Journal of Innovative Optical Health Sciences, 2015, 8 (1): 1540003, Published Online: Jan. 10, 2019  

Anti-tumor activities of a novel chlorin derivative for photodynamic therapy in vitro and in vivo

Author Affiliations
1 Department of Pharmaceutical Science & Technology College of Chemistry and Biology, Donghua University Shanghai 201620, P. R. China
2 Changhai Hospital, Second Military Medical University Shanghai 200433, P. R. China
Abstract
In this study, a novel photosensitizer meso-tetra (3-pyrrolidinomethyl-4-methoxyphenyl) chlorin (TPMC) was reported. It displays a characteristic long wavelength absorption peak at 656 nm and it shows a singlet oxygen quantum yield of 0.48. After light irradiation with 650 nm laser, it can kill Eca-109 and SMMC-7721 cells in vitro (25mW/cm2, 1.2 to 3.6 J/cm2) and destroy Eca-109 tumor in nude mice (50mW/cm2, 90 J/cm2). It has the perspective to be developed as a new anti-tumor drug in photodynamic therapy (PDT) photodiagnosis, and deserves further investigation.
References

[1] T. J. Dougherty, C. J. Gomer, B. W. Henderson, G. Jori, D. Kessel, M. Korbelik, J. Moan, Q. Peng, "Photodynamic therapy," J. Nat. Cancer Inst. 90, 889–905 (1998).

[2] S. M. Fien, A. R. Osero , "Photodynamic therapy for non-melanoma skin cancer," J. Nat. Compr. Canc. Netw. 5, 531–540 (2007).

[3] J. F. Lovell, T. W. Liu, J. Chen, G. Zheng, "Activatable photosensitizers for imaging and therapy," Chem. Rev. 110, 2839–2857 (2010).

[4] E. A. Giuliano, I. MacDonald, D. L. McCaw, T. J. Dougherty, G. Klauss, J. Ota, J. W. Pearce, P. J. Johnson, "Photodynamic therapy for the treatment of periocular squamous cell carcinoma in horses: A pilot study," Vet. Ophthalmol. 11, 27–34 (2008).

[5] L. B. Josefsen, R. W. Boyle, "Photodynamic therapy and the development of metal-based photosensitisers," Met. Based Drugs 2008, 276109 (2008).

[6] M. Triesscheijn, P. Baas, J. H. Schellens, F. A. Stewart, "Photodynamic therapy in oncology," Oncologist 11, 1034–1044 (2006).

[7] J. P. Celli, B. Q. Spring, I. Rizvi, C. L. Evans, K. S. Samkoe, S. Verma, B. W. Pogue, T. Hasan, Imaging and photodynamic therapy: Mechanisms, monitoring, and optimization, Chem. Rev. 110, 2795–2838 (2010).

[8] Y. J. Yan, M. Z. Zheng, Z. L. Chen, X. H. Yu, X. X. Yang, Z. L. Ding, L. Xu, "Studies on preparation and photodynamic mechanism of chlorin P6-13,15- N-(cyclohexyl)cycloimide (Chlorin-H) and its antitumor effect for photodynamic therapy in vitro and in vivo," Bioorg. Med. Chem. 18, 6282–6291 (2010).

[9] Z. Huang, "A review of progress in clinical photodynamic therapy," Technol. Cancer Res. Treat. 4, 283–293 (2005).

[10] M. R. Hamblin, J. L. Miller, I. Rizvi, B. Ortel, E. V. Maytin, T. Hasan, "Pegylation of a chlorin(e6) polymer conjugate increases tumor targeting of photosensitizer," Cancer Res. 61, 7155–7162 (2001).

[11] R. Asano, A. Nagami, Y. Fukumoto, F. Yazama, H. Ito, I. Sakata, A. Tai, "Synthesis and biological evaluation of new chlorin derivatives as potential photosensitizers for photodynamic therapy," Bioorg. Med. Chem. 21, 2298–2304 (2013).

[12] J. M. Dabrowski, M. Krzykawska, L. G. Arnaut, M. M. Pereira, C. J. Monteiro, S. Simoes, K. Urbanska, G. Stochel, "Tissue uptake study and photodynamic therapy of melanoma-bearing mice with a nontoxic, effective chlorin," ChemMedChem 6, 1715–1726 (2011).

[13] E. Hao, E. Friso, G. Miotto, G. Jori, M. Soncin, C. Fabris, M. Sibrian-Vazquez, M. G. Vicente, "Synthesis and biological investigations of tetrakis (p-carboranylthio-tetrafluorophenyl)chlorin (TPFC)," Org. Biomol. Chem. 6, 3732–3740 (2008).

[14] M. Wawrzynska, W. Kalas, D. Bialy, E. Ziolo, J. Arkowski, W. Mazurek, L. Strzadala, "In vitro photodynamic therapy with chlorin e6 leads to apoptosis of human vascular smooth muscle cells," Arch. Immunol. Ther. Exp. 58, 67–75 (2010).

[15] V. A. Ol'shevskaya, R. G. Nikitina, A. N. Savchenko, M. V. Malshakova, A. M. Vinogradov, G. V. Golovina, D. V. Belykh, A. V. Kutchin, M. A. Kaplan, V. N. Kalinin, V. A. Kuzmin, A. A. Shtil, "Novel boronated chlorin e6-based photosensitizers: Synthesis, binding to albumin and antitumour e±cacy," Bioorg. Med. Chem. 17, 1297–1306 (2009).

[16] H. B. Ris, H. J. Altermatt, B. Nachbur, C. M. Stewart, Q. Wang, C. K. Lim, R. Bonnett, U. Althaus, "Intraoperative photodynamic therapy with m-tetrahydroxyphenylchlorin for chest malignancies," Lasers Surg. Med. 18, 39–45 (1996).

[17] J. Svensson, A. Johansson, S. Grafe, B. Gitter, T. Trebst,N.Bendsoe,S.Andersson-Engels, K.Svanberg, "Tumor selectivity at short times following systemic administration of a liposomal temoporfin formulation in a murine tumor model," Photochem. Photobiol. 83, 1211–1219 (2007).

[18] N. Dragicevic-Curic, S. Grafe, B. Gitter, A. Fahr, "E±cacy of temoporfin-loaded invasomes in the photodynamic therapy in human epidermoid and colorectal tumour cell lines," J. Photochem. Photobiol. B, Biol. 101, 238–250 (2010).

[19] J. A. Howard, "The new wilderness," J. Am. Coll. Dent. 43, 15–22 (1976).

[20] Y. A. Cheng, C. S. A, J. D. Meyers, I. Panagopoulos, B. Fei, C. Burda, "Highly e±cient drug delivery with gold nanoparticle vectors for in vivo photodynamic therapy of cancer," J. Am. Chem. Soc. 130, 10643–10647 (2008).

[21] P. Zimcik, M. Miletin, K. Kopecky, Z.Musil,P.Berka, V. Horakova, H. Kucerova, J. Zbytovska, D. Brault, "Influence of aggregation on interaction of lipophilic, water-insoluble azaphthalocyanines with DOPC vesicles," Photochem. Photobiol. 83, 1497–1504 (2007).

[22] J. C. Finlay, S. Mitra, M. S. Patterson, T. H. Foster, "Photobleaching kinetics of Photofrin in vivo and in multicell tumour spheroids indicate two simultaneous bleaching mechanisms," Phys. Med. Biol. 49, 4837–4860 (2004).

[23] Y. Wang, Z. Zuo, Y. Gu, N. Huang, R. Chen, B. Li, H. Qiu, J. Zeng, J. Zhu, J. Liang, "New optional photodynamic therapy laser wavelength for infantile port wine stains: 457 nm," J. Biomed. Opt. 17, 068003 (2012).

[24] A. V. Evans, A. Robson, R. J. Barlow, H. A. Kurwa, "Treatment of port wine stains with photodynamic therapy, using pulsed dye laser as a light source, compared with pulsed dye laser alone: A pilot study," Lasers Surg. Med. 36, 266–269 (2005).

[25] W. W. Chin, P. S. Thong, R. Bhuvaneswari, K. C. Soo, P. W. Heng, M. Olivo, "In-vivo optical detection of cancer using chlorin e6–polyvinylpyrrolidone induced fluorescence imaging and spectroscopy," BMC Med. Imaging 9, 1 (2009).

[26] M. R. Hamblin, M. Rajadhyaksha, T. Momma, N. S. Soukos, T. Hasan, "In vivo fluorescence imaging of the transport of charged chlorin e6 conjugates in a rat orthotopic prostate tumour," Br. J. Cancer 81, 261–268 (1999).

[27] E. F. Silva, F. A. Schaberle, C. J. Monteiro, J. M. Dabrowski, L. G. Arnaut, "The challenging combination of intense fluorescence and high singlet oxygen quantum yield in photostable chlorins — a contribution to theranostics," Photochem. Photobiol. Sci. 12, 1187–1192 (2013).

[28] K. Stefflova, H. Li, J. Chen, G. Zheng, "Peptidebased pharmacomodulation of a cancer-targeted optical imaging and photodynamic therapy agent," Bioconjug. Chem. 18, 379–388 (2007).

[29] J. C. Stockert,M. Canete, A. Juarranz,A.Villanueva, R. W. Horobin, J. I. Borrell, J. Teixido, S. Nonell, "Porphycenes: Facts and prospects in photodynamic therapy of cancer," Curr. Med. Chem. 14, 997–1026 (2007).

[30] J. Berlanda, T. Kiesslich, V. Engelhardt, B. Krammer, K. Plaetzer, "Comparative in vitro study on the characteristics of different photosensitizers employed in PDT," J. Photochem. Photobiol. B Biol. 100, 173–180 (2010).

[31] E. Buytaert, M. Dewaele, P. Agostinis, "Molecular effectors of multiple cell death pathways initiated by photodynamic therapy," Biochim. Biophys. Acta 1776, 86–107 (2007).

[32] S. Rello-Varona, J.C. Stockert, M. Canete, P. Acedo, A. Villanueva, "Mitotic catastrophe induced in HeLa cells by photodynamic treatment with Zn(II)-phthalocyanine," Int. J. Oncology 32, 1189–1196 (2008).

[33] M. Dewaele, T. Verfaillie, W. Martinet, P. Agostinis, "Death and survival signals in photodynamic therapy," Methods Mol. Biol. 635, 7–33 (2010).

[34] P. Mroz, A. Yaroslavsky, G. B. Kharkwal, M. R. Hamblin, "Cell death pathways in photodynamic therapy of cancer," Cancers 3, 2516–2539 (2011).

[35] M. C. Alley, D. A. Scudiero, A. Monks, M. L. Hursey, M. J. Czerwinski, D. L. Fine, B. J. Abbott, J. G. Mayo, R. H. Schoemaker, M. R. Boyd, "Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay," Cancer Res. 48, 589–560 (1988).

Li-Jun Zhang, Lai-Xing Wang, Wei-Li Zhang, Yi-Jia Yan, Zhi-Long Chen. Anti-tumor activities of a novel chlorin derivative for photodynamic therapy in vitro and in vivo[J]. Journal of Innovative Optical Health Sciences, 2015, 8(1): 1540003.

关于本站 Cookie 的使用提示

中国光学期刊网使用基于 cookie 的技术来更好地为您提供各项服务,点击此处了解我们的隐私策略。 如您需继续使用本网站,请您授权我们使用本地 cookie 来保存部分信息。
全站搜索
您最值得信赖的光电行业旗舰网络服务平台!