Synthesis of Radioiodinated Compounds. Classical Approaches and Achievements of Recent Years
Abstract
:1. Introduction
2. Iodine Isotopes Used in Radiopharmaceuticals
- iobenguane 131I, a form of 131I-MIBG, for the treatment of paragangliomas and pheochromocytomas
- 131I-labeled HSA for the determination of total blood and plasma volume, cardiac output, cardiac and pulmonary blood volumes and circulation times; for the study of protein metabolism and borders of the heart and large vessels; and for localization of the placenta and cerebral neoplasms
- [131I]NaI for diagnostics and therapeutic applications
3. Synthetic Methods for Incorporation of Radioactive Iodine into Molecules
3.1. The Problem of Iodine-Containing Drugs’ Stability and the Optimal Position of Radioactive Iodine in a Molecule
3.2. General Methods for Incorporation of Radioactive Iodine into a Molecule
3.2.1. Introduction of Radioactive Iodine into Small Molecules
Substrate Choice
Oxidizing Agent Choice
3.2.2. Radioiodination of Macromolecules Using Prosthetic Groups
Direct Radioiodination
Choice of Bioconjugation Reaction
3.3. Synthesis of Radioiodinated Derivatives: Conclusion
4. Iodine-Containing Radiopharmaceuticals at the Stage of Clinical Trials
4.1. Low-Molecular-Weight Iodine-Containing Radiopharmaceuticals
4.1.1. meta-Iodobenzylguanidine (MIBG)
4.1.2. Radioiodinated Amino Acids
4.1.3. Radioiodinated Lipids
4.1.4. Radioiodinated Heterocyclic Compounds
4.1.5. para-Iodophenylpentadecanoic Acid (IPPA) and β-Methyliodophenylpentadecanoic Acid (BMIPP)
4.1.6. 4-(4-Fluoro-3-(4-(3-iodobenzoyl)piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one (MAPi)
4.1.7. 4-(6-Iodimidazo [1,2-a]pyridin-2-yl)-N,N-dimethylaniline (IMPY, TZDM)
4.1.8. Iodobenzovesamicol (IBVM)
4.1.9. 4-(2-(Bis(4-fluorophenyl)methoxy)ethyl)-1-(4-iodobenzyl)piperidine (β-CIT)
4.1.10. Ioflupan (FP-CIT)
4.1.11. (2R)-2-(2-Hydroxy-1-iodopropan-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno [3,4-b]fluoro [2,3-h] chromen-6(6aH)-one (CMICE-013)
4.1.12. N-(2-(Diethylamino)ethyl)-6-iodoquinoxaline-2-carboxamide (ICF01012)
4.1.13. Radioiodinated Drugs Based on Peptide Conjugates
4.2. Radioiodinated Drugs Based on Macromolecular Compounds
5. Conclusions
- Electrophilic and nucleophilic substitution reactions, especially the former, are the predominant synthetic approaches used in radioiodination.
- Iododestantnylation is the best and most widely used method for electrophilic radioiodination of low-molecular-weight compounds, provided that the product can be purified from the unreacted tin-containing precursor.
- Fixing tin precursors to insoluble resins or using ionic liquids may overcome the difficulties of separation from toxic tin derivatives.
- Isotopic exchange of iodine-127 is the most commonly used method of nucleophilic radioiodination of low-molecular-weight compounds.
- Direct radioactive iodination of peptides and proteins is very easy, and it cannot be recommended as a method for the synthesis of radiopharmaceuticals, because the products are rapidly deiodinated in vivo.
- The problem of deiodination of proteins and peptides is generally solved by the use of prosthetic groups.
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Abbreviations
A85380 | 5-Iodo-3-(2(S)-azetidinylmethoxy)pyridine |
AGI-5198 | N-Cyclohexyl-2-(N-(3-iodophenyl)-2-(2-methyl-1H-imidazol-1- yl)acetamido)-2-(o-tolyl)acetamide |
BMIPP | β-Methyliodophenylpentadecanoic acid |
β-CIT | 2β-Carbomethoxy-3β-(4-iodophenyl)tropane |
CLR-131 | Iopofosin I-131, 12-[4-(131I)iodophenyl]dodecylphosphocholine |
CMICE-013 | (2R)-2-(2-Hydroxy-1-iodopropan-2-yl)-8,9-dimethoxy-1,2,12,12a- tetrahydrochromeno [3,4-b]fluoro [2,3-h] chromen-6(6aH)-one |
CNS1261 | N-(1-Naphthyl)-N’-(3-iodophenyl)-N-methylguanidine |
(1-)-DABI | (4-isothiocyanatobenzylammonio)-undecahydro-closo-dodecaborate |
FDA | Food and Drug Administration (Food and Drug Administration, USA) |
FP-CIT | Ioflupane, N-ω-fluoropropyl-2β-carbomethoxy-3β-(4- iodophenyl)northropan |
HAS | Human serum albumin |
IAZA | 1-(5-Iodo-5-deoxy-β-D-arabinofuranosyl)-2-nitroimidazole |
IBOX | 2-(4’-Dimethylaminophenyl)-6-iodobenzoxazole |
IBM | N-(2-Aminoethyl)maleimide) |
IBVM | Iodobenzovemicol |
ICF01012 | N-(2-(Diethylamino)ethyl)-6-iodoquinoxaline-2-carboxyamide () |
IMPY, TZDM | 4-(6-Iodimidazo [1,2-a]pyridin-2-yl)-N,N-dimethylaniline |
IMTO | Iodomethomidate |
IMT | L-3-Iodine-α-methyltyrosine |
IPA | para-I-Iodo-L-Phenylalanine |
IPBM | 2-((2-Iodophenyloxy)(phenyl)methyl)-2-methylmorpholine |
IPM | 1-(3-Iodophenyl)maleimide |
IPPA | para-Iodophenylpentadecanoic acid |
mAb | Monoclonal antibodies |
MAPi | 4-(4-Fluoro-3-(4-(3-iodobenzoyl)piperazine-1-carbonyl)benzyl) phthalazin-1(2H)-one |
MIBG, MIBG | meta-Iodobenzylguanidine |
MIP-1072 | (S)-2-(3-((S)-1-carboxy-5-(4-iodobenzylamino)pentyl)ureido) pentanedioic acid |
MNI-187 | 4-(5-Iodo-2H-benzo[d][1,2,3]triazol-2-yl)-N,N-dimethylaniline |
MZINT | 2β-Carbomethoxy-3β-(4′-((Z)-2-iodoethenyl)phenyl)northropan |
NBS | N-Bromosuccinimide |
NCS | N-Chlorosuccinimide |
NCTFS | N-Chloro-tetra-fluorosuccinimide |
PET | Positron emission tomography |
PIB | N-Succinimidyl-4-iodobenzoate |
RCC | Radiochemical Conversion |
RCP | Radiochemical purity |
RCY | Radiochemical yield |
SIB | N-Succinimidyl-3-iodobenzoate |
SIPC | N-Succinimidyl-5-iodine-3-pyridinecarboxylate |
SPECT | Single photon emission tomography |
TCP | 2,3,5,6-Tetrafluorophenyl-3-(nidocarboranyl)propionate |
TFIB | Tetrafluorophenyl-4-fluoro-3-iodobenzoate. |
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Characteristic | SPECT | PET |
---|---|---|
Equipment | γ-Camera | Tomograph |
Radioisotopes | γ-Emitters | β+-emitters |
Average procedure duration | 30–40 min | 10–20 min |
Image reconstruction | Automatic | automatic |
Spatial resolution | 12–16 mm | 4–6 mm |
Sensitivity | Lower than that of PET | High |
Multimodality | It is possible to combine SPECT-CT and SPECT-MRI | It is possible to combine PET-CT and PET-MRI |
Availability | Wide | Less available than SPECT |
Resulting image | 2D or 3D reconstruction | 3D |
Quantification | Only semiquantitative assessment | Possible |
Dose load on tissues | Lower than that of PET | Higher, but balanced by higher sensitivity |
Radioisotope | 123I | 124I | 125I | 131I |
---|---|---|---|---|
Half-lifetime T1/2 | 13.22 h | 4.18 days | 59.39 days | 8.02 days |
Decay type | EC (100%) | EC (77%) β+ (23%) | EC (100%) | β− (90%) EC (10%) |
Energy of emitted particles * | γ (159 keV), 28.4 e−/decay (Auger electrons) | γ (603 keV) γ (511 keV upon annihilation of β+ with an electron) β+ (213.8 keV) | γ (35.5 keV), 19.5 e−/decay (Auger electrons) | γ (364 keV), β− (606 keV) |
Production ** | Cyclotron: 124Xe(p, pn) 123Xe → 123I 124Xe(p, 2n) 123Cs→ 123Xe → 123I | Cyclotron: 124Te(p, n) → 124I | Nuclear reactor: 124Xe(n, γ) → 125mXe → 125I; 124Xe (n, γ) → 125gXe → 125I | Nuclear reactor: 131Te(n, γ) → 131I or 235U fission |
Application | SPECT, radiotherapy | PET | Radiotherapy in vitro and in vivo experiments on small animals | Radiotherapy, SPECT |
Ref. | [25] | [26] | [27] | [28] |
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Petrov, S.A.; Yusubov, M.S.; Beloglazkina, E.K.; Nenajdenko, V.G. Synthesis of Radioiodinated Compounds. Classical Approaches and Achievements of Recent Years. Int. J. Mol. Sci. 2022, 23, 13789. https://doi.org/10.3390/ijms232213789
Petrov SA, Yusubov MS, Beloglazkina EK, Nenajdenko VG. Synthesis of Radioiodinated Compounds. Classical Approaches and Achievements of Recent Years. International Journal of Molecular Sciences. 2022; 23(22):13789. https://doi.org/10.3390/ijms232213789
Chicago/Turabian StylePetrov, Stanislav A., Mekhman S. Yusubov, Elena K. Beloglazkina, and Valentine G. Nenajdenko. 2022. "Synthesis of Radioiodinated Compounds. Classical Approaches and Achievements of Recent Years" International Journal of Molecular Sciences 23, no. 22: 13789. https://doi.org/10.3390/ijms232213789