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Original Articles

Synthesis, characterization, radiolabeling and biodistribution of a novel cyclohexane dioxime derivative as a potential candidate for tumor imaging

ORCID Icon, ORCID Icon, , &
Pages 590-596 | Received 14 Oct 2017, Accepted 20 Mar 2018, Published online: 27 Apr 2018

References

  • Alberto R. 2003. Technetium. In: McCleverty JA, Meyer TJ, editors. Comprehensive Coordination Chemistry–II from biology to nanotechnology. 2nd ed. Amsterdam: Elsevier Ltd; p. 127–270.
  • Al-Sha’alan NH. 2007. Antimicrobial activity and spectral, magnetic and thermal studies of some transition metal complexes of a schiff base hydrazone containing a quinoline moiety. Molecules. 12:1080–1091.
  • Alsibai W, Hahnenkamp A, Eisenblatter M, Eisenblätter M, Riemann B, Schäfers M, Bremer C, Haufe G, Höltke C. 2014. Fluorescent non-peptidic RGD mimetics with high selectivity for αVβ3 vs αIIbβ3 integrin receptor: novel probes for in vivo optical imaging. J Med Chem. 57:9971–9982.
  • Archer CM, Burke JF, Canning LR, Edwards B, King AC, inventors; Amersham International PLC, assignee. 1999 Dec 7. Radiometal complexes that localise in hypoxic tissue. United States patent US 5,997,843.
  • Archer CM, Edwards B, Kelly JD, King AC, Burke JF, Riley ALM. 1995. In: Nicolini M, Bandoli G, Mazzi U, editors. Technetium and rhenium in chemistry and nuclear medicine 4. Padova: S.G. Editorali; p. 535–539.
  • Babahan I, Coban EP, Biyik H. 2013. Synthesis, characterisation and antimicrobial activities of vicdioxime derivatives containing heteroaromatic hydrazine groups and their metal complexes. Maejo Int J Sci Technol. 7:26–41.
  • Baileya SE, Olin TJ, Bricka RM, Adrian DD. 1999. A review of potentially low-cost sorbents for heavy metals. Water Reserch. 33:2469–2479.
  • Chu E, Sartorelli AC. 2015. Cancer chemotherapy. In: Katzung BG, Trevor AJ, editors. Basic and clinical pharmacology. 13th ed. New York: McGraw-Hill Education; p. 1345.
  • Corner J, Bailey C. 2008. Cancer Nursing Care in Context. 2nd ed. Oxford: Wiley-Blackwell.
  • Demir I, Bayrakci M, Mutlu K, Pekacar AI. 2008. Synthesis and characterization of a novel iminooxime schiff base ligand and its complexation with copper(II), nickel(II), zinc(II), cadmium(II), and cobalt(II). Acta Chim Slov. 55:120–124.
  • Di Antonio M, McLuckie KIE, Balasubramanian S. 2014. Reprogramming the mechanism of action of chlorambucil by coupling to a G‐quadruplex ligand. J Am Chem Soc. 136:5860–5863.
  • Ding R, He Y, Xu J, Liu H, Wang X, Feng M, Qi C, Zhang J, Peng C. 2012. Preparation and bioevaluation of 99mTc nitrido radiopharmaceuticals with pyrazolo[1,5-a]pyrimidine as tumor imaging agents. Med Chem Res. 21:523–530.
  • El-Kawy OA, Talaat HM. 2016. Preparation, characterization and evaluation of 186Re-idarubicin: a novel agent for diagnosis and treatment of hepatocellular carcinoma. J Label Compd Radiopharm. 59:72–77.
  • Gabriel J. 2007. The biology of cancer. 2nd ed. Chichester (UK): John Wiley & Sons Ltd.
  • Gracheva MA, Ilyushchenko ON, Kodina GE, Levin VI. 1982. The reaction of technetium 99-m complex formation with the ligands used for the preparation of radiopharmaceutical medicines. In: Fourth international symposium on radiopharmaceutical chemistry. J Label Comp Radiopharm 19:1535–1536.
  • Hirabayashi RN, Lindsay S. 1961. Carcinoma of the thyroid gland: a statistical study of 390 patients. J Clin Endocrinol Metab. 21:1596–1610.
  • Johnson LL, Schofield L, Mastrofrancesco P, Donahay T, Nott L. 1998. Technetium-99m-nitroimidazole uptake in a swine model of demand ischemia. J Nucl Med. 39:468–1475.
  • Karapcin F, Arabali F. 2006. Synthesis and characterization of 4-arylaminobi- phenylglyoximes and their complexes. J Chil Chem Soc. 51:982–985.
  • Lin X, Fang S, Teng Y, Zhang J. 2017. Preparation and biological evaluation of a technetium-99m labeled 4-nitroimidazole derivative for imaging tumor hypoxia. J Radioanal Nucl Chem. 313:39–45.
  • Lin J, Qiu L, Lv G, Li K, Wang W, Liu G, Zhao X, Wang S. 2017. Synthesis and preliminary biological evaluation of a 99mTc-chlorambucil derivative as a potential tumor imaging agent. J Label Compd Radiopharm. 60:116–123.
  • Linder KE, Chan YW, Cyr JE, Malley MF, Nowotnik DP, Nunn AD. 1994. TcO(PnAO-1-(2-nitroimidazole)) [BMS-181321], a new technetium-containing nitroimidazole complex for imaging hypoxia: synthesis, characterization, and xanthine oxidase-catalyzed reduction. J Med Chem. 37:9–17.
  • Liu J, Wang H, Wang S, Xue Q, Wang D, Wang H, Zha H. 2017. Initial evaluation of 99mTc‐tricarbonyl-cyclopentadienyl fatty acids derivatives as SPECT tracers for myocardium. J Label Compd Radiopharm. 60:250–262.
  • Meegalla SK, Plossl K, Kung MP, Chumpradit S, Stevenson DA, Kushner SA, McElgin WT, Mozley PD, Kung HF. 1997. Synthesis and characterization of technetium-99m-labeled tropanes as dopamine transporter-imaging agents. J Med Chem. 40:9–17.
  • Meltzer PC, Blundell P, Jones AG, Mahmood A, Garada B, Zimmerman RE, Davison A, Holman BL, Madras BK. 1997. A technetium-99m SPECT imaging agent which targets the dopamine transporter in primate brain. J Med Chem. 40:1835–1844.
  • Méndez-Rojas MA, Kharisov BI, Tsivadze AY, Tsivadze AYu. 2006. Recent advances on technetium complexes: coordination chemistry and medical applications. J Coord Chem. 59:1–63.
  • Mirković M, Vranješ-Đurić DJS, Radović M, Stanković D, Mijin D, Nikolić N. 2012. Novel tetradentate diamine dioxime ligands: synthesis, characterization and in vivo behavior of their 99mTc-complexes. Appl Organometal Chem. 26:347–355.
  • Motaleb MA. 2007. Preparation and biodistribution of 99mTc-lomefloxacin and 99mTc-ofloxacin complexes. J Radioanal Nucl Chem. 272:95–99.
  • Motaleb MA, Adli ASA, El-Tawoosy M, Sanad MH, AbdAllah M. 2016. An easy and effective method for synthesis and radiolabelling of risedronate as a model for bone imaging. J Label Compd Radiopharm. 59:157–163.
  • Motaleb MA, El-Tawoosy M, Mohamed SB, Borei IH, Ghanem HM, Massoud AA. 2014. 99mTc-labeled teicoplanin and its biological evaluation in experimental animals for detection of bacterial infection. Radiochemistry 56:544–549.
  • Motaleb MA, Ibrahem IT, Ayoub VR, Geneidi AS. 2016. Preparation and biological evaluation of 99mTc–ropinirole as a novel radiopharmaceutical for brain imaging. J Label Compd Radiopharm. 59:147–152.
  • Motaleb MA, Selim AA, El-Tawoosy M, Sanad MH, El-Hashash MA. 2017. Synthesis, radiolabeling and biological distribution of a new dioxime derivative as a potential tumor imaging agent. J Radioanal Nucl Chem 314:1517–1522. [accessed 2017 June 6]: [6 P.] https://doi.org/10.1007/s10967-017-5310-2
  • Moustapha ME, Shweeta HA, Motaleb MA. 2014. Technetium-labeled danofloxacin complex as a model for infection imaging. Arab J Chem. 9:S1928–S1934.
  • Nowotnik DP, Canning LR, Cumming SA, Harrison RC, Higley B, Nechvatal G, Pickett RD, Piper IM, Bayne VJ, Forster AM, et al. 1985. Development of a 99Tcm-labeled radiopharmaceutical for cerebral blood flow imaging. Nucl Med Commun. 6:499–506.
  • Oshima M, Itoh K, Okae S, Tadokoro M, Kodama Y, Sakuma S. 1990. Evaluation of primary lung carcinoma using technetium 99m-hexamethylpropylene amine oxime: preliminary clinical experience. Eur J Nucl Med. 16:859–864.
  • Owunwanne A, Marinsky J, Blau M. 1977. Charge and nature of technetium species produced in the reduction of pertechnetate by stannous ion. J Nucl Med. 18:1099–1105.
  • Reichert DE, Lewis JS, Anderson CJ. 1999. Metal complexes as diagnostic tools. Coord Chem Rev. 184:3–66.
  • Rhodes BA. 1974. Considerations in the Radiolabeling of Albumin. Semin Nucl Med. 4:281–293.
  • Sakr TM, El-Safoury DM, Awad GAS, Motaleb MA. 2013. Biodistribution of 99mTc-sunitinib as a potential radiotracer for tumor hypoxia imaging. J Label Compd Radiopharm. 56:392–395.
  • Sanad MH, El-Bayoumy ASA, Ibrahim AA. 2017. Comparative biological evaluation between 99mTc (CO)3 and 99mTc-Sn (II) complexes of novel quinoline derivative: a promising infection radiotracer. J Radioanal Nucl Chem. 311:1–14.
  • Satpati D, Korde A, Venkatesh M, Banerjee S. 2009. Preparation and bioevaluation of a 99mTc-labeled chlorambucil analog as a tumor targeting agent. Appl Radiat Isot. 67:1644–1649.
  • Treher EN, Francesconi LC, Gougoutas JZ, Malley MF, Nunn AD. 1989. Mono-capped tris dioxime complexes of technetium(III): Synthesis and structural characterization of TcX(dioxime)3B-R(X) Cl, Br; dioxime) dimethylglyoxime, cyclohexanedionedioxime; R) CH3, C4H9). Inorg Chem. 28:3411–3416.
  • Tubergen K, Corlija M, Volkert WA, Holmes RA. 1991. Sensitivity of technetium-99m-d,1-HMPAO to radiolysis in aqueous solutions. J Nucl Med. 32:111–115.
  • Vallabhajosula S, Zimmerman RE, Picard M, Stritzke P, Mena I, Heliman RS, Tikofsky RS, Stabin MG, Morgan RA, Goldsmith SJ. 1989. Technetium-99m ECD: A new brain imaging agent: In vivo kinetics and biodistribution studies in normal human subjects. J Nucl Med. 30:599–604.
  • Yarbro CH, Wujcik D, Gobel BH. 2011. Cancer nursing: principles and practice. 7th ed. Boston (MA): Jones and Bartlett Publishers.
  • Yaul SR, Yaul AR, Pethe GB, Aswar AS. 2009. Synthesis and characterization of transition metal complexes with N, O-chelating hydrazone schiff base ligand. Am Euras J Sci Res. 4:229–234.
  • Zhang X, Melo T, Rauth AM, Ballinger JR. 2001. Cellular accumulation and retention of the technetium-99m-labelled hypoxia markers BRU59-21 and butylene amine oxime. Nucl Med Biol. 28:949–957.
  • Zhang J, Yu Q, Huo J, Pang Y, Yang S, He Y, Tang T, Yang C, Wang X. 2010. Synthesis and biodistribution of a novel 99mTc-DMSA metronidazole ester as a potential tumor hypoxia imaging agent. J Radioanal Nucl Chem. 283:481–485.

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