Synthesis of radiolabeled O 6 ‐benzylguanine derivatives as new potential PET tumor imaging agents for the DNA repair protein O 6 ‐alkylguanine‐DNA alkyltransferase
Novel radiolabeled O 6 ‐benzylguanine derivatives, 2‐amino‐6‐O‐[ 11 C]‐[(methoxymethyl)benzyloxy]‐9‐benzyl purines ([ 11 C] p ‐O 6 ‐AMBP, 1a ; [ 11 C] m ‐O 6 ‐AMBP, 1b ; [ 11 C] o ‐O 6 ‐AMBP, 1c ), have been synthesized for evaluation as new potential positron emission tomography (PET) tumor imaging...
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| Veröffentlicht in: | Journal of labelled compounds & radiopharmaceuticals 2002-12, Vol.45 (14), p.1239-1252 |
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| container_title | Journal of labelled compounds & radiopharmaceuticals |
| container_volume | 45 |
| creator | Zheng, Qi‐Huang Liu, Xuan Fei, Xiangshu Wang, Ji‐Quan Ohannesian, David W. Erickson, Leonard C. Stone, K. Lee Martinez, Tanya D. Miller, Kathy D. Hutchins, Gary D. |
| description | Novel radiolabeled O
6
‐benzylguanine derivatives, 2‐amino‐6‐O‐[
11
C]‐[(methoxymethyl)benzyloxy]‐9‐benzyl purines ([
11
C]
p
‐O
6
‐AMBP,
1a
; [
11
C]
m
‐O
6
‐AMBP,
1b
; [
11
C]
o
‐O
6
‐AMBP,
1c
), have been synthesized for evaluation as new potential positron emission tomography (PET) tumor imaging agents for the DNA repair protein, O
6
‐alkylguanine‐DNA alkyltransferase (AGT). The appropriate precursors for radiolabeling were obtained in three steps from starting material 2‐amino‐6‐chloropurine with moderate to excellent chemical yields. Tracers were prepared by O‐[
11
C]methylation of hydroxymethyl precursors using [
11
C]methyl triflate. Pure target compounds were isolated by solid‐phase extraction (SPE) purification procedure in 45–60% radiochemical yields (decay corrected to the end of bombardment), and a synthesis time of 20–25min. Copyright © 2002 John Wiley & Sons, Ltd. |
| doi_str_mv | 10.1002/jlcr.636 |
| format | Article |
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6
‐benzylguanine derivatives, 2‐amino‐6‐O‐[
11
C]‐[(methoxymethyl)benzyloxy]‐9‐benzyl purines ([
11
C]
p
‐O
6
‐AMBP,
1a
; [
11
C]
m
‐O
6
‐AMBP,
1b
; [
11
C]
o
‐O
6
‐AMBP,
1c
), have been synthesized for evaluation as new potential positron emission tomography (PET) tumor imaging agents for the DNA repair protein, O
6
‐alkylguanine‐DNA alkyltransferase (AGT). The appropriate precursors for radiolabeling were obtained in three steps from starting material 2‐amino‐6‐chloropurine with moderate to excellent chemical yields. Tracers were prepared by O‐[
11
C]methylation of hydroxymethyl precursors using [
11
C]methyl triflate. Pure target compounds were isolated by solid‐phase extraction (SPE) purification procedure in 45–60% radiochemical yields (decay corrected to the end of bombardment), and a synthesis time of 20–25min. Copyright © 2002 John Wiley & Sons, Ltd.</description><identifier>ISSN: 0362-4803</identifier><identifier>EISSN: 1099-1344</identifier><identifier>DOI: 10.1002/jlcr.636</identifier><language>eng</language><ispartof>Journal of labelled compounds & radiopharmaceuticals, 2002-12, Vol.45 (14), p.1239-1252</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c157t-8a3eeabbd6d773e45ab6a7fdc16bdd0ab24fc7db5939b87762b5d1419b5cc1293</citedby><cites>FETCH-LOGICAL-c157t-8a3eeabbd6d773e45ab6a7fdc16bdd0ab24fc7db5939b87762b5d1419b5cc1293</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Zheng, Qi‐Huang</creatorcontrib><creatorcontrib>Liu, Xuan</creatorcontrib><creatorcontrib>Fei, Xiangshu</creatorcontrib><creatorcontrib>Wang, Ji‐Quan</creatorcontrib><creatorcontrib>Ohannesian, David W.</creatorcontrib><creatorcontrib>Erickson, Leonard C.</creatorcontrib><creatorcontrib>Stone, K. Lee</creatorcontrib><creatorcontrib>Martinez, Tanya D.</creatorcontrib><creatorcontrib>Miller, Kathy D.</creatorcontrib><creatorcontrib>Hutchins, Gary D.</creatorcontrib><title>Synthesis of radiolabeled O 6 ‐benzylguanine derivatives as new potential PET tumor imaging agents for the DNA repair protein O 6 ‐alkylguanine‐DNA alkyltransferase</title><title>Journal of labelled compounds & radiopharmaceuticals</title><description>Novel radiolabeled O
6
‐benzylguanine derivatives, 2‐amino‐6‐O‐[
11
C]‐[(methoxymethyl)benzyloxy]‐9‐benzyl purines ([
11
C]
p
‐O
6
‐AMBP,
1a
; [
11
C]
m
‐O
6
‐AMBP,
1b
; [
11
C]
o
‐O
6
‐AMBP,
1c
), have been synthesized for evaluation as new potential positron emission tomography (PET) tumor imaging agents for the DNA repair protein, O
6
‐alkylguanine‐DNA alkyltransferase (AGT). The appropriate precursors for radiolabeling were obtained in three steps from starting material 2‐amino‐6‐chloropurine with moderate to excellent chemical yields. Tracers were prepared by O‐[
11
C]methylation of hydroxymethyl precursors using [
11
C]methyl triflate. Pure target compounds were isolated by solid‐phase extraction (SPE) purification procedure in 45–60% radiochemical yields (decay corrected to the end of bombardment), and a synthesis time of 20–25min. Copyright © 2002 John Wiley & Sons, Ltd.</description><issn>0362-4803</issn><issn>1099-1344</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNo9kEtOwzAQhi0EEqUgcYRZsgnYcR7NsirlIVUUibKOxvEkuKROZKdFZcUROAfH4iSkvFaj-f-Z-TQ_Y6eCnwvOw4tlXbjzRCZ7bCB4lgVCRtE-G3CZhEE04vKQHXm_5Lz3omjAPh62tnsibzw0JTjUpqlRUU0a5pDA59u7Ivu6ras1WmMJNDmzwc5syAN6sPQCbdOR7QzWcD9dQLdeNQ7MCitjK8CqtzyUvdRT4PJuDI5aNA5a168Z-0fB-vkf0re7wW-pc2h9SQ49HbODEmtPJ791yB6vpovJTTCbX99OxrOgEHHaBSOURKiUTnSaSopiVAmmpS5EorTmqMKoLFKt4kxmapSmSahiLSKRqbgoRJjJITv7uVu4xntHZd66_h-3zQXPdxnnu4zzPmP5BeIYdsk</recordid><startdate>200212</startdate><enddate>200212</enddate><creator>Zheng, Qi‐Huang</creator><creator>Liu, Xuan</creator><creator>Fei, Xiangshu</creator><creator>Wang, Ji‐Quan</creator><creator>Ohannesian, David W.</creator><creator>Erickson, Leonard C.</creator><creator>Stone, K. Lee</creator><creator>Martinez, Tanya D.</creator><creator>Miller, Kathy D.</creator><creator>Hutchins, Gary D.</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200212</creationdate><title>Synthesis of radiolabeled O 6 ‐benzylguanine derivatives as new potential PET tumor imaging agents for the DNA repair protein O 6 ‐alkylguanine‐DNA alkyltransferase</title><author>Zheng, Qi‐Huang ; Liu, Xuan ; Fei, Xiangshu ; Wang, Ji‐Quan ; Ohannesian, David W. ; Erickson, Leonard C. ; Stone, K. Lee ; Martinez, Tanya D. ; Miller, Kathy D. ; Hutchins, Gary D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c157t-8a3eeabbd6d773e45ab6a7fdc16bdd0ab24fc7db5939b87762b5d1419b5cc1293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zheng, Qi‐Huang</creatorcontrib><creatorcontrib>Liu, Xuan</creatorcontrib><creatorcontrib>Fei, Xiangshu</creatorcontrib><creatorcontrib>Wang, Ji‐Quan</creatorcontrib><creatorcontrib>Ohannesian, David W.</creatorcontrib><creatorcontrib>Erickson, Leonard C.</creatorcontrib><creatorcontrib>Stone, K. Lee</creatorcontrib><creatorcontrib>Martinez, Tanya D.</creatorcontrib><creatorcontrib>Miller, Kathy D.</creatorcontrib><creatorcontrib>Hutchins, Gary D.</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of labelled compounds & radiopharmaceuticals</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zheng, Qi‐Huang</au><au>Liu, Xuan</au><au>Fei, Xiangshu</au><au>Wang, Ji‐Quan</au><au>Ohannesian, David W.</au><au>Erickson, Leonard C.</au><au>Stone, K. Lee</au><au>Martinez, Tanya D.</au><au>Miller, Kathy D.</au><au>Hutchins, Gary D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of radiolabeled O 6 ‐benzylguanine derivatives as new potential PET tumor imaging agents for the DNA repair protein O 6 ‐alkylguanine‐DNA alkyltransferase</atitle><jtitle>Journal of labelled compounds & radiopharmaceuticals</jtitle><date>2002-12</date><risdate>2002</risdate><volume>45</volume><issue>14</issue><spage>1239</spage><epage>1252</epage><pages>1239-1252</pages><issn>0362-4803</issn><eissn>1099-1344</eissn><abstract>Novel radiolabeled O
6
‐benzylguanine derivatives, 2‐amino‐6‐O‐[
11
C]‐[(methoxymethyl)benzyloxy]‐9‐benzyl purines ([
11
C]
p
‐O
6
‐AMBP,
1a
; [
11
C]
m
‐O
6
‐AMBP,
1b
; [
11
C]
o
‐O
6
‐AMBP,
1c
), have been synthesized for evaluation as new potential positron emission tomography (PET) tumor imaging agents for the DNA repair protein, O
6
‐alkylguanine‐DNA alkyltransferase (AGT). The appropriate precursors for radiolabeling were obtained in three steps from starting material 2‐amino‐6‐chloropurine with moderate to excellent chemical yields. Tracers were prepared by O‐[
11
C]methylation of hydroxymethyl precursors using [
11
C]methyl triflate. Pure target compounds were isolated by solid‐phase extraction (SPE) purification procedure in 45–60% radiochemical yields (decay corrected to the end of bombardment), and a synthesis time of 20–25min. Copyright © 2002 John Wiley & Sons, Ltd.</abstract><doi>10.1002/jlcr.636</doi><tpages>14</tpages></addata></record> |
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| language | eng |
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| source | Wiley Journals |
| title | Synthesis of radiolabeled O 6 ‐benzylguanine derivatives as new potential PET tumor imaging agents for the DNA repair protein O 6 ‐alkylguanine‐DNA alkyltransferase |
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