Abstract
Schiff base ligands are biologically active compounds in having antimicrobial, antiviral and antitumor activities etc. In this study, we have synthesized a Schiff base ligand namely 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino) benzoic acid, by reacting 3-amino-4-hydroxybenzoic acid and 2-hydroxy-3-methoxy benzaldehyde in the presence of acetic acid and refluxing it. The resulting base ligand was characterized on HPLC and used for radiolabelling with technetium-99m. The ligand 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino) benzoic acid was labelled with 99mTc at pH 7, while reacting 230 µg of ligand with 15 mCi of 99mTcO−4 for 10 min at room temperature. The resulting 99mTc-ligand complex was characterized by paper chromatography, TLC, HPLC and electrophoresis technique. The stability of the complex was determined at room temperature and in human serum. The biodistribution of the complex was studied in mice and scintigraphy was performed in rabbit. The 99mTc-ligand complex showed high radiolabelling yield (up to 99 ± 1%) and high stability at room temperature and in human serum. The newly prepared complex exhibited no net charge. Our newly developed 99mTc-ligand complex demonstrated high accumulation in liver and spleen of mice as well as in rabbit. Based on these findings, we have suggested that this novel radioligand i.e., 99mTc- 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino) benzoic acid complex could be used for liver and spleen imaging.
Similar content being viewed by others
Change history
12 November 2018
In the published original version, the complete list of authors was omitted. The complete list of contributing authors is updated with this Correction.
References
Ghammamy S, Sedaghatb S (2013) Preparation and characterization of Co(III) and Ni(II) complexes of the new chiral Schiff base (z)-1-(pyridine-2-ylmethylene) thiosemicarbazide. Middle-East J Sci Res 13(9):1213–1216
Singh P, Dhakarey RK (2009) Synthesis, characterization and antimicrobial studies of metal complexes with Schiff bases derived from 2-thienyl glyoxal. Rasayan J Chem 2(4):869–874
Sharma A, Mehta T, Shah MK (2013) Synthesis and spectral studies of transition metal complexes supported by NO-bidentate Schiff-base ligand. Pelagia Res Libr 4(1):141–146
Akila E, Usharani M, Rajavel R (2012) Design, synthesis and interpretation of binuclear Schiff base metal complexes and their application; antibacterial activity. Int J Inorg Bioinorg Chem 2(2):15–19
Alaghaz A-NM, Bayoumi HA, Ammar YA, Aldhlmani SA (2013) Synthesis, characterization, and antipathogenic studies of some transition metal complexes with N, O-chelating Schiff’s base ligand incorporating azo and sulfonamide Moieties. J Mol Struct 1035:383–399
Pawar V, Uma V, Joshi S (2011) Synthesis, characterization and biological studies of schiff bases metal complexes Co(II), Zn(II), Ni(II), and Mn(II) derived from amoxicillin trihydrate with various aldehydes. Int J Pharm Bio Sci 2:240–250
Priyarega S, Tamizh MM, Karvembu R, Prabhakaran R, Natarajan K (2011) Synthesis, spectroscopic characterization and catalytic oxidation properties of ONO/ONS donor Schiff base ruthenium(III) complexes containing PPh 3/AsPh 3. J Chem Sci 123(3):319–325
Akbar MU, Zia KM, Akash MSH, Nazir A, Zuber M, Ibrahim M (2018) In-vivo anti-diabetic and wound healing potential of chitosan/alginate/maltodextrin/pluronic-based mixed polymeric micelles: curcumin therapeutic potential. Int J Biol Macromol. https://doi.org/10.1016/j.ijbiomac.2018.09.010
Akbar MU, Zia KM, Nazir A, Iqbal J, Ejaz SA, Akash MSH (2018) Pluronic-based mixed polymeric micelles enhance the therapeutic potential of curcumin. AAPS PharmSciTech 19(6):2719–2739
Akbar MU, Rehman K, Zia KM, Qadir MI, Akash MSH, Ibrahim M (2018) Critical review on curcumin as a therapeutic agent: from traditional herbal medicine to an ideal therapeutic agent. Crit Rev Eukaryot Gene Expr 28:17–24. https://doi.org/10.1615/CritRevEukaryotGeneExpr.2018020088
Akbar MU, Bokhari TH, Khalid M, Ahmad MR, Roohi S, Hina S et al (2017) Radiolabeling, quality control, and biological characterization of 177Lu-labeled kanamycin. Chem Biol Drug Des 90(3):425–431
Akbar MU, Ahmad MR, Shaheen A, Mushtaq S (2016) A review on evaluation of technetium-99m labeled radiopharmaceuticals. J Radioanal Nucl Chem 310(2):477–493
Bokhari TH, Roohi S, Hina S, Akbar MU, Sohaib M, Iqbal M (2018) Synthesis, quality control, and bio-evaluation of 99mTc-cyclophosphamide. Chem Biol Drug Des 91(2):456–462
Akbar MU, Bokhari TH, Roohi S, Zia KM, Zuber M, Parveen N et al (2016) Development, optimization, and biovalidation of 99mTc–insulin complex. Russ J Bioorg Chem 42(5):491–496
Bokhari TH, Akbar MU, Roohi S, Hina S, Sohaib M, Rizvi FA (2015) Synthesis, characterization and biological evaluation of 99mTc-labeled Mitomycin C. J Radioanal Nucl Chem 303(3):1779–1784
Bokhari T, Akbar M, Hina S, Usman M, Haq A, Roohi S et al (2016) Direct labelling of medically interesting 99 m Tc-benzyl penicillin. Oxid Commun 1:187–194
Acknowledgements
The authors are thankful to all lab staff of PINSTECH for their technical guidance, co-operation, and assistance for the completion of this research project.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
Author declare that do not have any conflict of interest for this article.
Rights and permissions
About this article
Cite this article
Akbar, M.U. Preparation, optimization and pharmacological evaluation of 99mTc- 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino) benzoic acid complex: as a novel potential radiopharmaceutical agent with hepatobiliary excretion. Mol Biol Rep 45, 2717–2723 (2018). https://doi.org/10.1007/s11033-018-4402-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11033-018-4402-6