Abstract

We report application of two-photon excitation of europium chelates to immunolabeling of epidermal growth factor receptor (EGFR) cell surface proteins on A431 cancer cells. The europium chelates are excited with two photons of infrared light and emit in the visible. Europium chelates are conjugated to antibodies for EGFR. A431 (human epidermoid carcinoma) cells are labeled with this conjugate and imaged using a multiphoton microscope. To minimize signal loss due to the relatively long-lived Eu3+ emission, the multiphoton microscope is used with scanning laser two-photon excitation and non-scanning detection with a CCD. The chelate labels show very little photobleaching (less than 1% during continuous illumination in the microscope for 20 minutes) and low levels of autofluorescence (less than 1% of the signal from labeled cells). The detection limit of the europium label in the cell assay is better than 100 zeptomoles.

© 2011 OSA

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2010 (1)

G. Shao, R. Han, Y. Ma, M. Tang, F. Xue, Y. Sha, and Y. Wang, “Bionanoprobes with excellent two-photon-sensitized Eu3+ luminescence properties for live cell imaging,” Chemistry 16(29), 8647–8651 (2010).
[CrossRef] [PubMed]

2009 (1)

C. Andraud and O. Maury, “Lanthanide complexes for nonlinear optics: from fundamental aspects to applications,” Eur. J. Inorg. Chem. 2009(29-30), 4357–4371 (2009).
[CrossRef]

2008 (2)

A. Picot, A. D’Aléo, P. L. Baldeck, A. Grichine, A. Duperray, C. Andraud, and O. Maury, “Long-lived two-photon excited luminescence of water-soluble europium complex: applications in biological imaging using two-photon scanning microscopy,” J. Am. Chem. Soc. 130(5), 1532–1533 (2008).
[CrossRef] [PubMed]

G. L. Law, K. L. Wong, C. W. Man, W. T. Wong, S. W. Tsao, M. H. Lam, and P. K. Lam, “Emissive terbium probe for multiphoton in vitro cell imaging,” J. Am. Chem. Soc. 130(12), 3714–3715 (2008).
[CrossRef] [PubMed]

2007 (1)

L. O. Pålsson, R. Pal, B. S. Murray, D. Parker, and A. Beeby, “Two-photon absorption and photoluminescence of europium based emissive probes for bioactive systems,” Dalton Trans. (48): 5726–5734 (2007).
[CrossRef] [PubMed]

2005 (1)

2004 (2)

X. Xiao, J. P. Haushalter, M. Weiss, and G. W. Faris, “Optical response measurement of upconverting luminescent reporters,” Proc. SPIE 5329, 229–238 (2004).
[CrossRef]

R. C. Leif, M. C. Becker, J. Alfred, J. Bromm, N. Chen, A. E. Cowan, L. M. Vallarino, S. Yang, and R. M. Zucker, “Lanthanide-enhanced luminescence (LEL) with one and two photon excitation of quantum dyes lanthanide(III)-macrocycles,” Proc. SPIE 5322, 187–199 (2004).
[CrossRef]

2003 (1)

L. D. Carlos, C. de Mello Donega, R. Q. Albuquerque, S. Alves, J. F. S. Menezes, and O. L. Malta, “Highly luminescent europium(III) complexes with naphtoiltrifluoroacetone and dimethyl sulphoxide,” Mol. Phys. 101(7), 1037–1045 (2003).
[CrossRef]

2001 (4)

J. Squier and M. Muller, “High resolution nonlinear microscopy: A review of sources and methods for achieving optimal imaging,” Rev. Sci. Instrum. 72(7), 2855–2867 (2001).
[CrossRef]

J. Hampl, M. P. Hall, N. A. Mufti, Y.-M. M. Yao, D. B. MacQueen, W. H. Wright, and D. E. Cooper, “Upconverting phosphor reporters in immunochromatographic assays,” Anal. Biochem. 288(2), 176–187 (2001).
[CrossRef] [PubMed]

A. Beeby, S. Faulkner, D. Parker, and J. A. G. Williams, “Sensitised luminescence from phenanthridine appended lanthanide complexes: analysis of triplet mediated energy transfer processes in terbium, europium and neodymium complexes,” J. Chem. Soc., Perkin Trans. 2 (8): 1268–1273 (2001).
[CrossRef]

G. Piszczek, B. P. Maliwal, I. Gryczynski, J. Dattelbaum, and J. R. Lakowicz, “Multiphoton ligand-enhanced excitation of lanthanides,” J. Fluoresc. 11(2), 101–107 (2001).
[CrossRef]

1998 (3)

M. Bruchez, M. Moronne, P. Gin, S. Weiss, and A. P. Alivisatos, “Semiconductor nanocrystals as fluorescent biological labels,” Science 281(5385), 2013–2016 (1998).
[CrossRef] [PubMed]

W. C. W. Chan and S. Nie, “Quantum dot bioconjugates for ultrasensitive nonisotopic detection,” Science 281(5385), 2016–2018 (1998).
[CrossRef] [PubMed]

J. Bewersdorf, R. Pick, and S. W. Hell, “Multifocal multiphoton microscopy,” Opt. Lett. 23(9), 655–657 (1998).
[CrossRef] [PubMed]

1995 (1)

1994 (1)

J. N. Mansbridge, W. A. Ausserer, M. A. Knapp, and R. M. Sutherland, “Adaptation of EGF receptor signal transduction to three-dimensional culture conditions: changes in surface receptor expression and protein tyrosine phosphorylation,” J. Cell. Physiol. 161(2), 374–382 (1994).
[CrossRef] [PubMed]

1984 (1)

I. Hemmilä, S. Dakubu, V. M. Mukkala, H. Siitari, and T. Lövgren, “Europium as a label in time-resolved immunofluorometric assays,” Anal. Biochem. 137(2), 335–343 (1984).
[CrossRef] [PubMed]

1977 (1)

R. C. Leif, R. A. Thomas, T. A. Yopp, B. D. Watson, V. R. Guarino, D. H. Hindman, N. Lefkove, and L. M. Vallarino, “Development of instrumentation and fluorochromes for automated multiparameter analysis of cells,” Clin. Chem. 23(8), 1492–1498 (1977).
[PubMed]

Albuquerque, R. Q.

L. D. Carlos, C. de Mello Donega, R. Q. Albuquerque, S. Alves, J. F. S. Menezes, and O. L. Malta, “Highly luminescent europium(III) complexes with naphtoiltrifluoroacetone and dimethyl sulphoxide,” Mol. Phys. 101(7), 1037–1045 (2003).
[CrossRef]

Alfred, J.

R. C. Leif, M. C. Becker, J. Alfred, J. Bromm, N. Chen, A. E. Cowan, L. M. Vallarino, S. Yang, and R. M. Zucker, “Lanthanide-enhanced luminescence (LEL) with one and two photon excitation of quantum dyes lanthanide(III)-macrocycles,” Proc. SPIE 5322, 187–199 (2004).
[CrossRef]

Alivisatos, A. P.

M. Bruchez, M. Moronne, P. Gin, S. Weiss, and A. P. Alivisatos, “Semiconductor nanocrystals as fluorescent biological labels,” Science 281(5385), 2013–2016 (1998).
[CrossRef] [PubMed]

Alves, S.

L. D. Carlos, C. de Mello Donega, R. Q. Albuquerque, S. Alves, J. F. S. Menezes, and O. L. Malta, “Highly luminescent europium(III) complexes with naphtoiltrifluoroacetone and dimethyl sulphoxide,” Mol. Phys. 101(7), 1037–1045 (2003).
[CrossRef]

Andraud, C.

C. Andraud and O. Maury, “Lanthanide complexes for nonlinear optics: from fundamental aspects to applications,” Eur. J. Inorg. Chem. 2009(29-30), 4357–4371 (2009).
[CrossRef]

A. Picot, A. D’Aléo, P. L. Baldeck, A. Grichine, A. Duperray, C. Andraud, and O. Maury, “Long-lived two-photon excited luminescence of water-soluble europium complex: applications in biological imaging using two-photon scanning microscopy,” J. Am. Chem. Soc. 130(5), 1532–1533 (2008).
[CrossRef] [PubMed]

Ausserer, W. A.

J. N. Mansbridge, W. A. Ausserer, M. A. Knapp, and R. M. Sutherland, “Adaptation of EGF receptor signal transduction to three-dimensional culture conditions: changes in surface receptor expression and protein tyrosine phosphorylation,” J. Cell. Physiol. 161(2), 374–382 (1994).
[CrossRef] [PubMed]

Baldeck, P. L.

A. Picot, A. D’Aléo, P. L. Baldeck, A. Grichine, A. Duperray, C. Andraud, and O. Maury, “Long-lived two-photon excited luminescence of water-soluble europium complex: applications in biological imaging using two-photon scanning microscopy,” J. Am. Chem. Soc. 130(5), 1532–1533 (2008).
[CrossRef] [PubMed]

Becker, M. C.

R. C. Leif, M. C. Becker, J. Alfred, J. Bromm, N. Chen, A. E. Cowan, L. M. Vallarino, S. Yang, and R. M. Zucker, “Lanthanide-enhanced luminescence (LEL) with one and two photon excitation of quantum dyes lanthanide(III)-macrocycles,” Proc. SPIE 5322, 187–199 (2004).
[CrossRef]

Beeby, A.

L. O. Pålsson, R. Pal, B. S. Murray, D. Parker, and A. Beeby, “Two-photon absorption and photoluminescence of europium based emissive probes for bioactive systems,” Dalton Trans. (48): 5726–5734 (2007).
[CrossRef] [PubMed]

A. Beeby, S. Faulkner, D. Parker, and J. A. G. Williams, “Sensitised luminescence from phenanthridine appended lanthanide complexes: analysis of triplet mediated energy transfer processes in terbium, europium and neodymium complexes,” J. Chem. Soc., Perkin Trans. 2 (8): 1268–1273 (2001).
[CrossRef]

Bewersdorf, J.

Bromm, J.

R. C. Leif, M. C. Becker, J. Alfred, J. Bromm, N. Chen, A. E. Cowan, L. M. Vallarino, S. Yang, and R. M. Zucker, “Lanthanide-enhanced luminescence (LEL) with one and two photon excitation of quantum dyes lanthanide(III)-macrocycles,” Proc. SPIE 5322, 187–199 (2004).
[CrossRef]

Bruchez, M.

M. Bruchez, M. Moronne, P. Gin, S. Weiss, and A. P. Alivisatos, “Semiconductor nanocrystals as fluorescent biological labels,” Science 281(5385), 2013–2016 (1998).
[CrossRef] [PubMed]

Carlos, L. D.

L. D. Carlos, C. de Mello Donega, R. Q. Albuquerque, S. Alves, J. F. S. Menezes, and O. L. Malta, “Highly luminescent europium(III) complexes with naphtoiltrifluoroacetone and dimethyl sulphoxide,” Mol. Phys. 101(7), 1037–1045 (2003).
[CrossRef]

Chan, W. C. W.

W. C. W. Chan and S. Nie, “Quantum dot bioconjugates for ultrasensitive nonisotopic detection,” Science 281(5385), 2016–2018 (1998).
[CrossRef] [PubMed]

Chen, N.

R. C. Leif, M. C. Becker, J. Alfred, J. Bromm, N. Chen, A. E. Cowan, L. M. Vallarino, S. Yang, and R. M. Zucker, “Lanthanide-enhanced luminescence (LEL) with one and two photon excitation of quantum dyes lanthanide(III)-macrocycles,” Proc. SPIE 5322, 187–199 (2004).
[CrossRef]

Cooper, D. E.

J. Hampl, M. P. Hall, N. A. Mufti, Y.-M. M. Yao, D. B. MacQueen, W. H. Wright, and D. E. Cooper, “Upconverting phosphor reporters in immunochromatographic assays,” Anal. Biochem. 288(2), 176–187 (2001).
[CrossRef] [PubMed]

Cowan, A. E.

R. C. Leif, M. C. Becker, J. Alfred, J. Bromm, N. Chen, A. E. Cowan, L. M. Vallarino, S. Yang, and R. M. Zucker, “Lanthanide-enhanced luminescence (LEL) with one and two photon excitation of quantum dyes lanthanide(III)-macrocycles,” Proc. SPIE 5322, 187–199 (2004).
[CrossRef]

D’Aléo, A.

A. Picot, A. D’Aléo, P. L. Baldeck, A. Grichine, A. Duperray, C. Andraud, and O. Maury, “Long-lived two-photon excited luminescence of water-soluble europium complex: applications in biological imaging using two-photon scanning microscopy,” J. Am. Chem. Soc. 130(5), 1532–1533 (2008).
[CrossRef] [PubMed]

Dakubu, S.

I. Hemmilä, S. Dakubu, V. M. Mukkala, H. Siitari, and T. Lövgren, “Europium as a label in time-resolved immunofluorometric assays,” Anal. Biochem. 137(2), 335–343 (1984).
[CrossRef] [PubMed]

Dattelbaum, J.

G. Piszczek, B. P. Maliwal, I. Gryczynski, J. Dattelbaum, and J. R. Lakowicz, “Multiphoton ligand-enhanced excitation of lanthanides,” J. Fluoresc. 11(2), 101–107 (2001).
[CrossRef]

de Mello Donega, C.

L. D. Carlos, C. de Mello Donega, R. Q. Albuquerque, S. Alves, J. F. S. Menezes, and O. L. Malta, “Highly luminescent europium(III) complexes with naphtoiltrifluoroacetone and dimethyl sulphoxide,” Mol. Phys. 101(7), 1037–1045 (2003).
[CrossRef]

Duperray, A.

A. Picot, A. D’Aléo, P. L. Baldeck, A. Grichine, A. Duperray, C. Andraud, and O. Maury, “Long-lived two-photon excited luminescence of water-soluble europium complex: applications in biological imaging using two-photon scanning microscopy,” J. Am. Chem. Soc. 130(5), 1532–1533 (2008).
[CrossRef] [PubMed]

Faris, G. W.

X. Xiao, J. P. Haushalter, and G. W. Faris, “Upconversion from aqueous phase lanthanide chelates,” Opt. Lett. 30(13), 1674–1676 (2005).
[CrossRef] [PubMed]

X. Xiao, J. P. Haushalter, M. Weiss, and G. W. Faris, “Optical response measurement of upconverting luminescent reporters,” Proc. SPIE 5329, 229–238 (2004).
[CrossRef]

Faulkner, S.

A. Beeby, S. Faulkner, D. Parker, and J. A. G. Williams, “Sensitised luminescence from phenanthridine appended lanthanide complexes: analysis of triplet mediated energy transfer processes in terbium, europium and neodymium complexes,” J. Chem. Soc., Perkin Trans. 2 (8): 1268–1273 (2001).
[CrossRef]

Gin, P.

M. Bruchez, M. Moronne, P. Gin, S. Weiss, and A. P. Alivisatos, “Semiconductor nanocrystals as fluorescent biological labels,” Science 281(5385), 2013–2016 (1998).
[CrossRef] [PubMed]

Grichine, A.

A. Picot, A. D’Aléo, P. L. Baldeck, A. Grichine, A. Duperray, C. Andraud, and O. Maury, “Long-lived two-photon excited luminescence of water-soluble europium complex: applications in biological imaging using two-photon scanning microscopy,” J. Am. Chem. Soc. 130(5), 1532–1533 (2008).
[CrossRef] [PubMed]

Gryczynski, I.

G. Piszczek, B. P. Maliwal, I. Gryczynski, J. Dattelbaum, and J. R. Lakowicz, “Multiphoton ligand-enhanced excitation of lanthanides,” J. Fluoresc. 11(2), 101–107 (2001).
[CrossRef]

Guarino, V. R.

R. C. Leif, R. A. Thomas, T. A. Yopp, B. D. Watson, V. R. Guarino, D. H. Hindman, N. Lefkove, and L. M. Vallarino, “Development of instrumentation and fluorochromes for automated multiparameter analysis of cells,” Clin. Chem. 23(8), 1492–1498 (1977).
[PubMed]

Hall, M. P.

J. Hampl, M. P. Hall, N. A. Mufti, Y.-M. M. Yao, D. B. MacQueen, W. H. Wright, and D. E. Cooper, “Upconverting phosphor reporters in immunochromatographic assays,” Anal. Biochem. 288(2), 176–187 (2001).
[CrossRef] [PubMed]

Hampl, J.

J. Hampl, M. P. Hall, N. A. Mufti, Y.-M. M. Yao, D. B. MacQueen, W. H. Wright, and D. E. Cooper, “Upconverting phosphor reporters in immunochromatographic assays,” Anal. Biochem. 288(2), 176–187 (2001).
[CrossRef] [PubMed]

Han, R.

G. Shao, R. Han, Y. Ma, M. Tang, F. Xue, Y. Sha, and Y. Wang, “Bionanoprobes with excellent two-photon-sensitized Eu3+ luminescence properties for live cell imaging,” Chemistry 16(29), 8647–8651 (2010).
[CrossRef] [PubMed]

Haushalter, J. P.

X. Xiao, J. P. Haushalter, and G. W. Faris, “Upconversion from aqueous phase lanthanide chelates,” Opt. Lett. 30(13), 1674–1676 (2005).
[CrossRef] [PubMed]

X. Xiao, J. P. Haushalter, M. Weiss, and G. W. Faris, “Optical response measurement of upconverting luminescent reporters,” Proc. SPIE 5329, 229–238 (2004).
[CrossRef]

Hell, S. W.

Hemmilä, I.

I. Hemmilä, S. Dakubu, V. M. Mukkala, H. Siitari, and T. Lövgren, “Europium as a label in time-resolved immunofluorometric assays,” Anal. Biochem. 137(2), 335–343 (1984).
[CrossRef] [PubMed]

Hindman, D. H.

R. C. Leif, R. A. Thomas, T. A. Yopp, B. D. Watson, V. R. Guarino, D. H. Hindman, N. Lefkove, and L. M. Vallarino, “Development of instrumentation and fluorochromes for automated multiparameter analysis of cells,” Clin. Chem. 23(8), 1492–1498 (1977).
[PubMed]

Knapp, M. A.

J. N. Mansbridge, W. A. Ausserer, M. A. Knapp, and R. M. Sutherland, “Adaptation of EGF receptor signal transduction to three-dimensional culture conditions: changes in surface receptor expression and protein tyrosine phosphorylation,” J. Cell. Physiol. 161(2), 374–382 (1994).
[CrossRef] [PubMed]

Lakowicz, J. R.

G. Piszczek, B. P. Maliwal, I. Gryczynski, J. Dattelbaum, and J. R. Lakowicz, “Multiphoton ligand-enhanced excitation of lanthanides,” J. Fluoresc. 11(2), 101–107 (2001).
[CrossRef]

Lam, M. H.

G. L. Law, K. L. Wong, C. W. Man, W. T. Wong, S. W. Tsao, M. H. Lam, and P. K. Lam, “Emissive terbium probe for multiphoton in vitro cell imaging,” J. Am. Chem. Soc. 130(12), 3714–3715 (2008).
[CrossRef] [PubMed]

Lam, P. K.

G. L. Law, K. L. Wong, C. W. Man, W. T. Wong, S. W. Tsao, M. H. Lam, and P. K. Lam, “Emissive terbium probe for multiphoton in vitro cell imaging,” J. Am. Chem. Soc. 130(12), 3714–3715 (2008).
[CrossRef] [PubMed]

Law, G. L.

G. L. Law, K. L. Wong, C. W. Man, W. T. Wong, S. W. Tsao, M. H. Lam, and P. K. Lam, “Emissive terbium probe for multiphoton in vitro cell imaging,” J. Am. Chem. Soc. 130(12), 3714–3715 (2008).
[CrossRef] [PubMed]

Lefkove, N.

R. C. Leif, R. A. Thomas, T. A. Yopp, B. D. Watson, V. R. Guarino, D. H. Hindman, N. Lefkove, and L. M. Vallarino, “Development of instrumentation and fluorochromes for automated multiparameter analysis of cells,” Clin. Chem. 23(8), 1492–1498 (1977).
[PubMed]

Leif, R. C.

R. C. Leif, M. C. Becker, J. Alfred, J. Bromm, N. Chen, A. E. Cowan, L. M. Vallarino, S. Yang, and R. M. Zucker, “Lanthanide-enhanced luminescence (LEL) with one and two photon excitation of quantum dyes lanthanide(III)-macrocycles,” Proc. SPIE 5322, 187–199 (2004).
[CrossRef]

R. C. Leif, R. A. Thomas, T. A. Yopp, B. D. Watson, V. R. Guarino, D. H. Hindman, N. Lefkove, and L. M. Vallarino, “Development of instrumentation and fluorochromes for automated multiparameter analysis of cells,” Clin. Chem. 23(8), 1492–1498 (1977).
[PubMed]

Lövgren, T.

I. Hemmilä, S. Dakubu, V. M. Mukkala, H. Siitari, and T. Lövgren, “Europium as a label in time-resolved immunofluorometric assays,” Anal. Biochem. 137(2), 335–343 (1984).
[CrossRef] [PubMed]

Ma, Y.

G. Shao, R. Han, Y. Ma, M. Tang, F. Xue, Y. Sha, and Y. Wang, “Bionanoprobes with excellent two-photon-sensitized Eu3+ luminescence properties for live cell imaging,” Chemistry 16(29), 8647–8651 (2010).
[CrossRef] [PubMed]

MacQueen, D. B.

J. Hampl, M. P. Hall, N. A. Mufti, Y.-M. M. Yao, D. B. MacQueen, W. H. Wright, and D. E. Cooper, “Upconverting phosphor reporters in immunochromatographic assays,” Anal. Biochem. 288(2), 176–187 (2001).
[CrossRef] [PubMed]

Maliwal, B. P.

G. Piszczek, B. P. Maliwal, I. Gryczynski, J. Dattelbaum, and J. R. Lakowicz, “Multiphoton ligand-enhanced excitation of lanthanides,” J. Fluoresc. 11(2), 101–107 (2001).
[CrossRef]

Malta, O. L.

L. D. Carlos, C. de Mello Donega, R. Q. Albuquerque, S. Alves, J. F. S. Menezes, and O. L. Malta, “Highly luminescent europium(III) complexes with naphtoiltrifluoroacetone and dimethyl sulphoxide,” Mol. Phys. 101(7), 1037–1045 (2003).
[CrossRef]

Man, C. W.

G. L. Law, K. L. Wong, C. W. Man, W. T. Wong, S. W. Tsao, M. H. Lam, and P. K. Lam, “Emissive terbium probe for multiphoton in vitro cell imaging,” J. Am. Chem. Soc. 130(12), 3714–3715 (2008).
[CrossRef] [PubMed]

Mansbridge, J. N.

J. N. Mansbridge, W. A. Ausserer, M. A. Knapp, and R. M. Sutherland, “Adaptation of EGF receptor signal transduction to three-dimensional culture conditions: changes in surface receptor expression and protein tyrosine phosphorylation,” J. Cell. Physiol. 161(2), 374–382 (1994).
[CrossRef] [PubMed]

Maury, O.

C. Andraud and O. Maury, “Lanthanide complexes for nonlinear optics: from fundamental aspects to applications,” Eur. J. Inorg. Chem. 2009(29-30), 4357–4371 (2009).
[CrossRef]

A. Picot, A. D’Aléo, P. L. Baldeck, A. Grichine, A. Duperray, C. Andraud, and O. Maury, “Long-lived two-photon excited luminescence of water-soluble europium complex: applications in biological imaging using two-photon scanning microscopy,” J. Am. Chem. Soc. 130(5), 1532–1533 (2008).
[CrossRef] [PubMed]

Menezes, J. F. S.

L. D. Carlos, C. de Mello Donega, R. Q. Albuquerque, S. Alves, J. F. S. Menezes, and O. L. Malta, “Highly luminescent europium(III) complexes with naphtoiltrifluoroacetone and dimethyl sulphoxide,” Mol. Phys. 101(7), 1037–1045 (2003).
[CrossRef]

Mertz, J.

Moronne, M.

M. Bruchez, M. Moronne, P. Gin, S. Weiss, and A. P. Alivisatos, “Semiconductor nanocrystals as fluorescent biological labels,” Science 281(5385), 2013–2016 (1998).
[CrossRef] [PubMed]

Mufti, N. A.

J. Hampl, M. P. Hall, N. A. Mufti, Y.-M. M. Yao, D. B. MacQueen, W. H. Wright, and D. E. Cooper, “Upconverting phosphor reporters in immunochromatographic assays,” Anal. Biochem. 288(2), 176–187 (2001).
[CrossRef] [PubMed]

Mukkala, V. M.

I. Hemmilä, S. Dakubu, V. M. Mukkala, H. Siitari, and T. Lövgren, “Europium as a label in time-resolved immunofluorometric assays,” Anal. Biochem. 137(2), 335–343 (1984).
[CrossRef] [PubMed]

Muller, M.

J. Squier and M. Muller, “High resolution nonlinear microscopy: A review of sources and methods for achieving optimal imaging,” Rev. Sci. Instrum. 72(7), 2855–2867 (2001).
[CrossRef]

Murray, B. S.

L. O. Pålsson, R. Pal, B. S. Murray, D. Parker, and A. Beeby, “Two-photon absorption and photoluminescence of europium based emissive probes for bioactive systems,” Dalton Trans. (48): 5726–5734 (2007).
[CrossRef] [PubMed]

Nie, S.

W. C. W. Chan and S. Nie, “Quantum dot bioconjugates for ultrasensitive nonisotopic detection,” Science 281(5385), 2016–2018 (1998).
[CrossRef] [PubMed]

Pal, R.

L. O. Pålsson, R. Pal, B. S. Murray, D. Parker, and A. Beeby, “Two-photon absorption and photoluminescence of europium based emissive probes for bioactive systems,” Dalton Trans. (48): 5726–5734 (2007).
[CrossRef] [PubMed]

Pålsson, L. O.

L. O. Pålsson, R. Pal, B. S. Murray, D. Parker, and A. Beeby, “Two-photon absorption and photoluminescence of europium based emissive probes for bioactive systems,” Dalton Trans. (48): 5726–5734 (2007).
[CrossRef] [PubMed]

Parker, D.

L. O. Pålsson, R. Pal, B. S. Murray, D. Parker, and A. Beeby, “Two-photon absorption and photoluminescence of europium based emissive probes for bioactive systems,” Dalton Trans. (48): 5726–5734 (2007).
[CrossRef] [PubMed]

A. Beeby, S. Faulkner, D. Parker, and J. A. G. Williams, “Sensitised luminescence from phenanthridine appended lanthanide complexes: analysis of triplet mediated energy transfer processes in terbium, europium and neodymium complexes,” J. Chem. Soc., Perkin Trans. 2 (8): 1268–1273 (2001).
[CrossRef]

Pick, R.

Picot, A.

A. Picot, A. D’Aléo, P. L. Baldeck, A. Grichine, A. Duperray, C. Andraud, and O. Maury, “Long-lived two-photon excited luminescence of water-soluble europium complex: applications in biological imaging using two-photon scanning microscopy,” J. Am. Chem. Soc. 130(5), 1532–1533 (2008).
[CrossRef] [PubMed]

Piszczek, G.

G. Piszczek, B. P. Maliwal, I. Gryczynski, J. Dattelbaum, and J. R. Lakowicz, “Multiphoton ligand-enhanced excitation of lanthanides,” J. Fluoresc. 11(2), 101–107 (2001).
[CrossRef]

Sha, Y.

G. Shao, R. Han, Y. Ma, M. Tang, F. Xue, Y. Sha, and Y. Wang, “Bionanoprobes with excellent two-photon-sensitized Eu3+ luminescence properties for live cell imaging,” Chemistry 16(29), 8647–8651 (2010).
[CrossRef] [PubMed]

Shao, G.

G. Shao, R. Han, Y. Ma, M. Tang, F. Xue, Y. Sha, and Y. Wang, “Bionanoprobes with excellent two-photon-sensitized Eu3+ luminescence properties for live cell imaging,” Chemistry 16(29), 8647–8651 (2010).
[CrossRef] [PubMed]

Siitari, H.

I. Hemmilä, S. Dakubu, V. M. Mukkala, H. Siitari, and T. Lövgren, “Europium as a label in time-resolved immunofluorometric assays,” Anal. Biochem. 137(2), 335–343 (1984).
[CrossRef] [PubMed]

Squier, J.

J. Squier and M. Muller, “High resolution nonlinear microscopy: A review of sources and methods for achieving optimal imaging,” Rev. Sci. Instrum. 72(7), 2855–2867 (2001).
[CrossRef]

Sutherland, R. M.

J. N. Mansbridge, W. A. Ausserer, M. A. Knapp, and R. M. Sutherland, “Adaptation of EGF receptor signal transduction to three-dimensional culture conditions: changes in surface receptor expression and protein tyrosine phosphorylation,” J. Cell. Physiol. 161(2), 374–382 (1994).
[CrossRef] [PubMed]

Tang, M.

G. Shao, R. Han, Y. Ma, M. Tang, F. Xue, Y. Sha, and Y. Wang, “Bionanoprobes with excellent two-photon-sensitized Eu3+ luminescence properties for live cell imaging,” Chemistry 16(29), 8647–8651 (2010).
[CrossRef] [PubMed]

Thomas, R. A.

R. C. Leif, R. A. Thomas, T. A. Yopp, B. D. Watson, V. R. Guarino, D. H. Hindman, N. Lefkove, and L. M. Vallarino, “Development of instrumentation and fluorochromes for automated multiparameter analysis of cells,” Clin. Chem. 23(8), 1492–1498 (1977).
[PubMed]

Tsao, S. W.

G. L. Law, K. L. Wong, C. W. Man, W. T. Wong, S. W. Tsao, M. H. Lam, and P. K. Lam, “Emissive terbium probe for multiphoton in vitro cell imaging,” J. Am. Chem. Soc. 130(12), 3714–3715 (2008).
[CrossRef] [PubMed]

Vallarino, L. M.

R. C. Leif, M. C. Becker, J. Alfred, J. Bromm, N. Chen, A. E. Cowan, L. M. Vallarino, S. Yang, and R. M. Zucker, “Lanthanide-enhanced luminescence (LEL) with one and two photon excitation of quantum dyes lanthanide(III)-macrocycles,” Proc. SPIE 5322, 187–199 (2004).
[CrossRef]

R. C. Leif, R. A. Thomas, T. A. Yopp, B. D. Watson, V. R. Guarino, D. H. Hindman, N. Lefkove, and L. M. Vallarino, “Development of instrumentation and fluorochromes for automated multiparameter analysis of cells,” Clin. Chem. 23(8), 1492–1498 (1977).
[PubMed]

Wang, Y.

G. Shao, R. Han, Y. Ma, M. Tang, F. Xue, Y. Sha, and Y. Wang, “Bionanoprobes with excellent two-photon-sensitized Eu3+ luminescence properties for live cell imaging,” Chemistry 16(29), 8647–8651 (2010).
[CrossRef] [PubMed]

Watson, B. D.

R. C. Leif, R. A. Thomas, T. A. Yopp, B. D. Watson, V. R. Guarino, D. H. Hindman, N. Lefkove, and L. M. Vallarino, “Development of instrumentation and fluorochromes for automated multiparameter analysis of cells,” Clin. Chem. 23(8), 1492–1498 (1977).
[PubMed]

Webb, W. W.

Weiss, M.

X. Xiao, J. P. Haushalter, M. Weiss, and G. W. Faris, “Optical response measurement of upconverting luminescent reporters,” Proc. SPIE 5329, 229–238 (2004).
[CrossRef]

Weiss, S.

M. Bruchez, M. Moronne, P. Gin, S. Weiss, and A. P. Alivisatos, “Semiconductor nanocrystals as fluorescent biological labels,” Science 281(5385), 2013–2016 (1998).
[CrossRef] [PubMed]

Williams, J. A. G.

A. Beeby, S. Faulkner, D. Parker, and J. A. G. Williams, “Sensitised luminescence from phenanthridine appended lanthanide complexes: analysis of triplet mediated energy transfer processes in terbium, europium and neodymium complexes,” J. Chem. Soc., Perkin Trans. 2 (8): 1268–1273 (2001).
[CrossRef]

Wong, K. L.

G. L. Law, K. L. Wong, C. W. Man, W. T. Wong, S. W. Tsao, M. H. Lam, and P. K. Lam, “Emissive terbium probe for multiphoton in vitro cell imaging,” J. Am. Chem. Soc. 130(12), 3714–3715 (2008).
[CrossRef] [PubMed]

Wong, W. T.

G. L. Law, K. L. Wong, C. W. Man, W. T. Wong, S. W. Tsao, M. H. Lam, and P. K. Lam, “Emissive terbium probe for multiphoton in vitro cell imaging,” J. Am. Chem. Soc. 130(12), 3714–3715 (2008).
[CrossRef] [PubMed]

Wright, W. H.

J. Hampl, M. P. Hall, N. A. Mufti, Y.-M. M. Yao, D. B. MacQueen, W. H. Wright, and D. E. Cooper, “Upconverting phosphor reporters in immunochromatographic assays,” Anal. Biochem. 288(2), 176–187 (2001).
[CrossRef] [PubMed]

Xiao, X.

X. Xiao, J. P. Haushalter, and G. W. Faris, “Upconversion from aqueous phase lanthanide chelates,” Opt. Lett. 30(13), 1674–1676 (2005).
[CrossRef] [PubMed]

X. Xiao, J. P. Haushalter, M. Weiss, and G. W. Faris, “Optical response measurement of upconverting luminescent reporters,” Proc. SPIE 5329, 229–238 (2004).
[CrossRef]

Xu, C.

Xue, F.

G. Shao, R. Han, Y. Ma, M. Tang, F. Xue, Y. Sha, and Y. Wang, “Bionanoprobes with excellent two-photon-sensitized Eu3+ luminescence properties for live cell imaging,” Chemistry 16(29), 8647–8651 (2010).
[CrossRef] [PubMed]

Yang, S.

R. C. Leif, M. C. Becker, J. Alfred, J. Bromm, N. Chen, A. E. Cowan, L. M. Vallarino, S. Yang, and R. M. Zucker, “Lanthanide-enhanced luminescence (LEL) with one and two photon excitation of quantum dyes lanthanide(III)-macrocycles,” Proc. SPIE 5322, 187–199 (2004).
[CrossRef]

Yao, Y.-M. M.

J. Hampl, M. P. Hall, N. A. Mufti, Y.-M. M. Yao, D. B. MacQueen, W. H. Wright, and D. E. Cooper, “Upconverting phosphor reporters in immunochromatographic assays,” Anal. Biochem. 288(2), 176–187 (2001).
[CrossRef] [PubMed]

Yopp, T. A.

R. C. Leif, R. A. Thomas, T. A. Yopp, B. D. Watson, V. R. Guarino, D. H. Hindman, N. Lefkove, and L. M. Vallarino, “Development of instrumentation and fluorochromes for automated multiparameter analysis of cells,” Clin. Chem. 23(8), 1492–1498 (1977).
[PubMed]

Zucker, R. M.

R. C. Leif, M. C. Becker, J. Alfred, J. Bromm, N. Chen, A. E. Cowan, L. M. Vallarino, S. Yang, and R. M. Zucker, “Lanthanide-enhanced luminescence (LEL) with one and two photon excitation of quantum dyes lanthanide(III)-macrocycles,” Proc. SPIE 5322, 187–199 (2004).
[CrossRef]

Anal. Biochem. (2)

J. Hampl, M. P. Hall, N. A. Mufti, Y.-M. M. Yao, D. B. MacQueen, W. H. Wright, and D. E. Cooper, “Upconverting phosphor reporters in immunochromatographic assays,” Anal. Biochem. 288(2), 176–187 (2001).
[CrossRef] [PubMed]

I. Hemmilä, S. Dakubu, V. M. Mukkala, H. Siitari, and T. Lövgren, “Europium as a label in time-resolved immunofluorometric assays,” Anal. Biochem. 137(2), 335–343 (1984).
[CrossRef] [PubMed]

Chemistry (1)

G. Shao, R. Han, Y. Ma, M. Tang, F. Xue, Y. Sha, and Y. Wang, “Bionanoprobes with excellent two-photon-sensitized Eu3+ luminescence properties for live cell imaging,” Chemistry 16(29), 8647–8651 (2010).
[CrossRef] [PubMed]

Clin. Chem. (1)

R. C. Leif, R. A. Thomas, T. A. Yopp, B. D. Watson, V. R. Guarino, D. H. Hindman, N. Lefkove, and L. M. Vallarino, “Development of instrumentation and fluorochromes for automated multiparameter analysis of cells,” Clin. Chem. 23(8), 1492–1498 (1977).
[PubMed]

Dalton Trans. (1)

L. O. Pålsson, R. Pal, B. S. Murray, D. Parker, and A. Beeby, “Two-photon absorption and photoluminescence of europium based emissive probes for bioactive systems,” Dalton Trans. (48): 5726–5734 (2007).
[CrossRef] [PubMed]

Eur. J. Inorg. Chem. (1)

C. Andraud and O. Maury, “Lanthanide complexes for nonlinear optics: from fundamental aspects to applications,” Eur. J. Inorg. Chem. 2009(29-30), 4357–4371 (2009).
[CrossRef]

J. Am. Chem. Soc. (2)

A. Picot, A. D’Aléo, P. L. Baldeck, A. Grichine, A. Duperray, C. Andraud, and O. Maury, “Long-lived two-photon excited luminescence of water-soluble europium complex: applications in biological imaging using two-photon scanning microscopy,” J. Am. Chem. Soc. 130(5), 1532–1533 (2008).
[CrossRef] [PubMed]

G. L. Law, K. L. Wong, C. W. Man, W. T. Wong, S. W. Tsao, M. H. Lam, and P. K. Lam, “Emissive terbium probe for multiphoton in vitro cell imaging,” J. Am. Chem. Soc. 130(12), 3714–3715 (2008).
[CrossRef] [PubMed]

J. Cell. Physiol. (1)

J. N. Mansbridge, W. A. Ausserer, M. A. Knapp, and R. M. Sutherland, “Adaptation of EGF receptor signal transduction to three-dimensional culture conditions: changes in surface receptor expression and protein tyrosine phosphorylation,” J. Cell. Physiol. 161(2), 374–382 (1994).
[CrossRef] [PubMed]

J. Chem. Soc., Perkin Trans. 2 (1)

A. Beeby, S. Faulkner, D. Parker, and J. A. G. Williams, “Sensitised luminescence from phenanthridine appended lanthanide complexes: analysis of triplet mediated energy transfer processes in terbium, europium and neodymium complexes,” J. Chem. Soc., Perkin Trans. 2 (8): 1268–1273 (2001).
[CrossRef]

J. Fluoresc. (1)

G. Piszczek, B. P. Maliwal, I. Gryczynski, J. Dattelbaum, and J. R. Lakowicz, “Multiphoton ligand-enhanced excitation of lanthanides,” J. Fluoresc. 11(2), 101–107 (2001).
[CrossRef]

Mol. Phys. (1)

L. D. Carlos, C. de Mello Donega, R. Q. Albuquerque, S. Alves, J. F. S. Menezes, and O. L. Malta, “Highly luminescent europium(III) complexes with naphtoiltrifluoroacetone and dimethyl sulphoxide,” Mol. Phys. 101(7), 1037–1045 (2003).
[CrossRef]

Opt. Lett. (3)

Proc. SPIE (2)

X. Xiao, J. P. Haushalter, M. Weiss, and G. W. Faris, “Optical response measurement of upconverting luminescent reporters,” Proc. SPIE 5329, 229–238 (2004).
[CrossRef]

R. C. Leif, M. C. Becker, J. Alfred, J. Bromm, N. Chen, A. E. Cowan, L. M. Vallarino, S. Yang, and R. M. Zucker, “Lanthanide-enhanced luminescence (LEL) with one and two photon excitation of quantum dyes lanthanide(III)-macrocycles,” Proc. SPIE 5322, 187–199 (2004).
[CrossRef]

Rev. Sci. Instrum. (1)

J. Squier and M. Muller, “High resolution nonlinear microscopy: A review of sources and methods for achieving optimal imaging,” Rev. Sci. Instrum. 72(7), 2855–2867 (2001).
[CrossRef]

Science (2)

M. Bruchez, M. Moronne, P. Gin, S. Weiss, and A. P. Alivisatos, “Semiconductor nanocrystals as fluorescent biological labels,” Science 281(5385), 2013–2016 (1998).
[CrossRef] [PubMed]

W. C. W. Chan and S. Nie, “Quantum dot bioconjugates for ultrasensitive nonisotopic detection,” Science 281(5385), 2016–2018 (1998).
[CrossRef] [PubMed]

Other (2)

G. W. Faris, W. H. Wright, S. Pati, L. V. Schneider, and D. A. Zarling, “Upconverting reporters for biomedical diagnostics: Applications in antibody and DNA detection,” in Biomedical Optical Spectroscopy and Diagnostics, Vol. 3 of OSA Trends in Optics and Photonics, E. Sevick-Muraca and D. Benaron, eds. (Optical Society of America, Washington, DC, 1996), pp. 225–228.

D. A. Zarling, M. Rossi, N. A. Peppers, J. Kane, G. W. Faris, M. J. Dyer, S. Y. Ng, and L. V. Schneider, “Up-converting reporters for biological and other assays using laser excitation techniques,” U.S. Patent 5,891,656 (6 April 1999).

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Figures (9)

Fig. 1
Fig. 1

Schematic of energy transfer from sensitizer to Eu3+.

Fig. 2
Fig. 2

Spectra of Eu DOTA-NHS before conjugation (a) and after conjugation to streptavidin with and without NTA added (b). These spectra were taken in a conventional fluorimeter.

Fig. 3
Fig. 3

Schematic of multiphoton microscope.

Fig. 4
Fig. 4

Schematic representation of cell-based assay using europium chelates.

Fig. 5
Fig. 5

Images of A431 cells labeled with EuDOTA (a) brightfield image; (b) two-photon-excited image; (c) two-photon-excited image (red) overlaid on brightfield image; (d) two-photon-excited image after addition of KHP.

Fig. 6
Fig. 6

Bright field (a) and two-photon-excited luminescence (b) images of A431 cells following protocol of Fig. 4 except without primary antibody.

Fig. 7
Fig. 7

Bright field (a) and two-photon-excited luminescence (b) images of bare A431 cells.

Fig. 8
Fig. 8

Positive (a) and negative (b) control images of A431 cells labeled with FITC.

Fig. 9
Fig. 9

Variation in two-photon-excited europium signal from labeled A431 cells as a function of time.

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