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Radiolabeling of gamma-irradiated rosmarinic acid by 67Gallium

Document Type : Research Paper

Authors

1 Gorgan University of Agricultural Sciences and Natural Resources, P.O.Box: 4913815739, Gorgan - Iran

2 Nuclear Science and Technology Research Institute, AEOI, P.O. Box 14395-836, Tehran - Iran

Abstract

Rosemary plant extract as a natural anti-oxidant is 4 times stronger than synthetic anti-oxidant like BHT and BHA. For this reason, it has been under attention not only for its anti-oxidant properties rather for its anti-inflammatory, anti-tumor, anti-bacterial, and anti-virus properties in different studies. This research investigates the effects of temperature, time, pH, and substance concentration in the labeling of irradiated rosmarinic acid by radioisotope gallium-67 as a high-resolution imaging agent for SPECT imaging. In this study, gamma irradiated rosmarinic acid nanoparticles at 20 kGy and 30 kGy levels in two concentrations of 0.5 and 1% were radiolabeled by gallium-67 radioisotope produced in Karaj cyclotron, and their efficiency and radiochemical purity were compared. Labeling conditions (including pH, temperature, time, and compound concentration) were investigated. Quality control was performed by thin-layer chromatography (RTLC). Resulting from the experiments, 30 kGy level and 1% concentration at 45 °C for 30 minutes at pH = 5.5-6 proved to be the best time for labeling rosemary nanoparticles, and the highest radiochemical purity achieved was 95%; radio conjugate also showed good stability after 12 hours.

Highlights

  1. P.P. McCue, K. Shetty, Inhibitory effects of rosmarinic acid extracts on porcine pancreatic amylase in vitro, Asia Pac J Clin Nutr, 13(1), 101-106 (2004).

 

  1. G. Nieto, et al., Antioxidant and Antimicrobial Properties of Rosemary (Rosmarinus officinalis, L.): A Review, Medicines (Basel), 5(3), 98 (2018).

 

  1. N. Erkan, et al., Antioxidant activities of rosemary (Rosmarinus Officinalis L.) extract, blackseed (Nigella sativa L.) essential oil, carnosic acid, rosmarinic acid and sesamol, Food Chem, 110(1), 76-82 (2008).

 

  1. L. Hajhosseini, et al., Effect of rosmarinic acid on sertoli cells apoptosis and serum antioxidant levels in rats after exposure to electromagnetic fields, Afr J Tradit Complement Altern Med, 10(6), 477–480 (2013).

 

  1. V.A. Tironi, et al., Quality loss during the frozen storage of sea salmon (Pseudopercis semifasciata) effect of rosemary (Rosmarinus officinalis L.) extract, J. Food. Sci. Tech, 43, 263–272 (2010).

 

  1. S.Y. Lin, et al., Hepatoprotective activities of rosmarinic acid against extrahepatic cholestasis in rats, Food Chem Toxicol, 108, 214-223 (2017).

 

  1. S.S. Chang, et al., Natural antioxidant from Rosemary and Sage, J. Food. Sci, 42, 1102-1106 (1977).

 

  1. R. Rezanejad, et al., Gamma-irradiated rosemary (Rosmarinus officinalis) dips treatment effect on quality of rainbow trout (Oncorhynchus mykiss) fillets during refrigerated storage, Bulg J Vet Med, (2020).

 

  1. R. Najafi, Sh. Khangholi, Investigating the antioxidant activity of methanolic, ethanolic extracts of rosemary leaves (Rosmarinus officinalis) under the influence of ultrasound waves, the third national conference on organic cultivation and propagation of medicinal plants, (2017) (In Persian).

 

  1. W. Hao, et al., Hydrogen peroxide is involved in salicylic acidelicited rosmarinic acid production in Salvia miltiorrhiza cell cultures, Sci World J, 1-7 (2014).

 

  1. R. Lucarini, et al., Hepatoprotective effect of Rosmarinus officinalis and rosmarinic acid on acetaminophen -induced liver damage, Emir J Food Agric, 878-884 (2014).

 

  1. G.S. Li, et al., In vitro and in vivo antifibrotic effects of rosmarinic acid on experimental liver fibrosis, Phytomedicine, 17(3-4), 282–288 (2010).

 

  1. W. Cao, et al., Rosmarinic acid inhibits inflammation and angiogenesis of hepatocellular carcinoma by suppression of NF-κB signaling in H22 tumor-bearing mice, J Pharmacol Sci, 132(2), 131–137 (2016).

 

  1. M. Dubois, et al., Reaction of rosmarinic acid with nitrite ions in acidic conditions: discovery of nitro- and dinitrorosmarinic acids as new anti-HIV-1 agents, J Med Chem, 51, 2575–2579 (2008).

 

  1. G. Jayanthy, S. Subramanian, Rosmarinic acid, a polyphenol, ameliorates hyperglycemia by regulating the key enzymes of carbohydrate metabolism in high fat diet –STZ induced experimental diabetes mellitus, Biomed Prev Nutr, 4(3), 431-437 (2014).

 

  1. A. Hamta, P. Parvini, Study of Cytotoxic Effects of Taxol and Rosemary Extracts on Cancerous Cells Derived From DMBA-induced Breast Cancer in SD Rats, Journal of Cell & Tissue, 2(2), 117-126 (2011) (In Persian).

 

  1. R. Torkashavand, et al., Evaluation of anticancer effects of rosemary extract and Leishmania extract on cervical cancer cells (HeLa), Razi Journal of Medical Sciences, 27(2), 103-112 (2020) (In Persian).

 

  1. M. Heidarieh, et al., Preparation and anatomical distribution study of 67Ga-alginic acid nanoparticles for SPECT purposes in rainbow trout (Oncorhynchus mykiss), Nukleonika, 59(4), 153-159 (2014).

 

  1. R. Rezanejad, et al., Characterization of gamma-irradiated Rosemary (Rosmarinus officinalis L.), Turk J Pharm Sci, 16, 4347 (2019).

 

  1. S.L. Kitson, et al., Modern Developments in Isotopic Labelling, Researchgate (2014).

 

  1. A.R. Jalilian, et al., Labeling, quality control and biodistribution of anti-CD 20 antibody with gallium-67, J Nucl Sci Technol, 46, 10-17 (2007) (In Persian).

 

  1. A. Taheri Borujeni, et al., Preparation and investigation of tissue distribution of gallium-67 labeled venom of Gadim Scorpion (Hemiscorpiuslepturus), doctoral thesis of Jundishapur University of Medical Sciences and Health Services, Ahvaz, (2013) (In Persian).

 

  1. D.M. El-Sharawy, et al., 99mTc-Luteolin: radiolabeling, in silico ADMET and biological evaluation as a natural tracer tumor imaging, J Radiat Res Appl Sci, 14, 125–132 (2021).

 

  1. D.M. Taylor, et al., The Scientific Background to Decorporation, Radiation Protection Dosimetry, 87(1), 11–18 (2000).

 

  1. B. Tepe, Antioxidant potentials and rosmarinic acid levels of the methanolic extracts of Salvia virgata (Jacq), Salvia staminea (Montbret and Aucher ex Bentham) and Salvia verbenaca (L.) from Turkey, Bioresour Technol, 99, 1584-1588 (2007).

 

  1. A.R. Jalilian, et al., Development of 67Ga-Bleomycin complex for tumor iamaging, J. of Nuclear Sci. & Tech, 25, 9-15 (2002).

 

  1. D.M. El-Sharawy, et al., Radiolabeling, biological distribution, docking and ADME studies of 99mTc-Ros as a promising natural tumor tracer, Appl Radiat Isot, 184, 110196 (2022).

 

  1. H.S. Ali, et al., Gold Nanoparticles in Cancer Diagnosis and Therapy, Elsevier, Amsterdam, The Netherlands, (2019) ISBN 9780128169605.

 

  1. A.B. De Barros, et al., Emerging role of radiolabeled nanoparticles as an effective diagnostic technique, EJNMMI Res, 2(39) (2012).

 

  1. R. Chakravarty, et al., Image-guided drug delivery with single-photon emission computed tomography: A review of literature, Curr Drug Targets, 16, 592-609 (2015).

 

  1. R. Chakravarty, et al., Positron emission tomography image-guided drug delivery: Current status and future perspectives, Mol Pharm, 11, 3777-3797 (2014).

 

  1. V.J. Chen, P. Ma, Nano-fibrous poly (L-lactic acid) scaffolds with interconnected spherical macropores, Biomaterials, 25(11), 2065–2073 (2004).

 

  1. M.A. Nematallahi, et al., Comparison between of effect of Ergosan particles and nano-particles as produced by using Gamma rays and ultrasonic waves on the growth and stress parameters indices of rainbow trout (Oncorhynchus mykiss), Aquaculture Sciences, 7(2), 123-131 (2020).

 

  1. M.R. Karim, et al., Synthesis of core-shell silver–polyaniline nanocomposites by gamma radiolysis method, J Polym Sci, 45, 5741-5747 (2007).

 

  1. J.K. Kim, et al., Structural and antioxidant properties of gamma irradiated hyaluronic acid, Food Chem, 109 (4), 763–770 (2008).

 

  1. E.H. Byun, et al., Effects of gamma irradiation on the physical and structural properties of β-glucan, Radiat.Phys.Chem, 77(6), 781–786 (2008).

 

  1. A. Charlesby, Crosslinking and degradation of polymers, Radiat. Phys. Chem, 18, 59–66 (1981).

 

  1. N. Damavandi Kamali, et al., Effect of pH Variation on Cross-linking of Water-soluble and Acid-soluble Chitosan with Sodium Tripolyphosphate and Gallium-67, Curr Radiopharm, (2021), DOI: 10.2174/1874471015666220204142608.

 

  1. B. Cekic, et al., Radiolabeling of methanol extracts of yarrow (Achillea millefolium l) in rats, Acta Cir Bras, 27 (5), 294-300 (2012).

 

  1. H.M. Rashed, et al., 99mTc-hexoprenaline and 131I-dapoxetine: preparation, in silico modeling and biological evaluation as promising lung scintigraphy radiopharmaceuticals, J Radioanal Nucl Chem, 314, 1297–1307 (2017).

 

  1. I.S. Ahmed, et al., Nanoparticlemediated dual targeting: an approach for enhanced baicalin delivery to the liver, Pharmaceutics, 12, 107 (2020).

Keywords

References
  1. P.P. McCue, K. Shetty, Inhibitory effects of rosmarinic acid extracts on porcine pancreatic amylase in vitro, Asia Pac J Clin Nutr, 13(1), 101-106 (2004).

 

  1. G. Nieto, et al., Antioxidant and Antimicrobial Properties of Rosemary (Rosmarinus officinalis, L.): A Review, Medicines (Basel), 5(3), 98 (2018).

 

  1. N. Erkan, et al., Antioxidant activities of rosemary (Rosmarinus Officinalis L.) extract, blackseed (Nigella sativa L.) essential oil, carnosic acid, rosmarinic acid and sesamol, Food Chem, 110(1), 76-82 (2008).

 

  1. L. Hajhosseini, et al., Effect of rosmarinic acid on sertoli cells apoptosis and serum antioxidant levels in rats after exposure to electromagnetic fields, Afr J Tradit Complement Altern Med, 10(6), 477–480 (2013).

 

  1. V.A. Tironi, et al., Quality loss during the frozen storage of sea salmon (Pseudopercis semifasciata) effect of rosemary (Rosmarinus officinalis L.) extract, J. Food. Sci. Tech, 43, 263–272 (2010).

 

  1. S.Y. Lin, et al., Hepatoprotective activities of rosmarinic acid against extrahepatic cholestasis in rats, Food Chem Toxicol, 108, 214-223 (2017).

 

  1. S.S. Chang, et al., Natural antioxidant from Rosemary and Sage, J. Food. Sci, 42, 1102-1106 (1977).

 

  1. R. Rezanejad, et al., Gamma-irradiated rosemary (Rosmarinus officinalis) dips treatment effect on quality of rainbow trout (Oncorhynchus mykiss) fillets during refrigerated storage, Bulg J Vet Med, (2020).

 

  1. R. Najafi, Sh. Khangholi, Investigating the antioxidant activity of methanolic, ethanolic extracts of rosemary leaves (Rosmarinus officinalis) under the influence of ultrasound waves, the third national conference on organic cultivation and propagation of medicinal plants, (2017) (In Persian).

 

  1. W. Hao, et al., Hydrogen peroxide is involved in salicylic acidelicited rosmarinic acid production in Salvia miltiorrhiza cell cultures, Sci World J, 1-7 (2014).

 

  1. R. Lucarini, et al., Hepatoprotective effect of Rosmarinus officinalis and rosmarinic acid on acetaminophen -induced liver damage, Emir J Food Agric, 878-884 (2014).

 

  1. G.S. Li, et al., In vitro and in vivo antifibrotic effects of rosmarinic acid on experimental liver fibrosis, Phytomedicine, 17(3-4), 282–288 (2010).

 

  1. W. Cao, et al., Rosmarinic acid inhibits inflammation and angiogenesis of hepatocellular carcinoma by suppression of NF-κB signaling in H22 tumor-bearing mice, J Pharmacol Sci, 132(2), 131–137 (2016).

 

  1. M. Dubois, et al., Reaction of rosmarinic acid with nitrite ions in acidic conditions: discovery of nitro- and dinitrorosmarinic acids as new anti-HIV-1 agents, J Med Chem, 51, 2575–2579 (2008).

 

  1. G. Jayanthy, S. Subramanian, Rosmarinic acid, a polyphenol, ameliorates hyperglycemia by regulating the key enzymes of carbohydrate metabolism in high fat diet –STZ induced experimental diabetes mellitus, Biomed Prev Nutr, 4(3), 431-437 (2014).

 

  1. A. Hamta, P. Parvini, Study of Cytotoxic Effects of Taxol and Rosemary Extracts on Cancerous Cells Derived From DMBA-induced Breast Cancer in SD Rats, Journal of Cell & Tissue, 2(2), 117-126 (2011) (In Persian).

 

  1. R. Torkashavand, et al., Evaluation of anticancer effects of rosemary extract and Leishmania extract on cervical cancer cells (HeLa), Razi Journal of Medical Sciences, 27(2), 103-112 (2020) (In Persian).

 

  1. M. Heidarieh, et al., Preparation and anatomical distribution study of 67Ga-alginic acid nanoparticles for SPECT purposes in rainbow trout (Oncorhynchus mykiss), Nukleonika, 59(4), 153-159 (2014).

 

  1. R. Rezanejad, et al., Characterization of gamma-irradiated Rosemary (Rosmarinus officinalis L.), Turk J Pharm Sci, 16, 4347 (2019).

 

  1. S.L. Kitson, et al., Modern Developments in Isotopic Labelling, Researchgate (2014).

 

  1. A.R. Jalilian, et al., Labeling, quality control and biodistribution of anti-CD 20 antibody with gallium-67, J Nucl Sci Technol, 46, 10-17 (2007) (In Persian).

 

  1. A. Taheri Borujeni, et al., Preparation and investigation of tissue distribution of gallium-67 labeled venom of Gadim Scorpion (Hemiscorpiuslepturus), doctoral thesis of Jundishapur University of Medical Sciences and Health Services, Ahvaz, (2013) (In Persian).

 

  1. D.M. El-Sharawy, et al., 99mTc-Luteolin: radiolabeling, in silico ADMET and biological evaluation as a natural tracer tumor imaging, J Radiat Res Appl Sci, 14, 125–132 (2021).

 

  1. D.M. Taylor, et al., The Scientific Background to Decorporation, Radiation Protection Dosimetry, 87(1), 11–18 (2000).

 

  1. B. Tepe, Antioxidant potentials and rosmarinic acid levels of the methanolic extracts of Salvia virgata (Jacq), Salvia staminea (Montbret and Aucher ex Bentham) and Salvia verbenaca (L.) from Turkey, Bioresour Technol, 99, 1584-1588 (2007).

 

  1. A.R. Jalilian, et al., Development of 67Ga-Bleomycin complex for tumor iamaging, J. of Nuclear Sci. & Tech, 25, 9-15 (2002).

 

  1. D.M. El-Sharawy, et al., Radiolabeling, biological distribution, docking and ADME studies of 99mTc-Ros as a promising natural tumor tracer, Appl Radiat Isot, 184, 110196 (2022).

 

  1. H.S. Ali, et al., Gold Nanoparticles in Cancer Diagnosis and Therapy, Elsevier, Amsterdam, The Netherlands, (2019) ISBN 9780128169605.

 

  1. A.B. De Barros, et al., Emerging role of radiolabeled nanoparticles as an effective diagnostic technique, EJNMMI Res, 2(39) (2012).

 

  1. R. Chakravarty, et al., Image-guided drug delivery with single-photon emission computed tomography: A review of literature, Curr Drug Targets, 16, 592-609 (2015).

 

  1. R. Chakravarty, et al., Positron emission tomography image-guided drug delivery: Current status and future perspectives, Mol Pharm, 11, 3777-3797 (2014).

 

  1. V.J. Chen, P. Ma, Nano-fibrous poly (L-lactic acid) scaffolds with interconnected spherical macropores, Biomaterials, 25(11), 2065–2073 (2004).

 

  1. M.A. Nematallahi, et al., Comparison between of effect of Ergosan particles and nano-particles as produced by using Gamma rays and ultrasonic waves on the growth and stress parameters indices of rainbow trout (Oncorhynchus mykiss), Aquaculture Sciences, 7(2), 123-131 (2020).

 

  1. M.R. Karim, et al., Synthesis of core-shell silver–polyaniline nanocomposites by gamma radiolysis method, J Polym Sci, 45, 5741-5747 (2007).

 

  1. J.K. Kim, et al., Structural and antioxidant properties of gamma irradiated hyaluronic acid, Food Chem, 109 (4), 763–770 (2008).

 

  1. E.H. Byun, et al., Effects of gamma irradiation on the physical and structural properties of β-glucan, Radiat.Phys.Chem, 77(6), 781–786 (2008).

 

  1. A. Charlesby, Crosslinking and degradation of polymers, Radiat. Phys. Chem, 18, 59–66 (1981).

 

  1. N. Damavandi Kamali, et al., Effect of pH Variation on Cross-linking of Water-soluble and Acid-soluble Chitosan with Sodium Tripolyphosphate and Gallium-67, Curr Radiopharm, (2021), DOI: 10.2174/1874471015666220204142608.

 

  1. B. Cekic, et al., Radiolabeling of methanol extracts of yarrow (Achillea millefolium l) in rats, Acta Cir Bras, 27 (5), 294-300 (2012).

 

  1. H.M. Rashed, et al., 99mTc-hexoprenaline and 131I-dapoxetine: preparation, in silico modeling and biological evaluation as promising lung scintigraphy radiopharmaceuticals, J Radioanal Nucl Chem, 314, 1297–1307 (2017).

 

  1. I.S. Ahmed, et al., Nanoparticlemediated dual targeting: an approach for enhanced baicalin delivery to the liver, Pharmaceutics, 12, 107 (2020).
Journal of Nuclear Science, Engineering and Technology (JONSAT)
Volume 44, Issue 4 - Serial Number 106
December 2024
Pages 163-169
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