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Chlorin e6

(Synonyms: 二氢卟吩E6,Ce6) 目录号 : GC43244

A photosensitizer

Chlorin e6 Chemical Structure

Cas No.:19660-77-6

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Sample solution is provided at 25 µL, 10mM.

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实验参考方法

Cell experiment [1]:

Cell lines

Human alveolar adenocarcinoma cells A549

Preparation Method

The 96-well plates were treated with 50μL of agar solution (1.5%(w/v)) made in serum free Dulbecco’s Modified Eagle’s Medium. A549 cells(1×104/well) were seeded in 96-well plates, centrifuged at 1500rcf for 15min at 25℃. The spheroids of 400-500μm size obtained after 4-5 days were utilized for the study

Reaction Conditions

3μg/mL for 4h(Growth Inhibition, Live/Dead Cell Assay), a serial concentration for 12h(0.5-3μg/mL In Vitro Phototoxicity)

Applications

A549 3D spheroids treated with Chlorin e6 micelles showed significant inhibition in growth, enhanced phototoxicity, and cellular apoptosis in comparison to free Chlorin e6.

Animal experiment [2]:

Animal models

SCC-7 tumor-bearing mice(1×106 SCC-7 cells(80μL) were injected into the left femoral regions of 4-week-old C3H/HeN male mice)

Preparation Method

Free Chlorin e6, and gelatin-Chlorin e6 solution were injected into the tail vein when the tumor volume reached approximately 150±30mm3. At 4 and 12h after the sample injection, the tumor site of each mouse was irradiated with a red laser (658nm, 0.3W, 200J). Then, the tumor sizes of all mice were monitored over 14 days.

Dosage form

Free Chlorin e6, gelatin-Ce6 2μM, or gelatin-Ce6 8μM solution, each containing 2.5mg/kg of Chlorin e6

Applications

In vivo tumor accumulation of gelatin-Chlorin e6-2 was much higher than that of free Chlorin e6 or gelatin-Chlorin e6-8 after intravenous injection into mice. After laser irradiation to the tumor site, gelatin-Chlorin e6-2 showed superior tumor suppression, indicating an enhanced PDT effect.

References:

[1]. Kumari P, Paul M, et al. Chlorin e6 Conjugated Methoxy-Poly (Ethylene Glycol)-Poly(D,L-Lactide) Glutathione Sensitive Micelles for Photodynamic Therapy. Pharm Res. 2020;37(2):18. Published 2020 Jan 2.

[2]. Son J, Yi G, et al. Gelatin-chlorin e6 conjugate for in vivo photodynamic therapy. J Nanobiotechnology. 2019;17(1):50. Published 2019 Apr 5.

产品描述

Chlorin e6(Ce6) is a second-generation photosensitizer. Compared to the first-generation photosensitizers, Chlorin e6 has the advantage of efficiently absorbing longer light wavelengths, which is favorable for deeper tissue penetration[1] .Chlorin e6-based photosensitizers are widely used in antitumor photodynamic therapy(PDT) due to high quantum output of single oxygen and a strong absorption band in a red region[2]

Chlorin e6-mediated PDT inhibits adipocyte differentiation and lipogenesis via regulating AMPK in 3T3-L1 cells, indicated that Chlorin e6-mediated PDT might serve as a potential therapy for the treatment of obesity and obesity-associated diseases[2]. Chlorin e6-Fu/AL@GG hydrogel can be a feasible nanocarrier for Chlorin e6-assisted PDT that possesses an excellent capability to selectively kill colon cancer cells[3]

Chlorin e6-loaded PEG-PCL nanoemulsions (Ce6-PCL-NEs) showed efficient cellular uptake and, upon laser irradiation, generated singlet oxygen to kill tumor cells. Particularly, Chlorin e6-PCL-NEs showed prolonged blood circulation and about 60% increased tumor accumulation compared to free Chlorin e6 after intravenous injection to 4T1 tumor-bearing mice(2.5mg/kg), indicated the promising potential of Chlorin e6-PCL-NEs for efficient PDT and in vivo drug delivery to tumor tissue[4]. Chlorin e6 nano-precipitations (Chlorin e6 NPs) can be prepared by a one-pot method for effective photodynamic therapy of colorectal cancer. The HT-29 tumour-bearing mice were randomly divided into three groups and were administered intravenously with saline, free Chlorin e6 and Chlorin e6 NPs (5mg/kg Chlorin e6) once every 2 days for 2 weeks. The laser was applied three times 24h post injection (680 nm, 0.5 W/cm2 for 5 min). Chlorin e6 NPs showed significantly enhanced anticancer benefits compared to free Chlorin e6, which almost obtained full ablation of tumours at the end of the study[5]

References:
[1].Ryu AR, Kim YW, et al. Chlorin e6-mediated photodynamic therapy modulates adipocyte differentiation and lipogenesis in 3T3-L1 cells. Photodiagnosis Photodyn Ther. 2020;31:101917.
[2].Papayan G.V., Akopov А.L. Photodynamic theranostics of central lung cancer: capabilities of early diagnosis and minimally invasive therapy (review). Sovremennye tehnologii v medicine 2021; 13(6): 78
[3].Karuppusamy S, Hyejin K, et al. Nanoengineered chlorin e6 conjugated with hydrogel for photodynamic therapy on cancer. Colloids Surf B Biointerfaces. 2019;181:778-788.
[4].Park C, Yoo J, et al. Chlorin e6-Loaded PEG-PCL Nanoemulsion for Photodynamic Therapy and In Vivo Drug Delivery. Int J Mol Sci. 2019;20(16):3958. Published 2019 Aug 14.
[5].Miao Z, Wang Y, et al. One-pot synthesis chlorin e6 nano-precipitation for colorectal cancer treatment Ce6 NPs for colorectal cancer treatment. IET Nanobiotechnol. 2021;15(8):680-685.

Chlorin e6(Ce6) 是第二代光敏剂。与第一代光敏剂相比,Chlorin e6具有高效吸收更长波长光的优势,有利于更深的组织穿透[1]。基于Chlorin e6的光敏剂广泛应用于抗肿瘤光动力治疗(PDT) 由于单氧的高量子输出和红色区域的强吸收带[2]

Chlorin e6 介导的 PDT 通过调节 3T3-L1 细胞中的 AMPK 抑制脂肪细胞分化和脂肪生成,表明 Chlorin e6 介导的 PDT 可能作为治疗肥胖和肥胖相关疾病的潜在疗法[2 ]。 Chlorin e6-Fu/AL@GG 水凝胶可作为 Chlorin e6 辅助 PDT 的纳米载体,具有出色的选择性杀死结肠癌细胞的能力[3]

负载二氢卟酚 e6 的 PEG-PCL 纳米乳剂 (Ce6-PCL-NEs) 显示出有效的细胞摄取,并且在激光照射下产生单线态氧以杀死肿瘤细胞。特别是,在静脉注射给 4T1 荷瘤小鼠(2.5mg/kg)后,与游离的 Chlorin e6 相比,Chlorin e6-PCL-NEs 显示出延长的血液循环和约 60% 的肿瘤积累,表明 Chlorin e6-PCL-用于有效 PDT 和体内药物递送至肿瘤组织的 NEs[4]。可通过一锅法制备二氢卟酚 e6 纳米沉淀物 (Chlorin e6 NPs),用于结直肠癌的有效光动力治疗。 HT-29 荷瘤小鼠随机分为三组,每 2 天一次静脉注射生理盐水、游离 Chlorin e6 和 Chlorin e6 NPs (5mg/kg Chlorin e6),持续 2 周。注射后 24 小时应用激光 3 次(680 nm,0.5 W/cm2,持续 5 分钟)。与游离的 Chlorin e6 相比,Chlorin e6 NPs 显示出显着增强的抗癌益处,后者在研究结束时几乎完全消融了肿瘤[5]

Chemical Properties

Cas No. 19660-77-6 SDF
别名 二氢卟吩E6,Ce6
化学名 (7S,8S)-3-carboxy-5-(carboxymethyl)-13-ethenyl-18-ethyl-7,8-dihydro-2,8,12,17-tetramethyl-21H,23H-porphine-7-propanoic acid
Canonical SMILES CC1=C2[NH]C(/C(CC(O)=O)=C([C@@H](CCC(O)=O)[C@@H]3C)\[N]=C3/C=C4[NH]/C(C(C=C)=C\4C)=C\C5=[N]/C(C(CC)=C5C)=C\2)=C1C(O)=O
分子式 C34H36N4O6 分子量 596.7
溶解度 DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:6): 0.14 mg/ml,Ethanol: slightly soluble 储存条件 Store at -20°C
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1 mM 1.6759 mL 8.3794 mL 16.7588 mL
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Research Update

Chlorin e6: A Promising Photosensitizer in Photo-Based Cancer Nanomedicine

ACS Appl Bio Mater 2023 Feb 20;6(2):349-364.PMID:36700563DOI:10.1021/acsabm.2c00891.

Conventional cancer treatment modalities are often associated with major therapeutic limitations and severe side effects. Photodynamic therapy is a localized noninvasive mode of treatment that has given a different direction to cancer research due to its effectivity against a wide range of cancers and minimal side effects. A photosensitizer is the key component of photodynamic therapy (PDT) that generates cytotoxic reactive oxygen species to eradicate cancer cells. As the therapeutic effectivity of PDT greatly depends upon the photosensitizer, great efforts have been made to search for an ideal photosensitizer. Chlorin e6 is a FDA approved second generation photosensitizer that meets the desired clinical properties for PDT. It is known for its high reactive oxygen species (ROS) generation ability and anticancer potency against many types of cancer. Hydrophobicity is a major drawback of Ce6 that leads to its poor biodistribution and rapid clearance from the circulatory system. To overcome this drawback, researchers have designed and fabricated several types of nanosystems, which can enhance Ce6 solubility and thereby enhance its bioavailability. These nanosystems also improve tumor accumulation of Ce6 by selectively targeting the cancer cells through passive and active targeting. In addition, Ce6 has been employed in many combination therapies like chemo-photodynamic therapy, photoimmunotherapy, and combined photodynamic-photothermal therapy. A combination therapy is more curative than a single therapy due to the synergistic effects of individual therapies. Ce6-based nanosystems for combination therapies have shown excellent results in various studies and provide a promising platform for cancer treatment.

Chlorin e6-Biotin Conjugates for Tumor-Targeting Photodynamic Therapy

Molecules 2021 Dec 3;26(23):7342.PMID:34885922DOI:10.3390/molecules26237342.

To improve the tumor-targeting efficacy of photodynamic therapy, biotin was conjugated with Chlorin e6 to develop a new tumor-targeting photosensitizer, Ce6-biotin. The Ce6-biotin had good water solubility and low aggregation. The singlet-oxygen generation rate of Ce6-biotin was slightly increased compared to Ce6. Flow cytometry and confocal laser scanning microscopy results confirmed Ce6-biotin had higher binding affinity toward biotin-receptor-positive HeLa human cervical carcinoma cells than its precursor, Ce6. Due to the BR-targeting ability of Ce6-biotin, it exhibited stronger cytotoxicity to HeLa cells upon laser irradiation. The IC50 against HeLa cells of Ce6-biotin and Ce6 were 1.28 µM and 2.31 µM, respectively. Furthermore, both Ce6-biotin and Ce6 showed minimal dark toxicity. The selectively enhanced therapeutic efficacy and low dark toxicity suggest that Ce6-biotin is a promising PS for BR-positive-tumor-targeting photodynamic therapy.

Chlorin e6 conjugated chitosan as an efficient photoantimicrobial agent

Int J Biol Macromol 2021 Jul 31;183:1309-1316.PMID:34000311DOI:10.1016/j.ijbiomac.2021.05.085.

The development of antibacterial agents with high bacteria-binding capability and antibacterial efficiency is highly desirable. Herein, cationic polysaccharide chitosan (CS) was combined with photosensitizer Chlorin e6 (Ce6) to construct a novel photodynamic antibacterial agent (CS-Ce6 conjugates) for combating gram-positive bacteria Staphylococcus aureus (S. aureus) and gram-negative bacteria Escherichia coli (E. coli). CS-Ce6 conjugates with different degrees of substitution (DS) were synthesized and characterized by a spectroscopic method and organic elemental analysis to understand the relationship between structure and antibacterial effect. CS-Ce6 conjugates revealed good reactive oxygen species (ROS) generation ability and photodynamic antibacterial effect. Meanwhile, they both were positively correlated with DS in the range of 4.81% ~ 11.56% resulting in stronger photodynamic antibacterial ability. These findings highlight that CS-Ce6 conjugates have the potential as an effective photodynamic bactericidal agent in the antibacterial field.

Chlorin e6-1,3-diphenylisobenzofuran polymer hybrid nanoparticles for singlet oxygen-detection photodynamic abaltion

Methods Appl Fluoresc 2021 Feb 13;9(2):025003.PMID:33524966DOI:10.1088/2050-6120/abe219.

A dual-functional nanosysterm is developed by means of Chlorin e6 (Ce6) as photosensitizer and 1,3-Diphenylisobenzofuran (DPBF) as fluorescent singlet oxygen (1O2) probe. Under 660 nm laser irradiation, Ce6 exhibites efficient 1O2 generation, and subsequently the production of 1O2 is assessed by the ratiometric fluorescence of PFO and DPBF under one-photon and two-photon excitation mode. The nanoparticles with excellent biocompatibility can be internalized into Hela cells and applied for tumor treatment. For intracellular PDT, the nanoparticles perform a high phototoxicity, while the PDT proccess can be evaluated in time by monitoring fluorescence signals of DPBF. This theranostic nanosysterm provides a facile strategy to fabricate 1O2-detection PDT, which can realize accurate and efficient photodynamic therapy based on singlet oxygen detection.

Water-soluble chlorin e6-hydroxypropyl chitosan as a high-efficiency photoantimicrobial agent against Staphylococcus aureus

Int J Biol Macromol 2022 May 31;208:669-677.PMID:35346676DOI:10.1016/j.ijbiomac.2022.03.140.

The development of new antimicrobial agents is important to combat infections caused by pathogenic bacteria. Herein, Hydroxypropyl chitosan (HPCS), a hydrophilic modified product of chitosan (CS), was employed as a carrier of the photosensitizer Chlorin e6 (Ce6) through an amide bond to obtain the products (HPCS-Ce6 conjugates) with a degree of substitution (DS) ranging from 2.95% to 5.25%. The UV-vis absorption spectra and 1H NMR spectra confirmed the successful synthesis of the products. The products have a better and more stable reactive oxygen species (ROS) generation capacity and higher bacterial affinity than Ce6. At a very low dose (1.8 μg/mL), the highest DS product (HPCS-Ce6-3) can effectively kill Staphylococcus aureus (S. aureus) under 660 nm irradiation. In addition, the HPCS-Ce6 conjugates showed high biocompatibility in the CCK-8 test. The HPCS-Ce6 conjugates could be a photodynamic antibacterial agent with good water solubility, high biocompatibility, and antibacterial activity.