Library synthesis, screening, and discovery of modified zinc(II)-bis(dipicolylamine) probe for enhanced molecular imaging of cell death

Bioconjugate Chemistry

Volumn 25, Issue 4, 2014, Pages 724-737

  Plaunt, Adam J ^a   Harmatys, Kara M ^a   Wolter, William R ^b   Suckow, Mark A ^b   Smith, Bradley D ^a  

^a 236 Nieuwland Science Hall   (United States)

^b UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; COORDINATION REACTIONS; DIAGNOSIS; FLUORESCENCE; MAGNETIC RESONANCE IMAGING; MAMMALS; MOLECULAR IMAGING; PROBES; ZINC COMPOUNDS;

COORDINATION COMPLEX; EQUILIBRIUM DIALYSIS; IMAGING APPLICATIONS; IMAGING CELLS; ITERATIVE CYCLES; MAMMALIAN CELLS; MOLECULAR PROBES; PHOSPHATIDYLSERINE; RAPID EQUILIBRIUM; RED FLUORESCENT;

CELL DEATH;

COORDINATION COMPOUND; LEAD; UNCLASSIFIED DRUG; ZINC BIS(DIPICOLYLAMINE); ZINC DERIVATIVE; BIS-DIPICOLYLAMINE-ZINC(II); MOLECULAR PROBE; ORGANOMETALLIC COMPOUND; PICOLINIC ACID DERIVATIVE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; CELL CULTURE; CELL DEATH; CONTROLLED STUDY; EQUILIBRIUM DIALYSIS; EX VIVO STUDY; IN VIVO STUDY; MOLECULAR IMAGING; NONHUMAN; RAT; SCREENING; SYNTHESIS; TITRIMETRY; ANALYSIS; ANIMAL; BREAST TUMOR; CHEMICAL STRUCTURE; CHEMISTRY; CHO CELL LINE; CRICETULUS; FLUORESCENCE RESONANCE ENERGY TRANSFER; HUMAN; MALE; MOLECULAR PROBE; PATHOLOGY; PHARMACOKINETICS; PROCEDURES; TISSUE DISTRIBUTION; TUMOR CELL LINE; WISTAR RAT;

ANIMALS; BREAST NEOPLASMS; CELL DEATH; CELL LINE, TUMOR; CHO CELLS; CRICETULUS; FLUORESCENCE RESONANCE ENERGY TRANSFER; HUMANS; MALE; MOLECULAR IMAGING; MOLECULAR PROBES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PICOLINIC ACIDS; RATS; RATS, WISTAR; TISSUE DISTRIBUTION;

EID: 84899026556     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc500003x     Document Type: Article

References (52)

1. Smith, B. A. and Smith, B. D. (2012) Biomarkers and molecular probes for cell death imaging and targeted therapeutics Bioconjugate Chem. 23, 1989-2006
2. Kepp, O., Galluzzi, L., Lipinski, M., Yuan, J., and Kroemer, G. (2011) Cell death assays for drug discovery Nat. Rev. Drug Discovery 10, 221-37
3. Huang, X., Lee, S., and Chen, X. (2011) Design of †smart†probes for optical imaging of apoptosis Am. J. Nucl. Med. Mol. Imaging 1, 3-17
4. Blankenberg, F. G. (2008) In vivo detection of apoptosis J. Nucl. Med. 49, 81S-95S
5. Smith, G., Nguyen, Q. D., and Aboagye, E. O. (2009) Translational imaging of apoptosis Anti-Cancer Agents Med. Chem. 9, 958-67
6. Balasubramanian, K. and Schroit, A. J. (2003) Aminophospholipid asymmetry: A matter of life and death Annu. Rev. Physiol. 65, 701-34
7. Belhocine, T. and Prato, F. (2011) Transbilayer phospholipids molecular imaging EJNMMI Res. 1, 17
8. Gao, J. M. and Zheng, H. (2013) Illuminating the lipidome to advance biomedical research: peptide-based probes of membrane lipids Future Med. Chem. 5, 947-59
9. Vance, J. E. and Steenbergen, R. (2005) Metabolism and functions of phosphatidylserine Prog. Lipid Res. 44, 207-34
10. Frey, B. and Gaipl, U. (2011) The immune functions of phosphatidylserine in membranes of dying cells and microvesicles Semin. Immunopathol. 33, 497-516
11. Fadeel, B. and Xue, D. (2009) The ins and outs of phospholipid asymmetry in the plasma membrane: roles in health and disease Crit. Rev. Biochem. Mol. Biol. 44, 264-77
12. Leventis, P. A. and Grinstein, S. (2010) The distribution and function of phosphatidylserine in cellular membranes Ann. Rev. Biophys. 39, 407-27
13. Schutters, K. and Reutelingsperger, C. (2010) Phosphatidylserine targeting for diagnosis and treatment of human diseases Apoptosis 15, 1072-82
14. Vanderheyden, J.-L., Liu, G., He, J., Patel, B., Tait, J. F., and Hnatowich, D. J. (2006) valuation of 99mTc-MAG3-annexin V: influence of the chelate on in vitro and in vivo properties in mice Nucl. Med. Biol. 33, 135-44
15. Ke, S., Wen, X. X., Wu, Q. P., Wallace, S., Charnsangavej, C., Stachowiak, A. M., Stephens, C. L., Abbruzzese, J. L., Podoloff, D. A., and Li, C. (2004) Imaging taxane-induced tumor apoptosis using PEGylated, In-111-labeled annexin V J. Nucl. Med. 45, 108-15
16. Beekman, C. A. C., Buckle, T., van Leeuwen, A. C., Valdés Olmos, R. A., Verheij, M., Rottenberg, S., and van Leeuwen, F. W. B. (2011) Questioning the value of 99mTc-HYNIC-annexin V based response monitoring after docetaxel treatment in a mouse model for hereditary breast cancer Appl. Radiat. Isot. 69, 656-62
17. 2+-dipicolylamine-based probe detects apoptosis during tumour treatment better than an annexin V-based probe Eur. Radiol. 1-8
18. Tavare, R., Torres Martin De Rosales, R., Blower, P., and Mullen, G. (2009) Efficient site-specific radiolabeling of a modified C2A domain synaptotagmin I with [99mTc(CO)3]+: a new radiopharmaceutical for imaging cell death Bioconjugate Chem. 20, 2071-81
19. Alam, I. S., Neves, A. A., Witney, T. H., Boren, J., and Brindle, K. M. (2010) Comparison of the C2A domain of synaptotagmin-I and annexin-V as probes for detecting cell death Bioconjugate Chem. 21, 884-91
20. Falborg, L., Waehrens, L., Alsner, J., Bluhme, H., Frokiaer, J., Heegaard, C., Horsman, M., Rasmussen, J., and Rehling, M. (2010) Biodistribution of 99mTc-HYNIC-lactadherin in mice - a potential tracer for visualizing apoptosis in vivo Scand. J. Clin. Lab. Invest. 70, 209-16
21. Burtea, C., Ballet, S., Laurent, S., Rousseaux, O., Dencausse, A., Gonzalez, W., Port, M., Corot, C., Elst, L. V., and Muller, R. N. (2012) Development of a magnetic resonance imaging protocol for the characterization of atherosclerotic plaque by using vascular cell adhesion molecule-1 and apoptosis-targeted ultrasmall superparamagnetic iron oxide derivatives Arterioscler., Thromb., Vasc. Biol. 32, E36-E48
22. Kapty, J., Banman, S., Goping, I. S., and Mercer, J. R. (2012) Evaluation of phosphatidylserine-binding peptides targeting apoptotic cells J. Biomol. Screen. 17, 1293-1301
23. Xiong, C. Y., Brewer, K., Song, S. L., Zhang, R., Lu, W., Wen, X. X., and Li, C. (2011) Peptide-based imaging agents targeting phosphatidylserine for the detection of apoptosis J. Med. Chem. 54, 1825-35
24. Zheng, H., Wang, F., Wang, Q., and Gao, J. M. (2011) Cofactor-free detection of phosphatidylserine with cyclic peptides mimicking lactadherin J. Am. Chem. Soc. 133, 15280-3
25. Oltmanns, D., Zitzmann-Kolbe, S., Mueller, A., Bauder-Wuest, U., Schaefer, M., Eder, M., Haberkorn, U., and Eisenhut, M. (2011) Zn(II)-bis(cyclen) complexes and the imaging of apoptosis/necrosis Bioconjugate Chem. 22, 2611-24
26. Cooley, C. M., Hettie, K. S., Klockow, J. L., Garrison, S., and Glass, T. E. (2013) A selective fluorescent chemosensor for phosphoserine Org. Biomol. Chem. 11, 7387-92
27. Lakshmi, C., Hanshaw, R. G., and Smith, B. D. (2004) Fluorophore-linked zinc(II)dipicolylamine coordination complexes as sensors for phosphatidylserine-containing membranes Tetrahedron 60, 11307-15
28. Smith, B. A., Xie, B. W., van Beek, E. R., Que, I., Blankevoort, V., Xiao, S. Z., Cole, E. L., Hoehn, M., Kaijzel, E. L., Lowik, C., and Smith, B. D. (2012) Multicolor fluorescence imaging of traumatic brain injury in a cryolesion mouse model ACS Chem. Neurosci. 3, 530-37
29. Smith, B. A., Gammon, S. T., Xiao, S. Z., Wang, W., Chapman, S., McDermott, R., Suckow, M. A., Johnson, J. R., Piwnica-Worms, D., Gokel, G. W., Smith, B. D., and Leevy, W. M. (2011) In vivo optical imaging of acute cell death using a near-infrared fluorescent zinc-dipicolylamine probe Mol. Pharmaceut. 8, 583-90
30. Smith, B. A., Akers, W. J., Leevy, W. M., Lampkins, A. J., Xiao, S., Wolter, W., Suckow, M. A., Achilefu, S., and Smith, B. D. (2010) Optical imaging of mammary and prostate tumors in living animals using a synthetic near infrared zinc(II)-dipicolylamine probe for anionic cell surfaces J. Am. Chem. Soc. 132, 67-9
31. Xiao, S. Z., Turkyilmaz, S., and Smith, B. D. (2013) Convenient synthesis of multivalent zinc(II)-dipicolylamine complexes for molecular recognition Tetrahedron Lett. 54, 861-4
32. Smith, B. A., Harmatys, K. M., Xiao, S., Cole, E. L., Plaunt, A. J., Wolter, W., Suckow, M. A., and Smith, B. D. (2013) Enhanced cell death imaging using multivalent zinc(II)-bis(dipicolylamine) fluorescent probes Mol. Pharmaceut. 10, 3296-303
33. OaNeil, E. J., Jiang, H., and Smith, B. D. (2013) Effect of bridging anions on the structure and stability of phenoxide bridged zinc dipicolylamine coordination complexes Supramol. Chem. 25, 315-22
34. Hanshaw, R. G., Stahelin, R. V., and Smith, B. D. (2008) Noncovalent keystone interactions controlling biomembrane structure Chem.î - ̧Eur. J. 14, 1690-7
35. Huang, F., Cheng, C., and Feng, G. (2012) Introducing ligand-based hydrogen bond donors to a receptor: both selectivity and binding affinity for anion recognition in water can be improved J. Org. Chem. 77, 11405-8
36. Drewry, J. A., Fletcher, S., Hassan, H., and Gunning, P. T. (2009) Novel asymmetrically functionalized bis-dipicolylamine metal complexes: peripheral decoration of a potent anion recognition scaffold Org. Biomol. Chem. 7, 5074-7
37. Lee, J. H., Park, J., Lah, M. S., Chin, A., and Hong, J.-I. (2007) High-affinity pyrophosphate by a synergistic effect receptor metal coordination and hydrogen bonding in water Org. Lett. 9, 3729-731
38. Mareque-Rivas, J. C., Torres Martin de Rosales, R., and Parsons, S. (2004) The affinity of phosphates to zinc(II) complexes can be increased with hydrogen bond donors Chem. Commun. 610-1
39. Pouessel, J., Le Bris, N., Bencini, A., Giorgi, C., Valtancoli, B., and Tripier, R. (2012) Glyphosate and ATP binding by mononuclear Zn(II) complexes with non-symmetric ditopic polyamine ligands Dalton Trans. 41, 10521-32
40. Drewry, J. A., Duodu, E., Mazouchi, A., Spagnuolo, P., Burger, S., Gradinaru, C. C., Ayers, P., Schimmer, A. D., and Gunning, P. T. (2012) Phosphopeptide selective coordination complexes as promising Src homology 2 domain mimetics Inorg. Chem. 51, 8284-91
41. Drewry, J. A., Burger, S., Mazouchi, A., Duodu, E., Ayers, P., Gradinaru, C. C., and Gunning, P. T. (2012) Src homology 2 domain proteomimetics: developing phosphopeptide selective receptors Med. Chem. Commun. 3, 763-70
42. Drewry, J. A., Fletcher, S., Yue, P., Marushchak, D., Zhao, W., Sharmeen, S., Zhang, X., Schimmer, A. D., Gradinaru, C., Turkson, J., and Gunning, P. T. (2010) Coordination complex SH2 domain proteomimetics: an alternative approach to disrupting oncogenic protein-protein interactions Chem. Commun. 46, 892-4
43. Scott, J. L., Musselman, C. A., Adu-Gyamfi, E., Kutateladze, T. G., and Stahelin, R. V. (2012) Emerging methodologies to investigate lipid-protein interactions Integr. Biol. 4, 247-58
44. Segers, J., Laumonier, C., Burtea, C., Laurent, S., Vander Elst, L., and Muller, R. N. (2007) From phage display to magnetophage, a new tool for magnetic resonance molecular imaging Bioconjugate Chem. 18, 1251-58
45. Waters, N. J., Jones, R., Williams, G., and Sohal, B. (2008) Validation of a rapid equilibrium dialysis approach for the measurement of plasma protein binding J. Pharm. Sci. 97, 4586-95
46. White, A. G., Gray, B. D., Pak, K. Y., and Smith, B. D. (2012) Deep-red fluorescent imaging probe for bacteria Bioorg. Med. Chem. Lett. 22, 2833-6
47. Connors, K. A. (1987) Binding Constants: The Measure of Complex Stability, John Wiley & Sons, New York.
48. Smith, B. A., Xiao, S. Z., Wolter, W., Wheeler, J., Suckow, M. A., and Smith, B. D. (2011) In vivo targeting of cell death using a synthetic fluorescent molecular probe Apoptosis 16, 722-31
49. Wyffels, L., Gray, B. D., Barber, C., Woolfenden, J. M., Pak, K. Y., and Liu, Z. L. (2011) Synthesis and preliminary evaluation of radiolabeled bis(zinc(II)-dipicolylamine) coordination complexes as cell death imaging agents Bioorg. Med. Chem. 19, 3425-33
50. McDunn, J. E., Muenzer, J. T., Dunne, B., Zhou, A., Yuan, K., Hoekzema, A., Hilliard, C., Chang, K. C., Davis, C. G., McDonough, J., Hunt, C., Grigsby, P., Piwnica-Worms, D., and Hotchkiss, R. S. (2009) An anti-apoptotic peptide improves survival in lethal total body irradiation Biochem. Biophys. Res. Commun. 382, 657-62
51. Ying, T., Li, Z. J., Juan, Z., and Pan, J. M. (2005) Recent advances of the derivatives of pyridylazo as reagents in analytical chemistry Rev. Anal. Chem. 24, 103-47
52. Xie, H. Z., Yi, S., and Wu, S. K. (1999) Study on host-guest complexation of anions based on tri-podal naphthylthiourea derivatives J. Chem. Soc., Perkin Trans. 2, 2751-4