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  Talaporfin  Sodium

Description of Talaporfin sodium: Talaporfin sodium is  a natural chlorophyll-based, and water soluble PDT photosensitizer consisting of chlorin e6, derived from chlorophyll, and L-aspartic acid with photosensitizing activity. After intratumoral activation by light emitting diodes, talaporfin sodium forms an extended high energy conformational state that generates singlet oxygen, which can kill target tissues with minimal side effects through vascular closure and apoptosis. Constant illumination can activate each molecule of talaporfin many times, resulting in a continuous supply of singlet oxygen molecules. Talaporfin kills all tumour cells in the targeted zone, rather than only the minority of cells undergoing rapid division, as in the case of chemotherapy. There are no serious toxicities to date. Talaporfin sodium was approved in 2004 in Japan, and is currently in phase III trials in USA. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Current developer: Light Sciences Oncology.

Talaporfin (INN, also known as aspartyl chlorin, mono-L-aspartyl chlorine e6, NPe6, or LS11) is a photosensitizer used in photodynamic therapy (PDT). It absorbs red light at 664nm normally provided by a laser tuned to this wavelength. Talaporfin was approved in Japan (in 2004) for PDT of lung cancer and marketed as Laserphyrin.

Development status: talaporfin was approved in Japan in 2004, but not yet in USA.  Light Sciences Oncology (LSO) is developing Aptocine™ (talaporfin sodium) for solid tumors as well as other indications such as BPH. Aptocine is a water-soluble drug targeted by a small, single-use, disposable drug activator included with the drug. Aptocine is designed to provide tolerable, effective, and repeatable treatments for patients. LSO has completed treatment of patients in a Phase 3 trial of Aptocine in hepatocellular carcinoma (HCC) and in a Phase 3 trial for metastatic colorectal cancer (MCRC). LSO is also conducting clinical trials in benign prostatic hyperplasia (BPH), or enlargement of the prostate, and has clinical or preclinical programs in cardiovascular, ophthalmic, and dermatologic diseases. Aptocine has three potential primary mechanisms of action: direct tumor cytotoxicity, apoptosis due to vascular shutdown, and anti-tumor immune stimulation. In clinical studies to date, Aptocine has been well-tolerated with no evidence that Aptocine causes the serious toxicities associated with traditional cancer treatments. (source: http://www.lsoncology.com/).

Chemical and physical properties of Talaporfin:
Talaporfin is dark blue-green powder, soluble in water. Talaporfin is also hygroscopic and light sensitive. Therefore talaporfin should be stored under dry and protected from light (easily way to this is to use alumina foil to wrap the container).  Talaporfin's absorption max (phosphate buffer, pH 7.4): 400 nm, 654 nm (e 180000, 40000). Absorption max (dioxane): 402 nm, 663 nm (EmM 111, 38).

Original Literature References of Talaporfin: Semisynthetic derivative of chlorin e6, q.v. Photosensitizer activated at 664 nm by laser or light-emitting diode-based light infusion device. Causes irreversible tumor blood vessel closure. Prepn: J. C. Bommer, B. F. Burnham, EP 168831; eidem, US 4675338 (1986, 1987 both to Nippon Petrochemicals). Photophysical properties: J. D. Spikes, J. C. Bommer, J. Photochem. Photobiol. B 17, 135 (1993); L. Li et al., ibid. 67, 51 (2002). Chemical and NMR structural studies: S. Gomi et al., Heterocycles 48, 2231 (1998). Safety assessment in treatment of refractory solid tumors: R. A. Lustig et al., Cancer 98, 1767 (2003). Clinical evaluation in lung cancer: H. Kato et al., Lung Cancer 42, 103 (2003).

Highlight of recent research using Talaporfin sodium

Sonodynamically-induced antitumor effect of NPe6. The rate of ultrasonically-induced damage on isolated sarcoma 180 cells in air-saturated suspension was enhanced two-fold with 80 μM NPe6. The co-administration of 25 mg/kg NPe6 followed by ultrasonic exposure at 2 MHz suppressed the growth of implanted colon 26 cell tumors at an intensity at which ultrasound alone showed only a slight antitumor effect. These in vitro and in vivo results suggest that NPe6 is a potential sensitizer for sonodynamic tumor treatment. The enhancement of cell damage by NPe6 was significantly inhibited by histidine, which may suggest reactive oxygen species plays a primary role in sonodynamically-induced antitumor effect. (source: Anticancer Res. 2011 Feb;31(2):501-6.)

Talaporfin sodium has a broad safety profile and a mode of action that could affect growth in treated and untreated tumors. Talaporfin sodium is a light-activated drug that causes tissue death through induction of apoptosis. Systemic antitumor effects mediated by CD8(+) T cells have been demonstrated in preclinical studies, providing a mechanism for distant response of tumors noted in clinical trials. Talaporfin sodium is approved in Japan for early-stage endobronchial cancer. Phase I and II studies in solid tumors have shown tumor regression in patients refractory to other therapies. Phase III pivotal studies against hepatocellular carcinoma as monotherapy and liver-metastatic colorectal cancer in combination with chemotherapy are ongoing. Talaporfin sodium is also in studies in men with symptomatic benign prostatic hyperplasia. Substantial safety data from clinical trials so far indicate that the drug is well tolerated. Talaporfin sodium has a broad safety profile and a mode of action that could affect growth in treated and untreated tumors. Clinical and preclinical studies indicate that talaporfin sodium treatment may offer a powerful option to synergize current therapies, as well as an alternative monotherapy in treating cancer. [source:  Expert Opin Pharmacother. 2010 Jan;11(1):133-40.]

A phase IIa study of  talaporfin sodium in patients with primary or recurrent glioblastoma multiforme. Background: Preclinical studies have shown that talaporfin sodium (LS11) can concentrate in brain-tumor cells and be activated by red light (664nm wavelength) from light-emitting diodes (LEDs). Singlet oxygen is released that induces blood-vessel occlusion and apoptosis in target tumor cells, which results in direct tumor-cell death and a potential antitumor immunogenic effect on untreated tumors. Preferential talaporfin uptake in tumor and clearance from normal surrounding brain occur by 24 hours after injection. A single center, open label phase IIa study was conducted to establish safety and acute antitumor effect of light-activated drug therapy in glioblastoma patients. Results: No dose-limiting toxicity was noted at the higher light-dose level. Seven adverse events (2 neurologic) occurred in four patients, none treatment related. Apoptosis was evident by TUNEL stain, and vessel closure was seen histologically. No acute inflammatory changes or cerebral edema were noted; normal brain was unaffected. No adverse neurologic sequelae were ascribable to the therapy, and no post-operative ICP elevation was noted. At 4 weeks, all patients were alive; two patients progressed and died shortly thereafter. Conclusions: Treatment of glioblastoma with this light-activated drug therapy was safe and tolerable in this study. An antivascular effect and tumor-cell apoptosis were seen histologically and confined to tumor. [source: J Clin Oncol 27, 2009 (suppl; abstr e13026)]

1: Bromley E, Briggs B, Keltner L, Wang SS. Characterization of cutaneous photosensitivity in healthy volunteers receiving talaporfin sodium. Photodermatol Photoimmunol Photomed. 2011 Apr;27(2):85-9. doi: 10.1111/j.1600-0781.2011.00573.x. PubMed PMID: 21392111.

2: Ito A, Kimura T, Miyoshi S, Ogawa S, Arai T. Photosensitization reaction-induced acute electrophysiological cell response of rat myocardial cells in short loading periods of talaporfin sodium or porfimer sodium. Photochem Photobiol. 2011 Jan-Feb;87(1):199-207. doi: 10.1111/j.1751-1097.2010.00846.x. Epub 2010 Nov 29. PubMed PMID: 21114668.

3: Kishi K, Yano M, Inoue M, Miyashiro I, Motoori M, Tanaka K, Goto K, Eguchi H, Noura S, Yamada T, Ohue M, Ohigashi H, Ishikawa O. Talaporfin-mediated photodynamic therapy for peritoneal metastasis of gastric cancer in an in vivo mouse model: drug distribution and efficacy studies. Int J Oncol. 2010 Feb;36(2):313-20. PubMed PMID: 20043064.

4: Wang S, Bromley E, Xu L, Chen JC, Keltner L. Talaporfin sodium. Expert Opin Pharmacother. 2010 Jan;11(1):133-40. Review. PubMed PMID: 20001435.

5: Tomioka Y, Kushibiki T, Awazu K. Evaluation of oxygen consumption of culture medium and in vitro photodynamic effect of talaporfin sodium in lung tumor cells. Photomed Laser Surg. 2010 Jun;28(3):385-90. PubMed PMID: 19860571.

6: Ohshiro T, Nakajima T, Ogata H, Kishi K. Histological responses of cutaneous vascular lesions following photodynamic therapy with talaporfin sodium: a chicken comb model. Keio J Med. 2009 Sep;58(3):176-84. PubMed PMID: 19826211.

7: Tsurubuchi T, Zoboronok A, Yamamoto T, Nakai K, Yoshida F, Shirakawa M, Matsuda M, Matsumura A. The optimization of fluorescence imaging of brain tumor tissue differentiated from brain edema--in vivo kinetic study of 5-aminolevulinic acid and talaporfin sodium. Photodiagnosis Photodyn Ther. 2009 Mar;6(1):19-27. Epub 2009 May 5. PubMed PMID: 19447368.

8: Namatame H, Akimoto J, Matsumura H, Haraoka J, Aizawa K. Photodynamic therapy of C6-implanted glioma cells in the rat brain employing second-generation photosensitizer talaporfin sodium. Photodiagnosis Photodyn Ther. 2008 Sep;5(3):198-209. Epub 2008 Oct 22. PubMed PMID: 19356656.

9: Nakagishi Y, Morimoto N, Fujita M, Ozeki Y, Maehara T, Kikuchi M, Morimoto Y. Amelioration of airway stenosis in rabbit models by photodynamic therapy with talaporfin sodium (NPe6). Photochem Photobiol. 2009 May-Jun;85(3):714-8. Epub 2008 Nov 19. PubMed PMID: 19067947.

10: Torikai E, Kageyama Y, Kohno E, Hirano T, Koide Y, Terakawa S, Nagano A. Photodynamic therapy using talaporfin sodium for synovial membrane from rheumatoid arthritis patients and collagen-induced arthritis rats. Clin Rheumatol. 2008 Jun;27(6):751-61. Epub 2007 Dec 8. PubMed PMID: 18066613.

11: Usuda J, Tsutsui H, Honda H, Ichinose S, Ishizumi T, Hirata T, Inoue T, Ohtani K, Maehara S, Imai K, Tsunoda Y, Kubota M, Ikeda N, Furukawa K, Okunaka T, Kato H. Photodynamic therapy for lung cancers based on novel photodynamic diagnosis using talaporfin sodium (NPe6) and autofluorescence bronchoscopy. Lung Cancer. 2007 Dec;58(3):317-23. Epub 2007 Aug 15. PubMed PMID: 17698240.

12: Kujundzić M, Vogl TJ, Stimac D, Rustemović N, Hsi RA, Roh M, Katicić M, Cuenca R, Lustig RA, Wang S. A Phase II safety and effect on time to tumor progression study of intratumoral light infusion technology using talaporfin sodium in patients with metastatic colorectal cancer. J Surg Oncol. 2007 Nov 1;96(6):518-24. PubMed PMID: 17671969.

13: Ohmori S, Arai T. In vitro behavior of Porfimer sodium and Talaporfin sodium with high intensity pulsed irradiation. Lasers Med Sci. 2006 Dec;21(4):213-23. Epub 2006 Sep 22. PubMed PMID: 17024319.

14: Tsukagoshi S; Tokyo Cooperative Oncology Group. [Development of a novel photosensitizer, talaporfin sodium, for the photodynamic therapy (PDT)]. Gan To Kagaku Ryoho. 2004 Jun;31(6):979-85. Review. Japanese. PubMed PMID: 15222124.

15: Lustig RA, Vogl TJ, Fromm D, Cuenca R, Alex Hsi R, D'Cruz AK, Krajina Z, Turić M, Singhal A, Chen JC. A multicenter Phase I safety study of intratumoral photoactivation of talaporfin sodium in patients with refractory solid tumors. Cancer. 2003 Oct 15;98(8):1767-71. PubMed PMID: 14534895.

16: Talaporfin sodium. LS 11, ME 2906, mono-L-aspartyl chlorine e6, NP e6, NPE 6, taporfin sodium. Drugs R D. 2003;4(2):135-7. PubMed PMID: 12723579.

17: Talaporfin: LS 11, LS11, ME 2906, mono-L-aspartyl chlorin e6, NP e6, NPE 6, taporfin sodium. Drugs R D. 2003;4(1):69-71. Review. Corrected and republished in: Drugs R D. 2003;4(2):135-7. PubMed PMID: 12568643.

1: Yumita N, Iwase Y, Nishi K, Ikeda T, Komatsu H, Fukai T, Onodera K, Nishi H, Takeda K, Umemura S, Okudaira K, Momose Y. Sonodynamically-induced antitumor effect of mono-l-aspartyl chlorin e6 (NPe6). Anticancer Res. 2011 Feb;31(2):501-6. PubMed PMID: 21378330.

2: Vermathen M, Vermathen P, Simonis U, Bigler P. Time-dependent interactions of the two porphyrinic compounds chlorin e6 and mono-L-aspartyl-chlorin e6 with phospholipid vesicles probed by NMR spectroscopy. Langmuir. 2008 Nov 4;24(21):12521-33. Epub 2008 Sep 30. PubMed PMID: 18823137.

3: Yumita N, Han QS, Kitazumi I, Umemura S. Sonodynamically-induced apoptosis, necrosis, and active oxygen generation by mono-l-aspartyl chlorin e6. Cancer Sci. 2008 Jan;99(1):166-72. Epub 2007 Oct 29. PubMed PMID: 17970784.

4: Mori K, Kanai K, Peyman GA, Yoneya S. Intraocular biodistribution of mono-L-aspartyl chlorin e6 in a primate choroidal neovascularization model. Ophthalmic Surg Lasers Imaging. 2007 Mar-Apr;38(2):142-7. PubMed PMID: 17396695.

5: Ohmori S, Masuda K, Arai T. Characteristics of Photocytotoxicity with high peak power pulsed irradiation: Comparison of Photodynamic Therapy with two photosensitizers, Photofrin® and mono-L-aspartyl chlorin e6 on prostate cancer cell in vitro. Conf Proc IEEE Eng Med Biol Soc. 2005;1:217-9. PubMed PMID: 17282151.

6: Nakagawa H, Matsumiya T, Sakaki H, Imaizumi T, Kubota K, Kusumi A, Kobayashi W, Kimura H. Expression of vascular endothelial growth factor by photodynamic therapy with mono-L-aspartyl chlorin e6 (NPe6) in oral squamous cell carcinoma. Oral Oncol. 2007 Jul;43(6):544-50. Epub 2007 Jan 25. PubMed PMID: 17257889.

7: Kobayashi W, Liu Q, Nakagawa H, Sakaki H, Teh B, Matsumiya T, Yoshida H, Imaizumi T, Satoh K, Kimura H. Photodynamic therapy with mono-L-aspartyl chlorin e6 can cause necrosis of squamous cell carcinoma of tongue: experimental study on an animal model of nude mouse. Oral Oncol. 2006 Jan;42(1):46-50. Epub 2005 Nov 2. PubMed PMID: 16266818.

8: Chan AL, Juarez M, Allen R, Volz W, Albertson T. Pharmacokinetics and clinical effects of mono-L-aspartyl chlorin e6 (NPe6) photodynamic therapy in adult patients with primary or secondary cancer of the skin and mucosal surfaces. Photodermatol Photoimmunol Photomed. 2005 Apr;21(2):72-8. PubMed PMID: 15752124.

9: Webber J, Leeson B, Fromm D, Kessel D. Effects of photodynamic therapy using a fractionated dosing of mono-L-aspartyl chlorin e6 in a murine tumor. J Photochem Photobiol B. 2005 Feb 1;78(2):135-40. PubMed PMID: 15664500.

10: Kikuchi T, Asakura T, Aihara H, Shiraki M, Takagi S, Kinouchi Y, Aizawa K, Shimosegawa T. Photodynamic therapy of intestinal tumors with mono-L-aspartyl chlorin e6 (NPe6): a basic study. Anticancer Res. 2003 Nov-Dec;23(6C):4897-900. PubMed PMID: 14981942.

11: Biały D, Derkacz A, Wawrzyńska M, Bednarkiewicz A, Ziółkowski P, Nowosad H, Strek W. In vitro photodynamic diagnosis of atherosclerotic wall changes with the use of mono-l-aspartyl chlorin e6. A preliminary report. Kardiol Pol. 2003 Oct;59(10):293-301. PubMed PMID: 14618213.

12: Wong TW, Aizawa K, Sheyhedin I, Wushur C, Kato H. Pilot study of topical delivery of mono-L-aspartyl chlorin e6 (NPe6): implication of topical NPe6-photodynamic therapy. J Pharmacol Sci. 2003 Oct;93(2):136-42. PubMed PMID: 14578580.

13: Kato H, Furukawa K, Sato M, Okunaka T, Kusunoki Y, Kawahara M, Fukuoka M, Miyazawa T, Yana T, Matsui K, Shiraishi T, Horinouchi H. Phase II clinical study of photodynamic therapy using mono-L-aspartyl chlorin e6 and diode laser for early superficial squamous cell carcinoma of the lung. Lung Cancer. 2003 Oct;42(1):103-11. PubMed PMID: 14512194.

14: Talaporfin: LS 11, LS11, ME 2906, mono-L-aspartyl chlorin e6, NP e6, NPE 6, taporfin sodium. Drugs R D. 2003;4(1):69-71. Review. Corrected and republished in: Drugs R D. 2003;4(2):135-7. PubMed PMID: 12568643.

15: Li L, Kodama K, Saito K, Aizawa K. Phase-resolved fluorescence study of mono-L-aspartyl chlorin E6. J Photochem Photobiol B. 2002 May;67(1):51-6. PubMed PMID: 12007467.

16: Nakamura H, Suzuki Y, Takeichi M, Saito T, Takayama M, Aizawa K. Morphologic evaluation of the antitumor activity of photodynamic therapy (PDT) using mono-L-aspartyl chlorin e6 (NPe6) against uterine cervical carcinoma cell lines. Int J Gynecol Cancer. 2002 Mar-Apr;12(2):177-86. PubMed PMID: 11975677.

17: Mori K, Yoneya S, Anzail K, Kabasawa S, Sodeyama T, Peyman GA, Moshfeghi DM. Photodynamic therapy of experimental choroidal neovascularization with a hydrophilic photosensitizer: mono-L-aspartyl chlorin e6. Retina. 2001;21(5):499-508. PubMed PMID: 11642380.

18: Nagae T, Aizawa K, Uchimura N, Tani D, Abe M, Fujishima K, Wilson SE, Ishimaru S. Endovascular photodynamic therapy using mono-L-aspartyl-chlorin e6 to inhibit Intimal hyperplasia in balloon-injured rabbit arteries. Lasers Surg Med. 2001;28(4):381-8. PubMed PMID: 11344521.

19: Saito K, Mikuniya N, Aizawa K. Effects of photodynamic therapy using mono-L-aspartyl chlorin e6 on vessels and its contribution to the antitumor effect. Jpn J Cancer Res. 2000 May;91(5):560-5. PubMed PMID: 10835502.

20: Sheyhedin I, Okunaka T, Kato H, Yamamoto Y, Sakaniwa N, Konaka C, Aizawa K. Localization of experimental submucosal esophageal tumor in rabbits by using mono-L-aspartyl chlorin e6 and long-wavelength photodynamic excitation. Lasers Surg Med. 2000;26(1):83-9. PubMed PMID: 10637007.

21: Nakamura J, Kajiwara H. Photodynamic therapy using mono-L-aspartyl chlorin e6 for rabbit experimental hepatoma. J Hepatobiliary Pancreat Surg. 1999;6(3):312-9. PubMed PMID: 10526068.

22: Mori K, Yoneya S, Ohta M, Sano A, Anzai K, Peyman GA, Moshfeghi DM. Angiographic and histologic effects of fundus photodynamic therapy with a hydrophilic sensitizer (mono-L-aspartyl chlorin e6). Ophthalmology. 1999 Jul;106(7):1384-91. PubMed PMID: 10406627.

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