Chlorin E6
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MedKoo CAT#: 500410

CAS#: 19660-77-6

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).


Chemical Structure

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Chlorin E6
CAS# 19660-77-6

Theoretical Analysis

MedKoo Cat#: 500410
Name: Chlorin E6
CAS#: 19660-77-6
Chemical Formula: C34H36N4O6
Exact Mass: 596.26348
Molecular Weight: 596.67
Elemental Analysis: C, 68.44; H, 6.08; N, 9.39; O, 16.09

Price and Availability

Size Price Availability Quantity
100.0mg USD 90.0 Ready to ship
200.0mg USD 150.0 Ready to ship
500.0mg USD 250.0 Ready to ship
1.0g USD 450.0 Ready to ship
2.0g USD 810.0 Ready to ship
5.0g USD 1820.0 Ready to ship
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Synonym: CE6; Chlorin E6; chlorin e6; Chlorine 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)=N\2

Appearance: black solid powder

Purity: >9 5 % (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

Biological target: Active against S. aureus, P. aeruginosa, E. coli, and S. typhimurium when used at a concentration of 20 µM in combination with photodynamic therapy (PDT).
In vitro activity: PDT may be a substitute treatment for cutaneous leishmaniasis. Chlorin E6 effected the viability and mitochondrial activity of L. major and L. braziliensis promastigotes. In addition, Chlorin E6 remained inside the parasites after an hour of incubation. Mitochondirial activity was found to be affected by interaction with chlorin, in the dark, and after PDT. However, changes in mitochondrial activity of incubated groups with the chlorin in the dark did not lead to cellular death. Only the groups treated with PDT had their viability affected. Reference: Photodiagnosis Photodyn Ther. 2016 Sep;15:19-24. https://www.sciencedirect.com/science/article/abs/pii/S1572100016300436?via%3Dihub
In vivo activity: Following corneal epithelium scratches, mouse corneas were infected with the multidrug resistant (MDR) P. aeruginosa strain PA54. 24 hours later, 0% (for control group), 0.01%, 0.05% or 0.1% Chlorin e6 (Ce6) was combined with red light for photodynamic inactivation (PDI). 1 hour or 2 days later, entire mouse eyes were enucleated and homogenized for counting colony forming units (CFU) of P. aeruginosa. For comparison, 0.1% Ce6 mediated PDI was started at 12 hours post infection, and 0.005% methylene blue mediated PDI 24 hours post infection. Compared to the control, CFU 1 hour after PDI started 24 hours post infection in the 0.01% Ce6 and 0.05% Ce6 groups were significantly lower (more than one log10 reduction), the CFU 2 days post PDI higher in the 0.1% Ce6 group, clinical score lower in the 0.1% Ce6 group at 1 day post PDI. Reference: Sci Rep. 2017; 7: 44537. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5353637/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DSMO 30.0 50.28
DMSO:PBS (pH 7.2) (1:6) 0.14 0.23
DMF 30.0 50.28

Preparing Stock Solutions

The following data is based on the product molecular weight 596.67 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. Paul S, Heng PWS, Chan LW. Improvement in dissolution rate and photodynamic efficacy of chlorin e6 by sucrose esters as drug carrier in nanosuspension formulation: optimisation and in vitro characterisation. J Pharm Pharmacol. 2018 Sep;70(9):1152-1163. doi: 10.1111/jphp.12947. Epub 2018 Jun 25. PMID: 29943465. 2. Mohsenian NB, Shanei A, Alavi SJ, Kheirollahi M, Nia AH, Tavakoli MB. Mn-doped ZnS quantum dots-chlorin e6 shows potential as a treatment for chondrosarcoma: an in vitro study. IET Nanobiotechnol. 2019 Jun;13(4):387-391. doi: 10.1049/iet-nbt.2018.5387. PMID: 31171743. 3. Son J, Yi G, Kwak MH, Yang SM, Park JM, Lee BI, Choi MG, Koo H. Gelatin-chlorin e6 conjugate for in vivo photodynamic therapy. J Nanobiotechnology. 2019 Apr 5;17(1):50. doi: 10.1186/s12951-019-0475-1. PMID: 30953510; PMCID: PMC6449946. 4. Wu MF, Deichelbohrer M, Tschernig T, Laschke MW, Szentmáry N, Hüttenberger D, Foth HJ, Seitz B, Bischoff M. Chlorin e6 mediated photodynamic inactivation for multidrug resistant Pseudomonas aeruginosa keratitis in mice in vivo. Sci Rep. 2017 Mar 15;7:44537. doi: 10.1038/srep44537. PMID: 28295043; PMCID: PMC5353637.
In vitro protocol: 1. Paul S, Heng PWS, Chan LW. Improvement in dissolution rate and photodynamic efficacy of chlorin e6 by sucrose esters as drug carrier in nanosuspension formulation: optimisation and in vitro characterisation. J Pharm Pharmacol. 2018 Sep;70(9):1152-1163. doi: 10.1111/jphp.12947. Epub 2018 Jun 25. PMID: 29943465. 2. Mohsenian NB, Shanei A, Alavi SJ, Kheirollahi M, Nia AH, Tavakoli MB. Mn-doped ZnS quantum dots-chlorin e6 shows potential as a treatment for chondrosarcoma: an in vitro study. IET Nanobiotechnol. 2019 Jun;13(4):387-391. doi: 10.1049/iet-nbt.2018.5387. PMID: 31171743.
In vivo protocol: 1. Son J, Yi G, Kwak MH, Yang SM, Park JM, Lee BI, Choi MG, Koo H. Gelatin-chlorin e6 conjugate for in vivo photodynamic therapy. J Nanobiotechnology. 2019 Apr 5;17(1):50. doi: 10.1186/s12951-019-0475-1. PMID: 30953510; PMCID: PMC6449946. 2. Wu MF, Deichelbohrer M, Tschernig T, Laschke MW, Szentmáry N, Hüttenberger D, Foth HJ, Seitz B, Bischoff M. Chlorin e6 mediated photodynamic inactivation for multidrug resistant Pseudomonas aeruginosa keratitis in mice in vivo. Sci Rep. 2017 Mar 15;7:44537. doi: 10.1038/srep44537. PMID: 28295043; PMCID: PMC5353637.

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Gong B, Shen Y, Li H, Li X, Huan X, Zhou J, Chen Y, Wu J, Li W. Thermo-responsive polymer encapsulated gold nanorods for single continuous wave laser-induced photodynamic/photothermal tumour therapy. J Nanobiotechnology. 2021 Feb 8;19(1):41. doi: 10.1186/s12951-020-00754-8. PMID: 33557807; PMCID: PMC7869504.

1: Li Q, Wang X, Wang P, Zhang K, Wang H, Feng X, Liu Q. Efficacy of Chlorin e6-Mediated Sono-Photodynamic Therapy on 4T1 Cells. 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 for targeted, NIR light induced, photodynamic therapy. Biomaterials. 2013 Dec;34(36):9160-70. doi: 10.1016/j.biomaterials.2013.08.041. Epub 2013 Sep 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 for photosensitizer 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 enhances the efficacy of chlorin E6-mediated photodynamic therapy in MDA-MB-231 cells. 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, Greer A. Synthesis and characterization of mono-, di-, and tri-poly(ethylene glycol) chlorin e6 conjugates for the photokilling of human ovarian cancer cells. J Org Chem. 2012 Dec 7;77(23):10638-47. doi: 10.1021/jo301889s. Epub 2012 Nov 14. PubMed PMID: 23126407; PubMed Central PMCID: PMC3815657.

6: Chen B, Zheng R, Liu D, Li B, Lin J, Zhang W. The tumor affinity of chlorin 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 superparamagnetic chitosan hydrogel/chlorin E6 nanocarriers. Med Chem. 2013 Feb;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. Photodiagnosis Photodyn 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 and retention of chlorin e6 in cationic nanolipoplexes potentiate the tumor ablation effects of photodynamic therapy. Nanotechnology. 2011 Sep 7;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 a novel sonosensitizer chlorin-e6 and its sonodynamic anti-cancer activity in hepatoma-22 tumor-bearing mice. Biopharm Drug Dispos. 2011 Sep;32(6):319-32. doi: 10.1002/bdd.761. Epub 2011 Aug 3. PubMed PMID: 21815170.



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 E6
make Chlorin E6
Chlorin 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).