Water-soluble porphyrins as a dual-function molecular imaging platform for MRI and fluorescence zinc sensing.

Water-soluble porphyrins as a dual-function molecular imaging platform for MRI and fluorescence zinc sensing. Research Abstract Details 

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Water-soluble porphyrins as a dual-function molecular imaging platform for MRI and fluorescence zinc sensing. Abstract Text:

Xiao-An Zhang,Katherine S Lovejoy,Alan Jasanoff,Stephen J Lippard,Xiao-An Zhang,Katherine S Lovejoy,Alan Jasanoff,Stephen J Lippard,

We report a molecular platform for dual-function fluorescence/MRI sensing of mobile zinc. Zinc-selective binding units were strategically attached to a water-soluble porphyrin template. The synthetic strategy for achieving the designed target ligand is flexible and convenient, and the key intermediates can be applied as general building blocks for the construction of other metal sensors based on a similar mechanism. The metal-free form, (DPA-C(2))(2)-TPPS(3) (1), where DPA is dipicolylamine and TPPS(3) is 5-phenyl-10,15,20-tris(4-sulfonatophenyl)porphine, is an excellent fluorescent sensor for zinc. It has certain superior physical properties compared with earlier-generation zinc sensors including emission in the red and near-IR regions [lambda(em) = 645 nm (s) and 715 nm (m)], with a large Stokes shift of >230 nm. The fluorescence intensity of 1 increases by >10-fold upon zinc binding. The fluorescence "turn-on" is highly selective for zinc versus other divalent metal ions and is relatively pH-insensitive within the biologically relevant pH window. The manganese derivative, [(DPA-C(2))(2)-TPPS(3)Mn(III)] (2), switches the function of the molecule to generate an MRI contrast agent. In the presence of zinc, the relaxivity of 2 in aqueous solution is significantly altered, which makes it a promising zinc MRI sensor. Both metal-free and Mn(III)-inserted forms are efficiently taken up by live cells, and the intracellular zinc can be imaged by either fluorescence or MR, respectively. We anticipate that in vivo applications of the probes will facilitate a deeper understanding of the physiological roles of zinc and allow detection of abnormal zinc homeostasis for pathological diagnoses.

Water-soluble porphyrins as a dual-function molecular imaging platform for MRI and fluorescence zinc sensing. Publishing Authors By Initials

XA Zhang,KS Lovejoy,A Jasanoff,SJ Lippard,XA Zhang,KS Lovejoy,A Jasanoff,SJ Lippard,

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Water-soluble porphyrins as a dual-function molecular imaging platform for MRI and fluorescence zinc sensing. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Proceedings of the National Academy of Sciences of

VOLUME: 104

Page Numbers: 10780-5

Journal Abbreviation: Proc. Natl. Acad. Sci. U.S.A.

ISSN: 1091-6490

DAY: 19

MONTH: 06

YEAR: 2007

Water-soluble porphyrins as a dual-function molecular imaging platform for MRI and fluorescence zinc sensing. Information

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LANGUAGE: eng

NlmUniqueID: 7505876

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Grant and Affiliation Information for Water-soluble porphyrins as a dual-function molecular imaging platform for MRI and fluorescence zinc sensing.

AFFILIATION: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: GM65519

ACRONYM: GM

MEDLINETA: Proc Natl Acad Sci U S A

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