MedKoo Cat#: 202750 | Name: Talaporfin sodium
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Talaporfin sodium
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: 0.0000

Molecular Weight: 799.70

Elemental Analysis: C, 57.07; H, 4.66; N, 8.76; Na, 11.50; O, 18.01

Price and Availability

Size Price Availability Quantity
10mg USD 150.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 450.00 Ready to ship
100mg USD 750.00 Ready to ship
200mg USD 1,350.00 Ready to ship
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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
More Info
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).
Biological target:
Talaporfin (ME2906; NPe6) is a photosensitizer used in photodynamic therapy (PDT).
In vitro activity:
The present study focused on the subacute or later (2 days onward) phase following NPe6-PDT (Talaporfin photodynamic therapy) of GBM (glioblastoma) cells and investigated the behaviors of kinases associated with cellular stress and survival. This study observed transient (specifically within 2–6 days after PDT) and constitutive (14 days or more after PDT) ERK activation following NPe6-PDT (Figure 3b and Figure 4b). In addition, pharmacological suppression of ERK activation at specific time points (days 3 and 14) after NPe6-PDT effectively inhibited the migration or invasion of NPe6-PDT-R GBM cells, whereas the pharmacological inhibition of ERK activation in NPe6-PDT-R cells at 14 days after PDT enhanced NPe6-PDT-induced NPe6-PDT-R cell death. Based on these results, sustained ERK1/2 activation during the subacute or later phase plays pivotal roles in the migration or invasion and survival of NPe6-PDT-R GBM cells. Reference: Cancers (Basel). 2020 Dec; 12(12): 3641. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7761910/
In vivo activity:
In addition to the evaluation using OMEGAZONE2, the tumors were excised from the various mouse groups and evaluated pathologically by immunohistochemical staining for CD31 (a marker for vascular endothelial cells) at 24 h after TS-PDT (Talaporfin sodium photodynamic therapy). It was found that TS-PDT led to significant reductions in the active areas and diameters of the tumor vessels compared with those of the control, although the number of active areas remained unchanged (Figure 7, Figure S4). Reference: Cancers (Basel). 2020 Sep; 12(9): 2369. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7563359/
Solvent mg/mL mM
Solubility
DMSO 2.0 2.50
Water 50.0 62.52
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 799.70 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
Formulation protocol:
1. Kobayashi T, Miyazaki M, Sasaki N, Yamamuro S, Uchida E, Kawauchi D, Takahashi M, Otsuka Y, Kumagai K, Takeuchi S, Toyooka T, Otani N, Wada K, Narita Y, Yamaguchi H, Muragaki Y, Kawamata T, Mori K, Ichimura K, Tomiyama A. Enhanced Malignant Phenotypes of Glioblastoma Cells Surviving NPe6-Mediated Photodynamic Therapy are Regulated via ERK1/2 Activation. Cancers (Basel). 2020 Dec 4;12(12):3641. doi: 10.3390/cancers12123641. PMID: 33291680; PMCID: PMC7761910. 2. Saito T, Tsukahara T, Suzuki T, Nojima I, Tadano H, Kawai N, Kubo T, Hirohashi Y, Kanaseki T, Torigoe T, Li L. Spatiotemporal metabolic dynamics of the photosensitizer talaporfin sodium in carcinoma and sarcoma. Cancer Sci. 2021 Feb;112(2):550-562. doi: 10.1111/cas.14735. Epub 2020 Dec 4. PMID: 33190360; PMCID: PMC7894003. 3. Suzuki T, Tanaka M, Sasaki M, Ichikawa H, Nishie H, Kataoka H. Vascular Shutdown by Photodynamic Therapy Using Talaporfin Sodium. Cancers (Basel). 2020 Aug 21;12(9):2369. doi: 10.3390/cancers12092369. PMID: 32825648; PMCID: PMC7563359. 4. Takahashi T, Suzuki S, Misawa S, Akimoto J, Shinoda Y, Fujiwara Y. Photodynamic therapy using talaporfin sodium induces heme oxygenase-1 expression in rat malignant meningioma KMY-J cells. J Toxicol Sci. 2018;43(5):353-358. doi: 10.2131/jts.43.353. PMID: 29743446.
In vitro protocol:
1. Kobayashi T, Miyazaki M, Sasaki N, Yamamuro S, Uchida E, Kawauchi D, Takahashi M, Otsuka Y, Kumagai K, Takeuchi S, Toyooka T, Otani N, Wada K, Narita Y, Yamaguchi H, Muragaki Y, Kawamata T, Mori K, Ichimura K, Tomiyama A. Enhanced Malignant Phenotypes of Glioblastoma Cells Surviving NPe6-Mediated Photodynamic Therapy are Regulated via ERK1/2 Activation. Cancers (Basel). 2020 Dec 4;12(12):3641. doi: 10.3390/cancers12123641. PMID: 33291680; PMCID: PMC7761910. 2. Saito T, Tsukahara T, Suzuki T, Nojima I, Tadano H, Kawai N, Kubo T, Hirohashi Y, Kanaseki T, Torigoe T, Li L. Spatiotemporal metabolic dynamics of the photosensitizer talaporfin sodium in carcinoma and sarcoma. Cancer Sci. 2021 Feb;112(2):550-562. doi: 10.1111/cas.14735. Epub 2020 Dec 4. PMID: 33190360; PMCID: PMC7894003.
In vivo protocol:
1. Suzuki T, Tanaka M, Sasaki M, Ichikawa H, Nishie H, Kataoka H. Vascular Shutdown by Photodynamic Therapy Using Talaporfin Sodium. Cancers (Basel). 2020 Aug 21;12(9):2369. doi: 10.3390/cancers12092369. PMID: 32825648; PMCID: PMC7563359. 2. Takahashi T, Suzuki S, Misawa S, Akimoto J, Shinoda Y, Fujiwara Y. Photodynamic therapy using talaporfin sodium induces heme oxygenase-1 expression in rat malignant meningioma KMY-J cells. J Toxicol Sci. 2018;43(5):353-358. doi: 10.2131/jts.43.353. PMID: 29743446.
1: Razizadeh M, Nikfar M, Liu Y. Small molecule therapeutics to destabilize the ACE2-RBD complex: A molecular dynamics study. Biophys J. 2021 Jul 20;120(14):2793-2804. doi: 10.1016/j.bpj.2021.06.016. Epub 2021 Jun 30. PMID: 34214539; PMCID: PMC8241573. 2: Razizadeh M, Nikfar M, Liu Y. Small Molecules to Destabilize the ACE2-RBD Complex: A Molecular Dynamics Study for Potential COVID-19 Therapeutics. ChemRxiv [Preprint]. 2020 Dec 16. doi: 10.26434/chemrxiv.13377119. Update in: Biophys J. 2021 Jul 20;120(14):2793-2804. doi: 10.1016/j.bpj.2021.06.016. PMID: 33469570; PMCID: PMC7814830. 3: Oany AR, Mia M, Pervin T, Junaid M, Hosen SMZ, Moni MA. Design of novel viral attachment inhibitors of the spike glycoprotein (S) of severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) through virtual screening and dynamics. Int J Antimicrob Agents. 2020 Dec;56(6):106177. doi: 10.1016/j.ijantimicag.2020.106177. Epub 2020 Sep 25. PMID: 32987103; PMCID: PMC7518233. 4: Bibi N, Gul S, Ali J, Kamal MA. Viroinformatics approach to explore the inhibitory mechanism of existing drugs repurposed to fight against COVID-19. Eur J Pharmacol. 2020 Oct 15;885:173496. doi: 10.1016/j.ejphar.2020.173496. Epub 2020 Aug 22. PMID: 32841640; PMCID: PMC7443089. 5: Adedeji AO, Severson W, Jonsson C, Singh K, Weiss SR, Sarafianos SG. Novel inhibitors of severe acute respiratory syndrome coronavirus entry that act by three distinct mechanisms. J Virol. 2013 Jul;87(14):8017-28. doi: 10.1128/JVI.00998-13. Epub 2013 May 15. PMID: 23678171; PMCID: PMC3700180.