• Journal of Innovative Optical Health Sciences
  • Vol. 8, Issue 1, 1530003 (2015)
Hong Deng, Jie Xie, and Jingquan Zhao*
Author Affiliations
  • Beijing National Laboratory for Molecular Sciences (BNLMS) Key Laboratory of Photochemistry, Institute of Chemistry Chinese Academy of Sciences P. O. Box 101, No. 2, 1st North Street Zhongguancun, Beijing 100190, P. R. China
  • show less
    DOI: 10.1142/s1793545815300037 Cite this Article
    Hong Deng, Jie Xie, Jingquan Zhao. Drug-delivery and multifunction possibilities of hypocrellin photosensitizers[J]. Journal of Innovative Optical Health Sciences, 2015, 8(1): 1530003 Copy Citation Text show less
    References

    [1] C. Hopper, "Photodynamic therapy: A clinical reality in the treatment of cancer," Lancet Oncol. 1, 212–229 (2000).

    [2] H. X. Qiu, Y. Gu, Y. Wang, N. Y. Huang, "Twenty years of clinical experience with a new modality of vascular-targeted photodynamic therapy for port wine stains," Dermatol. Surg. 37, 1603–1610 (2011).

    [3] H. R. Coleman, C. C. Chan, F. L. Ferris, E. Y. Chew, "Age-related macular degeneration," Lancet 372, 1835–1845 (2008).

    [4] M. Ishizuka, F. Abe, Y. Sano, K. Takahashi, K. Inoue, M. Nakajima, T. Kohda, N. Komatsu, S. Ogura, T. Tanaka, "Novel development of 5-aminolevurinic acid (ALA) in cancer diagnoses and therapy," Int. Immunopharma. 11, 358–365 (2011).

    [5] B. Khoobehi, R. Grinstead, E.Passos, "Experimental photodynamic effects of hypocrellin A on the choriocapillaris," Ophthalmic. Surg. Las. 33, 207–213 (2002).

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

    [7] G. G. Miller, K. Brown, A. M. Ballangrud, O. Barajas, Z. Xiao, J. Tulip, J. W. Lown, J. M. Leitho , M. J. Allalunis-Turner, R. D. Mehta, R. B. Moore, "Preclinical assessment of hypocrellin B and hypocrellin B derivatives as sensitizers for photodynamic therapy of cancer: Progress update," Photochem. Photobiol. 65, 714–722 (1997).

    [8] P. F. Santos, L. V. Reis, P. Almeida, J. P. Serrano, A. S. Oliveira, L. F. V. Ferreira, "E±ciency of singlet oxygen generation of aminosquarylium cyanines," J. Photochem. Photobiol. A-Chem. 163, 267–269 (2004).

    [9] V. Engelhardt, T. Kiesslich, J. Berlanda, S. Hofbauer, B. Krammer, K. Plaetzer, "Lipophilic rather than hydrophilic photosensitizers show strong adherence to standard cell culture microplates under cell-free conditions," J. Photochem. Photobiol. BBiol. 103, 222–229 (2011).

    [10] M. Ishikawa, Y. Hashimoto, "Improvement in aqueous solubility in small molecule drug discovery programs by disruption of molecular planarity and symmetry," J. Med. Chem. 54, 1539–1554 (2011).

    [11] S. H. Hautmann, V. B. Lokeshwar, G. L. Schroeder, F. Civantos, R. C. Duncan, R. Gnann, M. G. Friedrich, M. S. Soloway, "Elevated tissue expression of hyaluronic acid and hyaluronidase validates the HA-HAase urine test for bladder cancer," J. Urol. 165, 2068–2074 (2001).

    [12] C. Bing, S. T. Russell, E. E. Beckett, P. Collins, S. Taylor, R. Barraclough, M. J. Tisdale, G. Williams, "Expression of uncoupling proteins-1,-2 and -3 mRNA is induced by an adenocarcinoma-derived lipid-mobilizing factor," Brit. J. Cancer 86, 612–618 (2002).

    [13] S. J. Xu, S. Chen, M. H. Zhang, T. Shen, "First synthesis of methylated hypocrellin and its fluorescent excited state: A cautionary tale," J. Org. Chem. 68, 2048–2050 (2003).

    [14] K. Das, D. S. English, J. W. Petrich, "Solvent dependence on the intramolecular excited-state proton or hydrogen atom transfer in hypocrellin," J. Am. Chem. Soc. 119, 2763–2764 (1997).

    [15] S. Ebrahim, G. A. Peyman, P. J. Lee, "Applications of liposomes in ophthalmology," Surv. Ophthalmol. 50, 167–182 (2005).

    [16] C. L. Yu, S. Chen, M. H. Zhang, T. Shen, "Spectroscopic studies and photodynamic actions of hypocrellin B in liposomes," Photochem. Photobiol. 73, 482–488 (2001).

    [17] 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," Photochem. Photobiol. Sci. 8, 1676–1682 (2009).

    [18] 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," Photochem. Photobiol. 70, 773–780 (1999).

    [19] J. Q. Zhao, X. Y. Jin, J. Xie, "Solid powder preparation from liposome of Hypocrellin and producing method," Patent CN1539407-A. Oct. 27-(2005).

    [20] J. Xie, Y. Zhang, J. Zhao, "Hypocrellin liposome formulation, comprises hypocrellin, phospholipids, cholesterol and lyophilization protecting agent," Patent CN101371828-A. Feb. 25 (2009).

    [21] 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).

    [22] Z. Zhang, W. Zhang, H. Zhang, "Bio-insecticide containing hypocrelline A," Patent CN96120599-A. Jun. 3 (1998).

    [23] J. Zhao, H. An, J. Xie, "Pesticide useful in e.g. grain, cotton, fruit, vegetable and tobacco, comprising hypocrellin B and non-ionic surfactant such as octyl phenol polyethenoxy ether or octyl phenol polyethenoxy ether, except water," Patent CN1481680- A. Mar. 17 (2004).

    [24] H. B. An, J. Xie, J. Q. Zhao, Z. S. Li, "Photogeneration of free radicals ((OH)-O-center dot and HB center dot-) and singlet oxygen (O-1(2)) by hypocrellin b in TX-100 micelles microsurroundings," Free Radical Res. 37, 1107–1112 (2003).

    [25] J. Q. Zhao, X. Liu, Y. Gu, L. H. Liu, "Microemulsion of hypocrellin, and its preparing method," Patent CN101002757-A. Jul. 25 (2007).

    [26] J. Zhao, B. Zhao, J. Xie, "Hypocrellin water-soluble nanogranule containing protein and polysaccharide useful for intravenous injection," Patent CN03148147-A. Jan. 19 (2005).

    [27] B. Z. Zhao, J. Xie, J. Q. Zhao, "A novel water-soluble nanoparticles of hypocrellin B and their interaction with a model protein: C-phycocyanin," Biochim. Biophys. Acta 1670, 113–120 (2004).

    [28] L. Zhou, J. H. Liu, S. H. Wei, Y. Y. Feng, J. H. Zhou, B. Y. Yu, "DNA combining and photocleaving properties of photosensitizer-encapsulated silica nanoparticles," Monatsh. Chem. 140, 1167–1170 (2009).

    [29] L. Zhou, W. Wang, S. H. Wei, Y. Y. Feng, J. H. Zhou, J. H. Liu, J. Shen, "Encapsulation of hydrophobic anticancer drug in nano-scale porous ceramic materials for photodynamic therapy," J. Porous Mater. 18, 517–522 (2011).

    [30] Z. B. Li, J. G. Wang, J. R. Chen, W. H. Lei, X. S. Wang, B. W. Zhang, "Hypocrellin B doped and pHresponsive silica nanoparticles for photodynamic therapy," Sci. Chin. Chem. 53, 1994–1999 (2010).

    [31] G. Paramaguru, R. V. Solomon, P. Venuvanalingam, R. Renganathan, "Spectroscopic studies on TiO2 enhanced binding of hypocrellin B with DNA," J. Fluoresc. 21, 1887–1895 (2011).

    [32] D. X. Li, C. F. Li, A. H. Wang, Q. He, J. B. Li, "Hierarchical gold/copolymer nanostructures as hydrophobic nanotanks for drug encapsulation," J. Mater. Chem. 20, 7782–7787 (2010).

    [33] L. Gao, J. B. Fei, J. Zhao, H. Li, Y. Cui, J. B. Li, "Hypocrellin-loaded gold nanocages with high two- Photon e±ciency for photothermal/photodynamic cancer therapy in vitro," Acs Nano 6, 8030–8040 (2012).

    [34] 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).

    [35] 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).

    [36] H. L. Liu, F. G. Liu, Y. Gu, J. H. Ma, J. Q. Zhao, J. Zeng, X. S. Li, "An experimental study of photodynamic effect of hypocrelline B liposome on leghorn cock comb," Chin. J. Laser Med. Sur. 14, 1–5 (2005).

    [37] J. H. Ma, J. Q. Zhao, L. J. Jiang, "Photosensitization mechanism of active species by the complex of hypocrellin B with aluminum ion," Free Radical Res. 35, 607–617 (2001).

    [38] J. H. Zhou, S. Q. Xia, J. R. Chen, X. S. Wang, B. W. Zhang, "The photodynamic property improvement of hypocrellin A by chelation with lanthanum ions," Chem. Commun. 1372–1373 (2003).

    [39] J. H. Zhou, J. H. Liu, S. Q. Xia, X. S. Wang, B. W. Zhang, "Effect of chelation to lanthanum ions on the photodynamic properties of hypocrellin A," J. Phys. Chem. B 109, 19529–19535 (2005).

    [40] Y. Sun, Y. J. Hou, Q. X. Zhou, W. H. Lei, J. R. Chen, X. S. Wang, B. W. Zhang, "Dinuclear Cu(II) hypocrellin B complexes with enhanced photonuclease activity," Inorg. Chem. 49, 10108–10116 (2010).

    [41] Y. Sun, Y. J. Hou, Q. X. Zhou, J. R. Chen, B. W. Zhang, X. S. Wang, "A new Co(III)-hypocrellin B complex with enhanced photonuclease activity," J. Inorg. Biochem. 105, 978–984 (2011).

    [42] Y. Sun, Y. Zheng,W. H. Lei, Q. X. Zhou, Y. J. Hou, B. W. Zhang, X. S. Wang, "Oxovanadium(IV) based hypocrellin B complexes with enhanced photodynamic activity," Dalton T. 41, 651–657 (2012).

    [43] Y. Z. Hu, J. Y. An, L. J. Jiang, L. C. Chiang, "Studies of the sulfonation of hypocrellin-A and the photodynamic actions of the product," J. Photochem. Photobiol. B-Biol. 17, 195–201 (1993).

    [44] Y. Z. Hu, J. Y. An, L. C. Chiang, "Studies on the photoinduced sulfonation of hypocrellins," J. Photochem. Photobiol. A-Chem. 70, 301–308 (1993).

    [45] Y. Y. He, J. Y. An, L. J. Jiang, "Synthesis and ESR investigation of hypocrellin glycoside," Tetrahedron Lett. 39, 5069–5072 (1998).

    [46] Z. Z. Ou, J. R. Chen, X. S. Wang, B. W. Zhang, Y. Cao, "Synthesis of a water-soluble cyclodextrin modified hypocrellin and ESR study of its photodynamic therapy properties," New J. Chem. 26, 1130–1136 (2002).

    [47] Y. Y. He, J. Y. An, L. J. Jiang, "Synthesis of a new water-soluble phototherapeutic sensitizer from hypocrellin B with enhanced red absorption," Dyes Pigm. 41, 93–100 (1999).

    [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] J. Xie, J. H. Ma, J. Q. Zhao, "Prediction on amphiphilicity of hypocrellin derivatives," Sci. China Ser. B-Chem. 45, 251–256 (2002).

    [50] M. Weng, M. H. Zhang, L. Ma, T. Shen, L. J. Jiang, "New long-wavelength perylenequinones. The reaction between hypocrellin B and mercapto compounds," Dyes Pigm. 35, 297–310 (1997).

    [51] Y. J. Tang, H. Y. Liu, J. Y. An, R. Han, "Synthesis, characterization and photodynamic activity of amino-substituted hypocrellin derivatives," Photochem. Photobiol. 74, 201–205 (2001).

    [52] S. J. Xu, S. Chen, M. H. Zhang, T. Shen, X. X. Zhang, Z. P. Wang, "Synthesis and characterization of three novel amphiphilic aminated hypocrellins as photodynamic therapeutic agents," Photochem. Photobiol. 78, 411–415 (2003).

    [53] Z. H. Zeng, R. Qiao, J. H. Zhou, S. Q. Xia, Y. Zhang, Y. Y. Liu, J. R. Chen, X. S. Wang, B. W. Zhang, "Photodynamic properties of dipeptide-modified hypocrellin B derivatives: The role of tyrosine and tryptophan groups," J. Phys. Chem. B 111, 3742– 3749 (2007).

    [54] H. Y. Lee, S. Chen, M. H. Zhang, T. Shen, "Studies on the synthesis of two hydrophilic hypocrellin derivatives with enhanced absorption in the red spectral region and on their photogeneration of O-2 (center dot-) and O-2((1)Delta(g))," J. Photochem. Photobiol. B-Biol. 71, 43–50 (2003).

    [55] S. J. Xu, S. Chen, M. H. Zhang, T. Shen, Z. W. Liu, Y. P. Zhao, Y. D. Wu, "Cyclohexylamino-demethoxy- hypocrellin B and photodynamic therapy decreases human cancer in vitro," Anti-Cancer Drug Des. 16, 271–277 (2001).

    [56] S. J. Xu, S. Chen, M. H. Zhang, T. Shen, "Synthesis, characterization and photodynamic activity of phenmethylamino-demethoxy-hypocrellin B," J. Photochem. Photobiol. B-Biol. 72, 61–67 (2003).

    [57] S. J. Xu, S. Chen, M. H. Zhang, T. Shen, "Hypocrellin derivative with improvements of red absorption and active oxygen species generation," Bioorg. Med. Chem. Lett. 14, 1499–1501 (2004).

    [58] Y. Zhang, L. M. Song, J. Xie, H. X. Qiu, Y. Gu, J. Q. Zhao, "Novel surfactant-like hypocrellin derivatives to achieve simultaneous drug delivery in blood plasma and cell uptake," Photochem. Photobiol. 86, 667–672 (2010).

    [59] 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).

    [60] M. Verhille, P. Couleaud, R. Vanderesse, D. Brault, M. Barberi-Heyob, C. Frochot, "Modulation of photosensitization processes for an improved targeted photodynamic therapy," Curr. Med. Chem. 17, 3925–3943 (2010).

    [61] Y. Y. Liu, Q. X. Zhou, Z. H. Zeng, R. Qiao, X. S. Wang, B. W. Zhang, "Photodynamic properties of a bispyrrolecarboxamide-modified hypocrellin B: The role of a±nity and ascorbic acid," J. Phys. Chem. B 112, 9959–9965 (2008).

    [62] S. Q. Xia, J. H. Zhou, J. R. Chen, X. S. Wang, B. W. Zhang, "A tyrosine-modified hypocrellin B with a±nity for and photodamaging ability towards calf thymus DNA," Chem. Commun. 2900–2901 (2003).

    [63] L. Li, Y.W. Chen, J. Q. Shen, M. H. Zhang, T. Shen, "New long-wavelength perylenequinones: Synthesis and phototoxicity of hypocrellin B derivatives," Biochim. Biophys. Acta 1523, 6–12 (2000).

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

    [65] Y. W. Zhao, J. Q. Zhao, "Preparation of a novel hypocrellin derivative and its photochemical, photophysical properties," Dyes Pigm. 63, 175–179 (2004).

    [66] 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).

    [67] T. A. Heming, S. K. Dave, D. M. Tuazon, A. K. Chopra, J. W. Peterson, A. Bidani, "Effects of extracellular pH on tumour necrosis factor-alpha production by resident alveolar macrophages," Clin. Sci. 101, 267–274 (2001).

    [68] L. David, V. Dulong, D. Le Cerf, C. Chauzy, V. Norris, B. Delpech, M. Lamacz, J. P. Vannier, "Reticulated hyaluronan hydrogels: A model for examining cancer cell invasion in 3D," Matrix Biol. 23, 183–193 (2004).

    [69] Y. Aoyagi, T. Oda, T. Kinoshita, C. Nakahashi, T. Hasebe, N. Ohkohchi, A. Ochiai, "Overexpression of TGF-beta by infiltrated granulocytes correlates with the expression of collagen mRNA in pancreatic cancer," Brit. J. Cancer 91, 1316–1326 (2004).

    [70] M. Kongshaug, J. Moan, L. S. Cheng, G.M. Garbo, S. Kolboe, A. R. Morgan, C. Rimington, "Binding of drugs to human plasma-proteins, exemplified by Sn(Iv)-etiopurpurin dichloride delivered in cremophor and DMSO," International J. Biochem. 25, 739–760 (1993).

    [71] K. Das, A. V. Smirnov, J. Wen, P. Miskovsky, J. W. Petrich, "Photophysics of hypericin and hypocrellin A in complex with subcellular components: Interactions with human serum albumin," Photochem. Photobiol. 69, 633–645 (1999).

    [72] B. Z. Zhao, J. Xie, J. Q. Zhao, "Binding of hypocrellin B to human serum albumin and photo-induced interactions," Biochim. Biophys. Acta 1722, 124– 130 (2005).

    [73] B. Z. Zhao, L. M. Song, X. Liu, J. Xie, J. Q. Zhao, "Spectroscopic studies of the interaction between hypocrellin B and human serum albumin," Bioorg. Med. Chem. 14, 2428–2432 (2006).

    [74] J. Lesley, R. Hyman, N. English, J. B. Catterall, G. A. Turner, "CD44 in inflammation and metastasis," Glycoconjugate J. 14, 611–622 (1997).

    [75] L. M. Song, B. Z. Zhao, J. Xie, J. Q. Zhao, "Interactions of hypocrellin B with hyaluronan and photo-induced interactions," Biochim. Biophys. Acta 1760, 333–339 (2006).

    [76] L. M. Song, J. Xie, C. X. Zhang, C. Li, J. Q. Zhao, "Recognition of various biomolecules by the environment- sensitive spectral responses of hypocrellin B," Photochem. Photobiol. Sci. 6, 683–688 (2007).

    [77] G. P. van-Balen, C. A. M. Martinet, G. Caron, G. Bouchard, M. Reist, P. A. Carrupt, R. Fruttero, A. Gasco, B. Testa, "Liposome/water lipophilicity: Methods, information content, and pharmaceutical applications," Med. Res. Rev. 24, 299–324 (2004).

    [78] N. K. Srivastava, S. Pradhan, G. A. N. Gowda, R. Kumar, "In vitro, high-resolution H-1 and P-31 NMR based analysis of the lipid components in the tissue, serum, and CSF of the patients with primary brain tumors: One possible diagnostic view," NMR Biomed. 23, 113–122 (2010).

    [79] J. L. Wikehooley, J. Haveman, H. S. Reinhold, "The relevance of tumor pH to the treatment of malignant disease," Radiother. Oncol. 2, 343–366 (1984).

    [80] X. Y. Jin, Y. W. Zhao, J. Xie, J. Q. Zhao, "Fluorescence response of hypocrellin B to the environmental changes in a mimic biological membrane — liposome," Sci. China Ser. B-Chem. 47, 335–339 (2004).

    Hong Deng, Jie Xie, Jingquan Zhao. Drug-delivery and multifunction possibilities of hypocrellin photosensitizers[J]. Journal of Innovative Optical Health Sciences, 2015, 8(1): 1530003
    Download Citation