Skip to main content
SpringerLink
Log in

Bis(o-methylserotonin)-containing iridium(III) and ruthenium(II) complexes as new cellular imaging dyes: synthesis, applications, and photophysical and computational studies

  • Original Paper
  • Published:
JBIC Journal of Biological Inorganic Chemistry Aims and scope Submit manuscript

Abstract

We report the synthesis, characterization, and scope of a new versatile emissive molecular probe functionalized with a 1,10-phenanthroline moiety containing methylserotonin groups as binding sites for metal ion recognition. The synthesis, characterization, and evaluation of the in vitro imaging capability of the iridium(III) and ruthenium(II) complexes [Ir(ppy)2(N–N)]+ and [Ru(bpy)2(N–N)]2+, in which ppy is 2-phenylpyridine, bpy is 2,2′-bipyridine, and N–N is a 1,10-phenanthroline ligand functionalized with two methylserotonin groups to serve as binding sites for metal ion recognition, is reported. The uptake of these compounds by living freshwater fish (Carassius auratus) was studied by fluorescence microscopy, and the cytotoxicity of ligand N–N and [Ru(bpy)2(N–N)]2+ in this species was also investigated.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Dahlstrom A, Fuxe K (1964) Acta Physiol Scand 62:1–55

    Google Scholar 

  2. Rapport MM, Green AA, Page IH (1948) Science 108:329–330

    Article  PubMed  CAS  Google Scholar 

  3. Erspamer V, Asero B (1952) Nature 169:800–801

    Article  PubMed  CAS  Google Scholar 

  4. Reiter RJ (1991) Endocr Rev 12:151–180

    Article  PubMed  CAS  Google Scholar 

  5. Yavarone MS, Shuey DL, Tamir H, Sadler TW, Lauder JM (1993) Teratology 47:573–584

    Article  PubMed  CAS  Google Scholar 

  6. (2008) Nat Chem Biol 4:143

  7. Schatzschneider U (2010) Eur J Inorg Chem 10:1451–1467

    Article  Google Scholar 

  8. Yang H, Li L, Wan L, Zhou Z, Yang S (2010) Inorg Chem Commun 13:1387–1390

    Article  CAS  Google Scholar 

  9. Zhong W, Urayama P, Mycek M-A (2003) J Phys D Appl Phys 36:1689–1695

    Article  CAS  Google Scholar 

  10. Musatkina E, Amouri H, Lamoureux M, Chepurnykh T, Cordier C (2007) J Inorg Biochem 101:1086–1094

    Article  PubMed  CAS  Google Scholar 

  11. Puckett CA, Barton JK (2006) J Am Chem Soc 128:46–47

    Article  Google Scholar 

  12. Wu P, Wong EL-M, Ma D-L, Tong GS-M, Ng K-M, Che C-M (2009) Chem Eur J 15:3652–3656

    Article  PubMed  CAS  Google Scholar 

  13. Picot A, D’Aléo A, Baldeck PL, Grichine A, Duperray A, Andraud C, Maury O (2008) J Am Chem Soc 130:1532–1533

    Article  PubMed  CAS  Google Scholar 

  14. Fu L-M, Wen X-F, Ai X-C, Sun Y, Wu Y-S, Zhang J-P, Wang Y (2005) Angew Chem Int Ed 44:747–750

    Article  CAS  Google Scholar 

  15. Koo C-K, Wong K-L, Man CW-Y, Lam Y-W, So LK-Y, Tam H-L, Tsao S-W, Cheah K-W, Lau K-C, Yang Y-Y, Chen J-C, Lam MH-W (2009) Inorg Chem 48:872–878

    Article  PubMed  CAS  Google Scholar 

  16. Koo C-K, Wong K-L, Man CW-Y, Tam H-L, Tsao S-W, Cheah K-W, Lam MH-W (2009) Inorg Chem 48:7501–7503

    Article  PubMed  CAS  Google Scholar 

  17. Carraway ER, Demas JN, DeGraff BA, Bacon JR (1991) Anal Chem 63:337–342

    Article  CAS  Google Scholar 

  18. Baldo MA, O’Brien DF, You Y, Shoustikov A, Sibley S, Thompson ME, Forrest SR (1998) Nature 395:151–154

    Article  CAS  Google Scholar 

  19. O’Regan B, Grätzel M (1991) Nature 353:737–740

    Article  Google Scholar 

  20. Keefe MH, Benkstein KD, Hupp JT (2000) Coord Chem Rev 205:201–228

    Article  CAS  Google Scholar 

  21. DeRosa MC, Hodgson DJ, Enright GD, Dawson B, Evans CEB, Crutchley RJ (2004) J Am Chem Soc 126:7619–7626

    Article  PubMed  CAS  Google Scholar 

  22. Lo KKW, Hui WK, Chung CK, Tsang KHK, Ng DCM, Zhu NY, Cheung KK (2005) Coord Chem Rev 249:1434–1450

    Article  CAS  Google Scholar 

  23. Lowry MS, Goldsmith JI, Slinker JD, Rohl R, Pascal RA, Malliaras GG, Bernhard S (2005) Chem Mater 17:5712–5719

    Article  CAS  Google Scholar 

  24. Patel M, Day BJ (1999) Trends Pharmacol Sci 20:359–364

    Article  PubMed  CAS  Google Scholar 

  25. Dixon IM, Collin J-P, Sauvage J-P, Barigelletti F, Flamigni L (2000) Angew Chem Int Ed 39:1292–1295

    Article  CAS  Google Scholar 

  26. Ayala NP, Flynn CM, Sacksteder L, Demas JN, DeGraff B (1990) J Am Chem Soc 112:3837–3844

    Article  CAS  Google Scholar 

  27. Coppo P, Duati M, Kozhevnikov VN, Hofstraat JW, De Cola L (2005) Angew Chem Int Ed 44:1806–1810

    Article  CAS  Google Scholar 

  28. Lafolet F, Welter S, Popovi’c Z, De Cola L (2005) J Mater Chem 15:2820–2828

    Article  CAS  Google Scholar 

  29. Yu M, Zhao Q, Shi L, Li F, Zhou Z, Yang H, Yia T, Huang C (2008) Chem Commun 2115–2117

  30. Lamansky S, Djurovich P, Murphy D, Abdel-Razzaq F, Lee HE, Adachi C, Burrows PE, Forrest SR, Thompson ME (2001) J Am Chem Soc 123:4304–4312

    Article  PubMed  CAS  Google Scholar 

  31. You YM, Park SY (2005) J Am Chem Soc 127:12438–12439

    Article  PubMed  CAS  Google Scholar 

  32. Tsuboyama A, Iwawaki H, Furugori M, Mukaide T, Kamatani J, Igawa S, Moriyama T, Miura S, Takiguchi T, Okada S, Hoshino M, Ueno K (2003) J Am Chem Soc 125:12971–12979

    Article  PubMed  CAS  Google Scholar 

  33. Takizawa S, Nishida J, Tsuzuki T, Tokito S, Yamashita Y (2007) Inorg Chem 46:4308–4309

    Article  PubMed  CAS  Google Scholar 

  34. Zhen HY, Luo C, Yang W, Song WY, Du B, Jiang JX, Jiang CY, Zhang Y, Cao Y (2006) Macromolecules 39:1693–1700

    Article  CAS  Google Scholar 

  35. Chen X, Liao JL, Liang Y, Ahmed MO, Tseng HE, Chen SA (2003) J Am Chem Soc 125:636–637

    Article  PubMed  CAS  Google Scholar 

  36. Lo KKW, Lau JSY (2007) Inorg Chem 46:700–709

    Article  PubMed  CAS  Google Scholar 

  37. Lo KKW, Zhang KY, Cheng CK, Kwok KY (2007) Chem Eur J 13:7110–7121

    Article  PubMed  CAS  Google Scholar 

  38. Lo KKW, Cheng CK, Zhu N (2006) Chem Eur J 12:1500–1512

    Article  PubMed  CAS  Google Scholar 

  39. Gao RM, Ho DG, Hernández B, Selke M, Murphy D, Djurovich PI, Thompson ME (2002) J Am Chem Soc 124:14828–14829

    Article  PubMed  CAS  Google Scholar 

  40. Ho ML, Hwang FM, Chen PN, Hu YH, Cheng YM, Chen KS, Lee GH, Chi Y, Chou PT (2006) Org Biomol Chem 4:98–103

    Article  PubMed  CAS  Google Scholar 

  41. Zhao Q, Cao TY, Li FY, Li XH, Jing H, Yi T, Huang CH (2007) Organometallics 16:2077–2081

    Article  Google Scholar 

  42. Zhao Q, Liu SJ, Shi M, Li FY, Jing H, Yi T, Huang CH (2007) Organometallics 16:5922–5930

    Article  Google Scholar 

  43. Chen HL, Zhao Q, Wu Y, Li FY, Yang H, Yi T, Huang CH (2007) Inorg Chem 46:11075–11081

    Article  PubMed  CAS  Google Scholar 

  44. Neugebauer U, Pellegrin Y, Devocelle M, Forster RJ, Signac W, Morand N, Keyes TE (2008) Chem Commun 5307–5309

  45. Kale GV, Samoilenko SG (1997) J Appl Spectrosc 64:214

    Article  Google Scholar 

  46. Dwyer FP, Gyarfas EC, Rogers WP, Koch JH (1952) Nature 170:190–191

    Article  PubMed  CAS  Google Scholar 

  47. Puckett CA, Barton JK (2008) Biochemistry 47:11711–11716

    Article  PubMed  CAS  Google Scholar 

  48. Puckett CA, Barton JK (2007) J Am Chem Soc 129:46–47

    Article  PubMed  CAS  Google Scholar 

  49. Puckett CA, Barton JK (2009) J Am Chem Soc 131:8738–8739

    Article  PubMed  CAS  Google Scholar 

  50. O’Connor NA, Stevens N, Samaroo D, Solomon MR, Marti AA, Dyer J, Vishwasrao H, Akins DL, Kandel ER, Turro NJ (2009) Chem Commun 2640–2642

  51. Lo KK-W, Lee TK-M, Lau JS-Y, Poon W-L, Cheng S-H (2008) Inorg Chem 47:200–208

    Article  PubMed  CAS  Google Scholar 

  52. Sun RW-Y, Ng MF-Y, Wong EL-M, J Zhang, SS-Y Chui, L Shek, T-C Lau, Che C-M (2009) Dalton Trans 10712–10716

  53. Neugebauer U, Pellegrin Y, Devocelle M, Forster R J, Signac W, Morand N, Keyes TE (2008) Chem Commun 5307–5309

  54. Zhang CX, Lippard SJ (2003) Curr Opin Chem Biol 7:481–489

    Article  PubMed  CAS  Google Scholar 

  55. Boerner LJK, Zaleski JM (2005) Curr Opin Chem Biol 9:135–144

    Article  PubMed  CAS  Google Scholar 

  56. Brunner J, Barton JK (2006) Biochemistry 45:12295–12302

    Article  PubMed  CAS  Google Scholar 

  57. Hart JR, Glebov O, Ernst RJ, Kirsch IL, Barton JK (2006) Proc Natl Acad Sci USA 103:15359–15363

    Article  PubMed  CAS  Google Scholar 

  58. Bronner C, Veiga M, Guenet A, De Cola L, Hosseini MW, Strassert CA, Baudr SA (2012) Chem Eur J 18:4041–4050

    Article  PubMed  CAS  Google Scholar 

  59. Du B, Wang L, Wu H, Yang W, Zhang Y, Liu R, Sun M, Peng J, Cao Y (2007) Chem Eur J 13:7432–7442

    Article  PubMed  CAS  Google Scholar 

  60. Lowry MS, Bernhard S (2006) Chem Eur J 12:7970–7977

    Article  PubMed  CAS  Google Scholar 

  61. Shi H-F, Liu S-J, Sun H-B, Xu W-J, An Z-F, Chen J, Sun S, Lu X-M, Zhao Q, Huang W (2010) Chem Eur J 16:12158–12167

    Article  PubMed  CAS  Google Scholar 

  62. Aldrey A, Núñez C, García V, Bastida R, Lodeiro C, Macías A (2010) Tetrahedron 66:9223–9230

    Article  CAS  Google Scholar 

  63. Lodeiro C, Capelo JL, Mejuto JC, Oliveira E, Santos HM, Pedras B, Núñez C (2010) Chem Soc Rev 39:2948–2976

    Article  PubMed  CAS  Google Scholar 

  64. Lodeiro C, Pina F (2009) Coord Chem Rev 253:1353–1383

    Article  CAS  Google Scholar 

  65. Pedras B, Batista RMF, Tormo L, Costa SPG, Raposo MMM, Orellana G, Capelo JL, Lodeiro C (2012) Inorg Chim Acta 381:95–103

    Article  CAS  Google Scholar 

  66. Meech SR, Philips D (1983) J Photochem 23:193–217

    Article  CAS  Google Scholar 

  67. Montalti M, Credi A, Prodi L, Gandolfi MT (2006) Handbook of photochemistry, 3rd edn. CRC, Boca Raton

  68. Auffrant A, Barbieri A, Barigelletti F, Lacour J, Mobian P, Collin J-P, Sauvage J-P, Ventura B (2007) Inorg Chem 46:6911–6919

    Article  PubMed  CAS  Google Scholar 

  69. Hohenberg P, Kohn W (1964) Phys Rev 136:B864–B871

    Article  Google Scholar 

  70. Kohn W, Sham L (1965) Phys Rev A 140:A1133–A1138

    Google Scholar 

  71. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision A.1. Gaussian Inc., Wallingford, CT

  72. Zhao Y, Truhlar DG (2008) Theor Chem Acc 120:215–241

    Article  CAS  Google Scholar 

  73. Hay PJ, Wadt WR (1985) J Chem Phys 82:270–283

    Article  CAS  Google Scholar 

  74. Hay PJ, Wadt WR (1985) J Chem Phys 82:284–298

    Article  Google Scholar 

  75. Hay PJ, Wadt WR (1985) J Chem Phys 82:299–310

    Article  CAS  Google Scholar 

  76. Diniz MS, Peres I, Castro L, Freitas AC, Rocha-Santos TAP, Pereira R, Duarte AC (2010) J Environ Sci Health A 45:1858–1865

    Article  CAS  Google Scholar 

  77. Rand GM (1995) Fundamentals of aquatic toxicology. Effects, environmental fate, and risk assessment, 2nd edn. Taylor & Francis, Philiadelphia

  78. Bradford MM (1976) Anal Biochem 72:248–254

    Article  PubMed  CAS  Google Scholar 

  79. Aebi HE (1983) Methods of enzymatic analysis. VCH, Weinheim, pp 273–286

    Google Scholar 

  80. Habig WH, Pabst MJ, Jakoby WB (1974) J Biol Chem 246:7130–7139

    Google Scholar 

  81. Ohkawa H, Ohishi N, Yagi K (1979) Anal Biochem 95(2):351–358

    Article  PubMed  CAS  Google Scholar 

  82. Sprouse S, King KA, Spellane PJ, Watts RJ (1984) J Am Chem Soc 106:6647–6653

    Article  CAS  Google Scholar 

  83. Sullivan BP, Salmon DJ, Meyer TJ (1978) Inorg Chem 17:3334–3341

    Article  CAS  Google Scholar 

  84. Aragoni MC, Massimiliano A, Demartin F, Devillanova FA, Isaia F, Garau A, Lippolis V, Jalali F, Papke U, Shamsipur M, Tei L, Yari A, Verani G (2002) Inorg Chem 41:6623–6632

    Article  PubMed  CAS  Google Scholar 

  85. Przybylski P, Bejcar G, Huczynski A, Schroeder G, Brzezinski B, Bartl F (2006) Biopolymers 82:521–535

    Article  PubMed  CAS  Google Scholar 

  86. de Silva AP, Gunaratne HQ, Gunnlaugsson T, Huxley AJ, McCoy CP, Rademacher JT, Rice TE (1997) Chem Rev 97:1515–1566

    Article  PubMed  Google Scholar 

  87. Kimura E, Koike T (1998) Chem Soc Rev 27:179–183

    Article  CAS  Google Scholar 

  88. Fabbrizzi L, Lichelli M, Parodi L, Poggi A, Taglietti A (1999) Eur J Inorg Chem 35–39

  89. Bazzicalupi C, Bencini A, Bianchi A, Giorgi C, Fusi V, Valtancoli B, Bernardo MA, Pina F (1999) Inorg Chem 38:3806–3813

    Article  CAS  Google Scholar 

  90. Bencini A, Bernardo MA, Bianchi A, Fusi V, Giorgi C, Pina F, Valtancoli B (1999) Eur J Inorg Chem 1911–1918

  91. Bencini A, Bianchi A, Lodeiro C, Masotti A, Parola AJ, Pina F, Seixas de Melo J, Valtancoli B (2000) Chem Commun 1639–1640

  92. Sajoto T, Djurovich PI, Tamayo AB, Oxgaard J, Goodard WA III, Thompson ME (2009) J Am Chem Soc 131:9813–9822

    Article  PubMed  CAS  Google Scholar 

  93. Zhang KY, Liu H-W, Fong TT-H, Chen X-G, Lo KK-W (2010) Inorg Chem 49:5432–5443

    Article  PubMed  CAS  Google Scholar 

  94. Bilakhiya AK, Tyagi B, Paul P, Natarajan P (2002) Inorg Chem 41:3830–3842

    Article  PubMed  CAS  Google Scholar 

  95. Bhaumik C, Das S, Saha D, Dutta S, Baitalik S (2010) Inorg Chem 49:5049–5062

    Article  PubMed  CAS  Google Scholar 

  96. Gans P, Sabatini A, Vacca A (1996) Talanta 43:1739–1753

    Article  PubMed  CAS  Google Scholar 

  97. Lo KK-W, Choi AW-T, Law WH-T (2012) Dalton Trans 41:6021–6047

    Article  PubMed  CAS  Google Scholar 

  98. Schatzschneider U, Niesel J, Ott I, Gust R, Alborzinia H, Wölfl S (2008) Chem Med Chem 3:1104–1109

    PubMed  CAS  Google Scholar 

  99. Lo KK-W, Louie M-W, Zhang KY (2010) Coord Chem Rev 254:2603–2622

    Article  CAS  Google Scholar 

  100. Wicklund A, Runn P, Norrgren L (1988) Arch Environ Contam Toxicol 17:345–354

    Article  PubMed  CAS  Google Scholar 

  101. European Medicines Agency (2007) Guideline on the specification limits for residues of metal catalysts. European Medicines Agency, London

  102. Kumar A, Garg R (2009) Fundam Clin Pharmacol 23:89–95

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to Xunta de Galicia (Spain) for the project 09CSA043383PR (Biomedicine) and to the Scientific Association Proteomass (Portugal) for financial support. C.N. thanks the Fundação para a Ciência e a Tecnologia/FEDER (Portugal/EU) program for postdoctoral contract SFRH/BPD/65367/2009. C.S.L. thanks Xunta de Galicia for the Isidro Parga Pondal Research program. O.N.F. and C.S.L. also thank the Centro de Supercomputación de Galicia for generous allocation of computational resources. J.F.L. thanks Xunta de Galicia for a research contract under project 09CSA043383PR (Biomedicine). M.D. thanks REQUIMTE for financial support.

Author information

Authors and Affiliations

  1. BIOSCOPE Group, REQUIMTE/CQFB, Chemistry Department, Faculty of Science and Technology, University NOVA of Lisbon, 2829-516, Lisbon, Portugal

    Cristina Núñez, Javier Fernández-Lodeiro, Mario Diniz, Jose Luis Capelo & Carlos Lodeiro

  2. Organic Chemistry Department, Faculty of Chemistry, University of Vigo, As Lagoas Marcosende, 36310, Vigo, Spain

    Carlos Silva López

  3. Organic Chemistry Department, Faculty of Chemistry, University of Vigo, Ourense Campus, 32004, Ourense, Spain

    Olalla Nieto Faza

  4. Inorganic Chemistry Department, Faculty of Chemistry, University of Santiago de Compostela, 15782, Santiago de Compostela, Spain

    Rufina Bastida

Authors
  1. Cristina Núñez
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Carlos Silva López
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Olalla Nieto Faza
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Javier Fernández-Lodeiro
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mario Diniz
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Rufina Bastida
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Jose Luis Capelo
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Carlos Lodeiro
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Carlos Lodeiro.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Núñez, C., Silva López, C., Faza, O.N. et al. Bis(o-methylserotonin)-containing iridium(III) and ruthenium(II) complexes as new cellular imaging dyes: synthesis, applications, and photophysical and computational studies. J Biol Inorg Chem 18, 679–692 (2013). https://doi.org/10.1007/s00775-013-1013-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00775-013-1013-5

Keywords

Search

Navigation