Synthesis of 11C-labeled Kendine 91, a histone deacetylase inhibitor
In the present paper, the synthesis of 11C-labeled Kendine 91 (a HDAC inhibitor which has shown in vitro and in vivo activity in HCT 116 and MOLT 4 human cancer cell lines) is described for the first time. The radiosynthesis has been approached by reaction of the non-radioactive precursor 6-((3-(4-h...
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| Published in: | Applied radiation and isotopes Vol. 70; no. 10; pp. 2552 - 2557 |
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| Abstract | In the present paper, the synthesis of 11C-labeled Kendine 91 (a HDAC inhibitor which has shown in vitro and in vivo activity in HCT 116 and MOLT 4 human cancer cell lines) is described for the first time. The radiosynthesis has been approached by reaction of the non-radioactive precursor 6-((3-(4-hydroxyphenyl)-5-phenyl-1H-pyrrole-2-carboxamide))hexanehydroxamic acid with [11C]CH3I in basic media. Despite the presence of more than one reactive site in the chemical structure of the precursor, acceptable radiochemical yield (8.2±2.1%, decay corrected to the end of bombardment), specific activity (28.2±9.4GBq/μmol) and radiochemical purity values (>95%) were obtained in reasonably short preparation times (∼40min). Despite the moderate radiochemical yield, final radioactivity and radioactivity concentration values (1.8±0.3GBq and 180MBq/ml, respectively) should be sufficient for putative in vivo studies in animals.
► We labeled Kendine 91 with carbon-11. ► Despite low yields final radioactivity should allow in vivo studies. ► We synthesized the desmethylated precursor using two routes. ► Microwave assisted Paal–Knorr reaction was more efficient than (3+2) cycloaddition. |
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| AbstractList | In the present paper, the synthesis of 11C-labeled Kendine 91 (a HDAC inhibitor which has shown in vitro and in vivo activity in HCT 116 and MOLT 4 human cancer cell lines) is described for the first time. The radiosynthesis has been approached by reaction of the non-radioactive precursor 6-((3-(4-hydroxyphenyl)-5-phenyl-1H-pyrrole-2-carboxamide))hexanehydroxamic acid with [11C]CH3I in basic media. Despite the presence of more than one reactive site in the chemical structure of the precursor, acceptable radiochemical yield (8.2±2.1%, decay corrected to the end of bombardment), specific activity (28.2±9.4GBq/μmol) and radiochemical purity values (>95%) were obtained in reasonably short preparation times (∼40min). Despite the moderate radiochemical yield, final radioactivity and radioactivity concentration values (1.8±0.3GBq and 180MBq/ml, respectively) should be sufficient for putative in vivo studies in animals.
► We labeled Kendine 91 with carbon-11. ► Despite low yields final radioactivity should allow in vivo studies. ► We synthesized the desmethylated precursor using two routes. ► Microwave assisted Paal–Knorr reaction was more efficient than (3+2) cycloaddition. In the present paper, the synthesis of (11)C-labeled Kendine 91 (a HDAC inhibitor which has shown in vitro and in vivo activity in HCT 116 and MOLT 4 human cancer cell lines) is described for the first time. The radiosynthesis has been approached by reaction of the non-radioactive precursor 6-((3-(4-hydroxyphenyl)-5-phenyl-1H-pyrrole-2-carboxamide))hexanehydroxamic acid with [(11)C]CH(3)I in basic media. Despite the presence of more than one reactive site in the chemical structure of the precursor, acceptable radiochemical yield (8.2±2.1%, decay corrected to the end of bombardment), specific activity (28.2±9.4 GBq/μmol) and radiochemical purity values (>95%) were obtained in reasonably short preparation times (~40 min). Despite the moderate radiochemical yield, final radioactivity and radioactivity concentration values (1.8±0.3 GBq and 180 MBq/ml, respectively) should be sufficient for putative in vivo studies in animals. In the present paper, the synthesis of (11)C-labeled Kendine 91 (a HDAC inhibitor which has shown in vitro and in vivo activity in HCT 116 and MOLT 4 human cancer cell lines) is described for the first time. The radiosynthesis has been approached by reaction of the non-radioactive precursor 6-((3-(4-hydroxyphenyl)-5-phenyl-1H-pyrrole-2-carboxamide))hexanehydroxamic acid with [(11)C]CH(3)I in basic media. Despite the presence of more than one reactive site in the chemical structure of the precursor, acceptable radiochemical yield (8.2±2.1%, decay corrected to the end of bombardment), specific activity (28.2±9.4 GBq/μmol) and radiochemical purity values (>95%) were obtained in reasonably short preparation times (~40 min). Despite the moderate radiochemical yield, final radioactivity and radioactivity concentration values (1.8±0.3 GBq and 180 MBq/ml, respectively) should be sufficient for putative in vivo studies in animals. In the present paper, the synthesis of 11C-labeled Kendine 91 (a HDAC inhibitor which has shown in vitro and in vivo activity in HCT 116 and MOLT 4 human cancer cell lines) is described for the first time. The radiosynthesis has been approached by reaction of the non-radioactive precursor 6-((3-(4-hydroxyphenyl)-5-phenyl-1H-pyrrole-2-carboxamide))hexaneh y droxamic acid with [11C]CH3I in basic media. Despite the presence of more than one reactive site in the chemical structure of the precursor, acceptable radiochemical yield (8.2+/-2.1%, decay corrected to the end of bombardment), specific activity (28.2+/-9.4 GBq/Ammol) and radiochemical purity values (>95%) were obtained in reasonably short preparation times ( similar to 40 min). Despite the moderate radiochemical yield, final radioactivity and radioactivity concentration values (1.8+/-0.3 GBq and 180 MBq/ml, respectively) should be sufficient for putative in vivo studies in animals. |
| Author | Aginagalde, Maialen Vara, Yosu Gómez-Vallejo, Vanessa Llop, Jordi Cossío, Fernando P. |
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| Keywords | HDAC inhibitors Carbon-11 Kendine 91 PET |
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| SubjectTerms | Carbon Radioisotopes - chemistry Carbon-11 Chromatography, Liquid HDAC inhibitors Histone Deacetylase Inhibitors - chemical synthesis Hydroxamic Acids - chemical synthesis Kendine 91 Magnetic Resonance Spectroscopy PET Pyrroles - chemical synthesis |
| Title | Synthesis of 11C-labeled Kendine 91, a histone deacetylase inhibitor |
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