Abstract
Three vitamin B12 (cyanocobalamin) conjugates bearing one nido-carborane molecule or two nido-carborane molecules linked to the propionamide side chains via a four carbon linker have been synthesized. Reaction of o-carboranoylchloride with 1,4-diaminobutane in pyridine produced nido-carboranoyl(4-amidobutyl)amine, which was linked to the b- and d-monocarboxylic acids and the b,d-dicarboxylic acid of cyanocobalamin. Mass spectrometry analysis as well as 11B nuclear magnetic resonance demonstrated that during the reaction of o-carboranonylchloride with diaminobutane one of the boron atoms was eliminated. In vitro biological activity of the cyanocobalamin-nido-carborane conjugates was assessed by the unsaturated vitamin B12 binding capacity assay. When compared with 57Co cyanocobalamin, the biological activity of cyanocobalamin-b-nido-carborane, cyanocobalamin-d-nido-carborane, and cyanocobalamin-b-d-bis-nido-carborane conjugates were 92.93%, 35.75%, and 37.02%, respectively. These findings suggest that the 10B cobalamin conjugates might be useful agents in treating malignant tumors via neutron capture therapy. Copyright (C) 2000 Elsevier Science Inc.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 89-92 |
| Number of pages | 4 |
| Journal | Nuclear Medicine and Biology |
| Volume | 27 |
| Issue number | 1 |
| DOIs | |
| State | Published - Jan 2000 |
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Keywords
- Boron neutron capture therapy (BNCT)
- Boronated vitamin B
- Cyanocobalamin-nido-carborane conjugates
- Vitamin B
ASJC Scopus subject areas
- Cancer Research
- Molecular Medicine
- Radiology Nuclear Medicine and imaging
Cite this
Synthesis and characterization of nido-carborane-cobalamin conjugates. / Hogenkamp, H. P C; Collins, Douglas A.; Live, David; Benson, Linda M.; Naylor, Stephen.
In: Nuclear Medicine and Biology, Vol. 27, No. 1, 01.2000, p. 89-92.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and characterization of nido-carborane-cobalamin conjugates
AU - Hogenkamp, H. P C
AU - Collins, Douglas A.
AU - Live, David
AU - Benson, Linda M.
AU - Naylor, Stephen
PY - 2000/1
Y1 - 2000/1
N2 - Three vitamin B12 (cyanocobalamin) conjugates bearing one nido-carborane molecule or two nido-carborane molecules linked to the propionamide side chains via a four carbon linker have been synthesized. Reaction of o-carboranoylchloride with 1,4-diaminobutane in pyridine produced nido-carboranoyl(4-amidobutyl)amine, which was linked to the b- and d-monocarboxylic acids and the b,d-dicarboxylic acid of cyanocobalamin. Mass spectrometry analysis as well as 11B nuclear magnetic resonance demonstrated that during the reaction of o-carboranonylchloride with diaminobutane one of the boron atoms was eliminated. In vitro biological activity of the cyanocobalamin-nido-carborane conjugates was assessed by the unsaturated vitamin B12 binding capacity assay. When compared with 57Co cyanocobalamin, the biological activity of cyanocobalamin-b-nido-carborane, cyanocobalamin-d-nido-carborane, and cyanocobalamin-b-d-bis-nido-carborane conjugates were 92.93%, 35.75%, and 37.02%, respectively. These findings suggest that the 10B cobalamin conjugates might be useful agents in treating malignant tumors via neutron capture therapy. Copyright (C) 2000 Elsevier Science Inc.
AB - Three vitamin B12 (cyanocobalamin) conjugates bearing one nido-carborane molecule or two nido-carborane molecules linked to the propionamide side chains via a four carbon linker have been synthesized. Reaction of o-carboranoylchloride with 1,4-diaminobutane in pyridine produced nido-carboranoyl(4-amidobutyl)amine, which was linked to the b- and d-monocarboxylic acids and the b,d-dicarboxylic acid of cyanocobalamin. Mass spectrometry analysis as well as 11B nuclear magnetic resonance demonstrated that during the reaction of o-carboranonylchloride with diaminobutane one of the boron atoms was eliminated. In vitro biological activity of the cyanocobalamin-nido-carborane conjugates was assessed by the unsaturated vitamin B12 binding capacity assay. When compared with 57Co cyanocobalamin, the biological activity of cyanocobalamin-b-nido-carborane, cyanocobalamin-d-nido-carborane, and cyanocobalamin-b-d-bis-nido-carborane conjugates were 92.93%, 35.75%, and 37.02%, respectively. These findings suggest that the 10B cobalamin conjugates might be useful agents in treating malignant tumors via neutron capture therapy. Copyright (C) 2000 Elsevier Science Inc.
KW - Boron neutron capture therapy (BNCT)
KW - Boronated vitamin B
KW - Cyanocobalamin-nido-carborane conjugates
KW - Vitamin B
UR - http://www.scopus.com/inward/record.url?scp=0033951571&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033951571&partnerID=8YFLogxK
U2 - 10.1016/S0969-8051(99)00081-5
DO - 10.1016/S0969-8051(99)00081-5
M3 - Article
C2 - 10755651
AN - SCOPUS:0033951571
VL - 27
SP - 89
EP - 92
JO - International journal of radiation applications and instrumentation. Part B, Nuclear medicine and biology
JF - International journal of radiation applications and instrumentation. Part B, Nuclear medicine and biology
SN - 0969-8051
IS - 1
ER -