An isothiocyanato-functionalized phthalocyanine (Pc) was synthesized in good yield from the corresponding amine-substituted Pc. This Pc reacted with ethanolamine, biotin hydrazine, and biotin diethylamine under mild conditions (room temperature in DMF or DMSO in the presence of TEA) to produce the corresponding thiourea products in 60–75% yields. All Pcs showed intense Q absorptions in DMF around 677 nm, emissions centered at 683 nm, and fluorescence quantum yields in the range 0.18–0.27. The Pcs were phototoxic to human carcinoma HEp2 cells (IC $_{50}$ $\sim$ 7 at 1.5 J/cm $^{2})$ and localized in multiple organelles, including the lysosomes, Golgi and ER. One biotin-Pc conjugate was injected via tail vein into nude mice bearing HT-29 tumors and demonstrated selective localization in the tumor tissue.

This paper is part of the 2019 Women in Porphyrin Science special issue.

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References

1. Sharma D, Huijser A, Savolainen J, Steen G and Herek JL. Faraday Discuss. 2013; 163: 433–445. Crossref, Google Scholar
2. Vakoulovskaya EG, Shental VV, Oumnova LV and Vorozhcsov GN. Proceedings of the SPIE 2003; 4952: 149–151. Google Scholar
3. Baron ED, Malbasa CL, Santo-Domingo D, Fu P, Miller JD, Hanneman KK, Hsia AH, Oleinick NL, Colussi VC and Cooper KD. Lasers Surg. Med. 2010; 42: 728–735. Crossref, ISI, Google Scholar
4. Sekkat N, van den Bergh H, Nyokong T and Lange N. Molecules 2011; 17: 98–144. Crossref, ISI, Google Scholar
5. Weissleder R and Ntziachristos V. Nat. Med. 2003; 9: 123–128. Crossref, ISI, Google Scholar
6. Ntziachristos V, Bremer C and Weissleder R. Eur. Rad. 2003; 13: 195–208. Crossref, ISI, Google Scholar
7. Luo S, Zhang E, Su Y, Cheng T and Shi C. Biomaterials 2011; 32: 7127–7138. Crossref, ISI, Google Scholar
8. Ongarora BG, Hu X, Verberne-Sutton SD, Garno JC and Vicente MGH. Theranostics 2012; 2: 850–870. Crossref, ISI, Google Scholar
9. Vrouenraets MB, Visser GW, Stigter M, Oppelaar H, Snow GB and van Dongen GA. Cancer Res. 2001; 61: 1970–1975. ISI, Google Scholar
10. Vrouenraets MB, Visser GW, Stigter M, Oppelaar H, Snow GB and van Dongen GA. Int. J. Cancer 2002; 98: 793–798. Crossref, ISI, Google Scholar
11. Duan W, Smith K, Savoie H, Greenman J and Boyle RW. Org. Biomol. Chem. 2005; 3: 2384–2386. Crossref, Google Scholar
12. Ke MR, Yeung SL, Fong WP, Ng DK and Lo PC. Chem. —Eur. J. 2012; 18: 4225–4233. Crossref, ISI, Google Scholar
13. Rodriguez ME, Zhang P, Azizuddin K, Delos Santos GB, Chiu SM, Xue LY, Berlin JC, Peng X, Wu H, Lam M, Nieminen AL, Kenney ME and Oleinick NL. Photochem. Photobiol. 2009; 85: 1189–1200. Crossref, ISI, Google Scholar
14. Ongarora BG, Zhou Z, Okoth EA, Kolesnichenko I, Smith KM and Vicente MGH. J. Porphyrins Phthalocyanines 2014; 18: 1021–1033. Link, ISI, Google Scholar
15. Göksel M. Bioorg. Med. Chem. 2016; 24: 4152–4164. Crossref, ISI, Google Scholar
16. Hammer RP, Owens CV, Hwang SH, Sayes CM and Soper SA. Bioconjugate Chem. 2002; 13: 1244–1252. Crossref, Google Scholar
17. López-Duarte I, Dieu LQ, Dolamic I, Martínez-Díaz MV, Torres T, Calzaferri G and Brühwiler D. Chem. —Eur. J. 2011; 17: 1855–1862. Crossref, Google Scholar
18. Li H, Fronczek FR and Vicente MGH. Tetrahedron Lett. 2008; 49: 4828–4830. Crossref, ISI, Google Scholar
19. Zorlu Y, Dumoulin F, Bouchu D, Ahsen V and Lafont D. Tetrahedron Lett. 2010; 51: 6615–6618. Crossref, ISI, Google Scholar
20. Vrouenraets MB, Visser GWM, Stewart FA, Stigter M, Oppelaar H, Postmus PE, Snow GB and van Dongen GAMS. Cancer Res. 1999; 59: 1505–1513. ISI, Google Scholar
21. Carcenac M, Larroque C, Langlois R, van Lier JE, Artus JC and Pelegrin A. Photochem. Photobiol. 1999; 70: 930–936. ISI, Google Scholar
22. Sehgal I, Li H, Ongarora BG, Devillier D and Vicente MGH. J. Porphyrins Phthalocyanines 2013; 17: 150–156. Link, Google Scholar
23. Leznoff CC and Sosa-Sanchez JL. Chem. Commun. 2004; 0: 338–339. Crossref, Google Scholar
24. Li XY and Ng DKP. Tetrahedron Lett. 2001; 42: 305–309. Crossref, Google Scholar
25. Josefsen LB and Boyle RW. Br. J. Pharmacol. 2008; 154: 1–3. Crossref, ISI, Google Scholar
26. Hellebust A and Richards-Kortum R. Nanomedicine (London) 2012; 7: 429–445. Crossref, Google Scholar
27. Carcenac M, Dorvillius M, Garambois V, Glaussel F, Larroque C, Langlois R, Hynes NE, van Lier JE and Pèlegrin A. Br. J. Cancer 2001; 85: 1787–1793. Crossref, ISI, Google Scholar
28. Moret F and Reddi E. J. Porphyrins Phthalocyanines 2017; 21: 239–256. Link, ISI, Google Scholar
29. Russell-Jones G, McTavish K, McEwan J, Rice J and Nowotnik D. J. Inorg. Biochem. 2004; 98: 1625–1633. Crossref, ISI, Google Scholar
30. Tripodo G, Mandracchia D, Collina S, Rui M and Rossi D. Med. Chem. 2014; 8, 1–4. Google Scholar
31. Sibrian-Vazquez M, Ortiz J, Nesterova IV, Fernández-Lázaro F, Sastre-Santos A, Soper SA and Vicente MGH. Bioconjugate Chem. 2007; 18: 410–420. Crossref, ISI, Google Scholar
32. Chen S, Zhao X, Chen J, Chen J, Kuznetsova L, Wong SS and Ojima I. Bioconjugate Chem. 2010; 21: 979–987. Crossref, Google Scholar
33. Li X, Kim CY, Lee S, Lee D, Chung HM, Kim G, Heo SH, Kim C, Hong KS and Yoon J. J. Am. Chem. Soc. 2017; 139: 10880–10886. Crossref, ISI, Google Scholar
34. Stallivieri A, Baros F, Jetpisbayeva G, Myrzakhmetov B and Frochot C. Curr. Med. Chem. 2015; 22: 3185–3207. Crossref, ISI, Google Scholar
35. Meerovich IG, Jerdeva V, Derkacheva VM, Meerovich GA, Lukyanets EA, Kogan EA and Savitsky AP. J. Photochem. Photobiol. B 2005; 80: 57–64. Crossref, ISI, Google Scholar
36. Sutton JM, Clarke OJ, Fernandez N and Boyle RW. Bioconjugate Chem. 2002; 13: 249–263. Crossref, ISI, Google Scholar
37. Hudson R, Carcenac M, Smith K, Madden L, Clarke OJ, Pèlegrin A, Greenman J and Boyle RW. Br. J. Cancer 2005; 92: 1442–1449. Crossref, ISI, Google Scholar
38. Sibrian-Vazquez M, Jensen TJ, Fronczek FR, Hammer RP and Vicente MGH. Bioconjugate Chem. 2005; 16: 852–863. Crossref, ISI, Google Scholar
39. Clarke OJ and Boyle RW. Chem. Commun. 1999; 0: 2231–2232. Crossref, Google Scholar
40. Soini AE, Yashunsky DV, Meltola NJ and Ponomarev GV. Luminescence 2003; 18: 182–192. Crossref, Google Scholar
41. Malatesti N, Smith K, Savoie H, Greenman J and Boyle RW. Int. J. Oncol. 2006; 28: 1561–1569. ISI, Google Scholar
42. Kim S and Yi KY. J. Org. Chem. 1986; 51: 2613–2615. Crossref, ISI, Google Scholar
43. Ongarora BG, Hu X, Li H, Fronczek FR and Vicente MGH. MedChemComm 2012; 3: 179–194. Crossref, Google Scholar
44. Chaudhary PM, Murthy RV, Yadav R and Kikkeri R. Chem. Commun. 2015; 51: 8112–8115. Crossref, Google Scholar
45. Zorlu Y, Dumoulin F, Durmuş M and Ahsen V. Tetrahedron 2010; 66: 3248–3258. Crossref, ISI, Google Scholar

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Vol. 23, No. 01n02

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Received 14 December 2018

Accepted 15 January 2019

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Synthesis and investigation of phthalocyanine-biotin conjugates

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