Effects of Substituents on the Properties of Metal-Free MRI Contrast Agents

Ryoma Shiraishi, Tomoyo Kaneko, Kazuteru Usui, Tatsuya Naganuma, Naoko Iizuka, Kosuke Morishita, Shigeki Kobayashi, Yasufumi Fuchi, Yuta Matsuoka, Go Hirai, Ken Ichi Yamada, Satoru Karasawa

Research output: Contribution to journalArticle

Abstract

Materials possessing electron spin can shorten the T1 relaxation times in magnetic resonance imaging (MRI). For example, gadolinium (Gd) complexes with seven f-orbital electrons are widely used as contrast agents in clinical applications. However, Gd has severe potential side effects, and thus metal-free alternatives are needed. Toward this end, we synthesized seven NO radicals consisting of a dioxa-azaspiro[4.5]decane framework having various substituents, DAD-X (X = methyl, ethyl, n-propyl, c-propyl, vinyl, phenyl, and 2-pyridyl), that functioned as metal-free MRI contrast agents. The relationship between (i) water-proton relaxivity and log※P and (ii) reactivity for ascorbic acid and the spin density of the NO oxygen atom were established, which provided a basis for the rational design of practical metal-free contrast agents.

Original languageEnglish
Pages (from-to)20715-20723
Number of pages9
JournalACS Omega
Volume4
Issue number24
DOIs
Publication statusPublished - Dec 10 2019

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Magnetic resonance
Contrast Media
Gadolinium
Metals
Imaging techniques
Electrons
Ascorbic acid
Relaxation time
Ascorbic Acid
Protons
Oxygen
Atoms
Water

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Shiraishi, R., Kaneko, T., Usui, K., Naganuma, T., Iizuka, N., Morishita, K., ... Karasawa, S. (2019). Effects of Substituents on the Properties of Metal-Free MRI Contrast Agents. ACS Omega, 4(24), 20715-20723. https://doi.org/10.1021/acsomega.9b03003

Effects of Substituents on the Properties of Metal-Free MRI Contrast Agents. / Shiraishi, Ryoma; Kaneko, Tomoyo; Usui, Kazuteru; Naganuma, Tatsuya; Iizuka, Naoko; Morishita, Kosuke; Kobayashi, Shigeki; Fuchi, Yasufumi; Matsuoka, Yuta; Hirai, Go; Yamada, Ken Ichi; Karasawa, Satoru.

In: ACS Omega, Vol. 4, No. 24, 10.12.2019, p. 20715-20723.

Research output: Contribution to journalArticle

Shiraishi, R, Kaneko, T, Usui, K, Naganuma, T, Iizuka, N, Morishita, K, Kobayashi, S, Fuchi, Y, Matsuoka, Y, Hirai, G, Yamada, KI & Karasawa, S 2019, 'Effects of Substituents on the Properties of Metal-Free MRI Contrast Agents', ACS Omega, vol. 4, no. 24, pp. 20715-20723. https://doi.org/10.1021/acsomega.9b03003
Shiraishi R, Kaneko T, Usui K, Naganuma T, Iizuka N, Morishita K et al. Effects of Substituents on the Properties of Metal-Free MRI Contrast Agents. ACS Omega. 2019 Dec 10;4(24):20715-20723. https://doi.org/10.1021/acsomega.9b03003
Shiraishi, Ryoma ; Kaneko, Tomoyo ; Usui, Kazuteru ; Naganuma, Tatsuya ; Iizuka, Naoko ; Morishita, Kosuke ; Kobayashi, Shigeki ; Fuchi, Yasufumi ; Matsuoka, Yuta ; Hirai, Go ; Yamada, Ken Ichi ; Karasawa, Satoru. / Effects of Substituents on the Properties of Metal-Free MRI Contrast Agents. In: ACS Omega. 2019 ; Vol. 4, No. 24. pp. 20715-20723.
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