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Differential interaction of porphyrins used in photoradiation therapy with ferrochelatase
Open accessAbstract
The mechanism of porphyrin accumulation by tumours is not yet established. If metabolism aids porphyrin elimination, tumours, unlike normal tissues, may not metabolize porphyrins used clinically, such as proto-, haemato-, OO'-diacetyl-haemato- and monohydroxyethyl-monovinyl-deutero-porphyrin. Proto-, haemato- and monohydroxyethyl-monovinyl-deutero-porphyrin are substrates for the mitochondrial enzyme ferrochelatase (EC 4.99.1.1), which can form haem analogues from exogenous porphyrins. The Km values for proto-, haemato- and monohydroxyethyl-monovinyl-deutero-porphyrin are 11, 22 and 23 microM respectively. However, OO'-diacetyl-haematoporphyrin is an effective competitive inhibitor with Ki of 11 microM. Hepatic ferrochelatase specific activity is 5.9 and 5.5 nmol of haem/h per mg of protein respectively in normal Buffalo rat and in those bearing the extrahepatic Morris 7288C hepatoma, and is only 0.13 nmol/h per mg in the hepatomas. Therefore low ferrochelatase activity in cancerous cells may provide one means whereby some porphyrins accumulate in tumours, and the ability of certain porphyrins to act as ferrochelatase inhibitors may provide another.
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“Although the uptake of ALA is non-selective, accumulation of PpIX in tumor cells may occur selectively because of alterations in enzymatic activity in the heme synthesis pathway.”
From Photodynamic Therapy for Non-Melanoma Skin Cancers (2016) · cites this paper as [10]
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“The accumulation of PpIX in neoplastic tissue is further supplemented by decreased activity of ferrochelatase (FC), which converts PpIX to heme [9,10].”
From Photodynamic Therapy for Non-Melanoma Skin Cancers (2016) · cites this paper as [10]
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Photosensitiser delivery for photodynamic therapy. Part 1: Topical carrier platforms
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“Although debate exists over the exact reason for this, reports have suggested that the activity of the rate-limiting enzyme porphobilinogen deaminase is increased [12-14] , while the activity of ferrochelatase is decreased [12,15,16] .”
BackgroundCasas, A. G., Fukuda, H., & Batlle, A. M. D. C. (1999) · British Journal of Cancer · doi:10.1038/sj.bjc.6690644 · Cited by 24
“ALA-induced PpIX accumulation has been shown to be preferentially greater in certain tumoural cells (Batlle et al, 1975; Navone et al, 1988; Fukuda et al, 1989) primarily due to the reduced activity of ferrochelatase, the enzyme responsible for the conversion of PpIX into haem (Dailey and Smith, 1984; Van Hillesberg e…”
BackgroundThe role of arginyl residues in porphyrin binding to ferrochelatase.
Dailey, H. A., & Fleming, J. E. (1986) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)57488-9 · Cited by 26
Fischer, F. F., Dickson, E. F. G., Kennedy, J. C., & Pottier, R. (2001) · Lasers in Medical Science · doi:10.1007/pl00011356 · Cited by 25
Interstitial photodynamic therapy in a rat liver metastasis model
van Hillegersberg, R., Marijnissen, J., Kort, W. J., Zondervan, P. E., Terpstra, O. T., & Star, W. (1992) · British Journal of Cancer · doi:10.1038/bjc.1992.402 · Cited by 25
Bartošová, J., & Hrkal, Z. (2000) · Comparative Biochemistry and Physiology Part C Pharmacology Toxicology and Endocrinology · doi:10.1016/s0742-8413(00)00125-0 · Cited by 24
Ninomiya, Y., Itoh, Y., Tajima, S., & Ishibashi, A. (2001) · Journal of Dermatological Science · doi:10.1016/s0923-1811(01)00123-2 · Cited by 24
Palasuberniam, P., Kraus, D., Mansi, M., Braun, A., Howley, R., Myers, K. A., & Chen, B. (2019) · Photochemistry and Photobiology · doi:10.1111/php.13091 · Cited by 23
“activity in a variety of tumors including liver (29), gastric (14) and colorectal (14,30) cancers.”
BackgroundBressoud, D., Jomini, V., & Tyrrell, R. M. (1992) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/1011-1344(92)85110-g · Cited by 23
Wang, I. (1998) · Cancer Letters · doi:10.1016/s0304-3835(98)00271-7 · Cited by 23
Fluorescent contrast agents for tumor surgery (Review)
Xiao, Q., Chen, T., & Chen, S. (2018) · Experimental and Therapeutic Medicine · doi:10.3892/etm.2018.6401 · Cited by 22
“FECH Liver cancer (69) Enzyme activity decreased”
Background5-Aminolevulinic Acid: Production by Fermentation, and Agricultural and Biomedical Applications
Nishikawa, S., & Murooka, Y. (2001) · Biotechnology and Genetic Engineering Reviews · doi:10.1080/02648725.2001.10648012 · Cited by 23
Gederaas, O. A., Berg, K., & Romslo, I. (2000) · Cancer Letters · doi:10.1016/s0304-3835(99)00399-7 · Cited by 21
Smith, A. (1987) · Annals of the New York Academy of Sciences · doi:10.1111/j.1749-6632.1987.tb48786.x · Cited by 21
Minamikawa, T., Matsuo, H., Kato, Y., Harada, Y., Otsuji, E., Yanagisawa, A., Tanaka, H., & Takamatsu, T. (2016) · Scientific Reports · doi:10.1038/srep25530 · Cited by 20
Spectroscopic examination of the active site of bovine ferrochelatase
Dailey, H. A. (1985) · Biochemistry · doi:10.1021/bi00327a003 · Cited by 20
TMC-435, an NS3/4A protease inhibitor for the treatment of HCV infection.
Tsantrizos, Y. S. (2009) · PubMed · Cited by 19
Sl, G., Havens, J. J., Nguyen, M. L., & Hilf, R. (1999) · British Journal of Cancer · doi:10.1038/sj.bjc.6690454 · Cited by 17
“The promise of this photos tizer stems from reports that PPIX accumulates to a greater e in malignant compared to normal tissue after administration δ-aminolaevulinic acid ( δ-ALA) (Dailey and Smith, 1984; van Hillegersberg et al, 1992; Malik et al, 1995).”
BackgroundAkhtar, M. (1991) · New comprehensive biochemistry · doi:10.1016/s0167-7306(08)60109-x · Cited by 18
[48] Purification and characterization of bacterial ferrochelatase
Dailey, H. A. (1986) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/s0076-6879(86)23050-5 · Cited by 18
Photodynamic therapy and laser-based diagnostic studies of malignant tumours
Wang, I. (1999) · Lund University Publications (Lund University) · Cited by 17
Photodynamic Therapy Effectively Treats Actinic Keratoses Without Pre-Illumination Incubation Time.
Gandy, J. R., Labadie, B. W., Bierman, D., & Zachary, C. B. (2017) · PubMed · Cited by 16
Dailey, H. A., Fleming, J. E., & Harbin, B. M. (1986) · Journal of Bacteriology · doi:10.1128/jb.165.1.1-5.1986 · Cited by 16
“Experiments with N-methylprotoporphyrin and 2,4-disubstituted porphyrins were performed as described previously for bovine ferrochelatase (4, 6).”
BackgroundUnilesional mycosis fungoides treated with photodynamic therapy. A case report.
Hegyi, J., Frey, T., & Arenberger, P. (2008) · PubMed · Cited by 15
Metadata
- Authors
- Dailey, H. A., & Smith, A.
- ORCID
- Venue
- Biochemical Journal
- Publisher
- Portland Press Ltd.
- Published
- 1984-10-15
- Volume
- 223
- Issue
- 2
- Pages
- 441-445
- ISSN
- 0264-6021 (ISSN-L)
- 1470-8728
- PMC
- PMC1144316
- OpenAlex
- W2170447022
- Cited by
- 140
- References
- 30
- Citations by year
- 2025: 1 · 2023: 1 · 2022: 3 · 2020: 3 · 2019: 3 · 2018: 1 · 2017: 4 · 2016: 3 · 2015: 4 · 2014: 1 · 2012: 3
- FWCI
- 6.75
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Biochemical Journal (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Funders
- British Sedimentological Research Group
- National Institutes of Health
- U.S. Public Health Service
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Photodynamic Therapy Research Studies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Porphyrin Metabolism and Disorders
- Physical Sciences › Materials Science › Materials Chemistry › Porphyrin and Phthalocyanine Chemistry
- Keywords
- porphyrins, ferrochelatase, photodynamic therapy, hematoporphyrin, deuteroporphyrin, competitive inhibition, enzyme kinetics, hepatocellular carcinoma
- MeSH terms
- Animals, Ferrochelatase, Hematoporphyrins, Kinetics, Liver, Liver Neoplasms, Experimental, Lyases, Male, Porphyrins, Rats, Inbred BUF, Rats, In Vitro Techniques
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