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Journal articles on the topic 'Purpurin-18'

Author: Grafiati

Published: 22 February 2025

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1

Yoon, Il, Ho-Sung Park, Bing Cun Cui, Jung-Hwa Kim, and Young-Key Shim. "Synthesis and Photodynamic Activities of Pyrazolyl and Cyclopropyl Derivatives of Purpurin-18 Methyl Ester and Purpurin-18-N-butylimide." Bulletin of the Korean Chemical Society 32, no. 1 (January 20, 2011): 169–74. http://dx.doi.org/10.5012/bkcs.2011.32.1.169.

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2

Pavlíčková, Vladimíra, Jan Škubník, Michal Jurášek, and Silvie Rimpelová. "Advances in Purpurin 18 Research: On Cancer Therapy." Applied Sciences 11, no. 5 (March 4, 2021): 2254. http://dx.doi.org/10.3390/app11052254.

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How to make cancer treatment more efficient and enhance the patient’s outcome? By multimodal therapy, theranostics, or personalized medicine? These are questions asked by scientists and doctors worldwide. However, finding new unique approaches and options for cancer treatment as well as new selective therapeutics is very challenging. More frequently, researchers “go back in time” and use already known and well-described compounds/drugs, the structure of which further derivatize to “improve” their properties, extend the use of existing drugs to new indications, or even to obtain a completely novel drug. Natural substances, especially marine products, are a great inspiration in the discovery and development of novel anticancer drugs. These can be used in many modern approaches, either as photo- and sonosensitizers in photodynamic and sonodynamic cancer therapy, respectively, or in tumor imaging and diagnosis. This review is focused on a very potent natural product, the chlorophyll metabolite purpurin 18, and its derivatives, which is well suitable for all the mentioned applications. Purpurin 18 can be easily isolated from green plants of all kinds ranging from seaweed to spinach leaves and, thus, it presents an economically feasible source for a very promising anticancer drug.

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3

Pavlíčková, Vladimíra, Silvie Rimpelová, Michal Jurášek, Kamil Záruba, Jan Fähnrich, Ivana Křížová, Jiří Bejček, et al. "PEGylated Purpurin 18 with Improved Solubility: Potent Compounds for Photodynamic Therapy of Cancer." Molecules 24, no. 24 (December 6, 2019): 4477. http://dx.doi.org/10.3390/molecules24244477.

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Purpurin 18 derivatives with a polyethylene glycol (PEG) linker were synthesized as novel photosensitizers (PSs) with the goal of using them in photodynamic therapy (PDT) for cancer. These compounds, derived from a second-generation PS, exhibit absorption at long wavelengths; considerable singlet oxygen generation and, in contrast to purpurin 18, have higher hydrophilicity due to decreased logP. Together, these properties make them potentially ideal PSs. To verify this, we screened the developed compounds for cell uptake, intracellular localization, antitumor activity and induced cell death type. All of the tested compounds were taken up into cancer cells of various origin and localized in organelles known to be important PDT targets, specifically, mitochondria and the endoplasmic reticulum. The incorporation of a zinc ion and PEGylation significantly enhanced the photosensitizing efficacy, decreasing IC50 (half maximal inhibitory compound concentration) in HeLa cells by up to 170 times compared with the parental purpurin 18. At effective PDT concentrations, the predominant type of induced cell death was apoptosis. Overall, our results show that the PEGylated derivatives presented have significant potential as novel PSs with substantially augmented phototoxicity for application in the PDT of cervical, prostate, pancreatic and breast cancer.

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4

Yoon, Il, Ho Sung Park, Bing Cun Cui, Jung Hwa Kim, and Young Key Shim. "ChemInform Abstract: Synthesis and Photodynamic Activities of Pyrazolyl and Cyclopropyl Derivatives of Purpurin-18 Methyl Ester and Purpurin-18-N-butylimide." ChemInform 42, no. 22 (May 5, 2011): no. http://dx.doi.org/10.1002/chin.201122105.

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5

Drogat, Nicolas, Matthieu Barrière, Robert Granet, Vincent Sol, and Pierre Krausz. "High yield preparation of purpurin-18 from Spirulina maxima." Dyes and Pigments 88, no. 1 (January 2011): 125–27. http://dx.doi.org/10.1016/j.dyepig.2010.05.006.

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6

Liu, Ranran, Jungang Yin, Jiazhu Li, Jin Wu, Guanlong Chen, Yingxue Jin, and Jinjun Wang. "Halogenation Reaction of Purpurin-18 and Synthesis of Chlorin Derivatives." Chinese Journal of Organic Chemistry 32, no. 03 (2012): 544. http://dx.doi.org/10.6023/cjoc1105231.

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7

Nguyen, Minh Hieu, Binh Duong Le, Anh Tuan Mai, Thi Binh Nguyen, Thi Thanh Phuong Bui, Huong Son Pham, and Thi Lai Nguyen. "Some characteristics of purpurin-18synthesised from chlorophyll a of Spirulina." Ministry of Science and Technology, Vietnam 63, no. 11 (November 25, 2021): 40–43. http://dx.doi.org/10.31276/vjst.63(11).40-43.

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Research and synthesis of photosensitive purpurin 18 (Pp-18) from nature is one of the topics that many research groups are interested in and developing. In this study, the authors defined some characteristics of Pp-18 synthesised from chlorophyll a - a substance isolated from Spirulina. The results showed that Pp-18 had good dispersion in acetone at 478.5 nm (R2=0.98285) and reached 98%. Fluorescence spectroscopy of Pp-18 in acetone was measured at a concentration of 70 ppm, wavelengths 365.39, 417.62, and 557.96 nm. The fluorescence lifetime of Pp-18 in acetone solution was 2.85 ns.

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8

Liu, Hongyao, Guohua Zhu, Ranran Liu, Yingxue Jin, Caixia Qi, and Jinjun Wang. "Chemical Modifications of Purpurin-18 and Synthesis of Chlorophyllous Chlorins Derivatives." Chinese Journal of Organic Chemistry 35, no. 6 (2015): 1320. http://dx.doi.org/10.6023/cjoc201410003.

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9

Pogorilyy, Viktor, Anna Plyutinskaya, Nikita Suvorov, Ekaterina Diachkova, Yuriy Vasil’ev, Andrei Pankratov, Andrey Mironov, and Mikhail Grin. "The First Selenoanhydride in the Series of Chlorophyll a Derivatives, Its Stability and Photoinduced Cytotoxicity." Molecules 26, no. 23 (December 1, 2021): 7298. http://dx.doi.org/10.3390/molecules26237298.

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In this work, we obtained the first selenium-containing chlorin with a chalcogen atom in exlocycle E. It was shown that the spectral properties were preserved in the target compound and the stability increased at two different pH values, in comparison with the starting purpurin-18. The derivatives have sufficiently high fluorescence and singlet oxygen quantum yields. The photoinduced cytotoxicity of sulfur- and selenium-anhydrides of chlorin p6 studied for the first time in vitro on the S37 cell line was found to be two times higher that of purpurin-18 and purpurinimide studied previously. Moreover, the dark cytotoxicity increased four-fold in comparison with the latter compounds. Apparently, the increase in the dark cytotoxicity is due to the interaction of the pigments studied with sulfur- and selenium-containing endogenous intracellular compounds. Intracellular distributions of thioanhydride and selenoanhydride chlorin p6 in S37 cells were shown in cytoplasm by diffusion distribution. The intracellular concentration of the sulfur derivative turned out to be higher and, as a consequence, its photoinduced cytotoxicity was higher as well.

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10

Lkhagvadulam, Byambajav, Jung Hwa Kim, Il Yoon, and Young Key Shim. "Synthesis and photodynamic activities of novel water soluble purpurin-18-N-methyl-D-glucamine photosensitizer and its gold nanoparticles conjugate." Journal of Porphyrins and Phthalocyanines 16, no. 04 (April 2012): 331–40. http://dx.doi.org/10.1142/s1088424612500708.

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A new type of water soluble ionic photosensitizer (PS), purpurin-18-N-methyl-D-glucamine (Pu-18-NMGA) has been synthesized and it was conjugated into gold nanoparticles (GNPs) stabilized by the PS without adding any particular reducing agents and surfactants. In vitro anticancer efficacy of the PS and its PS–GNPs conjugate against A549 lung cancer cell lines was evaluated. The PS–GNPs conjugate based on water-soluble Pu-18-NMGA afforded good PDT efficacy which was three times greater than that of the water-soluble PS.

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11

Cui, Bing Cun, Min-Uk Cha, Jia Zhu Li, Ho-Sung Park, Il Yoon, and Young-Key Shim. "Efficient Synthesis and in vitro PDT Effect of Purpurin-18-N-Aminoimides." Bulletin of the Korean Chemical Society 31, no. 11 (November 20, 2010): 3313–17. http://dx.doi.org/10.5012/bkcs.2010.31.11.3313.

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12

Ocampo, Rubén, and Daniel J. Repeta. "Structural determination of purpurin-18 (as methyl ester) from sedimentary organic matter." Organic Geochemistry 30, no. 2-3 (March 1999): 189–93. http://dx.doi.org/10.1016/s0146-6380(98)00214-9.

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13

Olshevskaya, V. A., A. N. Savchenko, G. V. Golovina, V. V. Lazarev, E. G. Kononova, P. V. Petrovskii, V. N. Kalinin, A. A. Shtil’, and V. A. Kuz’min. "New boronated derivatives of purpurin-18: Synthesis and intereaction with serum albumin." Doklady Chemistry 435, no. 2 (December 2010): 328–33. http://dx.doi.org/10.1134/s0012500810120050.

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14

Walker, Ian, David I. Vernon, and Stanley B. Brown. "The solid-phase conjugation of purpurin-18 with a synthetic targeting peptide." Bioorganic & Medicinal Chemistry Letters 14, no. 2 (January 2004): 441–43. http://dx.doi.org/10.1016/j.bmcl.2003.10.041.

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15

NDZIMBOU, Luce Janice, Frédérique BREGIER, Gautier M. A. NDONG NTOUTOUTME, and Vincent SOL. "Purpurin-18 imide derivative synthesis and functionalization for the photodynamic cancer therapy." Photodiagnosis and Photodynamic Therapy 41 (March 2023): 103479. http://dx.doi.org/10.1016/j.pdpdt.2023.103479.

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16

Wang, Peng, Ze Yang, Jazhu Li, Nannan Yao, and Jinjun Wang. "Aminolysis Reaction of Purpurin-18 and Synthesis of Chlorin Derivatives Related to Chlorophyll." Chinese Journal of Organic Chemistry 32, no. 2 (2012): 368. http://dx.doi.org/10.6023/cjoc1107031.

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17

Liu, Ranran, Lumin Wang, Jungang Yin, Jin Wu, Chao Liu, Peng Zhang, and Jinjun Wang. "Synthesis of Benzimidazolo-Fused Purpurin-18 Derivatives with the Basic Skeleton of Chlorophyll." Chinese Journal of Organic Chemistry 32, no. 2 (2012): 318. http://dx.doi.org/10.6023/cjoc1107064.

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18

Ji, Jianye, Shangwen Xia, Lili Zhao, Jiazhu Li, Caixia Qi, and Jinjun Wang. "Chemical Reaction of Purpurin-18 Imide and Synthesis of Chlorins Related to Chlorophyll." Chinese Journal of Organic Chemistry 33, no. 7 (2013): 1457. http://dx.doi.org/10.6023/cjoc201301044.

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19

Liang, Boying, Yang Liu, Xisen Xu, Yingxue Jin, Caixia Qi, and Jinjun Wang. "Modifications for Peripheral Structures of Purpurin-18 and Synthesis of Chlorophyllous Chlorin Derivatives." Chinese Journal of Organic Chemistry 33, no. 11 (2013): 2357. http://dx.doi.org/10.6023/cjoc201305006.

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20

Ji, Jianye, Jungang Yin, Lili Zhao, Nannan Yao, Caixia Qi, and Jinjun Wang. "Hydroxyla(acyla)tion of Purpurin-18 Imide and Synthesis of Chlorophyllous Chlorin Derivatives." Chinese Journal of Organic Chemistry 34, no. 11 (2014): 2262. http://dx.doi.org/10.6023/cjoc201405009.

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21

Liu, Fuxian, Xingping Zhou, Zhilong Chen, Peng Huang, Xiaqin Wang, and Yong Zhou. "Preparation of purpurin-18 loaded magnetic nanocarriers in cottonseed oil for photodynamic therapy." Materials Letters 62, no. 17-18 (June 2008): 2844–47. http://dx.doi.org/10.1016/j.matlet.2008.01.123.

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22

Golovina, G. V., F. N. Novikov, V. A. Ol’shevskaya, V. N. Kalinin, A. A. Shtil, and V. A. Kuzmin. "Complex formation of Zn-, Ni-, and Pd-derivatives of purpurin-18 with serum albumin." Russian Journal of Physical Chemistry A 86, no. 11 (September 29, 2012): 1756–58. http://dx.doi.org/10.1134/s003602441211012x.

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23

Zhang, Ying, Hongyue Zhang, Zhiqiang Wang, and Yingxue Jin. "pH-Sensitive graphene oxide conjugate purpurin-18 methyl ester photosensitizer nanocomplex in photodynamic therapy." New Journal of Chemistry 42, no. 16 (2018): 13272–84. http://dx.doi.org/10.1039/c8nj00439k.

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24

Kozyrev, Andrei N., Gang Zheng, Elizabeth Lazarou, Thomas J. Dougherty, Kevin M. Smith, and Ravindra K. Pandey. "Syntheses of emeraldin and purpurin-18 analogs as target-specific photosensitizers for photodynamic therapy." Tetrahedron Letters 38, no. 19 (May 1997): 3335–38. http://dx.doi.org/10.1016/s0040-4039(97)00621-7.

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25

Cui, Bing Cun, Min Uk Cha, Jia Zhu Li, Ho Sung Park, Il Yoon, and Young Key Shim. "ChemInform Abstract: Efficient Synthesis and in vitro PDT Effect of Purpurin-18-N-aminoimides." ChemInform 42, no. 10 (February 10, 2011): no. http://dx.doi.org/10.1002/chin.201110112.

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26

Lkhagvadulam, Byambajav, Jung Hwa Kim, Il Yoon, and Young Key Shim. "Size-Dependent Photodynamic Activity of Gold Nanoparticles Conjugate of Water Soluble Purpurin-18-N-Methyl-D-Glucamine." BioMed Research International 2013 (2013): 1–10. http://dx.doi.org/10.1155/2013/720579.

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Gold nanoparticles (GNPs) conjugates of water soluble ionic photosensitizer (PS), purpurin-18-N-methyl-D-glucamine (Pu-18-NMGA), were synthesized using various molar ratios between HAuCl4and Pu-18-NMGA without adding any particular reducing agents and surfactants. The PS-GNPs conjugates showed long wavelength absorption of range 702–762 nm, and their different shapes and diameters depend on the molar ratios used in the synthesis.In vitroanticancer efficacy of the PS-GNPs conjugates was investigated by MTT assay against A549 cells, resulting in higher photodynamic activity than that of the free Pu-18-NMGA. Among the PS-GNPs conjugates, the GNPs conjugate from the molar ratio of 1 : 2 (Au(III): Pu-18-NMGA) exhibits the highest photodynamic activity corresponding to bigger size (~60 nm) of the GNPs conjugate which could efficiently transport the PS into the cells than that of smaller size of the GNPs conjugate.

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27

Stefano, Anna Di, Anna Ettorre, Silverio Sbrana, Cinzia Giovani, and Paolo Neri. "Purpurin-18 in Combination with Light Leads to Apoptosis or Necrosis in HL60 Leukemia Cells¶." Photochemistry and Photobiology 73, no. 3 (May 1, 2007): 290–96. http://dx.doi.org/10.1562/0031-8655(2001)0730290picwll2.0.co2.

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28

Stefano, Anna Di, Anna Ettorre, Silverio Sbrana, Cinzia Giovani, and Paolo Neri. "Purpurin-18 in Combination with Light Leads to Apoptosis or Necrosis in HL60 Leukemia Cells¶." Photochemistry and Photobiology 73, no. 3 (2001): 290. http://dx.doi.org/10.1562/0031-8655(2001)073<0290:picwll>2.0.co;2.

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29

Lee, Shwn-Ji H., Nadine Jagerovic, and Kevin M. Smith. "Use of the chlorophyll derivative, purpurin-18, for syntheses of sensitizers for use in photodynamic therapy." Journal of the Chemical Society, Perkin Transactions 1, no. 19 (1993): 2369. http://dx.doi.org/10.1039/p19930002369.

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30

Byambajav, Lkhagvadulam, Kim Jung Hua, IL Yoon, and ShimYoung Key. "Synthesis and characterization of gold nanoparticles based on water-soluble Purpurin-18-N-methyl-d-glucamine." Photodiagnosis and Photodynamic Therapy 8, no. 2 (June 2011): 209. http://dx.doi.org/10.1016/j.pdpdt.2011.03.284.

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31

Sharma, Sulbha, Alok Dube, Biplab Bose, and Pradeep K. Gupta. "Pharmacokinetics and phototoxicity of purpurin-18 in human colon carcinoma cells using liposomes as delivery vehicles." Cancer Chemotherapy and Pharmacology 57, no. 4 (August 2, 2005): 500–506. http://dx.doi.org/10.1007/s00280-005-0072-x.

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32

Liu, Yang, Sang Hyeob Lee, Woo Kyoung Lee, and Il Yoon. "Ionic Liquid‐dependent Gold Nanoparticles of Purpurin‐18 for Cellular Imaging and Photodynamic Therapy In Vitro." Bulletin of the Korean Chemical Society 41, no. 2 (December 20, 2019): 230–33. http://dx.doi.org/10.1002/bkcs.11943.

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33

Yeo, Sooho, Hyeon Ho Song, Min Je Kim, Seokhyeon Hong, Il Yoon, and Woo Kyoung Lee. "Synthesis and Design of Purpurin-18-Loaded Solid Lipid Nanoparticles for Improved Anticancer Efficiency of Photodynamic Therapy." Pharmaceutics 14, no. 5 (May 15, 2022): 1064. http://dx.doi.org/10.3390/pharmaceutics14051064.

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Purpurin-18 (P18) is one of the essential photosensitizers used in photodynamic therapy (PDT), but its hydrophobicity causes easy coalescence and poor bioavailability. This study aimed to synthesize P18 and design P18-loaded solid lipid nanoparticles (SLNs) to improve its bioavailability. The characteristics of the synthesized P18 and SLNs were evaluated by particle characteristics and release studies. The effects of P18 were evaluated using the 1,3-diphenylisobenzofuran (DPBF) assay as a nonbiological assay and a phototoxicity assay against HeLa and A549 cell lines as a biological assay. The mean particle size and zeta potential of the SLNs were 164.70–762.53 nm and −16.77–25.54 mV, respectively. These results indicate that P18-loaded SLNs are suitable for an enhanced permeability and retention effect as a passive targeting anti-cancer strategy. The formulations exhibited a burst and sustained release based on their stability. The DPBF assay indicated that the PDT effect of P18 improved when it was entrapped in the SLNs. The photocytotoxicity assay indicated that P18-loaded SLNs possessed light cytotoxicity but no dark cytotoxicity. In addition, the PDT activity of the formulations was cell type- and size-dependent. These results suggest that the designed P18-loaded SLNs are a promising tool for anticancer treatment using PDT.

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34

Chkair, Rayan, Justine Couvez, Frédérique Brégier, Mona Diab-Assaf, Vincent Sol, Mireille Blanchard-Desce, Bertrand Liagre, and Guillaume Chemin. "Activity of Hydrophilic, Biocompatible, Fluorescent, Organic Nanoparticles Functionalized with Purpurin-18 in Photodynamic Therapy for Colorectal Cancer." Nanomaterials 14, no. 19 (September 26, 2024): 1557. http://dx.doi.org/10.3390/nano14191557.

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Photodynamic therapy (PDT) is a clinically approved, non-invasive therapy currently used for several solid tumors, triggering cell death through the generation of reactive oxygen species (ROS). However, the hydrophobic nature of most of the photosensitizers used, such as chlorins, limits the overall effectiveness of PDT. To address this limitation, the use of nanocarriers seems to be a powerful approach. From this perspective, we have recently developed water-soluble and biocompatible, fluorescent, organic nanoparticles (FONPs) functionalized with purpurin-18 and its derivative, chlorin p6 (Cp6), as new PDT agents. In this study, we aimed to investigate the induced cell death mechanism mediated by these functionalized nanoparticles after PDT photoactivation. Our results show strong phototoxic effects of the FONPs[Cp6], mediated by intracellular ROS generation, and subcellular localization in HCT116 and HT-29 human colorectal cancer (CRC) cells. Additionally, we proved that, post-PDT, the FONPs[Cp6] induce apoptosis via the intrinsic mitochondrial pathway, as shown by the significant upregulation of the Bax/Bcl-2 ratio, the activation of caspases 9, 3, and 7, leading poly-ADP-ribose polymerase (PARP-1) cleavage, and DNA fragmentation. Our work demonstrates the photodynamic activity of these nanoparticles, making them promising candidates for the PDT treatment of CRC.

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35

Zheng, Gang, William R. Potter, Adam Sumlin, Thomas J. Dougherty, and Ravindra K. Pandey. "Photosensitizers related to purpurin-18- N -alkylimides: a comparative in vivo tumoricidal ability of ester versus amide functionalities." Bioorganic & Medicinal Chemistry Letters 10, no. 2 (January 2000): 123–27. http://dx.doi.org/10.1016/s0960-894x(99)00649-6.

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36

Wang, J. J., Y. F. Yin, and Z. Yang. "Synthesis of purpurin-18 imide derivatives from chlorophyll-a and -b by modifications and functionalizations along their peripheries." Journal of the Iranian Chemical Society 10, no. 3 (December 4, 2012): 583–91. http://dx.doi.org/10.1007/s13738-012-0194-0.

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37

LEE, S. J. H., N. JAGEROVIC, and K. M. SMITH. "ChemInform Abstract: Use of the Chlorophyll Derivative, Purpurin-18, for Syntheses of Sensitizers for Use in Photodynamic Therapy." ChemInform 25, no. 4 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199404214.

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38

Yeo, Sooho, Huiqiang Wu, Il Yoon, Hye-Soo Kim, Young Kyu Song, and Woo Kyoung Lee. "Enhanced Photodynamic Therapy Efficacy through Solid Lipid Nanoparticle of Purpurin-18-N-Propylimide Methyl Ester for Cancer Treatment." International Journal of Molecular Sciences 25, no. 19 (September 26, 2024): 10382. http://dx.doi.org/10.3390/ijms251910382.

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Photodynamic therapy (PDT) is an innovative cancer treatment that utilizes light. When light irradiates, purpurin-18-N-propylimide methyl ester (P18 N PI ME) generates reactive oxygen species that destroy cancer cells. The hydrophobic nature of P18 N PI ME presents challenges regarding its aggregation in the body, which can affect its effectiveness. This study aimed to enhance the bioavailability and effectiveness of cancer treatment by synthesizing P18 N PI ME and formulating P18 N PI ME-loaded solid lipid nanoparticles (SLNs). The efficacy of PDT was estimated using the 1,3-diphenylisobenzofuran (DPBF) assay and photocytotoxicity tests on the HeLa (human cervical carcinoma) and A549 (human lung carcinoma) cell lines. The P18 N PI ME-loaded SLNs demonstrated particle sizes in the range of 158.59 nm to 248.43 nm and zeta potentials in the range of –15.97 mV to –28.73 mV. These SLNs exhibited sustained release of P18 N PI ME. DPBF analysis revealed enhanced PDT effects with SLNs containing P18 N PI ME compared with standalone P18 N PI MEs. Photocytotoxicity assays indicated toxicity under light irradiation but no toxicity in the dark. Furthermore, the smallest-sized formulation exhibited the most effective photodynamic activity. These findings indicate the potential of P18 N PI ME-loaded SLNs as promising strategies for PDT in cancer therapy.

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39

Jain, Beena, Abha Uppal, Kaustuv Das, Alok Dube, and Pradeep Kumar Gupta. "Conversion of purpurin 18 to chlorin P6 in the presence of silica, liposome and polymeric nanoparticles: A spectroscopic study." Journal of Molecular Structure 1060 (February 2014): 24–29. http://dx.doi.org/10.1016/j.molstruc.2013.12.019.

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40

Roeslan, Moehamad Orliando, Thaweephol Dechatiwongse Na Ayudhya, Boon-ek Yingyongnarongkul, and Sittichai Koontongkaew. "Anti-biofilm, nitric oxide inhibition and wound healing potential of purpurin-18 phytyl ester isolated from Clinacanthus nutans leaves." Biomedicine & Pharmacotherapy 113 (May 2019): 108724. http://dx.doi.org/10.1016/j.biopha.2019.108724.

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41

Cheng, Dong-Bing, Guo-Bin Qi, Jing-Qi Wang, Yong Cong, Fu-Hua Liu, Haijun Yu, Zeng-Ying Qiao, and Hao Wang. "In Situ Monitoring Intracellular Structural Change of Nanovehicles through Photoacoustic Signals Based on Phenylboronate-Linked RGD-Dextran/Purpurin 18 Conjugates." Biomacromolecules 18, no. 4 (March 14, 2017): 1249–58. http://dx.doi.org/10.1021/acs.biomac.6b01922.

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42

Zheng, Gang, William R. Potter, Adam Sumlin, Thomas J. Dougherty, and Ravindra K. Pandey. "ChemInform Abstract: Photosensitizers Related to Purpurin-18-N-alkylimides: A Comparative in vivo Tumoricidal Ability of Ester versus Amide Functionalities." ChemInform 31, no. 21 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200021112.

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43

Mishra, Padmaja P., and Anindya Datta. "Difference in the effects of surfactants and albumin on the extent of deaggregation of purpurin 18, a model of hydrophobic photosensitizer." Biophysical Chemistry 121, no. 3 (June 2006): 224–33. http://dx.doi.org/10.1016/j.bpc.2006.01.009.

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44

Hynninen, Paavo H., Tuomo S. Leppäkases, and Markku Mesilaakso. "Demethoxycarbonylation and oxidation of 132(S/R)-hydroxy-chlorophyll a to 132-demethoxycarbonyl-132-oxo-chlorophyll a and Mg-purpurin-18 phytyl ester." Tetrahedron Letters 47, no. 10 (March 2006): 1663–68. http://dx.doi.org/10.1016/j.tetlet.2005.12.106.

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45

Kang, Eun Seon, Tae Heon Lee, Yang Liu, Ki-Ho Han, Woo Kyoung Lee, and Il Yoon. "Graphene Oxide Nanoparticles Having Long Wavelength Absorbing Chlorins for Highly-Enhanced Photodynamic Therapy with Reduced Dark Toxicity." International Journal of Molecular Sciences 20, no. 18 (September 5, 2019): 4344. http://dx.doi.org/10.3390/ijms20184344.

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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.

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Tamiaki, Hitoshi, Yasuhide Shimamura, Hideaki Yoshimura, Suresh K. Pandey, and Ravindra K. Pandey. "Self-aggregation of Synthetic Zinc 3-Hydroxymethyl-purpurin-18 andN-Hexylimide Methyl Esters in an Aqueous Solution as Models of Green Photosynthetic Bacterial Chlorosomes." Chemistry Letters 34, no. 10 (October 2005): 1344–45. http://dx.doi.org/10.1246/cl.2005.1344.

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Frye, William J. E., Lyn M. Huff, José M. González Dalmasy, Paula Salazar, Rachel M. Carter, Ryan T. Gensler, Dominic Esposito, Robert W. Robey, Suresh V. Ambudkar, and Michael M. Gottesman. "The multidrug resistance transporter P-glycoprotein confers resistance to ferroptosis inducers." Cancer Drug Resistance 6 (2023): 468–80. http://dx.doi.org/10.20517/cdr.2023.29.

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Aim: Ferroptosis is a non-apoptotic form of cell death caused by lethal lipid peroxidation. Several small molecule ferroptosis inducers (FINs) have been reported, yet little information is available regarding their interaction with the ATP-binding cassette (ABC) transporters P-glycoprotein (P-gp, ABCB1) and ABCG2. We thus sought to characterize the interactions of FINs with P-gp and ABCG2, which may provide information regarding oral bioavailability and brain penetration and predict drug-drug interactions. Methods: Cytotoxicity assays with ferroptosis-sensitive A673 cells transfected to express P-gp or ABCG2 were used to determine the ability of the transporters to confer resistance to FINs; confirmatory studies were performed in OVCAR8 and NCI/ADR-RES cells. The ability of FINs to inhibit P-gp or ABCG2 was determined using the fluorescent substrates rhodamine 123 or purpuin-18, respectively. Results: P-gp overexpression conferred resistance to FIN56 and the erastin derivatives imidazole ketone erastin and piperazine erastin. P-gp-mediated resistance to imidazole ketone erastin and piperazine erastin was also reversed in UO-31 renal cancer cells by CRISPR-mediated knockout of ABCB1. The FINs ML-162, GPX inhibitor 26a, and PACMA31 at 10 µM were able to increase intracellular rhodamine 123 fluorescence over 10-fold in P-gp-expressing MDR-19 cells. GPX inhibitor 26a was able to increase intracellular purpurin-18 fluorescence over 4-fold in ABCG2-expressing R-5 cells. Conclusion: Expression of P-gp may reduce the efficacy of these FINs in cancers that express the transporter and may prevent access to sanctuary sites such as the brain. The ability of some FINs to inhibit P-gp and ABCG2 suggests potential drug-drug interactions.

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Sasaki, Isabelle, Frédérique Brégier, Guillaume Chemin, Jonathan Daniel, Justine Couvez, Rayan Chkair, Michel Vaultier, Vincent Sol, and Mireille Blanchard-Desce. "Hydrophilic Biocompatible Fluorescent Organic Nanoparticles as Nanocarriers for Biosourced Photosensitizers for Photodynamic Therapy." Nanomaterials 14, no. 2 (January 19, 2024): 216. http://dx.doi.org/10.3390/nano14020216.

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Most photosensitizers of interest for photodynamic therapy—especially porphyrinoids and chlorins—are hydrophobic. To circumvent this difficulty, the use of nanocarriers is an attractive strategy. In this perspective, we have developed highly water-soluble and biocompatible fluorescent organic nanoparticles (FONPs) made from citric acid and diethyltriamine which are then activated by ethlynene diamine as nanoplatforms for efficient photosensitizers (PSs). Purpurin 18 (Pp18) was selected as a biosourced chlorin photosensitizer combining the efficient single oxygen generation ability and suitable absorption in the biological spectral window. The simple reaction of activated FONPs with Pp18, which contains a reactive anhydride ring, yielded nanoparticles containing both Pp18 and Cp6 derivatives. These functionalized nanoparticles combine solubility in water, high singlet oxygen generation quantum yield in aqueous media (0.72) and absorption both in the near UV region (FONPS) and in the visible region (Soret band approximately 420 nm as well as Q bands at 500 nm, 560 nm, 660 nm and 710 nm). The functionalized nanoparticles retain the blue fluorescence of FONPs when excited in the near UV region but also show deep-red or NIR fluorescence when excited in the visible absorption bands of the PSs (typically at 520 nm, 660 nm or 710 nm). Moreover, these nanoparticles behave as efficient photosensitizers inducing colorectal cancer cell (HCT116 and HT-29 cell lines) death upon illumination at 650 nm. Half maximal inhibitory concentration (IC50) values down to, respectively, 0.04 and 0.13 nmol/mL were observed showing the potential of FONPs[Cp6] for the PDT treatment of cancer. In conclusion, we have shown that these novel biocompatible nanoparticles, which can be elaborated from biosourced components, both show deep-red emission upon excitation in the red region and are able to produce singlet oxygen with high efficiency in aqueous environments. Moreover, they show high PDT efficiency on colorectal cancer cells upon excitation in the deep red region. As such, these functional organic nanoparticles hold promise both for PDT treatment and theranostics.

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Huang, Pengyun, Baoting Zhang, Qiuju Yuan, Xie Zhang, Wingnang Leung, and Chuanshan Xu. "Photodynamic treatment with purpurin 18 effectively inhibits triple negative breast cancer by inducing cell apoptosis." Lasers in Medical Science, July 5, 2020. http://dx.doi.org/10.1007/s10103-020-03035-w.

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Yeo, Sooho, Huiqiang Wu, Young Kyu Song, Juseung Lee, Il Yoon, and Woo Kyoung Lee. "Application of PLGA Nanoparticles to Photodynamic Cancer Therapy by encapsulating Purpurin-18-N-hydroxylimide methyl ester." Colloids and Surfaces A: Physicochemical and Engineering Aspects, December 2024, 136064. https://doi.org/10.1016/j.colsurfa.2024.136064.

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