Reactions of methyl, hydroxyl and peroxyl radicals with the DOTA chelating agent used in medical imaging

Elad Avraham; Dan Meyerstein; Ana Lerner; Guy Yardeni; Svetlana Pevzner; Israel Zilbermann; Philippe Moisy; Eric Maimon; Inna Popivker

doi:10.1016/j.freeradbiomed.2021.12.313

Reactions of methyl, hydroxyl and peroxyl radicals with the DOTA chelating agent used in medical imaging

Elad Avraham, Dan Meyerstein, Ana Lerner, Guy Yardeni, Svetlana Pevzner, Israel Zilbermann, Philippe Moisy, Eric Maimon, Inna Popivker

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

The mechanism of reaction of DOTA (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) with ·CH₃, CH₃O₂· and ·OH radicals were studied. The radicals were formed in situ radiolytically. The methyl radicals react orders of magnitude slower with DOTA and with M^III(DOTA)^- than the hydroxyl radicals. The various final products were identified and mechanisms for their formation are proposed. CH₃O₂· radicals do not react, or react too slowly to be observed, with DOTA and with M^III(DOTA)^- as long as the central cation is not oxidized by the peroxyl radical. The results imply that synthesis of the M^III(DOTA)^-(M^III = radioisotope) complexes in a water-organic solvent (ethanol or 2-propanol or acetonitrile) mixture is not only kinetically desired but the so formed complex also decreases the radiolytic decomposition of DOTA.

Original language	English
Pages (from-to)	134-142
Number of pages	9
Journal	Free Radical Biology and Medicine
Volume	180
DOIs	https://doi.org/10.1016/j.freeradbiomed.2021.12.313
State	Published - 20 Feb 2022

ASJC Scopus subject areas

Physiology (medical)
Biochemistry

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10.1016/j.freeradbiomed.2021.12.313

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title = "Reactions of methyl, hydroxyl and peroxyl radicals with the DOTA chelating agent used in medical imaging",

abstract = "The mechanism of reaction of DOTA (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) with ·CH3, CH3O2· and ·OH radicals were studied. The radicals were formed in situ radiolytically. The methyl radicals react orders of magnitude slower with DOTA and with MIII(DOTA)- than the hydroxyl radicals. The various final products were identified and mechanisms for their formation are proposed. CH3O2· radicals do not react, or react too slowly to be observed, with DOTA and with MIII(DOTA)- as long as the central cation is not oxidized by the peroxyl radical. The results imply that synthesis of the MIII(DOTA)-(MIII = radioisotope) complexes in a water-organic solvent (ethanol or 2-propanol or acetonitrile) mixture is not only kinetically desired but the so formed complex also decreases the radiolytic decomposition of DOTA.",

author = "Elad Avraham and Dan Meyerstein and Ana Lerner and Guy Yardeni and Svetlana Pevzner and Israel Zilbermann and Philippe Moisy and Eric Maimon and Inna Popivker",

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AU - Avraham, Elad

AU - Meyerstein, Dan

AU - Lerner, Ana

AU - Yardeni, Guy

AU - Pevzner, Svetlana

AU - Zilbermann, Israel

AU - Moisy, Philippe

AU - Maimon, Eric

AU - Popivker, Inna

PY - 2022/2/20

Y1 - 2022/2/20

N2 - The mechanism of reaction of DOTA (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) with ·CH3, CH3O2· and ·OH radicals were studied. The radicals were formed in situ radiolytically. The methyl radicals react orders of magnitude slower with DOTA and with MIII(DOTA)- than the hydroxyl radicals. The various final products were identified and mechanisms for their formation are proposed. CH3O2· radicals do not react, or react too slowly to be observed, with DOTA and with MIII(DOTA)- as long as the central cation is not oxidized by the peroxyl radical. The results imply that synthesis of the MIII(DOTA)-(MIII = radioisotope) complexes in a water-organic solvent (ethanol or 2-propanol or acetonitrile) mixture is not only kinetically desired but the so formed complex also decreases the radiolytic decomposition of DOTA.

AB - The mechanism of reaction of DOTA (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) with ·CH3, CH3O2· and ·OH radicals were studied. The radicals were formed in situ radiolytically. The methyl radicals react orders of magnitude slower with DOTA and with MIII(DOTA)- than the hydroxyl radicals. The various final products were identified and mechanisms for their formation are proposed. CH3O2· radicals do not react, or react too slowly to be observed, with DOTA and with MIII(DOTA)- as long as the central cation is not oxidized by the peroxyl radical. The results imply that synthesis of the MIII(DOTA)-(MIII = radioisotope) complexes in a water-organic solvent (ethanol or 2-propanol or acetonitrile) mixture is not only kinetically desired but the so formed complex also decreases the radiolytic decomposition of DOTA.

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JO - Free Radical Biology and Medicine

JF - Free Radical Biology and Medicine

ER -

Reactions of methyl, hydroxyl and peroxyl radicals with the DOTA chelating agent used in medical imaging

Abstract

ASJC Scopus subject areas

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