Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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.

PubMed Disclaimer

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

References

    1. Mottu F.; Rufenacht D. A.; Doelker E. Radiopaque polymeric materials for medical applications. Current aspects of biomaterial research. Invest. Radiol. 1999, 34, 323–335. 10.1097/00004424-199905000-00001. - DOI - PubMed
    1. Torchilin V. P. PEG-based micelles as carriers of contrast agents for different imaging modalities. Adv. Drug Delivery Rev. 2002, 54, 235–252. 10.1016/S0169-409X(02)00019-4. - DOI - PubMed
    1. Torchilin V. P.The Use of Polychelating and Amphiphilic Polymers in Gamma, MR and CT Imaging. In Biomedical Polymers and Polymer Therapeutics, 1st ed.; Chiellini E.; Sunamoto J.; Migliaresi C.; Ottenbrite R. M.; Cohn D., Eds.; Springer: Boston, MA, 2002; pp 268–284.
    1. Torchilin V. P. Polymeric contrast agents for medical imaging. Curr. Pharm. Biotechnol. 2000, 1, 183–215. 10.2174/1389201003378960. - DOI - PubMed
    1. Lei K.; Chen Y.; Wang J.; Peng X.; Ding J.; et al. Non-invasive monitoring of in vivo degradation of a radiopaque thermoreversible hydrogel and its efficacy in preventing post-operative adhesions. Acta Biomater. 2017, 55, 396–409. 10.1016/j.actbio.2017.03.042. - DOI - PubMed