3–CB)]-for tumor imaging. J Radioanal Nucl Chem 287(2):465–469

    Article  CAS  Google Scholar 

  18. Ding R, He Y, Xu J, Liu H, Wang X, Feng M, Qi C, Zhang J, Peng C (2012) Preparation and bioevaluation of 99m Tc nitrido radiopharmaceuticals with pyrazolo [1, 5-a] pyrimidine as tumor imaging agents. Med Chem Res 21(4):523–530

    Article  CAS  Google Scholar 

  19. Hruska CB, Conners AL, Jones KN, Weinmann AL, Lingineni RK, Carter RE, Rhodes DJ, O’Connor MK (2014) Half-time Tc-99m sestamibi imaging with a direct conversion molecular breast imaging system. EJNMMI Res 4(1):5

    Article  PubMed  PubMed Central  Google Scholar 

  20. Shamsel-Din HA, Gizawy MA, Zaki EG, Elgendy A (2020) A novel 99mTc-diester complex as tumor targeting agent: Synthesis, radiolabeling, and biological distribution study. J Label Compd Radiopharm 63(8):376–385

    Article  CAS  Google Scholar 

  21. Shamsel-Din H, Ibrahim A (2017) A novel radiolabeled indole derivative as solid tumor imaging agent: in silico and preclinical pharmacological study. J Radioanal Nucl Chem 314(3):2263–2269

    Article  CAS  Google Scholar 

  22. Alsabagh A, Van Os N (1998) Non-ionic surfactant organic chemistry surfactant science series 72. Marcel Dekker, New York

    Google Scholar 

  23. Lang R (1999) Diaz. PD and Jocobs. D. J Surf Det 7:503

    Article  Google Scholar 

  24. Migahed M, Al-Sabagh A, Zaki E, Mostafa H, Fouda A (2014) Synthesis of some novel cationic surfactants and evaluation of their performance as corrosion inhibitors for X-65 type carbon steel under H2S environment. Int J Electrochem Sci 9:7693–7711

    Google Scholar 

  25. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. JNCI J Natl Cancer Inst 82(13):1107–1112

    Article  CAS  PubMed  Google Scholar 

  26. Gambino D, Kremer C, Cartesio S, León A, Kremer E (1989) Using Tc-Re chemical analogy to synthesize and identify new99mTc complexes. J Radioanal Nucl Chem 136(5):341–351

    Article  CAS  Google Scholar 

  27. Joyard Y, Le Joncour V, Castel H, Diouf CB, Bischoff L, Papamicaël C, Levacher V, Vera P, Bohn P (2013) Synthesis and biological evaluation of a novel 99mTc labeled 2-nitroimidazole derivative as a potential agent for imaging tumor hypoxia. Bioorg Med Chem Lett 23(13):3704–3708

    Article  CAS  PubMed  Google Scholar 

  28. Ruan Q, Zhang X, Lin X, Duan X, Zhang J (2018) Novel 99m Tc labelled complexes with 2-nitroimidazole isocyanide: design, synthesis and evaluation as potential tumor hypoxia imaging agents. MedChemComm 9(6):988–994

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Li Z, Lin X, Zhang J, Wang X, Jin Z, Zhang W, Zhang Y (2016) Kit formulation for preparation and biological evaluation of a novel 99mTc-oxo complex with metronidazole xanthate for imaging tumor hypoxia. Nucl Med Biol 43(2):165–170

    Article  CAS  PubMed  Google Scholar 

  30. Giglio J, Rey A (2019) 99mTc labelling strategies for the development of potential nitroimidazolic hypoxia imaging agents. Inorganics 7(11):128

    Article  CAS  Google Scholar 

  31. Alberto R, Abram U (2011) 99mTc: Labeling chemistry and labeled compounds. In: Vértes A, Nagy S, Klencsár Z, Lovas RG, Rösch F (eds) Handbook of nuclear Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4419-0720-2_43

    Chapter  Google Scholar 

  32. Rhodes BA (1974) Considerations in the radiolabeling of albumin. Sem nucl med 4(3):281–293

    Article  CAS  Google Scholar 

  33. Abu-Zeid M, Hori H, Nagasawa H, Uto Y, Inayama S (2000) Studies of Methyl 2-Nitroimidazole-1-acetohydroxamate (KIN-804) 2: effect on certain antioxidant enzyme systems in mice bearing Ehrlish ascites carcinoma. Biol Pharm Bull 23(2):195–198

    Article  CAS  PubMed  Google Scholar 

  34. Motaleb M, Abdel-Ghaney I, Abdel-Bary H, Shamsel-Din H (2016) Synthesis, radioiodination and biological evaluation of a novel phthalimide derivative. J Radioanal Nucl Chem 307(1):363–372

    Article  CAS  Google Scholar 

  35. Abdelaziz G, Shamsel-Din HA, Sarhan MO, Gizawy MA (2020) Tau protein targeting via radioiodinated Azure a for brain theranostics: radiolabeling, molecular docking, in vitro and in vivo biological evaluation. J Label Compd Radiopharm 63(1):33–42

    Article  CAS  Google Scholar 

  36. Abdel-Ghany I, Moustafa K, Abdel-Bary H, Shamsel-Din H (2013) Synthesis, radioiodination and biological evaluation of novel dipeptide attached to triazole-pyridine moiety. J Radioanal Nucl Chem 295(2):1273–1281

    Article  CAS  Google Scholar 

  37. Inukai J, Ohnishi A, Tagawa S, Hayashi K, Sakamoto N, Nakamura T, Hase M (2019) Diseases showing diffuse bone uptake on FDG-PET. J Nucl Med 60(supplement 1):1155

    Google Scholar 

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Authors and Affiliations

  1. Labeled Compounds Department, Hot Labs Center, Atomic Energy Authority, P.O. Box 13759, Cairo, Egypt

    H. A. Shamsel-Din

  2. Egyptian Petroleum Research Institute, P.O. Box 11727, Nasr City, Cairo, Egypt

    E. G. Zaki

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  1. H. A. Shamsel-Din
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  2. E. G. Zaki
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Shamsel-Din, H.A., Zaki, E.G. Synthesis, 99mTc-radiolabeling and in vivo evaluation of a new sulphonamide derivative for solid tumor imaging. J Radioanal Nucl Chem 326, 129–136 (2020). https://doi.org/10.1007/s10967-020-07317-z

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