Elsinochrome A photosensitizers: Alternative drugs for photodynamic therapy

Tinghui Li; Hong Deng; Jingquan Zhao; Ying Gu

doi:10.1142/s1793545815300013

[1] C. A. Robertson, D. H. Evans, H. Abraharnse, "Photodynamic therapy (PDT): A short review on cellular mechanisms and cancer research applications for PDT," J. Photochem. Photobiol. B-Biol. 96, 1–8 (2009).

[2] S. Yano, S. Hirohara, M. Obata, Y. Hagiya, S. Ogura, A. Ikeda, H. Kataoka, M. Tanaka, T. Joh, "Current states and future views in photodynamic therapy," J. Photochem. Photobiol. C-Photochem. Rev. 12, 46–67 (2011).

[3] J. Usuda, H. Kato, T. Okunaka, K. Furukawa, H. Tsutsui, K. Yamada, Y. Suga, H. Honda, Y. Nagatsuka, T. Ohira, M. Tsuboi, T. Hirano, "Photodynamic therapy (PDT) for lung cancers," J. Thorac. Oncol. 1, 489–493 (2006).

[4] R. Hornung, H. Walt, N. E. A. Crompton, K. A. Keefe, B. Jentsch, G. Perewusnyk, U. Haller, O. R. Kochli, "m-THPC-mediated photodynamic therapy (PDT) does not induce resistance to chemotherapy, radiotherapy or PDT on human breast cancer cells in vitro," J. Photochem. Photobiol. 68, 569–574 (1998).

[5] L. M. Davids, B. Kleemann, "Combating melanoma: The use of photodynamic therapy as a novel, adjuvant therapeutic tool," Cancer Treat. Rev. 37, 465– 475 (2011).

[6] A. R. Montazerabadi, A. Sazgarnia, M. H. Bahreyni- Toosi, A. Ahmadi, A. Shakeri-Zadeh, A. Aledavood, "Mitoxantrone as a prospective photosensitizer for photodynamic therapy of breast cancer," J. Photodiagn. Photodyn. 9, 46–51 (2012).

[7] A. R. Montazerabadi, A. Sazgarnia, M. H. Bahreyni- Toosi, A. Ahmadi, A. Aledavood, "The effects of combined treatment with ionizing radiation and indocyanine green-mediated photodynamic therapy on breast cancer cells," J. Photochem. Photobiol. B-Biol. 109, 42–49 (2012).

[8] A. Sazgarnia, A. R. Montazerabadi, M. H. Bahreyni- Toosi, A. Ahmadi, A. Aledavood, "In vitro survival of MCF-7 breast cancer cells following combined treatment with ionizing radiation and mitoxantrone-mediated photodynamic therapy," Photodiagn. Photodyn. 10, 72–78 (2013).

[9] A. Sazgarnia, A. R. Montazerabadi, M. H. Bahreyni- Toosi, A. Ahmadi, "Photosensitizing and radiosensitizing effects ofmitoxantrone: Combined chemo-, photo-, and radiotherapy of DFW human melanoma cells," Laser Med. Sci. 28, 1533–1539 (2013).

[10] L. Benov, J. Craik, I. Batinic-Haberle, "Protein damage by photo-activated Zn(II) Nalkylpyridylporphyrins," Amino Acids 42, 117–128 (2012).

[11] N. Sekkat, H. van den Bergh, T. Nyokong, N. Lange, "Like a bolt from the blue: Phthalocyanines in biomedical optics," Molecules 17, 98–144 (2012).

[12] A. Kamuhabwa, P. Agostinis, B. Ahmed, W. Landuyt, B. Van Cleynenbreugel, H. Van Poppel, P. de Witte, "Hypericin as a potential phototherapeutic agent in superficial transitional cell carcinoma of the bladder," Photochem. Photobiol. Sci. 3, 772–780 (2004).

[13] A. Karioti, A. R. Bilia, "Hypericins as potential leads for new therapeutics," Int. J. Mol. Sci. 11, 562–594 (2010).

[14] L. J. Jiang, Y. Y. He, "Photophysics, photochemistry and photobiology of hypocrellin photosensitizers," Chin. Sci. Bull. 46, 6–16 (2001).

[15] U. Weiss, H. Flon, W. C. Burger, "The photodynamic pigment of some species of Elsinoe and Sphaceloma," Arch. Biochem. Biophys. 69, 311–319 (1957).

[16] U. Weiss, H. Zi er, T. J. Batterha, M. Blumer, W. H. Hackeng, H. Copier, C. A. Salemink, "Pigments of elsinoe species.I. pigment production by elsinoe species — isolation of pure elsinochromes A B and C," Can. J. Microbiol. 11, 57–66 (1965).

[17] R. J. Lousberg, C. A. Salemink, U. Weiss, "Pigments of Elsinoe Species 5. Structure of Elsinochrome- D," J. Chem. Soc. C-Org. 2159–2162 (1970).

[18] C. Li, Y. P. He, L. C. Ou, M. J. Tian, Z. Yao, M. B. Guo, "Photophysical and photosensitive properties of Elsinochrome A," Chin. Sci. Bull. 51, 1050–1054 (2006).

[19] C. Li, Y. T. Chen, H. Tai, L. C. Ou, Y. P. He, "Biosynthesis method of perilenoquinoid pigments," Patent CN 1680562-A. Oct. 12 (2005).

[20] Y. Cai, J. Cao, J. Cui, D. Kim, "New Shiraia bambusicola WW67 strain useful in production of metabolite product chosen from bamboo hypocrellin, hypocrellin B, elsinochrome A, elsinochrome B, elsinochrome C and elsinochrome D," Patent CN 102703328-A. Oct. 3 (2012).

[21] Y. Zhang, J. Xie, L. Y. Zhang, C. Li, H. X. Chen, Y. Gu, J. Q. Zhao, "A novel elsinochrome A derivative: A study of drug delivery and photodynamic activity," J. Photochem. Photobiol. Sci. 8, 1676– 1682 (2009).

[22] L. F. Wang, H. Y. Zhang, "A theoretical study on physicochemical properties of elsinochrome A in ground state," J. Mol. Struct.-Theochem. 726, 135– 140 (2005).

[23] L. Shen, "Theoretical study on the photophysical and photochemical properties of elsinochrome a," J. Biomol. Struct. Dyn. 25, 321–325 (2007).

[24] M. J. Fehr, S. L. Carpenter, Y. Wannemuehler, J. W. Petrich, "Roles of oxygen and photoinduced acidification in the light-dependent antiviral activity of Hypocrellin-A," Biochemistry 34, 15845–15848 (1995).

[25] M. J. Fehr, M. A. Mccloskey, J. W. Petrich, "Light- Induced acidification by the antiviral agent Hypericin," J. Am. Chem. Soc. 117, 1833–1836 (1995).

[26] W. Liu, H. Y. Zhang, D. Z. Chen, Z. Y. Zhang, M. H. Zhang, "Theoretical study on intramolecular hydrogen transfer involving amino-substituted perylenequinone," Dyes Pigm. 47, 277–284 (2000).

[27] K. Lang, D. M. Wagnerova, P. Stopka, W. Damerau, "Reduction of dioxygen to superoxide photosensitized by Anthraquinone-2-Sulfonate," J. Photochem. Photobiol. a-Chem. 67, 187–195 (1992).

[28] Y. K. Chen, C. Li, H. Tai, Y. T. Chen, K. Gu, H. Q. Wang, "Photochemistry of amino substituted elsinochrome a: ESR study on the photogeneration of active radical species," Chin. J. Magn. Reson. 20, 167–172 (2003).

[29] L. Ma, H. Tai, C. Li, Y. Zhang, Z. H. Wang, W. Z. Ji, "Photodynamic inhibitory effects of three perylenequinones on human colorectal carcinoma cell line and primate embryonic stem cell line," World J. Gastroenterol. 9, 485–490 (2003).

[30] W. Zhou, C. Li, "Photosensitive properties and antitumor mechanisms of perylenequinones," Chem. life 31, 246–247 (2001).

[31] J. Zhang, X. J. Wu, Y. Luo, Q. Wang, "Photodynamic therapy of elsinochrome A for animal entity tumor," Sichuan J. Zoology 25, 884–886 (2006).

[32] L. Liu, F. Liu, Y. Gu, H. Qiu, J. Zhen, "Killing effect of Elsinochrome A and Hypocrellin B-mediated photodynamic therapy on ECV304 cells: A comparative study," Chin. J. Laser Med. Surg. 15, 93– 97 (2006).

[33] J. Zhang, X. J. Wu, G. H. Yin, Y. X. Chen, L. Ma, "Study on the bacteriostasis effect of elsinochrome A in vitro," Lishizhen Med. Mater. Medica Res. 17, 2414–2415 (2006).

[34] F. Ma, J. Tang, C. Yang, Y. Y. Feng, S. H. Wei, J. Shen, J. H. Zhou, L. Zhou, "DNA binding and photo-induced DNA cleavage activity of Elsinochrome A in visible light," Spectroscopy-Biomed. Appl. 26, 289–296 (2011).

[35] F. Ma, L. Zhou, W. Wang, Y. Feng, J. Zhou, X. Wang, J. Shen, "Spectroscopic studies on interaction of Elsinochrome A with Hemoglobin," J. Nanjing Norm. Univ. Nat. Sci. 33, 46 (2010).

[36] F. Ma, L. Zhou, W. Wang, Y. Y. Feng, J. H. Zhou, X. H. Wang, J. Shen "Spectroscopic studies on the interaction of Elsinochrome A with myoglobin," Spectroscopy Spectral. Anal. 31, 1601–1605 (2011).

[37] W. Tu, Y. Zhao, A. Xia, G. Zhao, "Study on the tissue distribution and excretion kinetics of elsinochrome A in mice," Chin. J. Hosp. Pharma. 33, 852–856 (2013).

[38] J. Zhang, W. Dai, J. Guo, J. Liu, "Study on the acute toxicity of Elsinochrome A in mice," Lishizhen Med. Mater. Medica Res. 20, 1663–1664 (2009).

[39] R. J. Lousberg, C. A. Salemink, U. Weiss, T. Batterha, "Pigments of Elsinoe Species 2. Structure of Elsinochromes a B and C," J. Chem. Soc. C-Org. 1219–1227 (1969).

[40] C. Dong, F. Ma, L. Zhou, D. Dai, Y. Feng, S. Wei, J. Zhou, "Studies of preparation and photodynamic properties of water-soluble Elsinochrome A-Silica Nanospheres," J. Nanjing Norm. Univ. Nat. Sci. 32, 95–98 (2009).

[41] L. Zhou, C. Dong, S. H. Wei, Y. Y. Feng, J. H. Zhou, J. H. Liu, "Water-soluble soft nano-colloid for drug delivery," Mater. Let. 63, 1683–1685 (2009).

[42] K. Huang, H. Zhu, C. Li, K. Gu, Y. Chen, "The bromination of elsinochrome A and photosensitivity of its derivatives," J. Yunnan Univ. Nat. Sci. 25, 352–354 (2003).

[43] R. Qiao, L. Zhou, J. H. Zhou, S. H. Wei, J. Shen, B. W. Zhang, X. S. Wang, "The synthesis and characterization of ethylenediamine-modified Elsinochrome A," Dyes Pigm. 94, 99–102 (2012).

[44] M. O. Ahonsi, D. Boss, M. Maurhofer, G. Defago, "Potential environmental fate of elsinochrome A, a perylenequinone toxin produced in culture by bindweed biocontrol fungus Stagonospora convolvuli LA39," Environmentalist 26, 183–193 (2006).

[45] Z. J. Wang, Y. Y. He, C. G. Huang, J. S. Huang, Y. C. Huang, J. Y. An, Y. Gu, L. J. Jiang, "Pharmacokinetics, tissue distribution and photodynamic therapy e±cacy of liposomal-delivered hypocrellin A, a potential photosensitizer for tumor therapy," J. Photochem. Photobiol. 70, 773–780 (1999).

[46] H. X. Chen, Z. F. Yang, X. B. Zou, J. G. Zhu, H. Deng, J. Q. Zhao, Y. Gu, "Photodynamic e±cacy of liposome-delivered hypocrellin B in microvascular endothelial cells in vitro and chicken combs in vivo: A potential photosensitizer for port wine stain," Laser Phys. 23, 025605 (2013).

[47] C. L. L. Saw, P. W. S. Heng, M. Olivo, "Potentiation of the photodynamic action of hypericin," J.Environ. Pathol. Tox. 27, 23–33 (2007).

[48] S. J. Xu, X. X. Zhang, S. Chen, M. H. Zhang, T. Shen, Z. P. Wang, "Novel phototherapeutic agents: Investigation and progress of hypocrellin derivatives," Chin. Sci. Bull. 48, 1775–1785 (2003).

[49] M. Waser, H. Falk, "Progress in the chemistry of second generation Hypericin based photosensitizers," Curr. Org. Chem. 15, 3894–3907 (2011).

[50] Y. W. Zhao, J. Xie, J. S. Ma, J. Q. Zhao, "A novel amphiphilic 2-taurine substituted hypocrellin B (THB) and its photodynamic activity," New J. Chem. 28, 484–489 (2004).

[51] X. Liu, J. Xie, L. Y. Zhang, H. X. Chen, Y. Gu, J. Q. Zhao, "A novel hypocrellin B derivative designed and synthesized by taking consideration to both drug delivery and biological photodynamic activity," J. Photochem. Photobiol. B-Biol. 94, 171– 178 (2009).

[52] H. Deng, X. Liu, J. Xie, R. Yin, N. Y. Huang, Y. Gu, J. Q. Zhao, "Quantitative and site-directed chemical modification of Hypocrellins toward direct drug delivery and effective photodynamic activity," J. Med. Chem. 55, 1910–1919 (2012).

[53] J. Q. Zhao, H. Deng, J. Xie, X. Liu, Y. Zhang, N. Y. Huang, Y. Gu, "Towards characteristics of photodynamic drugs specifically aimed at microvascular diseases," Mini-Rev. Med. Chem. 10, 332–341 (2010).

[54] H. Deng, T. H. Li, J. Xie, N. Y. Huang, Y. Gu, J. Q. Zhao, "Synthesis and bio-evaluation of novel hypocrellin derivatives: Potential photosensitizers for photodynamic therapy of age-related macular degeneration," Dyes Pigm. 99, 930–939 (2013).