Synthesis, radioiodination and biological evaluation of novel dipeptide attached to triazole-pyridine moiety

Abdel-Ghany, I. Y.; Moustafa, K. A.; Abdel‐Bary, Hamed M.; Shamsel-Din, Hesham A.

doi:10.1007/s10967-012-2237-5

Cited by 12 publications

(4 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…During the reaction, chloramine-T has a crucial role in converting iodide to a more reactive form [34]. The number of attempts was performed by increasing the amount of chloramine-T (Entry [13][14][15][16][17][18]. The results suggest that increasing the amount of chloramine-T significantly impacts the RCYs.…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, the introduction of iodine into the substrate negligibly alters the structure, and therefore could be crucial in maintaining biological activities [15]. Until recently, radioiodination of organic molecules has gained much attention among scientists in developing suitable radiotracers for the diagnosis and treatment of human ailments, such as cancer treatment (e.g., [ 125 I]-iodothioguanine, [ 131 I]-metaiodobenzylguanidine (MIBG), and [ 131 I]-anti-CD20) and cancer imaging (e.g., [ 123 I]iodocelecoxib, [ 123 I]-MIBG) [16][17][18]. Although some xanthine derivatives have been explored for their potential as imaging or therapeutic agents in nuclear medicine, xanthine and hypoxanthine have not been radiolabeled with therapeutic radionuclides, especially iodine-131.…”

Section: Introduction mentioning

confidence: 99%

See 1 more Smart Citation

Efficient and Practical Radiosynthesis of Novel [131I]-Xanthine and [131I]-Hypoxanthine

Wongso¹,

Nuraeni²,

Rosyidiah³

2022

Atom Indo.

View full text Add to dashboard Cite

Natural products (NPs) have been the basis for the discovery and development of pharmacologically relevant drug-related molecules, including radiopharmaceuticals. Xanthine (3,7-dihydropurine-2,6-dione) and hypoxanthine (1,9-dihydro-6H-purin-6-one) are purine-based natural heterocyclic alkaloids that are generally found in some plants, animals, and the human body (e.g., muscle tissue, blood, and urine). The purpose of this study was to label xanthine and hypoxanthine with radioactive iodine-131 (a theranostic radionuclide) by a direct labeling method using chloramine-T as an oxidizing agent. Several experiments were performed to optimize the labeling efficiency by changing reaction conditions, including the ratio of starting material and chloramine-T, pH, solvent, temperature, and reaction time. Overall, labeling at acidic conditions in dimethyl sulfoxide (DMSO) resulted in considerable low radiochemical yields (RCYs) (< 4.0 %), and therefore the focus was shifted to exploit the alkaline reaction conditions.The optimized reaction condition: pH (10.5-11.0), xanthine:chloramine-T ratio (1:2), reaction temperature (27 ºC), and reaction time (30 min), provided [ 131 I]-xanthine with a RCY of 65.8 ± 0.1 %. After purification with extraction using chloroform (CHCl 2 ), the radiochemical purity (RCP) of 95.1 % was achieved, as indicated by radio-thin layer chromatography (radio-TLC) analysis. In addition, the labeling of hypoxanthine was accomplished in a maximum 60.3 ± 0.2 % RCY, and after purification a RCP of 94.2 % was obtained. The present results provide an efficient and practical labeling method for xanthine and hypoxanthine with iodine-131, suggesting that these radiolabeled compounds can be further investigated in in vitro and in vivo studies for their theranostics potential.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introduction mentioning

confidence: 99%

Efficient and Practical Radiosynthesis of Novel [131I]-Xanthine and [131I]-Hypoxanthine

Wongso¹,

Nuraeni²,

Rosyidiah³

2022

Atom Indo.

View full text Add to dashboard Cite

show abstract

“…The measurement was repeated three times. The partition coefficient value was expressed as log P .

boldLog p_{oct . / wat .} = boldLog ((), {[solute]}_{octanol} / {[solute]}_{deionized water})

…”

Section: Methodsmentioning

confidence: 99%

“Tau Protein Targeting Via Radioiodinated Azure A For Brain Theranostics: Radiolabeling, Molecular Docking, in vitro And in vivo Biological Evaluation”

Abdelaziz

Shamsel-Din

Sarhan

et al. 2019

Labelled Comp Radiopharmac

View full text Add to dashboard Cite

Azure-A is one of the phenothiazines (PTZs) derivatives which for decades have been used as antipsychotic drugs due to good lipophilic characteristics which enable them to pass through the blood brain barrier (BBB), besides the important property of enabeling investigation of the pathological forms of aggregated tau protein found in the neurons of the central nervous system.Radioiodination of Azure-A was carried out via an electrophilic substitution reaction using chloramine-T as oxidizing agent. The influence of various reaction parameters and conditions on radioiodination efficiency was investigated, and a high radiochemical yield of 92.07 ± 0.9 % was obtained. An in vitro cytotoxicity study of iodinated Azure-A on three cell lines (HCT-116, human colon carcinoma cell line; Hep-G2, liver carcinoma cell line and HFB-4, normal human melanocytes) was carried out, and the data revealed that ioiodinated Azure A has no to very low toxic effect. The in vivo biodistribution study of 131 I-Azure A showed a high brain uptake of 6.15 ± 0.09 % injected dose/g tissue organ at 30 minutes post-injection, and its retention in brain remained high up to 2 hours, whereas the clearance from the body appeared to proceed via the renal system. The experimental data were confirmed by the molecular docking studies to predict the effect of radioiodination on the binding affinity of the parent molecule (Azure A) to tau paired helical filaments (PHFs). Both ligands showed better binding to S2 and S3 pockets of (PHFs). Consequently, radioiodinated Azure A seems to be a good candidate as an imaging agent for taupathies such as Alzheimer's disease, chronic traumatic encephalopathy, and corticobasal degeneration. Furthermore, it could be a very potent theranostics agent for brain tumors. K E Y W O R D SAzure A, blood brain barrier (BBB)

show abstract

“…Chloramine T is hydrolyzed in an acidic medium to form hypohalous acid (HOCl), which will be further hydrolyzed to form H2OCl + , so the possible oxidizing agents in acidified CAT solution are HOCl and H2OCl + , while the alkaline CAT solution is HOCl and ClO [36]. Therefore, it reacts quickly with olmesartan at any site where it can enter the electrophilic substitution reaction [37][38][39][40]. 4) showed the effect of different concentrations of parathion on the variation of the radiochemical yield, whereas different concentrations ranging from 10 to 100µg.…”

Section: Optimization Of Reactionmentioning

confidence: 99%

Distribution of Iodine125 Labeled Parathion and the Protective Effect of Dried Banana Peel in Experimental Mice

et al. 2021

View full text Add to dashboard Cite

Parathion (PA) one of the organophosphorus pesticides, is widespread in agriculture crops. Several studies reported the detection of this pesticide residue in food at high concentrations. Accordingly, the purpose of this study was to determine the accumulation of iodine [ 125 I] labeled parathion ([ 125 I] PA) in mice organs and to study the protecting reflex of dried banana peel. In this study, two groups of mice were used. Iodine [ 125 I] labeled parathion (10 mg/kg body weight) was applied only to one group of mice. Meanwhile, [ 125 I] PA (10 mg/kg body weight) and dried banana peel (20% were added to the diet) were applied to the other group of mice. The mice were injected by [ 125 I] PA through the tail vein and were given the dried banana peel through the mouth. The mice were kept under observation for 180 min. for monitoring. The result of the first group of mice, which was injected with [ 125 I] PA, only indicated that [ 125 I] PA was distributed primarily in the kidneys (18.6%), liver (18.9%), and intestine (6.11%), after 180 min. In the second group of mice which received both [ 125 I] PA, and dried banana peels, [ 125 I] PA accumulated at a lower percentage in the kidneys (10.2%), liver (5.2%), and intestine (4.67%) after 180 min. These results indicated the decrease of [ 125 I] PA in the liver and kidneys could be due to the effect of dried banana peels, and draw attention to the use of agricultural waste to remove pesticide residues contaminating food and feed.

show abstract

Synthesis, radioiodination and biological evaluation of novel dipeptide attached to triazole-pyridine moiety

Cited by 12 publications

References 31 publications

Efficient and Practical Radiosynthesis of Novel [131I]-Xanthine and [131I]-Hypoxanthine

Efficient and Practical Radiosynthesis of Novel [131I]-Xanthine and [131I]-Hypoxanthine

“Tau Protein Targeting Via Radioiodinated Azure A For Brain Theranostics: Radiolabeling, Molecular Docking, in vitro And in vivo Biological Evaluation”

Distribution of Iodine125 Labeled Parathion and the Protective Effect of Dried Banana Peel in Experimental Mice

Contact Info

Product

Resources

About