Fimaporfin

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

MedKoo CAT#: 206129

CAS#: 1443547-43-0

Description: Fimaporfin, also known as TPCS2a, is a potent chlorin-based photosensitizer, Fimaporfin is consisted of a mixture of three isomers A, B and C (25%,50%,25%). Fimaporfin has been developed by di-imide reduction of disulfonated tetraphenyl porphine (TPPS(2a)). The synthesized TPCS(2a) contains 3 isomers as shown by HPLC with low (<4%) inter-batch variation with respect to isomer formation, less than 0.5% (w/w) of the starting material TPPS(2a) and absorbs light at 652 nm. TPCS(2a) was found to be a clinically suitable PCI photosensitizer for photochemical activation of molecules that do not readily penetrate the cellular plasma membrane.


Chemical Structure

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Fimaporfin
CAS# 1443547-43-0

Theoretical Analysis

MedKoo Cat#: 206129
Name: Fimaporfin
CAS#: 1443547-43-0
Chemical Formula: C44H32N4O6S2
Exact Mass: 776.17633
Molecular Weight: 776.88
Elemental Analysis: C, 68.02; H, 4.15; N, 7.21; O, 12.36; S, 8.25

Size Price Shipping out time Quantity
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Pricing updated 2021-02-24. Prices are subject to change without notice.

Fimaporfin is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Synonym: Fimaporfin; TPCS2a; Disulfonated tetraphenyl chlorin.

IUPAC/Chemical Name: NONE

Appearance:
Solid powder

Purity:
>98% (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 DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 776.88 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.

Select a batch to recalculate based on the batch molecular weight:
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: Baglo Y, Hagen L, Høgset A, Drabløs F, Otterlei M, Gederaas OA. Enhanced efficacy of bleomycin in bladder cancer cells by photochemical internalization. Biomed Res Int. 2014;2014:921296. doi: 10.1155/2014/921296. Epub 2014 Jun 30. PubMed PMID: 25101299; PubMed Central PMCID: PMC4101207.

2: Bostad M, Kausberg M, Weyergang A, Olsen CE, Berg K, Høgset A, Selbo PK. Light-Triggered, Efficient Cytosolic Release of IM7-Saporin Targeting the Putative Cancer Stem Cell Marker CD44 by Photochemical Internalization. Mol Pharm. 2014 Aug 4;11(8):2764-76. doi: 10.1021/mp500129t. Epub 2014 Jul 2. PubMed PMID: 24960585.

3: Weyergang A, Cheung LH, Rosenblum MG, Mohamedali KA, Peng Q, Waltenberger J, Berg K. Photochemical internalization augments tumor vascular cytotoxicity and specificity of VEGF(121)/rGel fusion toxin. J Control Release. 2014 Apr 28;180:1-9. doi: 10.1016/j.jconrel.2014.02.003. Epub 2014 Feb 13. PubMed PMID: 24531010.

4: Lund K, Bostad M, Skarpen E, Braunagel M, Kiprijanov S, Krauss S, Duncan A, Høgset A, Selbo PK. The novel EpCAM-targeting monoclonal antibody 3-17I linked to saporin is highly cytotoxic after photochemical internalization in breast, pancreas and colon cancer cell lines. MAbs. 2014 Jul-Aug;6(4):1038-50. PubMed PMID: 24525727.

5: Aubertin K, Bonneau S, Silva AK, Bacri JC, Gallet F, Wilhelm C. Impact of photosensitizers activation on intracellular trafficking and viscosity. PLoS One. 2013 Dec 27;8(12):e84850. doi: 10.1371/journal.pone.0084850. eCollection 2013. PubMed PMID: 24386423; PubMed Central PMCID: PMC3874004.

6: Håkerud M, Waeckerle-Men Y, Selbo PK, Kündig TM, Høgset A, Johansen P. Intradermal photosensitisation facilitates stimulation of MHC class-I restricted CD8 T-cell responses of co-administered antigen. J Control Release. 2014 Jan 28;174:143-50. doi: 10.1016/j.jconrel.2013.11.017. Epub 2013 Nov 23. PubMed PMID: 24280261.

7: Arentsen HC, Falke J, Høgset A, Oosterwijk E, Alfred Witjes J. The effect of photochemical internalization of bleomycin in the treatment of urothelial carcinoma of the bladder: an in vitro study. Urol Oncol. 2014 Jan;32(1):49.e1-6. doi: 10.1016/j.urolonc.2013.07.005. Epub 2013 Oct 17. PubMed PMID: 24140247.

8: Stratford EW, Bostad M, Castro R, Skarpen E, Berg K, Høgset A, Myklebost O, Selbo PK. Photochemical internalization of CD133-targeting immunotoxins efficiently depletes sarcoma cells with stem-like properties and reduces tumorigenicity. Biochim Biophys Acta. 2013 Aug;1830(8):4235-43. doi: 10.1016/j.bbagen.2013.04.033. Epub 2013 May 2. PubMed PMID: 23643966.

9: Bostad M, Berg K, Høgset A, Skarpen E, Stenmark H, Selbo PK. Photochemical internalization (PCI) of immunotoxins targeting CD133 is specific and highly potent at femtomolar levels in cells with cancer stem cell properties. J Control Release. 2013 Jun 28;168(3):317-26. doi: 10.1016/j.jconrel.2013.03.023. Epub 2013 Apr 6. PubMed PMID: 23567040.

10: Berg K, Nordstrand S, Selbo PK, Tran DT, Angell-Petersen E, Høgset A. Disulfonated tetraphenyl chlorin (TPCS2a), a novel photosensitizer developed for clinical utilization of photochemical internalization. Photochem Photobiol Sci. 2011 Oct;10(10):1637-51. doi: 10.1039/c1pp05128h. Epub 2011 Jul 20. PubMed PMID: 21773635.



Additional Information

The absorption and fluorescence spectra of TPCS(2a) were examined in a range of solvents together with fluorescence lifetime measurements. The fluorescence lifetime of TPCS(2a) was found to be 8.5 ns in methanol, whereas non-exponential decays were observed in distilled water due to sensitiser dimerisation. The singlet oxygen quantum yield of TPCS(2a) was determined as 0.62 in deuterated methanol by direct observation of singlet oxygen phosphorescence. In a human oral squamous carcinoma (HN5) cell line, intracellular co-localisation of TPCS(2a) and Alexa488-labelled saporin, a macromolecular toxin, was observed corresponding predominantly to a lysosomal distribution. Intracellular fluorescence redistribution of TPCS(2a) and Alexa488-saporin was observed after 405 nm irradiation. Using two-photon confocal microscopy at 840 nm, and fluorescence lifetime imaging (FLIM), the lifetime was measured as 6 ns in HN5 cells. PCI using TPCS(2a) was shown to be very effective, and a synergistic increase in saporin toxicity was achieved in HN5 cells where viability was significantly reduced after light exposure compared to saporin (25 nM) treatment alone. The results demonstrate the favourable photophysical and photobiological properties of TPCS(2a) for PCI, which induces the relocalisation of a macromolecular anti-cancer toxin inside cells and significantly enhances cell death. ( Photochem Photobiol Sci. 2013 Mar;12(3):519-26.)