5594-30-9Relevant articles and documents
Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C. cyrtophyllum
Cheng,Wang,Ito,Bastow,Tachibana,Nakanishi,Xu,Luo,Lee
, p. 915 - 919 (2001)
Three pheophorbide-related compounds (1-3) were isolated from the leaves and stems of Clerodendrum calamitosum. The methyl ester of 3 (6) and the known (10S)-hydroxypheophytin a (7) also were isolated from leaves of the related plant Clerodendrum cyrtophyllum. Compounds 1 and 6 were isolated for the first time as naturally occurring products from a plant source. All structures were elucidated by detailed spectroscopic analysis. Biological evaluation showed that 1 and 2 exhibited strong cytotoxicity against human lung carcinoma (A549), ileocecal carcinoma (HCT-8), kidney carcinoma (CAKI-1), breast adenocarcinoma (MCF-7), malignant melanoma (SK-MEL-2), ovarian carcinoma (1A9), and epidermoid carcinoma of the nasopharynx (KB), and its etoposide- (KB-7d), vincristine- (KB-VCR), and camptothecin-resistant (KB-CPT) subclones. Compound 3 was less cytotoxic than 1 and 2. Compounds 4-6, the methyl esters of 1-3, showed strongly increased cytotoxicity compared with the parent acids. Interestingly, 6 was the most active derivative among these compounds. Compound 7 was inactive.
Double helices of a pyridine-appended zinc chlorophyll derivative
Shinozaki, Yoshinao,Richards, Gary,Ogawa, Keizo,Yamano, Akihito,Ohara, Kazuaki,Yamaguchi, Kentaro,Kawano, Shin-Ichiro,Tanaka, Kentaro,Araki, Yasuyuki,Wada, Takehiko,Otsuki, Joe
, p. 5262 - 5265 (2013)
Self-assembled structures formed from a pyridine-appended zinc chlorophyll derivative are reported. While the zinc complex forms cyclic oligomers in chloroform solution, as indicated by 1H NMR studies (including diffusion-ordered spectroscopy), vapor pressure osmometry, and cold-spray ionization mass spectrometry, it forms double-stranded helical coordination polymers in the solid state, as revealed by single-crystal X-ray analysis.
Preparation and in vitro biological evaluation of tetrapyrrole ethanolamide derivatives as potential anticancer agents
Girard, Denis,Weagle, Glenn,Gupta, Atul,Berube, Gervais,Chapados, Camille
, p. 360 - 365 (2008)
Tetrapyrrole ethanolamide derivatives, 1 and 2, were prepared from hematoporphyrin IX (HPIX, 3) and methyl pheophorbide a (mPheo, 6). These were evaluated for their dual action as chemotherapeutics and photosensitizers in treatment of cancer. The novel compounds showed significant in vitro anticancer activity as measured in different cell lines using the MTT assay and photodynamic activity measured by erythrocytes' photohemolysis.
Synthesis, photophysical and electrochemistry of near-IR absorbing bacteriochlorins related to bacteriochlorophyll a
Kozyrev, Andrei,Ethirajan, Manivannan,Chen, Ping,Ohkubo, Kei,Robinson, Byron C.,Barkigia, Kathleen M.,Fukuzumi, Shunichi,Kadish, Karl M.,Pandey, Ravindra K.
, p. 10260 - 10271 (2012)
A series of new bacteriochlorins was synthesized using 13 2-oxo-bacteriopyropheophorbide a (derived from bacteriochlorophyll a) as a starting material, which on reacting with o-phenylenediamine and 1,10-diaminonaphthalene afforded highly conjug
Physicochemical and biochemical properties of synthetic zinc 131-(un)substituted chlorophyll-a derivatives
Hirose, Mitsuaki,Harada, Jiro,Maeda, Hiroaki,Tamiaki, Hitoshi
, (2021/04/23)
Zinc methyl pheophorbides a/a’, which possess oxo and methoxycarbonyl groups at the C131- and C132-positions, respectively, on the exo-five membered ring fusing the cyclic tetrapyrrole of their chlorin π-skeletons, were prepared via chemical modifications of chlorophyll a produced in phototrophs. The C131-hydroxylated and unsubstituted analogues were synthesized by reduction of the ketone moiety. The C131- and C132-stereochemistry of these semi-synthetic compounds was confirmed by 1H NMR and circular dichroism spectroscopies. A methoxycarbonyl group at the chiral C132-position in the ketone was stereo-inverted under basic conditions, whereas those in the corresponding alcoholic and dihydro-forms were not. The in vitro BciC enzymatic reaction of the (132R)-ketone was found to stereoselectively hydrolyze the C132-methoxycarbonyl group, followed by spontaneous decarboxylation. Similarly, the (132R)-COOCH3 group in the (131S)-alcohol was hydrolyzed, whereas the (132R)-COOCH3 group in the (131R)-alcohol was not. After the enzymatic reaction of the C131-dihydro-compound, its (132S)-demethoxycarbonylated and hydroxylated product was observed.
Chlorin e6 ferrocene conjugate with photo- and acoustic-sensitive activity as well as preparation method and application
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Paragraph 0061-0063, (2020/08/07)
The invention provides a chlorin e6 ferrocene conjugate with photo- and acoustic-sensitive activity as well as a preparation method and application thereof, and belongs to the technical field of chemical medicines. The chlorin e6 ferrocene conjugate disclosed by the invention has different degrees of inhibition effects on Hela cells in in-vitro anti-tumor activity evaluation. The introduction of the ferrocene group significantly improves the proliferation inhibition activity of the compound on tumor cells, and the proliferation inhibition activity of the chlorin e6 ferrocene conjugate on tumorcells is much higher than that of chlorin e6 used as a control group. The method can be used for preparing photosensitizers and sonosensitizers in photodynamic therapy and sonodynamic therapy methodsfor tumor therapy.
Synthesis of a chlorophyll-a derivative fused with an additional exo-five-membered ring and its optical properties
Doi,Tamiaki, Hitoshi
, (2019/07/30)
A C20-free chlorophyll-a derivative with an additional exo-five-membered ring was successfully prepared using an ethylene linkage at the C3- and C5-positions. A bromination at the C20-position was requisite for the cyclization of a 1-hydroxyethyl or vinyl group at the C3-position of methyl bacteriopheophorbide-d or methyl pyropheophorbide-a, respectively. By comparing optical properties of the cyclized product with those of its 3-ethyl uncyclized analog in a diluted dichloromethane solution, it was shown that the cyclization shifted the Qx and Bx absorption maxima to longer wavelengths and reduced the Stokes shift.
Graphene oxide nanoparticles having long wavelength absorbing chlorins for highly-enhanced photodynamic therapy with reduced dark toxicity
Kang, Eun Seon,Lee, Tae Heon,Liu, Yang,Han, Ki-Ho,Lee, Woo Kyoung,Yoon, Il
, (2019/10/21)
The long wavelength absorbing photosensitizer (PS) is important in allowing deeper penetration of near-infrared light into tumor tissue for photodynamic therapy (PDT). A suitable drug delivery vehicle is important to attain a sufficient concentration of PS at the tumor site. Presently, we developed graphene oxide (GO) nanoparticles containing long wavelength absorbing PS in the form of the chlorin derivative purpurin-18-N-ethylamine (maximum absorption wavelength [λmax] 707 nm). The GO-PS complexes comprised a delivery system in which PS was loaded by covalent and noncovalent bonding on the GO nanosheet. The two GO-PS complexes were fully characterized and compared concerning their synthesis, stability, cell viability, and dark toxicity. The GO-PS complexes produced significantly-enhanced PDT activity based on excellent drug delivery effect of GO compared with PS alone. In addition, the noncovalent GO-PS complex displayed higher photoactivity, corresponding with the pH-induced release of noncovalently-bound PS from the GO complex in the acidic environment of the cells. Furthermore, the noncovalently bound GO-PS complex had no dark toxicity, as their highly organized structure prevented GO toxicity. We describe an excellent GO complex-based delivery system with significantly enhanced PDT with long wavelength absorbing PS, as well as reduced dark toxicity as a promising cancer treatment.
Regioisomeric synthesis of chlorin-e 6 dimethyl esters and their optical properties
Nagano, Yasunobu,Ogasawara, Shin,Tamiaki, Hitoshi
, p. 1039 - 1046 (2018/11/23)
Chlorin-e6 dimethyl esters possessing a single carboxy group at the 13-, 151-,or 172-position were prepared by chemically modifying chlorophyll-A. These three synthetic regioisomers were fully characterized by their mass, NMR, and visible absorption spectra. Their molecular structures were unambiguously identified by the specific 1H-13C correlation at the 13-, 15-, and/or 17-substituents in their respective HMBC spectra. Methyl esterification of 13/151-COOH and hydrolysis of 13/151-COOMe affected small shifts of the Qy absorption and fluorescence emission maxima in a diluted CH2Cl2 solution, while no substitution effect of 172-COOH/Me was observed.
An amidochlorin-based colorimetric fluorescent probe for selective Cu2+ detection
Li, Wenting,Zhu, Guohua,Li, Jinghua,Wang, Zhiqiang,Jin, Yingxue
, (2016/02/05)
The design and synthesis of selective and sensitive chemosensors for the quantification of environmentally and biologically important ionic species has attracted widespread attention. Amidochlorin p6 (ACP); an effective colorimetric and fluorescent probe for copper ions (Cu2+) in aqueous solution derived from methyl pheophorbide-a (MPa) was designed and synthesized. A remarkable color change from pale yellow to blue was easily observed by the naked eye upon addition of Cu2+; and a fluorescence quenching was also determined. The research of fluorescent quenching of ACP-Cu2+ complexation showed the detection limit was 7.5 ×10-8 mol/L; which suggested that ACP can act as a high sensitive probe for Cu2+ and can be used to quantitatively detect low levels of Cu2+ in aqueous solution. In aqueous solution the probe exhibits excellent selectivity and sensitivity toward Cu2+ ions over other metal ions (M = Zn2+; Ni2+; Ba2+; Ag+; Co2+; Na+; K+; Mg2+; Cd2+; Pb2+; Mn2+; Fe3+; and Ca2+). The obvious change from pale yellow to blue upon the addition of Cu2+ could make it a suitable "naked eye" indicator for Cu2+.
