Chlorin E6

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

Description:Chlorin E6 is a natural molecule and a promising photosensitizer. Chlorin E6 usually can be made from Live chlorella and other green plants . Chlorin E6 is an attractive photodynamic therapy (PDT) drug candidate because of (1) its high absorption in the red spectral region , and (2) its low cost to make compared to other porphyrin-based PDT drugs . Chlorin E6 exhibits advantageous photophysical properties for PDT such as having long lifetimes in their photoexcited triplet states and high molar absorption in the red region of the visible spectrum. Moreover, a 664-nm laser light can penetrate tissue deeper that the 630-nm laser light used for Photofrin. Chlorin E6 is also an important starting material for making PDT drug Talaporfin sodium (mono-L-aspartyl chlorin e6, NPe6).

Price and Availability

Chlorin E6, purity > 95%, is in stock. The same day shipping out after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 500410Name: Chlorin E6CAS#: 19660-77-6Chemical Formula: C34H36N4O6Exact Mass: 596.26348Molecular Weight: 596.67Elemental Analysis:C, 68.44; H, 6.08; N, 9.39; O, 16.09

Synonym:CE6; Chlorin E6; chlorin e6.

IUPAC/Chemical Name: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]acetic acid

InChi Key:VAJLRIOJDADNAT-HHGNVTQFSA-N

InChi Code:InChI=1S/C34H36N4O6/c1-7-19-15(3)23-12-25-17(5)21(9-10-29(39)40)32(37-25)22(11-30(41)42)33-31(34(43)44)18(6)26(38-33)14-28-20(8-2)16(4)24(36-28)13-27(19)35-23/h7,12-14,17,21,35,38H,1,8-11H2,2-6H3,(H,39,40)(H,41,42)(H,43,44)/b23-12-,24-13-,25-12-,26-14-,27-13-,28-14-,32-22-,33-22-/t17-,21-/m0/s1

SMILES Code:O=C(O)C/C1=C2[C@@H](CCC(O)=O)[C@H](C)C(/C=C3C(C)=C(C=C)/C(N/3)=C/C(C(C)=C/4CC)=NC4=C/C5=C(C)C(C(O)=O)=C1N5)=N2

Technical Data

Additional Information

Photodynamic therapy (PDT) is currently being used as an alternative therapeutic modality for a variety of malignant tumors. This study was performed to show an efficient preparation of second generation of photosensitizer chlorin e6 (Ce6) with high yield and purity, and to test antitumor activity of Ce6-induced PDT (Ce6-PDT) both in vitro and in vivo using a rat tumor model. Three-week-old male Sprague-Dawley (SD) rats were inoculated s.c. on the right flank with 5x106 RK3E-ras cells. The animals were admin-istered i.v. with Ce6 (10 mg/kg) and 24 h later, PDT was performed using a laser diode at a light dose of 100 J/cm2. Ce6-PDT generated reactive oxygen species and led to significant growth inhibition in RK3E-ras cell. In addition, Ce6-PDT induced apoptosis through the activation of caspase-3 and its downstream target, PARP cleavage. The protein level of anti-apoptotic bcl-2 was also reduced by Ce6-PDT in RK3E-ras cells. In in vivo experiments, application of Ce6-PDT led to a significant reduction of tumor size. PCNA immunostaining and TUNEL assay revealed that Ce6-PDT inhibited tumor cell proliferation and increased apoptosis. These findings suggest that the newly purified Ce6-PDT can effectively arrest tumor growth by inhibiting cell proliferation and inducing apoptosis.  ( source: Oncology Reports, 2009, 22(5). 1085-1091. Doi: 10.3892/or_00000540. Efficient preparation of highly pure chlorin e6 and its photodynamic anti-cancer activity in a rat tumor model. Authors: Yeon-Hee Moon, Seong-Min Kwon, Hyo-Jun Kim, Kwan-Young Jung, Jong-Hwan Park, Soo-A Kim, Yong-Chul Kim, Sang-Gun Ahn, Jung-Hoon Yoon. Affiliations: Department of Pathology, School of Dentistry, Chosun University, Gwangju 500-759, Korea, http://www.spandidos-publications.com/or/22/5/1085 ).Photodynamic therapy (PDT) is currently being used as an alternative therapeutic modality for a variety of malignant tumors. This study was performed to show an efficient preparation of second generation of photosensitizer chlorin e6 (Ce6) with high yield and purity, and to test antitumor activity of Ce6-induced PDT (Ce6-PDT) both in vitro and in vivo using a rat tumor model. Three-week-old male Sprague-Dawley (SD) rats were inoculated s.c. on the right flank with 5x106 RK3E-ras cells. The animals were admin-istered i.v. with Ce6 (10 mg/kg) and 24 h later, PDT was performed using a laser diode at a light dose of 100 J/cm2. Ce6-PDT generated reactive oxygen species and led to significant growth inhibition in RK3E-ras cell. In addition, Ce6-PDT induced apoptosis through the activation of caspase-3 and its downstream target, PARP cleavage. The protein level of anti-apoptotic bcl-2 was also reduced by Ce6-PDT in RK3E-ras cells. In in vivo experiments, application of Ce6-PDT led to a significant reduction of tumor size. PCNA immunostaining and TUNEL assay revealed that Ce6-PDT inhibited tumor cell proliferation and increased apoptosis. These findings suggest that the newly purified Ce6-PDT can effectively arrest tumor growth by inhibiting cell proliferation and inducing apoptosis.  ( source: Oncology Reports, 2009, 22(5). 1085-1091.Doi: 10.3892/or_00000540.Efficient preparation of highly pure chlorin e6 and its photodynamic anti-cancer activity in a rat tumor model. Authors: Yeon-Hee Moon, Seong-Min Kwon, Hyo-Jun Kim, Kwan-Young Jung, Jong-Hwan Park, Soo-A Kim, Yong-Chul Kim, Sang-Gun Ahn, Jung-Hoon Yoon. Affiliations: Department of Pathology, School of Dentistry, Chosun University, Gwangju 500-759, Korea, http://www.spandidos-publications.com/or/22/5/1085 ).        Methods to make Chlorin E6make Chlorin E6Chlorin E6 is a natural product, and usually can be made from Live chlorella (Chlorella ellipsoidea, see the following pictures)Chlorin E6 is a natural product, and usually can be made from Live chlorella (Chlorella ellipsoidea, see the following pictures)              The following procedure was reported in Oncology Reports, 2009, 22(5). 1085-1091 by Korean scientists Yeon-Hee Moon et al.   Live chlorella (Chlorella ellipsoidea) 100 g (dried weight) was sequentially washed with 500 ml of water and 300 ml of 50% ethanol in water to remove polar materials and the residue was extracted twice with 500 ml of 100% ethanol to obtain chlorophyll a rich fraction (extraction yield 4.3%). Stirring the combined ethanol solution of chlorophyll a in 1 N HCl (pH 2.5) for 3 h at room temperature afforded pheophytin in the form of precipitates. The precipitate was dissolved in dichloromethane washed with distilled water, dried with anhydrous sodium sulfate, and rotary-evaporated to dryness. The residue was purified by a chromatography using neutral alumina (Aldrich, Brockmann, ~150 mesh) with a gradient elution from 30% dichloromethane in n-hexane to 100% dichloromethane. The main green band was collected and evaporated to dryness. The crystalline powder was dissolved in acetone, adjusted pH 12.0 with 1 N NaOH, and stirred for 12 h. The precipitated Ce6 was filtered, washed with acetone and dissolved in 100 ml of water, and filtered to remove insoluble impurity. After lyophilization of the filtered water solution, a fine black powder of Ce6 was obtained. The purity of Ce6 is 93-98% (yield of Ce6: 1% from dried weight of chlorella).The following procedure was reported in Live chlorella (Chlorella ellipsoidea) 100 g (dried weight) was sequentially washed with 500 ml of water and 300 ml of 50% ethanol in water to remove polar materials and the residue was extracted twice with 500 ml of 100% ethanol to obtain chlorophyll a rich fraction (extraction yield 4.3%). Stirring the combined ethanol solution of chlorophyll a in 1 N HCl (pH 2.5) for 3 h at room temperature afforded pheophytin in the form of precipitates. The precipitate was dissolved in dichloromethane washed with distilled water, dried with anhydrous sodium sulfate, and rotary-evaporated to dryness. The residue was purified by a chromatography using neutral alumina (Aldrich, Brockmann, ~150 mesh) with a gradient elution from 30% dichloromethane in n-hexane to 100% dichloromethane. The main green band was collected and evaporated to dryness. The crystalline powder was dissolved in acetone, adjusted pH 12.0 with 1 N NaOH, and stirred for 12 h. The precipitated Ce6 was filtered, washed with acetone and dissolved in 100 ml of water, and filtered to remove insoluble impurity. After lyophilization of the filtered water solution, a fine black powder of Ce6 was obtained. The purity of Ce6 is 93-98% (yield of Ce6: 1% from dried weight of chlorella).    

References

1: Li Q, Wang X, Wang P, Zhang K, Wang H, Feng X, LiuQ. Efficacy of Chlorin e6-Mediated Sono-Photodynamic Therapy on 4T1Cells. Cancer Biother Radiopharm. 2013 Nov 9. [Epub ahead of print]PubMed PMID: 24206161.

2: Li Z, Wang C, Cheng L, Gong H, Yin S, Gong Q, Li Y, Liu Z.PEG-functionalized iron oxide nanoclusters loaded with chlorin e6 fortargeted, NIR light induced, photodynamic therapy. Biomaterials. 2013Dec;34(36):9160-70. doi: 10.1016/j.biomaterials.2013.08.041. Epub 2013Sep 3. PubMed PMID: 24008045.

3: Skripka A, Valanciunaite J, Dauderis G, Poderys V, Kubiliute R,Rotomskis R. Two-photon excited quantum dots as energy donors forphotosensitizer chlorin e6. J Biomed Opt. 2013 Jul;18(7):078002. doi:10.1117/1.JBO.18.7.078002. PubMed PMID: 23864017.

4: Wang H, Wang X, Wang P, Zhang K, Yang S, Liu Q. Ultrasound enhancesthe efficacy of chlorin E6-mediated photodynamic therapy in MDA-MB-231cells. Ultrasound Med Biol. 2013 Sep;39(9):1713-24. doi:10.1016/j.ultrasmedbio.2013.03.017. Epub 2013 Jul 3. PubMed PMID:23830103.

5: Kimani S, Ghosh G, Ghogare A, Rudshteyn B, Bartusik D, Hasan T, GreerA. Synthesis and characterization of mono-, di-, and tri-poly(ethyleneglycol) chlorin e6 conjugates for the photokilling of human ovariancancer cells. J Org Chem. 2012 Dec 7;77(23):10638-47. doi:10.1021/jo301889s. Epub 2012 Nov 14. PubMed PMID: 23126407; PubMedCentral PMCID: PMC3815657.

6: Chen B, Zheng R, Liu D, Li B, Lin J, Zhang W. The tumor affinity ofchlorin e6 and its sonodynamic effects on non-small cell lung cancer.Ultrason Sonochem. 2013 Mar;20(2):667-73. doi:10.1016/j.ultsonch.2012.09.008. Epub 2012 Oct 2. PubMed PMID: 23073382.

7: Saboktakin MR, Tabatabaie RM, Amini FS, Maharramov A, Ramazanov MA.Synthesis and in-vitro photodynamic studies of the superparamagneticchitosan hydrogel/chlorin E6 nanocarriers. Med Chem. 2013Feb;9(1):112-7. PubMed PMID: 22762166.

8: Li P, Zhou G, Zhu X, Li G, Yan P, Shen L, Xu Q, Hamblin MR.Photodynamic therapy with hyperbranched poly(ether-ester) chlorin(e6)nanoparticles on human tongue carcinoma CAL-27 cells. PhotodiagnosisPhotodyn Ther. 2012 Mar;9(1):76-82. doi: 10.1016/j.pdpdt.2011.08.001.Epub 2011 Oct 4. PubMed PMID: 22369732; PubMed Central PMCID:PMC3292741.

9: Shim G, Lee S, Kim YB, Kim CW, Oh YK. Enhanced tumor localization andretention of chlorin e6 in cationic nanolipoplexes potentiate the tumorablation effects of photodynamic therapy. Nanotechnology. 2011 Sep7;22(36):365101. doi: 10.1088/0957-4484/22/36/365101. Epub 2011 Aug 12.PubMed PMID: 21841215.

10: Shi H, Liu Q, Qin X, Wang P, Wang X. Pharmacokinetic study of anovel sonosensitizer chlorin-e6 and its sonodynamic anti-cancer activityin hepatoma-22 tumor-bearing mice. Biopharm Drug Dispos. 2011Sep;32(6):319-32. doi: 10.1002/bdd.761. Epub 2011 Aug 3. PubMed PMID:21815170.