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/lp/springer-journals/novel-radiochemical-and-biological-characterization-of-99m-tc-X0xERjZtdD
- Publisher
- Springer Journals
- Copyright
- 2014 Sanad; licensee Springer.
- eISSN
- 2093-3371
- DOI
- 10.1186/s40543-014-0023-4
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- See Article on Publisher Site
Abstract
99m Background: Histamine was successfully labeled with technetium-99 m ( Tc). The studied reaction parameters included substrate concentration, reducing agent concentration, pH of the reaction mixture, reaction time, in vitro 99m stability of the Tc-histamine, and biodistribution in experimental animals. Method: Accurately weighed 3 mg histamine was dissolved and transferred to an evacuated penicillin vial. Exactly 50 μg SnCl dihydrate was added and the pH of the mixture was adjusted to 4 using 0.1N HCl, then the volume of 99m the mixture was adjusted to one ml by N -purged distilled water. One ml of freshly eluted TcO4- (~ 400MBq) was added to the above mixture. The reaction mixture was vigorously shaken and allowed to react at room temperature for sufficient time to complete the reaction Result: The complex gives a maximum labeling yield of 98.0% ± 0.34%, and maintained stability throughout the 99m working period (6 h). Biodistribution investigation showed that the maximum uptake of the Tc-histamine in the brain was 7.1% ± 0.12% of the injected activity/g tissue organ, at 5 min post-injection. The clearance from the mice appeared to proceed via the circulation mainly through the kidneys and urine (approximately 37.8% of the injected dose at 2 h after injection of the tracer). 99m 99m 99m Conclusions: Brain uptake of Tc-histamine is higher than that of ( Tc-ECD and Tc-HMPAO) therefore 99m Tc-histamine could be used for brain single-photon emission computed tomography (SPECT). Furthermore, 99m Tc-histamine could be considered as a novel radiopharmaceutical for brain imaging. Keywords: Histamine; Hexamethylpropyleneamine oxime and ethyl cysteinate dimer; Technetium-99 m; Labeling; Biodistribution; Brain; Imaging Background Brooks 2005; Heinz et al. 2000; Dickerson and Sperling Several recent reviews describe the use of single-photon 2005; Bammer et al. 2005; Eckert and Eidelberg 2005; emission computed tomography (SPECT) alone or in com- Kuzniecky 2005). Brain SPECT is now commonly used in bination with PET and/or functional magnetic resonance the diagnosis, prognosis assessment, evaluation of res- imaging (fMRI) in studies of human cognition, imaging of ponse to therapy, risk stratification, detection of benign or neuroreceptor systems, aiding diagnosis or assessment of malignant viable tissue, and choice of medical or surgical progression or treatment response in various psychiatric therapy, especially in head injury, malignant brain tumors, and neurologic disorders, neuropharmacologic challenge cerebrovascular disease, movement disorders, dementia, studies and in the new field of molecular imaging, includ- and epilepsy (Lee and Newberg 2005; Bonte and Devous ing imaging of transgene expression (Devous 2002; 2003; Devous Sr 1998; Brooks 2005; Heinz et al. 2000; Catafau 2001; Mazziotta and Toga 2002; Lee and Dickerson and Sperling 2005; Bammer et al. 2005; and Newberg 2005; Bonte and Devous 2003; Devous Sr 1998; Kuzniecky 2005). The selection of the proper isotope to be used in labeling and in imaging is important because it Correspondence: msanad74@yahoo.com should have a suitable short half-life to avoid unwarranted Labeled Compounds Department, Radioisotopes Production and Radioactive harmful exposure to radiation and suitable photon energy Sources Division, Hot Laboratories Center, Atomic Energy Authority, P.O. Box 13759, Cairo, Egypt © 2014 Sanad; licensee Springer. This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Sanad Journal of Analytical Science and Technology 2014, 5:23 Page 2 of 7 http://www.jast-journal.com/content/5/1/23 within the range of gamma camera. The two most proper 123 99m isotopes that fulfill these two precautions are Iand Tc. H H Brain imaging in humans is currently achieved by using 99m 99m 99m Tc-ethyl cysteinate dimer ( Tc-ECD), Tc-hexam- 99m 125 N N Tc ethylpropyleneamine oxime ( Tc-HMPAO), I-sibutra- mine, and I-fluoxetine (Ogasawara et al. 2001; Chang et al. 2002; Bonte et al. 2010; and El-Ghany et al. 2007). N The major disadvantage of these compounds is their poor 99m brain uptake in experimental animals (4.7% for Tc-ECD 99m and 2.25% for Tc-HMPAO) (Walovitch et al. 1989; H H Neirinckx et al. 1987). Such low uptake enforces us to try to find novel radiopharmaceuticals that can overcome this (a) (b) limitation and can be used as more efficient brain imaging agents. Histamine [2-(1H-imidazol-4-yl)] ethanamine is an Figure 1 The chemical structure of histamine (a), proposed 99m structure of the Tc-histamine (b). organic nitrogen compound involved in local immune re- sponsesaswellasregulatingphysiological function in the 99m molecules of histamine. Tc-histamine complex coordi- gut and acting as a neurotransmitter (Marieb 2001). Hista- nated as a Tc (V) oxocore, leading to complexes in which a mine increases the permeability of the capillaries to white 3+ TcO core exists (Jurisson et al. 1986; Abrams et al. 1991). blood cells and some proteins to allow them to engage path- ogens in the infected tissues (Di Giuseppe et al. 2003). Hista- Factors affecting % labeling yield mine is known to be involved in so many physiological This experiment was conducted to study the different factors functions because of its chemical properties that allow it to that affect labeling yield such as tin content as (SnCl · be so versatile in binding (Noszal et al. 2004). In this paper, 2H O), substrate content, pH of the reaction, and reaction histamine was labeled with the most widely used imaging 99m time. In the process of labeling, trials and errors were per- radionuclide, Tc. Factors affecting the labeling yield of 99m formed for each factor under investigations till obtains the Tc-histamine complex and biological distribution in Swiss optimum value. The experiment was repeated with all factors Albino mice (25 to 30 g) were studied in detail (Motaleb and kept at optimum changing except the factor under study, till Sanad 2012). The radiochemical yield of the product was de- the optimal conditions are achieved (Robbins 1984). termined by paper chromatography, paper electrophoresis, and high-performance liquid chromatography (HPLC). Quality control Paper chromatography Methods 99m Radiochemical yield of Tc-histamine was checked by Drugs and chemicals paper chromatography method in which, the reaction Histamine was purchased from Sigma-Aldrich Chemical product was spotted on ascending paper chromatogra- Company, St. Louis, MO, USA, and all other chemicals 99m − phy strips (10 × 1.5 cm). Free TcO in the preparation were purchased from Merck (Whitehouse Station, NJ, was determined using acetone as the mobile phase. Re- USA) and they were reactive grade. The water used is duced hydrolyzed technetium was determined by using an purged deoxygenated bidistilled water. ethanol/water/ammonium hydroxide mixture (2:5:1) or 5 N NaOH as the mobile phase. After complete develop- Labeling of histamine ment, the strips were dried then cut into 0.5-cm pieces Accurately weighed 3 mg histamine was dissolved and and counted in a well-type γ-scintillation counter. transferred to an evacuated penicillin vial. Exactly 50 μg SnCl dihydratewas addedand thepHof the mixturewas adjusted to 4 using 0.1 N HCl, then the volume of the mix- HPLC analysis ture was adjusted to 1 ml by N -purged distilled water. One An HPLC analysis of histamine solution was done by an in- 99m − milliliter of freshly eluted TcO (approximately jection of 10 μl from the reaction mixture into the column 400 MBq) was added to the above mixture. The reaction (RP-18-250 × 4.6 mm ,5 μm, Lischrosorb) built in an HPLC mixture was vigorously shaken and allowed to react at room Shimadzu model (Kyoto, Japan) which consists of pumps LC- temperature for sufficient time to complete the reaction 9A, Rheohydron injector and UV spectrophotometer detector 99m (Boyd 1986). The proposed structure of the Tc-histamine (SPD-6A) adjusted to the 256-nm wavelength. The column 99m − via reaction of histamine with TcO in the presence of was eluted with mobile phase methanol/H O (50:50) and the 4 2 stannous chloride dihydrate at pH 4 at room temperature is flow rate was adjusted to 1 ml/min. Then fractions of 1 ml 99m showninFigure1b, wherethe oxidationstate of Tc were collected separately using a fraction collector up to changed from +7 into +5 to form a complex with two 20 ml and counted in a well-type γ-scintillation counter. Sanad Journal of Analytical Science and Technology 2014, 5:23 Page 3 of 7 http://www.jast-journal.com/content/5/1/23 10.3 4.4 0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 Retention time, min 99m Figure 2 HPLC radiochromatogram of Tc-histamine complex. 99m Stability of Tc-histamine in human serum vein and kept alive in metabolic cage for different intervals 99m The stability of Tc-histamine was studied in vitro by mixing of time under normal conditions. For quantitative determin- 99m 1.8mlofnormalhuman serumand 0.2mlof Tc-histamine ation of organ distribution, five mice were used for each ex- and incubated at 37°C for (24 h). Exactly 0.2 ml aliquots were periment and the mice were sacrificed at different times withdrawn during the incubation at different time intervals post-injection. Samples of fresh blood, bone, and muscle up to 6 h and subjected to paper chromatography for de- were collected in pre-weighed vials and counted. The differ- 99m termination of the percent of Tc-histamine, reduced ent organs were removed, counted, and compared to a hydrolyzed technetium and free pertechnetate standard solution of the labeled histamine. The average per- cent values of the administrated dose/organ were calculated. Animal studies Blood, bone, and muscles were assumed to be 7%, 10%, and The study was approved by the animal ethics committee, 40%, respectively, of the total body weight (Motaleb 2001). Labeled Compound Department, and was in accordance Corrections were made for background radiation and phy- with the guidelines set out by the Egyptian Atomic Energy sical decay during experiment. Differences in the data were Authority. Swiss Albino mice (25 to 30 g) were in- evaluated with the Student's t test. Results for P using the travenously injected with 100 μl (100 to 150 MBq) of sterile two-tailed test are reported and all the results are given as 99m Tc-histamine adjusted to physiological pH via the tail mean ± SEM. The level of significance was set at P <0.05. % Labeled compound 99m % Free Tc % Colloid 0 25 50 75 100 125 150 SnCl .2H O amount,µg 2 2 99m Figure 3 Effect of Sn (II) amount on the labeling yield of Tc-histamine, complex. Conditions: 3 mg histamine, 25-150 µg Sn (II), pH 4 and 30 min. reaction time, n=3. % Labeling yield count/min Sanad Journal of Analytical Science and Technology 2014, 5:23 Page 4 of 7 http://www.jast-journal.com/content/5/1/23 % Labeled compound 99m % Free Tc % Colloid 0 1 2 3 4 5 6 7 8 9 10 11 Ligand amount,mg 99m Figure 4 Effect of histamine amount on the labeling yield of Tc-histamine complex. Conditions: 1-10 mg of histamine, 50 µg Sn (II), pH 4 and 30 min. reaction time, n=3. 99m Determination of the partition coefficient of Tc-histamine Results and discussion 99m 99m The partition coefficient was determined by mixing Tc- Separation of Tc-histamine complex histamine with equal volumes of 1-octanol and phosphate In the case of the ascending paper chromatographic buffer (0.025 M at pH 7.4) in a centrifuge tube. method, acetone was used as the developing solvent; free 99m − The mixture was vortexed at room temperature for TcO moved with the solvent front (R = 1), while 4 f 99m 1 min and then centrifuged at 5,000 rpm for 5 min. Sub- Tc-histamine and reduced hydrolyzed technetium sequently, 100 μl samples from the 1-octanol and aqueous remained at the point of spotting. In the case of the as- layers were pipetted into other test tubes and counted cending paper chromatographic method, mixture was in a gamma counter. The measurement was repeated used as the developing solvent; reduced hydrolyzed tech- five times. The partition coefficient value was expressed as netium remains at the origin (R = 0), while other species log p (Motaleb et al. 2011). migrate with the solvent front (R = 1). The radiochem- ical purity was determined by subtracting the sum of the percent of reduced hydrolyzed technetium and free per- Counts per min in octanole – Counts per min back ground technetate from 100%. The radiochemical yield is the P ¼ Counts per min in buffer – Counts per min back ground mean value of five experiments. % Labeled compound 99m % Free Tc Colloid 234 5 6 pH 99m Figure 5 Effect of pH of the reaction mixture of Tc-histamine complex. Conditions: 3 mg histamine, 50 µg Sn (II), pH 2-6 and 30 min. reaction time, n=3. % Labeling yield % Labeling yield Sanad Journal of Analytical Science and Technology 2014, 5:23 Page 5 of 7 http://www.jast-journal.com/content/5/1/23 % Labeled compound 99m % Free Tc Colloid 0 50 100 150 200 250 300 350 400 Reaction time,min. 99m Figure 6 Effect of reaction time on the labeling yield of Tc-histamine complex. Conditions: 1-360 min. at optimum conditions, reaction time, n=3. 99m − HPLC chromatogram was presented in Figure 2 and pertechnetate so the percentage of TcO was relatively shows two peaks, one at fraction No. 4.4, which corres- high (16.6%). The labeling yield significantly increased by 99m − ponds to TcO , while the second peak was collected increasing the amount of SnCl ·2H Ofrom25to 50 μg 4 2 2 99m at fraction No. 10.3 for Tc-histamine, which was found (optimum amount), at which a maximum labeling yield to coincide with the UV signal. of 98% was obtained. By increasing the amount of SnCl ·2H O above the optimum concentration value, 2 2 Factors affecting labeling yield the labeling yield decreased again because the excess Effect of SnCl ·2H O amount SnCl ·2H O was converted to colloid (50.6% at 150 μg 2 2 2 2 As shown in Figure 3, the radiochemical yield was de- SnCl ·2H O) (Liu et al. 2004). 2 2 pendent on the amount of SnCl ·2H O present in the 2 2 reaction mixture. At 25 μg SnCl ·2H O, the labeling Effect of histamine amount 2 2 99m 99m yield of Tc-histamine was 81.6% due to the fact The labeling yield of Tc-histamine complex was 55.5% that SnCl ·2H O amount was insufficient to reduce all at 1 mg histamine and increased with increasing the 2 2 99m Table 1 Biodistribution of Tc-histamine in normal mice Organs and body fluid % I.D./organ and body fluid at different post-injection times 5 min 15 min 30 min 120 min 240 min Liver 8.11 ± 0.3 6.2 ± 0.1 5.2 ± 0.2 3.2 ± 0.1 1.3 ± 0.02 Urine 5.10 ± 0.2 8.60 ± 0.11 18.1 ± 1.1 23.0 ± 2.3 31.5 ± 2.3 Kidneys 10.5 ± 0.1 12.25 ± 0.3 16.8 ± 1.2 15.2 ± 0.3 6.30 ± 22 Blood 28.4 ± 0.5 24.8 ± 0.9 6.1 ± 0.12 3.50 ± 0.1 1.2 ± 0.05 Heart 1.3 ± 0.01 1.40 ± 0.02 1.6 ± 0.01 0.9 ± 0.03 0.70 ± 0.02 Lung 30.5 ± 0.2 12.8 ± 0.3 11.30 ± 0.2 5.40 ± 0.10 3.25 ± 0.6 Intestine 3.50 ± 0.1 2.80 ± 0.2 1.4 ± 0.02 1.2 ± 0.03 0.9 ± 0.02 Stomach 1.6 ± 0.06 1.20 ± 0.02 2.2 ± 0.05 3.3 ± 0.13 3.70 ± 0.2 Spleen 1.6 ± 0.03 4.52 ± 0.21 6.20 ± 0.2 5.3 ± 0.32 3.80 ± 0.16 Bone 1.90 ± 0.1 1.6 ± 0.3 2.0 ± 0.11 1.80 ± 0.30 1.70 ± 0.13 Muscle 1.8 ± 0.01 1.6 ± 0.03 1.5 ± 0.01 1.2 ± 0.06 1.10 ± 0.02 Brain 7.1 ± 0.12 4.85 ± 0.6 1.4 ± 0.02 0.83 ± 0.06 0.62 ± 0.03 Thyroid 1.3 ± 0.05 0.9 ± 0.02 0.7 ± 0.03 0.55 ± 0.01 0.32 ± 0.01 Brain/blood 0.25 0.2 0.23 0.24 0.52 % Labeling yield Sanad Journal of Analytical Science and Technology 2014, 5:23 Page 6 of 7 http://www.jast-journal.com/content/5/1/23 99m amount of histamine till reaching the maximum value of The high accumulation of Tc-histamine in lungs is de- 98% at 3 mg (Figure 4). The formed complex remained creased markedly with time from 30.5 ± 0.2, at 5 min till stable with increasing the amount of histamine up to reaching 3.5 ± 0.6 at 4 h (Suhara et al. 1998; Sanad and 10 mg. So the optimum amount of histamine was 3 mg Ibrahim 2013; Ibrahim and Sanad 2013; Sanad and El- (Liu et al. 2004; Sanad 2007). Tawoosy 2013). The biodistribution data showed substan- tial uptake of 7.1 ± 0.12 (%ID/g ± SD) in the brain at 5 min Effect of pH of the reaction mixture post-injection. After this time point, radioactivity dropped As shown in Figure 5, at pH 2, the labeling yield of to 4.85 ± 0.6 at 15 min post-injection. The maximum 99m 99m Tc-histamine complex was small and equal to 75.5% brain uptake of Tc-histamine (7.1 ± 0.12) is higher than and this yield increased with increasing the pH of the that of currently used radiopharmaceuticals for brain 99m 99m reaction mixture where pH 4 gave the maximum label- imaging, Tc-ethyl cysteinate dimer ( Tc-ECD) and 99m 99m ing yield of 98%. By increasing the pH greater than 4, Tc- hexamethylpropyleneamine oxime ( Tc-HMPAO) the labeling yield decreased again till it became 55.5% at which have maximum brain uptake of 4.7% and 2.25%, re- pH 6 where colloid was the main impurity (35.2% at spectively (Walovitch et al. 1989; Neirinckx et al. 1987); 99m pH 6) after pH 6 more colloidal solutions are formed therefore, Tc-histamine could be successfully used for (Liu et al. 2004). brain SPECT. Effect of reaction time Conclusion Figure 6 describes the effect of incubation time on the 99m Histamine can be labeled easily with Tc using 50 μgstan- 99m radiochemical purity of Tc-histamine complex. At nous chloride dihydrate (SnCl ·2H O) as a reducing agent 2 2 1 min post labeling, the yield was small and equal to and 3 mg histamine at pH 4 for 30 min at room 85.6% which increased with time till reaching its max- 99m temperature to give Tc-histamine complex with a radio- imum value of 98% at 30 min. The yield remains stable chemical yield of 98%, which is higher than that of the com- at 97.9% for a time up to 6 h (Liu et al. 2004). mercially available kit. Biodistribution studies showed that 99m the uptake of Tc-histamine in the brain (7.1% ± 0.12) is Stability test higher than that of currently used radiopharmaceuticals for 99m In vitro stability of Tc- histamine was studied in 99m 99m brain imaging, Tc-ethyl cysteinate dimer ( Tc-ECD) order to determine the suitable time for injection to 99m 99m and Tc-hexamethylpropyleneamine oxime ( Tc- avoid the formation of the undesired products that result 99m HMPAO), respectively. Tc-histamine couldbeusedfor from the radiolysis of complex. These undesired radio- 99m brain SPECT. Furthermore, Tc histamine could be con- active products might be accumulated in non-target sidered as a novel radiopharmaceutical for brain imaging. 99m organs. The results of stability showed that the Tc- histamine is stable up to 24 h and that at 37°C, resulted Competing interests in no release of radioactivity (n = five experiments) from The author declares that he has no competing interests. 99m the Tc-histamine, as determined by paper chroma- Received: 9 June 2013 Accepted: 5 February 2014 tography (Motaleb et al. 2011). 99m Partition coefficient for Tc- histamine References The partition coefficient values were 1.48 ± 0.02, showing Abrams MJ, Larsen S, Zubieta J (1991) Fluoride as a terminal bridging ligand 99m for copper: isolation and X-ray crystallographic characterization of monomeric that the Tc-histamines are lipophilic and can cross the and dimeric forms of a copper (II)-fluoride complex. Inorg Chem 30:2031–2035 blood–brain barrier. Bammer R, Skare S, Newbould R, Liu C, Thijs V, Ropele S, Clayton DB, Krueger G, Moseley ME, Glover GH (2005) Foundations of advanced magnetic resonance 99m imaging. 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Society of Nuclear Medicine, New York, NY, USA journal and benefi t from: Sanad MH (2007) Synthesis and labeling of some organic compounds with one of the most radioactive isotope; Ph.D. Thesis, Chemistry Department, Faculty 7 Convenient online submission of Science, Ain-Shams University, Cairo, Egypt 7 Rigorous peer review Sanad MH (2013) Labeling of omeprazole with technetium-99 m for diagnosis of 7 Immediate publication on acceptance stomach. J Radiochemistry 55(6):605–609 Sanad MH, El-Tawoosy M (2013) Labeling of ursodeoxycholic acid with 7 Open access: articles freely available online technetium-99 m for hepatobiliary imaging. J Radioanal Nucl Chem 7 High visibility within the fi eld 298(2):1105–1109 7 Retaining the copyright to your article Sanad MH, Ibrahim IT (2013) Radiodiagnosis of peptic ulcer with technetium-99 m pantoprazole. J Radiochemistry 55(3):341–345 Submit your next manuscript at 7 springeropen.com
Journal
"Journal of Analytical Science and Technology" – Springer Journals
Published: Dec 1, 2014
Keywords: Analytical Chemistry; Characterization and Evaluation of Materials; Monitoring/Environmental Analysis