Synthesis of Nitric Oxide Probes with Fluorescence Lifetime Sensitivity

Overview

Journal Org Biomol Chem

Publisher Royal Society of Chemistry

Specialties Biochemistry
Chemistry

Date 2013 Oct 30

PMID 24166035

Citations 5

Authors

Natalia G Zhegalova

Garrett Gonzales

Mikhail Y Berezin

Affiliations

Soon will be listed here.

Abstract

We present the rationale, synthesis and evaluation of the first activatable fluorescent probe that utilizes fluorescence lifetime change for detection of nitric oxide. The new probe DAP-LT1 features a near-infrared polymethine skeleton with a diaminobenzene functionality incorporated into the meso-position. The probe is partially quenched, and upon reaction with nitric oxide shows an increase in the fluorescence lifetime from 1.08 ns to 1.24 ns.

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References

Hall C, Garthwaite J . What is the real physiological NO concentration in vivo?. Nitric Oxide. 2009; 21(2):92-103. PMC: 2779337. DOI: 10.1016/j.niox.2009.07.002. View

de Silva A, Gunaratne H, Gunnlaugsson T, Huxley A, McCoy C, Rademacher J . Signaling Recognition Events with Fluorescent Sensors and Switches. Chem Rev. 1997; 97(5):1515-1566. DOI: 10.1021/cr960386p. View

Kuwana E, Liang F, Sevick-Muraca E . Fluorescence lifetime spectroscopy of a pH-sensitive dye encapsulated in hydrogel beads. Biotechnol Prog. 2004; 20(5):1561-6. DOI: 10.1021/bp034328i. View

Sevick-Muraca E, Houston J, Gurfinkel M . Fluorescence-enhanced, near infrared diagnostic imaging with contrast agents. Curr Opin Chem Biol. 2002; 6(5):642-50. DOI: 10.1016/s1367-5931(02)00356-3. View

Yu F, Song P, Li P, Wang B, Han K . A fluorescent probe directly detect peroxynitrite based on boronate oxidation and its applications for fluorescence imaging in living cells. Analyst. 2012; 137(16):3740-9. DOI: 10.1039/c2an35246j. View

Berezin M, Lee H, Akers W, Achilefu S . Near infrared dyes as lifetime solvatochromic probes for micropolarity measurements of biological systems. Biophys J. 2007; 93(8):2892-9. PMC: 1989699. DOI: 10.1529/biophysj.107.111609. View

Fujita K, Wada K, Nozaki Y, Yoneda M, Endo H, Takahashi H . Serum nitric oxide metabolite as a biomarker of visceral fat accumulation: clinical significance of measurement for nitrate/nitrite. Med Sci Monit. 2011; 17(3):CR123-31. PMC: 3524723. DOI: 10.12659/msm.881445. View

Kobayashi H, Choyke P . Target-cancer-cell-specific activatable fluorescence imaging probes: rational design and in vivo applications. Acc Chem Res. 2010; 44(2):83-90. PMC: 3040277. DOI: 10.1021/ar1000633. View

Berezin M, Guo K, Akers W, Livingston J, Solomon M, Lee H . Rational approach to select small peptide molecular probes labeled with fluorescent cyanine dyes for in vivo optical imaging. Biochemistry. 2011; 50(13):2691-700. PMC: 3068226. DOI: 10.1021/bi2000966. View

10.

Lee H, Berezin M, Tang R, Zhegalova N, Achilefu S . Pyrazole-substituted near-infrared cyanine dyes exhibit pH-dependent fluorescence lifetime properties. Photochem Photobiol. 2012; 89(2):326-31. PMC: 3578979. DOI: 10.1111/php.12009. View

11.

Gaupels F, Spiazzi-Vandelle E, Yang D, Delledonne M . Detection of peroxynitrite accumulation in Arabidopsis thaliana during the hypersensitive defense response. Nitric Oxide. 2011; 25(2):222-8. DOI: 10.1016/j.niox.2011.01.009. View

12.

Lin L, Lin X, Lin F, Wong K . A new spirobifluorene-bridged bipolar system for a nitric oxide turn-on fluorescent probe. Org Lett. 2011; 13(9):2216-9. DOI: 10.1021/ol200463m. View

13.

Pi J, Kumagai Y, Sun G, Yamauchi H, Yoshida T, Iso H . Decreased serum concentrations of nitric oxide metabolites among Chinese in an endemic area of chronic arsenic poisoning in inner Mongolia. Free Radic Biol Med. 2000; 28(7):1137-42. DOI: 10.1016/s0891-5849(00)00209-4. View

14.

Wurth C, Grabolle M, Pauli J, Spieles M, Resch-Genger U . Relative and absolute determination of fluorescence quantum yields of transparent samples. Nat Protoc. 2013; 8(8):1535-50. DOI: 10.1038/nprot.2013.087. View

15.

Broadbelt N, Stahl P, Chen J, Mizrahi M, Lal A, Bozkurt A . Early upregulation of iNOS mRNA expression and increase in NO metabolites in pressurized renal epithelial cells. Am J Physiol Renal Physiol. 2007; 293(6):F1877-88. DOI: 10.1152/ajprenal.00238.2007. View

16.

Berezin M, Guo K, Akers W, Northdurft R, Culver J, Teng B . Near-infrared fluorescence lifetime pH-sensitive probes. Biophys J. 2011; 100(8):2063-72. PMC: 3077686. DOI: 10.1016/j.bpj.2011.02.050. View

17.

Magalotti S, Gustafson T, Cao Q, Abendschein D, Pierce R, Berezin M . Evaluation of inflammatory response to acute ischemia using near-infrared fluorescent reactive oxygen sensors. Mol Imaging Biol. 2013; 15(4):423-30. PMC: 3940059. DOI: 10.1007/s11307-013-0614-2. View

18.

Keefer L, Nims R, Davies K, Wink D . "NONOates" (1-substituted diazen-1-ium-1,2-diolates) as nitric oxide donors: convenient nitric oxide dosage forms. Methods Enzymol. 1996; 268:281-93. DOI: 10.1016/s0076-6879(96)68030-6. View

19.

Berezin M, Achilefu S . Fluorescence lifetime measurements and biological imaging. Chem Rev. 2010; 110(5):2641-84. PMC: 2924670. DOI: 10.1021/cr900343z. View

20.

Benson R, Kues H . Fluorescence properties of indocyanine green as related to angiography. Phys Med Biol. 1978; 23(1):159-63. DOI: 10.1088/0031-9155/23/1/017. View