Phenols as Diamagnetic T2-Exchange Magnetic Resonance Imaging Contrast Agents

Jia Zhang; Yuguo Li; Stephanie Slania; Nirbhay N. Yadav; Jing Liu; Rongfu Wang; Jianhua Zhang; Martin G. Pomper; Peter C. van Zijl; Xing Yang; Guanshu Liu

doi:10.1002/chem.201705772

Phenols as Diamagnetic T₂-Exchange Magnetic Resonance Imaging Contrast Agents

Jia Zhang, Yuguo Li, Stephanie Slania, Nirbhay N. Yadav, Jing Liu, Rongfu Wang, Jianhua Zhang, Martin G. Pomper, Peter C. van Zijl, Xing Yang, Guanshu Liu

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

9 Scopus citations

Abstract

Although T₂-exchange (T_2ex) NMR phenomena have been known for decades, there has been a resurgence of interest to develop T_2ex MRI contrast agents. One indispensable advantage of T_2ex MR agents is the possibility of using non-toxic and/or bio-compatible diamagnetic compounds with intermediate exchangeable protons. Herein a library of phenol-based compounds is screened and their T_2ex contrast (exchange relaxivity, r_2ex) at 9.4 T determined. The T_2ex contrast of phenol protons allows direct detection by MRI at a millimolar concentration level. The effect of chemical modification of the phenol on the T_2ex MRI contrast through modulation of exchange rate and chemical shift was also studied and provides a guideline for use of endogenous and exogenous phenols for T_2ex MRI contrast. As a proof-of-principle application, phenol T_2ex contrast can be used to detect enzyme activity in a tyrosinase-catalyzed catechol oxidation reaction.

Original language	English (US)
Pages (from-to)	1259-1263
Number of pages	5
Journal	Chemistry - A European Journal
Volume	24
Issue number	6
DOIs	https://doi.org/10.1002/chem.201705772
State	Published - Jan 26 2018

Keywords

T-exchange
contrast agents
magnetic resonance imaging
phenols
tyrosinase

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201705772

Cite this

@article{0b448fb813ac496ea2513b90834e3a18,

title = "Phenols as Diamagnetic T2-Exchange Magnetic Resonance Imaging Contrast Agents",

abstract = "Although T2-exchange (T2ex) NMR phenomena have been known for decades, there has been a resurgence of interest to develop T2ex MRI contrast agents. One indispensable advantage of T2ex MR agents is the possibility of using non-toxic and/or bio-compatible diamagnetic compounds with intermediate exchangeable protons. Herein a library of phenol-based compounds is screened and their T2ex contrast (exchange relaxivity, r2ex) at 9.4 T determined. The T2ex contrast of phenol protons allows direct detection by MRI at a millimolar concentration level. The effect of chemical modification of the phenol on the T2ex MRI contrast through modulation of exchange rate and chemical shift was also studied and provides a guideline for use of endogenous and exogenous phenols for T2ex MRI contrast. As a proof-of-principle application, phenol T2ex contrast can be used to detect enzyme activity in a tyrosinase-catalyzed catechol oxidation reaction.",

keywords = "T-exchange, contrast agents, magnetic resonance imaging, phenols, tyrosinase",

author = "Jia Zhang and Yuguo Li and Stephanie Slania and Yadav, {Nirbhay N.} and Jing Liu and Rongfu Wang and Jianhua Zhang and Pomper, {Martin G.} and {van Zijl}, {Peter C.} and Xing Yang and Guanshu Liu",

note = "Funding Information: Financial support from the NIH grants R03CA197470, R03EB021573, R01CA211087, R21CA215860, R01EB019934, and R01EB015032, and the Chinese National Thousand Young Talents Program is acknowledged. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = jan,

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doi = "10.1002/chem.201705772",

language = "English (US)",

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T1 - Phenols as Diamagnetic T2-Exchange Magnetic Resonance Imaging Contrast Agents

AU - Zhang, Jia

AU - Li, Yuguo

AU - Slania, Stephanie

AU - Yadav, Nirbhay N.

AU - Liu, Jing

AU - Wang, Rongfu

AU - Zhang, Jianhua

AU - Pomper, Martin G.

AU - van Zijl, Peter C.

AU - Yang, Xing

AU - Liu, Guanshu

N1 - Funding Information: Financial support from the NIH grants R03CA197470, R03EB021573, R01CA211087, R21CA215860, R01EB019934, and R01EB015032, and the Chinese National Thousand Young Talents Program is acknowledged. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/1/26

Y1 - 2018/1/26

N2 - Although T2-exchange (T2ex) NMR phenomena have been known for decades, there has been a resurgence of interest to develop T2ex MRI contrast agents. One indispensable advantage of T2ex MR agents is the possibility of using non-toxic and/or bio-compatible diamagnetic compounds with intermediate exchangeable protons. Herein a library of phenol-based compounds is screened and their T2ex contrast (exchange relaxivity, r2ex) at 9.4 T determined. The T2ex contrast of phenol protons allows direct detection by MRI at a millimolar concentration level. The effect of chemical modification of the phenol on the T2ex MRI contrast through modulation of exchange rate and chemical shift was also studied and provides a guideline for use of endogenous and exogenous phenols for T2ex MRI contrast. As a proof-of-principle application, phenol T2ex contrast can be used to detect enzyme activity in a tyrosinase-catalyzed catechol oxidation reaction.

AB - Although T2-exchange (T2ex) NMR phenomena have been known for decades, there has been a resurgence of interest to develop T2ex MRI contrast agents. One indispensable advantage of T2ex MR agents is the possibility of using non-toxic and/or bio-compatible diamagnetic compounds with intermediate exchangeable protons. Herein a library of phenol-based compounds is screened and their T2ex contrast (exchange relaxivity, r2ex) at 9.4 T determined. The T2ex contrast of phenol protons allows direct detection by MRI at a millimolar concentration level. The effect of chemical modification of the phenol on the T2ex MRI contrast through modulation of exchange rate and chemical shift was also studied and provides a guideline for use of endogenous and exogenous phenols for T2ex MRI contrast. As a proof-of-principle application, phenol T2ex contrast can be used to detect enzyme activity in a tyrosinase-catalyzed catechol oxidation reaction.

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