Abstract
Search and synthesis of glucose derivatives for nuclear medicine is of great current interest. Being a promising analogue of glucose, D-glucosamine iodine labeled glucose derivatives can be applied in rheumatoid arthritis radionuclide diagnostics and therapy as a radiopharmaceutical. The purpose of the study. Synthesis of a new iodine labeled D-glucosamine derivative; development of the iodine-123 labeling method and the obtained glucose derivative biostudy. Materials and methods. Synthesis of 2-N-(6-iodohexanoyl)-D-glucosamine was carried out through established techniques in organic chemistry. Infrared spectroscopy and nuclear magnetic resonance spectroscopy were used to establish the test compound structure. Isotope change between iodine-127 and iodine-123 of glucosamine derivative was conducted using the heating of mix of the compound and Na123I in acetone. The radio-TLC method was applied to estimate the radiochemical purity of 2-N- (6-iod-123-hexanoyl) -D-glucosamine. The safe application and test of drug pharmacokinetic parameters study was performed on intact Wistar male rats. Results. An original 2-N-(6-iodohexanoyl)-D-glucosamine synthesis method was proposed. According to the method, an intermediate synthesis succimide-1-yl 6-iodohexanoate was obtained by the cyclohexanone oxidative cleavage reaction. The radiochemical purity of 2-N-(6-iodo-123-hexanoyl)-D-glucosamine was more than 97%. Conclusion. 2-N-(6-iodohexanoyl)-D-glucosamine was synthesized and iodine-123 labeled. When investigating the proposed radiopharmaceutical safety and pharmacokinetics, it was shown the drug lacks acute toxicity through intravenous injection and is excreted renally by glomerular filtration.
| Original language | English |
|---|---|
| Pages (from-to) | 102-111 |
| Number of pages | 10 |
| Journal | Bulletin of Siberian Medicine |
| Volume | 17 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 1 Jan 2018 |
Fingerprint
Keywords
- 2-N-(6-iodohexanoyl)-D-glucosamine
- Cyclohexanone
- D-glucosamine
- Iodine-123
- RFP
ASJC Scopus subject areas
- Molecular Medicine
Cite this
Preparation of 123-iodine labeled glucosamine derivative and investigation of its biological properties. / Larkina, M. S.; Semenov, A. S.; Zelchan, R. V.; Podrezova, E. V.; Bragina, O. D.; Yusubov, M. S.; Skuridin, V. S.; Chernov, V. I.; Belousov, M. V.; Timofeev, M. S.
In: Bulletin of Siberian Medicine, Vol. 17, No. 1, 01.01.2018, p. 102-111.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Preparation of 123-iodine labeled glucosamine derivative and investigation of its biological properties
AU - Larkina, M. S.
AU - Semenov, A. S.
AU - Zelchan, R. V.
AU - Podrezova, E. V.
AU - Bragina, O. D.
AU - Yusubov, M. S.
AU - Skuridin, V. S.
AU - Chernov, V. I.
AU - Belousov, M. V.
AU - Timofeev, M. S.
PY - 2018/1/1
Y1 - 2018/1/1
N2 - Search and synthesis of glucose derivatives for nuclear medicine is of great current interest. Being a promising analogue of glucose, D-glucosamine iodine labeled glucose derivatives can be applied in rheumatoid arthritis radionuclide diagnostics and therapy as a radiopharmaceutical. The purpose of the study. Synthesis of a new iodine labeled D-glucosamine derivative; development of the iodine-123 labeling method and the obtained glucose derivative biostudy. Materials and methods. Synthesis of 2-N-(6-iodohexanoyl)-D-glucosamine was carried out through established techniques in organic chemistry. Infrared spectroscopy and nuclear magnetic resonance spectroscopy were used to establish the test compound structure. Isotope change between iodine-127 and iodine-123 of glucosamine derivative was conducted using the heating of mix of the compound and Na123I in acetone. The radio-TLC method was applied to estimate the radiochemical purity of 2-N- (6-iod-123-hexanoyl) -D-glucosamine. The safe application and test of drug pharmacokinetic parameters study was performed on intact Wistar male rats. Results. An original 2-N-(6-iodohexanoyl)-D-glucosamine synthesis method was proposed. According to the method, an intermediate synthesis succimide-1-yl 6-iodohexanoate was obtained by the cyclohexanone oxidative cleavage reaction. The radiochemical purity of 2-N-(6-iodo-123-hexanoyl)-D-glucosamine was more than 97%. Conclusion. 2-N-(6-iodohexanoyl)-D-glucosamine was synthesized and iodine-123 labeled. When investigating the proposed radiopharmaceutical safety and pharmacokinetics, it was shown the drug lacks acute toxicity through intravenous injection and is excreted renally by glomerular filtration.
AB - Search and synthesis of glucose derivatives for nuclear medicine is of great current interest. Being a promising analogue of glucose, D-glucosamine iodine labeled glucose derivatives can be applied in rheumatoid arthritis radionuclide diagnostics and therapy as a radiopharmaceutical. The purpose of the study. Synthesis of a new iodine labeled D-glucosamine derivative; development of the iodine-123 labeling method and the obtained glucose derivative biostudy. Materials and methods. Synthesis of 2-N-(6-iodohexanoyl)-D-glucosamine was carried out through established techniques in organic chemistry. Infrared spectroscopy and nuclear magnetic resonance spectroscopy were used to establish the test compound structure. Isotope change between iodine-127 and iodine-123 of glucosamine derivative was conducted using the heating of mix of the compound and Na123I in acetone. The radio-TLC method was applied to estimate the radiochemical purity of 2-N- (6-iod-123-hexanoyl) -D-glucosamine. The safe application and test of drug pharmacokinetic parameters study was performed on intact Wistar male rats. Results. An original 2-N-(6-iodohexanoyl)-D-glucosamine synthesis method was proposed. According to the method, an intermediate synthesis succimide-1-yl 6-iodohexanoate was obtained by the cyclohexanone oxidative cleavage reaction. The radiochemical purity of 2-N-(6-iodo-123-hexanoyl)-D-glucosamine was more than 97%. Conclusion. 2-N-(6-iodohexanoyl)-D-glucosamine was synthesized and iodine-123 labeled. When investigating the proposed radiopharmaceutical safety and pharmacokinetics, it was shown the drug lacks acute toxicity through intravenous injection and is excreted renally by glomerular filtration.
KW - 2-N-(6-iodohexanoyl)-D-glucosamine
KW - Cyclohexanone
KW - D-glucosamine
KW - Iodine-123
KW - RFP
UR - http://www.scopus.com/inward/record.url?scp=85049973601&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85049973601&partnerID=8YFLogxK
U2 - 10.20538/1682-0363-2018-1-102-111
DO - 10.20538/1682-0363-2018-1-102-111
M3 - Article
AN - SCOPUS:85049973601
VL - 17
SP - 102
EP - 111
JO - Bulletin of Siberian Medicine
JF - Bulletin of Siberian Medicine
SN - 1682-0363
IS - 1
ER -