Chlorin E6

• CAT Number: R043668
• CAS Number: 19660-77-6
• Molecular Formula: C34H36N4O6
• Molecular Weight: 596.684
• Purity: ≥95%
• Synonyms: (7S,8S)-3-Carboxy-5-(carboxymethyl)-13-ethenyl-18-ethyl-7,8-dihydro-2,8,12,17-tetramethyl-21H,23H-porphine-7-propanoic Acid;?18-Carboxy-20-(carboxymethyl)-13-ethyl-2β,3-dihydro-3β,7,12,17-tetramethyl-8-vinyl-2-porphinepropionic Acid; (2S-trans)-18-Ca
• Storage: -20°C
• IUPAC Name: (17S,18S)-18-(2-carboxyethyl)-20-(carboxymethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18,22,23-tetrahydroporphyrin-2-carboxylic acid
• InChI: 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/h7,12-14,17,21,35-36H,1,8-11H2,2-6H3,(H,39,40)(H,41,42)(H,43,44)/t17-,21-/m0/s1
• InChIKey: OYINILBBZAQBEV-UWJYYQICSA-N
• SMILES: CCC1=C2C=C3C(=C(C(=N3)C(=C4C(C(C(=N4)C=C5C(=C(C(=CC(=C1C)N2)N5)C=C)C)C)CCC(=O)O)CC(=O)O)C(=O)O)C

Chlorin E6 (CAS 19660-77-6) 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 its high absorption in the red spectral region , and 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).

Reference

1:Chlorin e6 conjugated copper sulfide nanoparticles for photodynamic combined photothermal therapy. Bharathiraja S, Manivasagan P, Moorthy MS, Bui NQ, Lee KD, Oh J.Photodiagnosis Photodyn Ther. 2017 Apr 29. pii: S1572-1000(17)30233-8. doi: 10.1016/j.pdpdt.2017.04.005. [Epub ahead of print] PMID: 28465165
2:Energy Transfer in Ce0.85Tb0.15F3 Nanoparticles-CTAB Shell-Chlorin e6 System. Losytskyy MY, Kuzmenko LV, Shcherbakov OB, Gamaleia NF, Marynin AI, Yashchuk VM.Nanoscale Res Lett. 2017 Dec;12(1):294. doi: 10.1186/s11671-017-2077-x. Epub 2017 Apr 24. PMID: 28445996 Free PMC Article
3:Quantification of a Novel Photosensitizer of Chlorin e6-C15-Monomethyl Ester in Beagle Dog Plasma Using HPLC: Application to Pharmacokinetic Studies. Li X, Wen J, Jiang J, Zhao X, Zhou T, Fan G.Molecules. 2017 Apr 26;22(5). pii: E693. doi: 10.3390/molecules22050693. PMID: 28445409 Free Article
4:Chlorin e6 mediated photodynamic inactivation for multidrug resistant Pseudomonas aeruginosa keratitis in mice in vivo. Wu MF, Deichelbohrer M, Tschernig T, Laschke MW, Szentmáry N, Hüttenberger D, Foth HJ, Seitz B, Bischoff M.Sci Rep. 2017 Mar 15;7:44537. doi: 10.1038/srep44537. PMID: 28295043 Free PMC Article
5:Size-Tunable Gd2O3@Albumin Nanoparticles Conjugating Chlorin e6 for Magnetic Resonance Imaging-Guided Photo-Induced Therapy. Zhou L, Yang T, Wang J, Wang Q, Lv X, Ke H, Guo Z, Shen J, Wang Y, Xing C, Chen H.Theranostics. 2017 Jan 25;7(3):764-774. doi: 10.7150/thno.15757. eCollection 2017. PMID: 28255365 Free PMC Article
6:Firmly anchored photosensitizer Chlorin e6 to layered double hydroxide nanoflakes for highly efficient photodynamic therapy in vivo. Yan L, Wang Z, Chen X, Gou XJ, Zhang Z, Zhu X, Lan M, Chen W, Zhu G, Zhang W.Chem Commun (Camb). 2017 Feb 16;53(15):2339-2342. doi: 10.1039/c6cc09510k. PMID: 28164197
7:Chlorin e6-Mediated Photodynamic Therapy Suppresses P. acnes-Induced Inflammatory Response via NFκB and MAPKs Signaling Pathway. Wang YY, Ryu AR, Jin S, Jeon YM, Lee MY.PLoS One. 2017 Jan 24;12(1):e0170599. doi: 10.1371/journal.pone.0170599. eCollection 2017. PMID: 28118375 Free PMC Article
8:Biodegradable nanocomplex from hyaluronic acid and arginine based poly(ester amide)s as the delivery vehicles for improved photodynamic therapy of multidrug resistant tumor cells: An in vitro study of the performance of chlorin e6 photosensitizer. Ji Y, Zhao J, Chu CC.J Biomed Mater Res A. 2017 May;105(5):1487-1499. doi: 10.1002/jbm.a.35982. Epub 2017 Mar 20. PMID: 27997760
9:Cerenkov Radiation Induced Photodynamic Therapy Using Chlorin e6-Loaded Hollow Mesoporous Silica Nanoparticles. Kamkaew A, Cheng L, Goel S, Valdovinos HF, Barnhart TE, Liu Z, Cai W.ACS Appl Mater Interfaces. 2016 Oct 12;8(40):26630-26637. Epub 2016 Sep 30. PMID: 27657487
10:Dual-Modality Positron Emission Tomography/Optical Image-Guided Photodynamic Cancer Therapy with Chlorin e6-Containing Nanomicelles. Cheng L, Kamkaew A, Sun H, Jiang D, Valdovinos HF, Gong H, England CG, Goel S, Barnhart TE, Cai W.ACS Nano. 2016 Aug 23;10(8):7721-30. doi: 10.1021/acsnano.6b03074. Epub 2016 Jul 28. PMID: 27459277