Literature DB >> 30968442

Free-base porphyrins as CEST MRI contrast agents with highly upfield shifted labile protons.

Xiaoxiao Zhang1, Yaping Yuan1,2, Sha Li1,2, Qingbin Zeng1,2, Qianni Guo1,2, Na Liu1,2, Minghui Yang1,2, Yunhuang Yang1,2, Maili Liu1,2, Michael T McMahon3,4, Xin Zhou1,2.   

Abstract

PURPOSE: CEST has become a preeminent technology for the rapid detection and grading of tumors, securing its widespread use in both laboratory and clinical research. However, many existing CEST MRI agents exhibit a sensitivity limitation due to small chemical shifts between their exchangeable protons and water. We propose a new group of CEST MRI agents, free-base porphyrins and chlorin, with large exchangeable proton chemical shifts from water for enhanced detection.
METHODS: To test these newly identified CEST agents, we acquired a series of Z-spectra at multiple pH values and saturation field strengths to determine their CEST properties. The data were analyzed using the quantifying exchange using saturation power method to quantify exchange rates. After identifying several promising candidates, a porphyrin solution was injected into tumor-bearing mice, and MR images were acquired to assess detection feasibility in vivo.
RESULTS: Based on the Z-spectra, the inner nitrogen protons in free-base porphyrins and chlorin resonate from -8 to -13.5 ppm from water, far shifted from the majority of endogenous metabolites (0-4 ppm) and Nuclear Overhauser enhancements (-1 to -3.5 ppm) and far removed from the salicylates, imidazoles, and anthranillates (5-12 ppm). The exchange rates are sufficiently slow to intermediate (500-9000 s-1 ) to allow robust detection and were sensitive to substituents on the porphyrin ring.
CONCLUSION: These results highlight the capabilities of free-base porphyrins and chlorin as highly upfield CEST MRI agents and provide a new scaffold that can be integrated into a variety of diagnostic or theranostic agents for biomedical applications.
© 2019 International Society for Magnetic Resonance in Medicine.

Entities:  

Keywords:  CEST imaging; contrast agents; free-base porphyrin; molecular imaging; upfield-shifted protons

Mesh:

Substances:

Year:  2019        PMID: 30968442      PMCID: PMC7294594          DOI: 10.1002/mrm.27753

Source DB:  PubMed          Journal:  Magn Reson Med        ISSN: 0740-3194            Impact factor:   4.668


  47 in total

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3.  Salicylic Acid Conjugated Dendrimers Are a Tunable, High Performance CEST MRI NanoPlatform.

Authors:  Wojciech G Lesniak; Nikita Oskolkov; Xiaolei Song; Bachchu Lal; Xing Yang; Martin Pomper; John Laterra; Sridhar Nimmagadda; Michael T McMahon
Journal:  Nano Lett       Date:  2016-03-01       Impact factor: 11.189

4.  Amide proton transfer imaging with improved robustness to magnetic field inhomogeneity and magnetization transfer asymmetry using saturation with frequency alternating RF irradiation.

Authors:  Rachel Scheidegger; Elena Vinogradov; David C Alsop
Journal:  Magn Reson Med       Date:  2011-05-23       Impact factor: 4.668

5.  Transforming thymidine into a magnetic resonance imaging probe for monitoring gene expression.

Authors:  Amnon Bar-Shir; Guanshu Liu; Yajie Liang; Nirbhay N Yadav; Michael T McMahon; Piotr Walczak; Sridhar Nimmagadda; Martin G Pomper; Keri A Tallman; Marc M Greenberg; Peter C M van Zijl; Jeff W M Bulte; Assaf A Gilad
Journal:  J Am Chem Soc       Date:  2013-01-16       Impact factor: 15.419

6.  Nuclear Overhauser enhancement (NOE) imaging in the human brain at 7T.

Authors:  Craig K Jones; Alan Huang; Jiadi Xu; Richard A E Edden; Michael Schär; Jun Hua; Nikita Oskolkov; Domenico Zacà; Jinyuan Zhou; Michael T McMahon; Jay J Pillai; Peter C M van Zijl
Journal:  Neuroimage       Date:  2013-04-06       Impact factor: 6.556

7.  Human protamine-1 as an MRI reporter gene based on chemical exchange.

Authors:  Amnon Bar-Shir; Guanshu Liu; Kannie W Y Chan; Nikita Oskolkov; Xiaolei Song; Nirbhay N Yadav; Piotr Walczak; Michael T McMahon; Peter C M van Zijl; Jeff W M Bulte; Assaf A Gilad
Journal:  ACS Chem Biol       Date:  2013-10-25       Impact factor: 5.100

8.  A general MRI-CEST ratiometric approach for pH imaging: demonstration of in vivo pH mapping with iobitridol.

Authors:  Dario L Longo; Phillip Zhe Sun; Lorena Consolino; Filippo C Michelotti; Fulvio Uggeri; Silvio Aime
Journal:  J Am Chem Soc       Date:  2014-10-02       Impact factor: 15.419

9.  In vivo imaging of glucose uptake and metabolism in tumors.

Authors:  Simon Walker-Samuel; Rajiv Ramasawmy; Francisco Torrealdea; Marilena Rega; Vineeth Rajkumar; S Peter Johnson; Simon Richardson; Miguel Gonçalves; Harold G Parkes; Erik Arstad; David L Thomas; R Barbara Pedley; Mark F Lythgoe; Xavier Golay
Journal:  Nat Med       Date:  2013-07-07       Impact factor: 53.440

10.  MRI-detectable pH nanosensors incorporated into hydrogels for in vivo sensing of transplanted-cell viability.

Authors:  Kannie W Y Chan; Guanshu Liu; Xiaolei Song; Heechul Kim; Tao Yu; Dian R Arifin; Assaf A Gilad; Justin Hanes; Piotr Walczak; Peter C M van Zijl; Jeff W M Bulte; Michael T McMahon
Journal:  Nat Mater       Date:  2013-01-27       Impact factor: 43.841

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  4 in total

1.  Amplified detection of phosphocreatine and creatine after supplementation using CEST MRI at high and ultrahigh magnetic fields.

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Journal:  J Magn Reson       Date:  2020-02-27       Impact factor: 2.229

Review 2.  Repurposing Clinical Agents for Chemical Exchange Saturation Transfer Magnetic Resonance Imaging: Current Status and Future Perspectives.

Authors:  Zelong Chen; Zheng Han; Guanshu Liu
Journal:  Pharmaceuticals (Basel)       Date:  2020-12-24

3.  Paracetamol and other acetanilide analogs as inter-molecular hydrogen bonding assisted diamagnetic CEST MRI contrast agents.

Authors:  Subhayan Chakraborty; S Peruncheralathan; Arindam Ghosh
Journal:  RSC Adv       Date:  2021-02-08       Impact factor: 3.361

4.  Preparation of Hydrothermal Carbon Quantum Dots as a Contrast Amplifying Technique for the diaCEST MRI Contrast Agents.

Authors:  Shalini Pandey; Rimilmandrita Ghosh; Arindam Ghosh
Journal:  ACS Omega       Date:  2022-09-12
  4 in total

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