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. 2021 Sep 16;6(38):24826-24833.
doi: 10.1021/acsomega.1c03671. eCollection 2021 Sep 28.

Organic Compound with Potential for X-ray Imaging Applications

Gopika V Gopan  1 , K Kezia Susan  1 , Enakshy Rajan Jayadevan  2 , Roy Joseph  1
Affiliations

Organic Compound with Potential for X-ray Imaging Applications

Gopika V Gopan et al. ACS Omega. .

Abstract

A radiopaque compound, namely, 4,4-bis(4-hydroxy-3,5-diiodophenyl)pentanoic acid, was synthesized by the electrophilic aromatic iodination of 4,4-bis(4-hydroxyphenyl)pentanoic acid using sodium iodide and sodium hypochlorite. The active iodines created by hypochlorite were selectively bound to the ortho positions of the diphenolic acid and obtained a tetraiodo compound. Characterization of this iodinated compound was accomplished by routine methods such as Fourier transform infrared (FTIR) spectroscopy, 1H nuclear magnetic resonance (NMR) spectroscopy, energy-dispersive X-ray spectroscopy, mass spectroscopy, UV-Vis spectroscopy, and thermogravimetry. The iodine content in the compound was as high as 64% by weight and therefore expected to possess substantial radiopacity. A 5% solution of the compound in dimethyl sulfoxide exhibited radiopacity of 885 ± 7 Hounsfield Units when tested with computed tomography (CT) scanner. In vitro cytotoxicity test performed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay demonstrated that the compound was noncytotoxic to L929 fibroblast cells up to the level of 0.8 mg/mL concentration. Overall results indicate that this highly radiopaque compound has the potential to be used for X-ray imaging in the clinical scenario.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
1H NMR spectrum of BHP.
Figure 2
Figure 2
1H NMR spectrum of IBHP.
Scheme 1
Scheme 1. Iodination of 4,4-Bis(4-Hydroxyphenyl) Pentanoic Acid
Figure 3
Figure 3
EDAX spectrum of IBHP.
Figure 4
Figure 4
FTIR spectra of BHP and IBHP.
Figure 5
Figure 5
UV absorption spectrum of BHP.
Figure 6
Figure 6
UV absorption spectrum of IBHP.
Figure 7
Figure 7
Mass spectra of (a) BHP and (b) IBHP.
Figure 8
Figure 8
TGA traces of BHP and IBHP.
Figure 9
Figure 9
X-ray opacity of different concentrations IBHP and control material (20% iodixanol).
Figure 10
Figure 10
Cell viability of L929 fibroblasts by the MTT assay.
See this image and copyright information in PMC

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