Talaporfin sodium
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MedKoo CAT#: 202750

CAS#: 220201-34-3 (sodium)

Description: 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.


Chemical Structure

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Talaporfin sodium
CAS# 220201-34-3 (sodium)

Theoretical Analysis

MedKoo Cat#: 202750
Name: Talaporfin sodium
CAS#: 220201-34-3 (sodium)
Chemical Formula: C38H37N5Na4O9
Exact Mass:
Molecular Weight: 799.6991
Elemental Analysis: C, 57.07; H, 4.66; N, 8.76; Na, 11.50; O, 18.01

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10.0mg USD 150.0 Ready to ship
25.0mg USD 250.0 Ready to ship
50.0mg USD 450.0 Ready to ship
100.0mg USD 750.0 Ready to ship
200.0mg USD 1250.0 Ready to ship
500.0mg USD 1950.0 Ready to ship
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2.0g USD 5850.0 Ready to ship
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Related CAS #: 220201-34-3 (sodium)   110230-98-3 (free acid)    

Synonym: LS11, LS-11, LS 11, ME2906, ME 2906, ME-2906, NPe6, mono-L-aspartyl chlorin e6, Talaporfin sodium, Laserphyrin

IUPAC/Chemical Name: N-[2-[(7S,8S)-3-Carboxy-7-(2-carboxyethyl)-13-ethenyl-18-ethyl-7,8-dihydro-2,8,12,17-tetramethyl-21H,23H-porphin-5-yl]acetyl]-L-aspartate, tetrasodium.

InChi Key: KPALSRNVSRWOPA-YJFNSWLASA-J

InChi Code: InChI=1S/C38H41N5O9.4Na/c1-7-20-16(3)24-12-26-18(5)22(9-10-32(45)46)35(42-26)23(11-31(44)41-30(37(49)50)15-33(47)48)36-34(38(51)52)19(6)27(43-36)14-29-21(8-2)17(4)25(40-29)13-28(20)39-24;;;;/h7,12-14,18,22,30,39,43H,1,8-11,15H2,2-6H3,(H,41,44)(H,45,46)(H,47,48)(H,49,50)(H,51,52);;;;/q;4*+1/p-4/b24-12-,25-13-,26-12-,27-14-,28-13-,29-14-,35-23-,36-23-;;;;/t18-,22-,30-;;;;/m0..../s1

SMILES Code: O=C(C[C@H](NC(C/C1=C2[C@H]([C@@H](C(/C=C3C(C)=C(/C(N/3)=C/C(C(C)=C/4CC)=NC4=C/C5=C(C(C(O[Na])=O)=C1N5)C)C=C)=N\2)C)CCC(O[Na])=O)=O)C(O[Na])=O)O[Na]

Appearance: Black solid powder

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in water.

Shelf Life: >2 years if stored properly.

Drug Formulation: This drug may be formulated in water.

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 799.6991 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Ogawa E, Ito A, Arai T. Detailed in vitro study of the photosensitization reaction of extracellular Talaporfin sodium in rat myocardial cells. Lasers Surg Med. 2013 Dec;45(10):660-7. doi: 10.1002/lsm.22192. Epub 2013 Nov 6. PubMed PMID: 24339254.

2: Takahashi M, Ito A, Kimura T, Takatsuki S, Fukuda K, Arai T. Myocardial necrosis depth prediction during extracellular photosensitization reaction of talaporfin sodium by defined index using fluorescence measurement. Lasers Med Sci. 2013 Dec 7. [Epub ahead of print] PubMed PMID: 24318629.

3: Muragaki Y, Akimoto J, Maruyama T, Iseki H, Ikuta S, Nitta M, Maebayashi K, Saito T, Okada Y, Kaneko S, Matsumura A, Kuroiwa T, Karasawa K, Nakazato Y, Kayama T. Phase II clinical study on intraoperative photodynamic therapy with talaporfin sodium and semiconductor laser in patients with malignant brain tumors. J Neurosurg. 2013 Oct;119(4):845-52. doi: 10.3171/2013.7.JNS13415. Epub 2013 Aug 16. PubMed PMID: 23952800.

4: Tsutsumi M, Miki Y, Akimoto J, Haraoka J, Aizawa K, Hirano K, Beppu M. Photodynamic therapy with talaporfin sodium induces dose-dependent apoptotic cell death in human glioma cell lines. Photodiagnosis Photodyn Ther. 2013 May;10(2):103-10. doi: 10.1016/j.pdpdt.2012.08.002. Epub 2012 Sep 25. PubMed PMID: 23769275.

5: Miki Y, Akimoto J, Yokoyama S, Homma T, Tsutsumi M, Haraoka J, Hirano K, Beppu M. Photodynamic therapy in combination with talaporfin sodium induces mitochondrial apoptotic cell death accompanied with necrosis in glioma cells. Biol Pharm Bull. 2013;36(2):215-21. Epub 2012 Nov 29. PubMed PMID: 23196427.

6: Nanashima A, Abo T, Nonaka T, Nonaka Y, Morisaki T, Uehara R, Ohnita K, Fukuda D, Murakami G, Tou K, Kunizaki M, Hidaka S, Tsuchiya T, Takeshita H, Nakao K, Nagayasu T. Photodynamic therapy using talaporfin sodium (Laserphyrin®) for bile duct carcinoma: a preliminary clinical trial. Anticancer Res. 2012 Nov;32(11):4931-8. PubMed PMID: 23155262.

7: Nonaka Y, Nanashima A, Nonaka T, Uehara M, Isomoto H, Abo T, Nagayasu T. Synergic effect of photodynamic therapy using talaporfin sodium with conventional anticancer chemotherapy for the treatment of bile duct carcinoma. J Surg Res. 2013 May;181(2):234-41. doi: 10.1016/j.jss.2012.06.047. Epub 2012 Jul 13. PubMed PMID: 22835954.

8: Yano T, Muto M, Yoshimura K, Niimi M, Ezoe Y, Yoda Y, Yamamoto Y, Nishisaki H, Higashino K, Iishi H. Phase I study of photodynamic therapy using talaporfin sodium and diode laser for local failure after chemoradiotherapy for esophageal cancer. Radiat Oncol. 2012 Jul 23;7:113. doi: 10.1186/1748-717X-7-113. PubMed PMID: 22824179; PubMed Central PMCID: PMC3410784.

9: Horimatsu T, Muto M, Yoda Y, Yano T, Ezoe Y, Miyamoto S, Chiba T. Tissue damage in the canine normal esophagus by photoactivation with talaporfin sodium (laserphyrin): a preclinical study. PLoS One. 2012;7(6):e38308. doi: 10.1371/journal.pone.0038308. Epub 2012 Jun 13. PubMed PMID: 22719875; PubMed Central PMCID: PMC3374776.

10: Akimoto J, Haraoka J, Aizawa K. Preliminary clinical report on safety and efficacy of photodynamic therapy using talaporfin sodium for malignant gliomas. Photodiagnosis Photodyn Ther. 2012 Jun;9(2):91-9. doi: 10.1016/j.pdpdt.2012.01.001. Epub 2012 Feb 28. PubMed PMID: 22594978.



Additional Information

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).
 
Useful data about talaporfin sodium:
The singlet oxygen quantum yield of  talaporfin was 0.5– 0.8 (0.56 in water and 0.77 in methanol). Talaporfin sodium has a serum t1⁄2 alpha of 9 hours and is excreted unmetabolized, predominantly by the biliary system. ( Cancer . 2003 Oct 15;98(8):1767-71.)
 
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).