ArticlesNo Access

Polyoligopeptides functionalized zinc(II)porphyrins: Step towards artificial hemes

Shawkat M. Aly

Département de chimie, Université de Sherbrooke, Sherbrooke, PQ, Canada

On leave from Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt.

Search for more papers by this author

Hannah Guernon

Département de chimie, Université de Sherbrooke, Sherbrooke, PQ, Canada

Search for more papers by this author

Brigitte Guérin

Centre d'imagerie moléculaire de Sherbrooke (CIMS) and Département of Médecine Nucléaire et de Radiobiologie, Faculty of Medicine and Health Sciences, Université de Sherbrooke, 3001, 12e Avenue Nord, Sherbrooke, Québec J1H 5N4, Canada

Corresponding author.

Search for more papers by this author

, and

Pierre D. Harvey

Département de chimie, Université de Sherbrooke, Sherbrooke, PQ, Canada

Corresponding author, tel: +1 819-821-7092, fax: +1 819-821-8017.

SPP full member in good standing.

Search for more papers by this author

https://doi.org/10.1142/S1088424611003756Cited by:9 (Source: Crossref)

Abstract

Two new zinc(II)porphyrin oligopeptide conjugates (zinc(II)-5,10,15,20-bis[4-(peptide)- phenyl]porphyrin (5) and -tetrakis[3,5-di(peptide)phenyl]porphyrin (9; peptide = -CH₂(CO)Gly-Phe-Ala-CNH₂) were prepared using the click chemistry with azides and ethynyl-containing precursors. The spectroscopic signature (S₀→S₁ and transient T₁→T_n absorption, excitation and emission spectra) are typical for zinc(II)porphyrin and shows no perturbation upon anchoring the oligopeptides, whereas some small decreases in the photophysical parameters (𝜏_F and Φ_F), and larger decrease in T₁ lifetimes are noted, which are attributable to the known "loose bolt" effect. The structure for 9 in solution was addressed qualitatively using computer modeling and the comparison of the bimolecular fluorescence quenching rate constants between 5 and 9 using C₆₀ as a photooxidative agent. While 5 exhibits a totally accessible zinc(II)porphyrin unit for a C₆₀ approach, 9 shows a slower quenching rate constant meaning some steric hindrance must be present.

Dedicated to Professor Karl M. Kadish on the occasion of his 65^th birthday

Keywords:

Most comprehensive & up-to-date research on PORPHYRINS
Handbook of Porphyrin Science now available in 46 volumes

References

a) Hernandez-Eguia LP, Brea RJ, Castedo L, Ballester P and Granja JR. Chem. Eur. J. 2011; 17: 1220–1229. b) Umezawa N, Matsumoto N, Iwama Sh, Kato N and Higuchi T. Bioorg. Med. Chem. 2010; 18: 6340–6350. c) Carvalho IMM and Ogawa MY. J. Braz. Chem. Soc. 2010; 21: 1390–1394. d) Bakleh M-E, Sol V, Granet R, Deleris G, Estieu-Gionnet K and Krausz P. Chem. Comm. 2010; 46: 2115–2117. e) Jintoku H, Sagawa T, Sawada T, Takafuji M and Ihara H. Org. Biomol. Chem. 2010; 8: 1344–1350. f) Setnicka V, Hlavacek J and Urbanova M. J. Porphyrins Phthalocyanines 2008; 12: 1270–1278. g) Ikawa Y, Harada H, Toganoh M and Furuta H. Bioorg. Med. Chem. Lett. 2009; 19: 2448–2452. h) Habdas J and Boduszek B. J. Peptides Sci. 2009; 15: 305–311. i) Sol V, Chaleix V, Granet R and Krausz P. Tetrahedron 2008; 64: 364–371. j) Wang J, Rosenblatt MM and Suslick KS. J. Am. Chem. Soc. 2007; 129: 14124–14125 . Google Scholar
a) Dmitriev RI, Ropiak HM, Yashunsky DV, Ponomarev GV, Zhdanov AV and Papkovsky DB. FEBS J. 2010; 277: 4651–4661. b) Li Z-Y, Wang H-Y, Li C, Zhang X-L, Wu X-J, Qin S-Y, Zhang X-Z and Zhuo R-X. J. Pol. Sci. A: Pol. Chem. 2011; 49: 286–292. c) Bourre L, Giuntini F, Eggleston IM, Mosse CA, MacRobert AJ and Wilson M. Photochem. Photobiol. 2010; 9: 1613–1620. d) Dosselli R, Gobbo M, Bolognini E, Campestrini S and Reddi E. ACS Med. Chem. Lett. 2010; 1: 35–38. e) Biron E and Voyer N. Org. Biomol. Chem. 2008; 6: 2507–2515. f) Sibrian VM, Jensen TJ and Vicente MGH. J. Med. Chem. 2008; 51: 2915–2923. g) Schroeder T, Schmitz K, Niemeier N, Balaban TS, Krug HF and Schepers UBS. Biocon. Chem. 2007; 18: 342–354. h) Conway CL, Walker I, Bell A, Roberts DJH, Brown SB and Vernon DI. Photochem. Photobiol. 2008; 7: 290–298. i) Habdas J and Boduszek B. Hetero. Chem. 2008; 19: 107–111 . Google Scholar
a) Ochiai T, Nagata M, Shimoyama K, Amano M, Kondo M, Dewa T, Hashimoto H and Nango M. Langmuir 2010; 26: 14419–14422. b) Aziat F, Rein R, Peon J, Rivera E and Solladie N. J. Porphyrins Phthalocyanines 2008; 12: 1232–1241. c) Ochiai T, Asaoka T, Kato T, Osaka Sh, Dewa T, Yamashita K, Gardiner AT, Hashimoto H and Nango M. Photosyn. Research 2008; 95: 353–361. d) Hasobe T, Saito K, Kamat PV, Troiani V, Qiu H, Solladie N, Kim KS, Park JK, Kim D, D'Souza F and Fukuzumi S. J. Mat. Chem. 2007; 17: 4160–4170. e) Hasobe T, Murata H, Fukuzumi S and Kamat PV. Mol. Crys. Liq. Crys. 2007; 471: 39–51. f) Jintoku H, Sagawa T, Miyamoto K, Takafuji M and Ihara H. Chem. Comm. 2010; 46: 7208–7210 . Google Scholar
D. V. Zaytsevet al., Biomacromol. 11, 2602 (2010), DOI: 10.1021/bm100540t. Crossref, Web of Science, Google Scholar
a) Maurer K, Grimm B, Wessendorf F, Hartnagel K, Guldi DM and Hirsch A. Eur. J. Org. Chem. 2010; 5010–5029. b) Kobata K, Ogawa J, Pandey SS, Oshima H, Arai T, Kato T and Nishino N. Syn. Met. 2007; 157: 311–317 . Google Scholar
J.-F. Gnichwitzet al., J. Am. Chem. Soc. 130, 8491 (2008), DOI: 10.1021/ja8018065. Crossref, Web of Science, Google Scholar
K. Saitoet al., ECS Trans. 157 (2007), DOI: 10.1149/1.2408962. Google Scholar
V. Krishnanet al., J. Am. Chem. Soc. 132, 11083 (2010), DOI: 10.1021/ja1010702. Crossref, Web of Science, Google Scholar
D. Kuciauskas and G. A. Caputo, J. Phys. Chem. B 113, 14439 (2009), DOI: 10.1021/jp905468y. Crossref, Web of Science, Google Scholar
M. Fujitsukaet al., J. Photochem. Photobiol. A 188, 346 (2007), DOI: 10.1016/j.jphotochem.2006.12.034. Crossref, Web of Science, Google Scholar
Y. Ikawaet al., Bioorg. Med. Chem. Lett. 19, 2448 (2009), DOI: 10.1016/j.bmcl.2009.03.066. Crossref, Web of Science, Google Scholar
a) Adrian R, McDonald NF, Gerard PM van K and Gerard van K. J. Organomet. Chem. 2009; 694: 2153–2162. b) Li F, Yang SI, Ciringh Y, Seth J, Martin CH, Singh DL, Kim D, Birge RR, Bocian DF, Holten D and Lindsey JS. J. Am. Chem. Soc. 1998; 120: 10001–10017 . Google Scholar
F. Robey and R. L. Fields, Anal. Biochem. 177, 373 (1989). Crossref, Web of Science, Google Scholar
J. Marik and J. L. Sutcliffe, Tet. Lett. 47, 6681 (2006), DOI: 10.1016/j.tetlet.2006.06.176. Crossref, Web of Science, Google Scholar
G. D. Egorovaet al., Opt. Spektrosk. 48, 1101 (1980). Google Scholar
L. Liu, D. Fortin and P. D. Harvey, Inorg. Chem. 48, 5891 (2009), DOI: 10.1021/ic900198h. Crossref, Web of Science, Google Scholar
P. D. Harvey, C. Stern and R. Guilard, Handbook of Porphyrin Science With Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medicine, eds. K. M. Kadish, K. M. Smith and R. Guilard (World Scientific Publishing, Singapore, 2011) pp. 1–179. Link, Google Scholar
N. J. Turro , V. Ramamurthy and J. C. Scaiano , Modern Molecular Photochemistry of Organic Molecules ( University Science Books , Sausalito, California , 2010 ) . Google Scholar
a) Imahori H and Sakata Y. Eur. J. Org. Chem. 1999; 24452–24457. b) Krasnov PO, Milyutina YM and Eliseeva NS. Internet Elec. J. Mol. Design 2010; 9: 20–32. c) Basiuk VA. J. Phys. Chem.A2005; 109, 3704–3710 . Google Scholar
F. D'Souzaet al., J. Phys. Chem. B 109, 10107 (2005), DOI: 10.1021/jp050591l. Crossref, Web of Science, Google Scholar
a) Filatov M, Laquai F, Fortin D, Guilard R and Harvey PD. Chem. Comm. 2010; 48: 9176–9178. b) Filatov MA, Guilard R and Harvey PD. Org. Lett., 2010; 12: 196–199 . Google Scholar