5-Aminolevulinic acid and its derivatives: physical chemical properties and protoporphyrin IX formation in cultured cells
Open accessAbstract
Protoporphyrin IX (PpIX) is used as a fluorescence marker and photosensitizing agent in photodynamic therapy (PDT). A temporary increase of PpIX in tissues can be obtained by administration of 5-aminolevulinic acid (ALA). Lipophilicity is one of the key parameters defining the bioavailability of a topically applied drug. In the present work, octanol-water partition coefficients of ALA and several of its esters have been determined to obtain a parameter related to their lipophilicity. The influence of parameters such as lipophilicity, concentration, time, and pH value on PpIX formation induced by ALA and its esters is then investigated in human cell lines originating from the lung and bladder. ALA esters are found to be more lipophilic than the free acid. The optimal concentration (c(opt), precursor concentration at which maximal PpIX accumulation is observed) is then measured for each precursor. Long-chained ALA esters are found to decrease the c(opt) value by up to two orders of magnitude as compared to ALA. The reduction of PpIX formation observed at higher concentrations than c(opt) is correlated to reduced cell viability as determined by measuring the mitochondrial activity. Under optimal conditions, the PpIX formation rate induced by the longer-chained esters is higher than that of ALA or the shorter-chained esters. A biphasic pH dependence on PpIX generation is observed for ALA and its derivatives. Maximal PpIX formation is measured under physiological conditions (pH 7.0-7.6), indicating that further enhancement of intracellular PpIX content may be achieved by adjusting the pharmaceutical formulation of ALA or its derivatives to these pH levels.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Topically applied ALA has slow and limited tissue penetration due to its hydrophilicity; hexaminolevulinate with increased lipophilicity was developed to overcome these limitations.
“Since topically applied ALA has slow and limited tissue penetration due to its hydrophilicity, hexaminolevulinate (HAL) with increased lipophilicity was developed to overcome these limitations [59].”
From 5-Aminolevulinic Acid as a Theranostic Agent for Tumor Fluorescence Imaging and Photodynamic Therapy (2023) · cites this paper as [59]
Cites
Kennedy (1992) · doi:10.1016/1011-1344(92)85108-7 · Cited by 1,166 · see citing works
Walter, S., Susanne, S., Simon, W., Herbert, S., Clemens, F., Claudia, G., Alwin, E. G., Rainer, K., & Hans, J. R. (1998) · Neurosurgery · doi:10.1097/00006123-199803000-00017 · Cited by 690 · see citing works
5-Aminolevulinic Acid-Based Photodynamic Therapy: Principles and Experimental Research
Peng, Q., Berg, K., Moan, J., Kongshaug, M., & Nesland, J. M. (1997) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1997.tb08549.x · Cited by 615 · see citing works
Detection of Early Bladder Cancer by 5-Aminolevulinic Acid Induced Porphyrin Fluorescence
Kriegmair, M., Baumgartner, R., Knüchel, R., Stepp, H. G., Hofstädter, F., & Hofstetter, A. G. (1996) · The Journal of Urology · doi:10.1016/s0022-5347(01)66559-5 · Cited by 436 · see citing works
Goßner, L., Stolte, M., Sroka, R. C., Rick, K., May, A. D., Hahn, E. G., & Ell, C. (1998) · Gastroenterology · doi:10.1016/s0016-5085(98)70527-x · Cited by 397 · see citing works
Kriegmair, M., Ehsan, A., Baumgartner, R., Lumper, W., Knuechel, R., Hofstädter, F., Steinbach, P., & Hofstetter, A. (1994) · Urology · doi:10.1016/s0090-4295(94)80167-3 · Cited by 265 · see citing works
Use of 5-aminolevulinic acid esters to improve photodynamic therapy on cells in culture.
Gaullier, J., Berg, K., Peng, Q., Anholt, H., Selbo, P. K., Ma, L. W., & Moan, J. E. (1997) · PubMed · Cited by 257 · see citing works
A mechanistic study of cellular photodestruction with 5-aminolaevulinic acid-induced porphyrin
Iinuma, S., Farshi, S., Ortel, B., & Hasan, T. (1994) · British Journal of Cancer · doi:10.1038/bjc.1994.244 · Cited by 240 · see citing works
Lange, N., Jichlinski, P., Zellweger, M., Forrer, M., Martí, A., Guillou, L., Kučera, P., Wagnières, G., & van den Bergh, H. (1999) · British Journal of Cancer · doi:10.1038/sj.bjc.6690338 · Cited by 229 · see citing works
Self-citationSide Effects and Photosensitization of Human Tissues after Aminolevulinic Acid
Webber, J. D., Kessel, D. H., & Fromm, D. (1997) · Journal of Surgical Research · doi:10.1006/jsre.1997.5004 · Cited by 189 · see citing works
Prodrugs of 5‐Aminolevullinic Acid for Photodynamic Therapy
Kloek, J., & van Henegouwen, G. M. J. B. (1996) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1996.tb01868.x · Cited by 182 · see citing works
Kloek, J., Akkermans, W., & van Henegouwen, G. M. J. B. (1998) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1998.tb05178.x · Cited by 175 · see citing works
Baumgärtner, R., Huber, R. M., Schulz, H., Stepp, H. G., Rick, K., Gamarra, F., Leberig, A., & Roth, C. (1996) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/s1011-1344(96)07365-4 · Cited by 155 · see citing works
Kriegmair, M., Baumgärtner, R., Lumper, W., Waidelich, R. M., & Hofstetter, A. G. (1996) · British Journal of Urology · doi:10.1046/j.1464-410x.1996.09717.x · Cited by 148 · see citing works
Tope, W. D., Martín, A., Grevelink, J. M., STARR, J. C., Fewkes, J. L., Flotte, T. J., Deutsch, T. F., & Anderson, R. R. (1995) · Archives of Dermatological Research · doi:10.1007/bf00371740 · Cited by 145 · see citing works
Berg, K., Anholt, H., Bech, Ø., & Moan, J. (1996) · British Journal of Cancer · doi:10.1038/bjc.1996.423 · Cited by 142 · see citing works
Jichlinski, P., Forrer, M., Mizeret, J. C., Glanzmann, T. M., Braichotte, D. R., Wagnières, G., Zimmer, G., Guillou, L., Schmidlin, F. R., Graber, P., et al. (1997) · Lasers in Surgery and Medicine · doi:10.1002/(sici)1096-9101(1997)20:4 · Cited by 130 · see citing works
Self-citationHinnen, P., de Rooij, F., van Velthuysen, M., Edixhoven, A., van Hillegersberg, R., Tilanus, H., Wilson, J., & Siersema, P. (1998) · British Journal of Cancer · doi:10.1038/bjc.1998.559 · Cited by 130 · see citing works
Photobleaching of protoporphyrin IX in cells incubated with 5-aminolevulinic acid
Moan, J. E., Streckytė, G., Bagdonas, S., Gadmar, Ø. B., & Berg, K. (1997) · International Journal of Cancer · doi:10.1002/(sici)1097-0215(19970106)70:1 · Cited by 118 · see citing works
Musgrove, E. A., Seaman, M., & Hedley, D. W. (1987) · Experimental Cell Research · doi:10.1016/0014-4827(87)90093-0 · Cited by 101 · see citing works
OPTIMISATION OF THE FORMATION AND DISTRIBUTION OF PROTOPORPHYRIN IX IN THE UROTHELIUM
Martí, A., Lange, N., van den Bergh, H., Sedmera, D., Jichlinski, P., & Kučera, P. (1999) · The Journal of Urology · doi:10.1016/s0022-5347(05)68625-9 · Cited by 92 · see citing works
Self-citationWyld, L., Reed, M., & Brown, N. (1998) · British Journal of Cancer · doi:10.1038/bjc.1998.265 · Cited by 82 · see citing works
Chemical instability of 5-aminolevulinic acid used in the fluorescence diagnosis of bladder tumours
Novo, M., Hüttmann, G., & Diddens, H. C. (1996) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/1011-1344(96)07285-5 · Cited by 82 · see citing works
Kondo, M., Hirota, N., Takaoka, T., & Kajiwara, M. (1993) · Cell Biology and Toxicology · doi:10.1007/bf00755143 · Cited by 69 · see citing works
Clinical Evaluation of the Cutaneous Phototoxicity of 5,10,15,20-Tetra (m-hydroxyphenyl)chlorin
Wagnières, G., Hadjur, C., Grosjean, P., Braichotte, D. R., Savary, J., Monnier, P., & van den Bergh, H. (1998) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1998.tb09696.x · Cited by 68 · see citing works
Self-citationHow do Ca2+ and 5-aminolevulinic acid-derived oxyradicals promote injury to isolated mitochondria?
Hermes‐Lima, M. (1995) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(95)00015-p · Cited by 65 · see citing works
Fraga, C. G., Onuki, J., Lucesoli, F., Bechara, E. J. H., & Mascio, P. D. (1994) · Carcinogenesis · doi:10.1093/carcin/15.10.2241 · Cited by 56 · see citing works
In-vitro investigation of ALA-induced protopoyphyrin IX
Krammer, B. E., & Überriegler, K. P. (1996) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/s1011-1344(96)07358-7 · Cited by 51 · see citing works
Does δ-aminolaevulinic acid induce genotoxic effects?
Fiedler, D. M., Eckl, P., & Krammer, B. E. (1996) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/1011-1344(95)07229-2 · Cited by 47 · see citing works
Gibson, S. L., Havens, J. J., Foster, T. H., & Hilf, R. (1997) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1997.tb08580.x · Cited by 41 · see citing works
Rossi, F. M., Campbell, D., Pottier, R., Kennedy, J. C., & Dickson, E. F. G. (1996) · British Journal of Cancer · doi:10.1038/bjc.1996.452 · Cited by 37 · see citing works
pH-Dependent formation of 5-aminolaevulinic acid-induced protoporphyrin IX in fibrosarcoma cells
Fuchs, C., Riesenberg, R., Siegert, J., & Baumgärtner, R. (1997) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/s1011-1344(97)00026-2 · Cited by 29 · see citing works
δ-Aminolevulinic acid transport in Saccharomyces cerevisiae
Moretti, M. B., Garcı́a, S. C., Stella, C. A., Ramos, E. H., & Batlle, A. M. D. C. (1993) · International Journal of Biochemistry · doi:10.1016/0020-711x(88)90325-4 · Cited by 28 · see citing works
THE EFFECT OF ALA AND RADIATION ON PORPHYRIN/HEME BIOSYNTHESIS IN ENDOTHELIAL CELLS
He, D., Behar, S., Nomura, N., Sassa, S., & Lim, H. W. (1995) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1995.tb09884.x · Cited by 24 · see citing works
Bridges, J. W., Sargent, N. S. E., & Upshall, D. G. (1979) · British Journal of Pharmacology · doi:10.1111/j.1476-5381.1979.tb13677.x · Cited by 21 · see citing works
Feasibility of photodynamic endometrial ablation without anesthesia
Wyss, P. A., Fehr, M. K., van den Bergh, H., & Haller, U. (1998) · International Journal of Gynecology & Obstetrics · doi:10.1016/s0020-7292(98)00004-6 · Cited by 16 · see citing works
Grönlund-Pakkanen, S., Mäkinen, K. T., Talja, M. T., Kuusisto, A., & ALHAVA, E. M. (1997) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/s1011-1344(96)00007-3 · Cited by 12 · see citing works
Flagged first, then by citations
1 of the 39 references couldn’t be matched to a known paper.
Cited by
Sorted by citations
Necrotic death as a cell fatePreprint
Zong, W., & Thompson, C. B. (2006) · Genes & Development · doi:10.1101/gad.1376506 · Cited by 912 · see citing works
Chemotherapeutic Approaches for Targeting Cell Death Pathways
Ricci, M., & Zong, W. (2006) · The Oncologist · doi:10.1634/theoncologist.11-4-342 · Cited by 512 · see citing works
Pariser, D. M., Lowe, N. J., Stewart, D. M., Jarratt, M. T., Lucky, A. W., Pariser, R. J., & Yamauchi, P. S. (2003) · Journal of the American Academy of Dermatology · doi:10.1067/mjd.2003.49 · Cited by 302 · see citing works
Photodynamic therapy: update 2006 Part 1: Photochemistry and photobiology
Calzavara‐Pinton, P., Venturini, M., & Sala, R. (2007) · Journal of the European Academy of Dermatology and Venereology · doi:10.1111/j.1468-3083.2006.01902.x · Cited by 244 · see citing works
5‐Aminolevulinic Acid Derivatives in Photomedicine: Characteristics, Application and Perspectives
Fotinos, N., Campo, M. A., Popowycz, F., Gurny, R., & Lange, N. (2006) · Photochemistry and Photobiology · doi:10.1562/2006-02-03-ir-794 · Cited by 238 · see citing works
Self-citationPhotodynamic therapy of skin cancer: controlled drug delivery of 5-ALA and its esters
Lopez, R. F. V. (2003) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2003.09.002 · Cited by 225 · see citing works
Peng, Q., Soler, A. M., Warloe, T., Nesland, J. M., & Giercksky, K.-E. (2001) · Journal of Photochemistry and Photobiology B: Biology · doi:10.1016/s1011-1344(01)00173-7 · Cited by 218 · see citing works
Garland, M. J., Cassidy, C. M., Woolfson, D., & Donnelly, R. F. (2009) · Future Medicinal Chemistry · doi:10.4155/fmc.09.55 · Cited by 207 · see citing works
Regulation in Plant Stress Tolerance by a Potential Plant Growth Regulator, 5-Aminolevulinic Acid
Akram, N. A., & Ashraf, M. (2013) · Journal of Plant Growth Regulation · doi:10.1007/s00344-013-9325-9 · Cited by 200 · see citing works
Perrett, C. M., McGregor, J. M., Warwick, J., Karran, P., Leigh, I. M., Proby, C. M., & Harwood, C. A. (2006) · British Journal of Dermatology · doi:10.1111/j.1365-2133.2006.07616.x · Cited by 188 · see citing works
Donnelly, R. F., Morrow, D. I. J., McCarron, P. A., Woolfson, A. D., Morrissey, A., Juzenas, P., Juzeniene, A., Iani, V., McCarthy, H. O., & Moan, J. E. (2008) · Journal of Controlled Release · doi:10.1016/j.jconrel.2008.05.002 · Cited by 173 · see citing works
Zhu, J., Zhang, L., Li, T., Dong, S., & Wang, E. (2013) · Advanced Materials · doi:10.1002/adma.201205360 · Cited by 162 · see citing works
Contrast Agents for Optical Imaging
Licha, K. (2002) · Topics in current chemistry · doi:10.1007/3-540-46009-8_1 · Cited by 158 · see citing works
Photodynamic therapy for acne vulgaris: A critical review from basics to clinical practice
Sakamoto, F. H., Lopes, J. D., & Anderson, R. R. (2010) · Journal of the American Academy of Dermatology · doi:10.1016/j.jaad.2009.09.056 · Cited by 150 · see citing works
Kojima, C., Toi, Y., Harada, A., & Kono, K. (2007) · Bioconjugate Chemistry · doi:10.1021/bc060244u · Cited by 147 · see citing works
The use of photodynamic therapy in dermatology: results of a consensus conference.
Nestor, M. S., Gold, M. H., Kauvar, A. N. B., Taub, A. F., Geronemus, R. G., Ritvo, E. C., Goldman, M. P., Gilbert, D. J., Richey, D. F., Alster, T. S., et al. (2006) · PubMed · Cited by 128 · see citing works
Ding, H., Sumer, B. D., Kessinger, C. W., Dong, Y., Huang, G., Boothman, D. A., & Gao, J. (2011) · Journal of Controlled Release · doi:10.1016/j.jconrel.2011.01.004 · Cited by 128 · see citing works
Photodynamic therapy for acne vulgaris: A critical review from basics to clinical practice
Sakamoto, F. H., Torezan, L. A. R., & Anderson, R. R. (2010) · Journal of the American Academy of Dermatology · doi:10.1016/j.jaad.2009.09.057 · Cited by 127 · see citing works
Fluorescence Detection of Bladder Cancer: A Review
D’Hallewin, M., Bezdetnaya, L., & Guillemin, F. H. (2002) · European Urology · doi:10.1016/s0302-2838(02)00402-5 · Cited by 121 · see citing works
Noninvasive fluorescence excitation spectroscopy during application of 5-aminolevulinic acid in vivo
Juzenas, P., Juzeniene, A., Kaalhus, O., Iani, V., & Moan, J. E. (2002) · Photochemical & Photobiological Sciences · doi:10.1039/b203459j · Cited by 116 · see citing works
Lipid cubic phases for improved topical drug delivery in photodynamic therapy
Bender, J., Ericson, M. B., Merclin, N., Iani, V., Rosén, A., Engström, S., & Moan, J. E. (2005) · Journal of Controlled Release · doi:10.1016/j.jconrel.2005.05.010 · Cited by 113 · see citing works
Diagnosis of urothelial carcinoma of the bladder using fluorescence endoscopy
Zaak, D., Karl, A., Knüchel, R., Stepp, H. G., Hartmann, A., Reich, O. M., Bachmann, A., Siebels, M., Popken, G., & Stief, C. G. (2005) · British Journal of Urology · doi:10.1111/j.1464-410x.2005.05604.x · Cited by 111 · see citing works
Dysart, J. S., & Patterson, M. S. (2005) · Photochemical & Photobiological Sciences · doi:10.1039/b511807g · Cited by 111 · see citing works
Fotinos, N., Convert, M., Piffaretti, J.-C., Gurny, R., & Lange, N. (2008) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.01372-07 · Cited by 105 · see citing works
Self-citationRosa, F. S. D., Tedesco, A. C., Lopez, R. F. V., Pierre, M. B. R., Lange, N., Marchetti, J. M., Rotta, J. C. G., & Bentley, M. V. L. B. (2003) · Journal of Controlled Release · doi:10.1016/s0168-3659(03)00125-1 · Cited by 104 · see citing works
Self-citationPhotodynamic Therapy and the Biophysics of the Tumor Microenvironment
Sorrin, A. J., Ruhi, M. K., Ferlic, N. A., Karimnia, V., Polacheck, W. J., Celli, J. P., Huang, H., & Rizvi, I. (2020) · Photochemistry and Photobiology · doi:10.1111/php.13209 · Cited by 101 · see citing works
Battah, S., Balaratnam, S., Casas, A. G., O’Neill, S., Edwards, C., Batlle, A. M. D. C., Dobbin, P. S., & MacRobert, A. J. (2007) · Molecular Cancer Therapeutics · doi:10.1158/1535-7163.mct-06-0359 · Cited by 99 · see citing works
Casas, A. G., Fukuda, H., Venosa, G. M. D., & Batlle, A. M. D. C. (2001) · British Journal of Cancer · doi:10.1054/bjoc.2001.1875 · Cited by 91 · see citing works
Topical photodynamic therapy in clinical dermatology
Kormeili, T., Yamauchi, P. S., & Lowe, N. J. (2004) · British Journal of Dermatology · doi:10.1111/j.1365-2133.2004.05940.x · Cited by 88 · see citing works
Donnelly, R. F., Morrow, D. I. J., Fay, F., Scott, C. J., Abdelghany, S. M., Singh, R. R. T., Garland, M. J., & Woolfson, A. D. (2010) · Photodiagnosis and Photodynamic Therapy · doi:10.1016/j.pdpdt.2010.09.001 · Cited by 86 · see citing works
Photosensitizers Used in the Photodynamic Therapy of Rheumatoid Arthritis
Gallardo‐Villagrán, M., Leger, D. Y., Liagre, B., & Therrien, B. (2019) · International Journal of Molecular Sciences · doi:10.3390/ijms20133339 · Cited by 80 · see citing works
Juzeniene, A., Juzenas, P., Iani, V., & Moan, J. E. (2002) · Photochemistry and Photobiology · doi:10.1562/0031-8655(2002)0760329taoaaa2.0.co2 · Cited by 79 · see citing works
Pharmacology of protoporphyrin IX in nude mice after application of ALA and ALA esters
Moan, J. E., Ma, L., Juzeniene, A., Iani, V., Juzenas, P., Apricena, F., & Peng, Q. (2002) · International Journal of Cancer · doi:10.1002/ijc.10802 · Cited by 75 · see citing works
Targets and Mechanisms of Photodynamic Therapy in Lung Cancer Cells: A Brief Overview
Chiaviello, A., Postiglione, I., & Palumbo, G. A. (2011) · Cancers · doi:10.3390/cancers3011014 · Cited by 69 · see citing works
Hædersdal, M., Sakamoto, F. H., Farinelli, W. A., Doukas, A. G., Tam, J., & Anderson, R. R. (2014) · Lasers in Surgery and Medicine · doi:10.1002/lsm.22259 · Cited by 65 · see citing works
Gederaas, O. A., Holroyd, A., Brown, S. B., Vernon, D. I., Moan, J. E., & Berg, K. (2001) · Photochemistry and Photobiology · doi:10.1562/0031-8655(2001)0730164aameto2.0.co2 · Cited by 62 · see citing works
Juzeniene, A., Juzenas, P., Ma, L.-W., Iani, V., & Moan, J. E. (2006) · British Journal of Dermatology · doi:10.1111/j.1365-2133.2006.07484.x · Cited by 61 · see citing works
Berger, Y., Greppi, A., Siri, O., Neier, R., & Juillerat‐Jeanneret, L. (2000) · Journal of Medicinal Chemistry · doi:10.1021/jm000981q · Cited by 61 · see citing works
Self-citationCasas, A. G., Battah, S., Venosa, G. M. D., Dobbin, P. S., Rodríguez, L., Fukuda, H., Batlle, A. M. D. C., & MacRobert, A. J. (2009) · Journal of Controlled Release · doi:10.1016/j.jconrel.2009.01.002 · Cited by 61 · see citing works
Steluti, R., DEROSA, F., Collett, J. H., Tedesco, A. C., & Bentley, M. V. L. B. (2005) · European Journal of Pharmaceutics and Biopharmaceutics · doi:10.1016/j.ejpb.2005.01.011 · Cited by 61 · see citing works
Photodynamic Therapy for Basal Cell Carcinoma: The Clinical Context for Future Research Priorities
Collier, N. J., & Rhodes, L. E. (2020) · Molecules · doi:10.3390/molecules25225398 · Cited by 61 · see citing works
Rodríguez, L., Batlle, A. M. D. C., Venosa, G. M. D., MacRobert, A. J., Battah, S., Daniel, H., & Casas, A. G. (2006) · The International Journal of Biochemistry & Cell Biology · doi:10.1016/j.biocel.2006.03.002 · Cited by 58 · see citing works
Protoporphyrin IX-dependent photodynamic production of endogenous ROS stimulates cell proliferation
Blázquez‐Castro, A., Carrasco, E., Calvo-Sánchez, M. I., Jaén, P., STOCKERT, J. C., Juarranz, Á., Sanz-Rodrı́guez, F., & Espada, J. (2012) · European Journal of Cell Biology · doi:10.1016/j.ejcb.2011.12.001 · Cited by 57 · see citing works
Battah, S., O’Neill, S., Edwards, C., Balaratnam, S., Dobbin, P. S., & MacRobert, A. J. (2006) · The International Journal of Biochemistry & Cell Biology · doi:10.1016/j.biocel.2006.02.001 · Cited by 57 · see citing works
Zawacka‐Pankau, J., Issaeva, N., Hossain, S., Pramanik, A., Selivanova, G., & Podhajska, A. J. (2006) · Journal of Biological Chemistry · doi:10.1074/jbc.m608906200 · Cited by 56 · see citing works
Photodynamic Therapy for Bladder Cancers, A Focused Review †
Rahman, K. M. M., Giram, P. S., Foster, B. A., & You, Y. (2022) · Photochemistry and Photobiology · doi:10.1111/php.13726 · Cited by 55 · see citing works
Tewari, K. M., & Eggleston, I. M. (2018) · Photochemical & Photobiological Sciences · doi:10.1039/c8pp00362a · Cited by 53 · see citing works
Drug Delivery of Aminolevulinic Acid from Topical Formulations Intended for Photodynamic Therapy¶
Donnelly, R. F., McCarron, P. A., & Woolfson, A. D. (2005) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2005.tb01439.x · Cited by 65 · see citing works
The advantages of aminolevulinic acid photodynamic therapy in dermatology
Taylor, E. G., & Brown, S. (2002) · Journal of Dermatological Treatment · doi:10.1080/095466302317414645 · Cited by 52 · see citing works
de Souza, A. L. R., Marra, K., Gunn, J., Samkoe, K. S., Kanick, S. C., Davis, S. C., Chapman, M. S., Maytin, E. V., Hasan, T., & Pogue, B. W. (2016) · British Journal of Cancer · doi:10.1038/bjc.2016.267 · Cited by 51 · see citing works
Derivatives of 5-Aminolevulinic Acid for Photodynamic Therapy
Donnelly, R. F., McCarron, P. A., & Woolfson, D. A. (2007) · Perspectives in Medicinal Chemistry · doi:10.1177/1177391x0700100005 · Cited by 50 · see citing works
Investigation of a novel dendritic derivative of 5-aminolaevulinic acid for photodynamic therapy
Venosa, G. M. D., Casas, A. G., Battah, S., Dobbin, P. S., Fukuda, H., MacRobert, A. J., & Batlle, A. M. D. C. (2005) · The International Journal of Biochemistry & Cell Biology · doi:10.1016/j.biocel.2005.08.001 · Cited by 50 · see citing works
Delivery of hypericin for photodynamic applications
Saw, C. L. L., Olivo, M., Soo, K. C., & Heng, P. W. S. (2005) · Cancer Letters · doi:10.1016/j.canlet.2005.10.020 · Cited by 48 · see citing works
Juzeniene, A., Juzenas, P., Kaalhus, O., Iani, V., & Moan, J. E. (2002) · Photochemistry and Photobiology · doi:10.1562/0031-8655(2002)0760452teoaop2.0.co2 · Cited by 48 · see citing works
Perotti, C., Casas, A. G., Fukuda, H., SACCA, P. A., & Batlle, A. M. D. C. (2002) · British Journal of Cancer · doi:10.1038/sj.bjc.6600559 · Cited by 44 · see citing works
Hoda, M. R., & Popken, G. (2009) · Journal of Surgical Research · doi:10.1016/j.jss.2008.12.027 · Cited by 44 · see citing works
5-Aminolaevulinic acid peptide prodrugs enhance photosensitization for photodynamic therapy
Bourré, L., Giuntini, F., Eggleston, I. M., Wilson, M., & MacRobert, A. J. (2008) · Molecular Cancer Therapeutics · doi:10.1158/1535-7163.mct-08-0092 · Cited by 44 · see citing works
van den Akker, J. T. H. M., Holroyd, J. A., Vernon, D. I., Sterenborg, H. J. C. M., & Brown, S. B. (2003) · Lasers in Surgery and Medicine · doi:10.1002/lsm.10212 · Cited by 44 · see citing works
Kantelhardt, S. R., Diddens, H., Leppert, J., Rohde, V., Hüttmann, G., & Giese, A. (2008) · Lasers in Surgery and Medicine · doi:10.1002/lsm.20623 · Cited by 43 · see citing works
Protoporphyrin IX photodynamic therapy for synovitis
Kirdaitė, G., Lange, N., Busso, N., van den Bergh, H., Kučera, P., & So, A. K.-L. (2002) · Arthritis & Rheumatism · doi:10.1002/art.10199 · Cited by 43 · see citing works
Self-citationDrug Delivery of Aminolevulinic Acid from Topical Formulations Intended for Photodynamic Therapy¶
Donnelly, R. F., McCarron, P. A., & Woolfson, A. D. (2005) · Photochemistry and Photobiology · doi:10.1562/2004-08-23-ir-283r1.1 · Cited by 43 · see citing works
Bigelow, C. E., Mitra, S., Knuechel, R., & Foster, T. H. (2001) · British Journal of Cancer · doi:10.1054/bjoc.2001.1977 · Cited by 41 · see citing works
Ito, S., Miyoshi, N., DeGraff, W., Nagashima, K., Kirschenbaum, L. J., & Riesz, P. (2009) · Free Radical Research · doi:10.3109/10715760903271249 · Cited by 42 · see citing works
Juzenas, P., Sharfaei, S., Moan, J. E., & Bissonnette, R. (2002) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/s1011-1344(02)00269-5 · Cited by 42 · see citing works
Rosa, F. S. D., Lopez, R. F. V., Thomazine, J. A., Tedesco, A. C., Lange, N., & Bentley, M. V. L. B. (2004) · Pharmaceutical Research · doi:10.1007/s11095-004-7677-3 · Cited by 41 · see citing works
Self-citationComparison of ALA- and ALA hexyl-ester-induced PpIX depth distribution in human skin carcinoma
Dögnitz, N., Salomon, D., Zellweger, M., Ballini, J.-P., Gabrecht, T., Lange, N., van den Bergh, H., & Wagnières, G. (2008) · Journal of Photochemistry and Photobiology B: Biology · doi:10.1016/j.jphotobiol.2008.07.012 · Cited by 39 · see citing works
Self-citationRadunović, M., Petrini, M., Tovilović, T. V., Iezzi, G., Lodovico, S. D., Piattelli, A., & D’Ercole, S. (2020) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/j.jphotobiol.2020.111826 · Cited by 39 · see citing works
Winkler, A., & Müller-Goymann, C. C. (2002) · European Journal of Pharmaceutics and Biopharmaceutics · doi:10.1016/s0939-6411(02)00006-1 · Cited by 38 · see citing works
Rodriguez, L., de Bruijn, H. S., Di Venosa, G., Mamone, L., Robinson, D. J., Juarranz, A., Batlle, A., & Casas, A. (2009) · Journal of Photochemistry and Photobiology B: Biology · doi:10.1016/j.jphotobiol.2009.07.001 · Cited by 37 · see citing works
Glycoside Esters of 5-Aminolevulinic Acid for Photodynamic Therapy of Cancer
Vallinayagam, R., Schmitt, F., Barge, J., Wagnières, G., Wenger, V., Neier, R., & Juillerat‐Jeanneret, L. (2008) · Bioconjugate Chemistry · doi:10.1021/bc700324r · Cited by 37 · see citing works
Self-citationALA- and ALA-ester-mediated Photodynamic Therapy of Human Glioma Spheroids
Hirschberg, H., Sun, C., Tromberg, B. J., & Madsen, S. J. (2002) · Journal of Neuro-Oncology · doi:10.1023/a:1015784926550 · Cited by 37 · see citing works
Tunstall, R. G., Barnett, A. A., Schofield, J., Griffiths, J., Vernon, D. I., Brown, S. B., & Roberts, D. J. H. (2002) · British Journal of Cancer · doi:10.1038/sj.bjc.6600460 · Cited by 37 · see citing works
Giuntini, F., Bourré, L., MacRobert, A. J., Wilson, M., & Eggleston, I. M. (2009) · Journal of Medicinal Chemistry · doi:10.1021/jm900224r · Cited by 36 · see citing works
Berger, Y., Ingrassia, L., Neier, R., & Juillerat‐Jeanneret, L. (2003) · Bioorganic & Medicinal Chemistry · doi:10.1016/s0968-0896(02)00619-3 · Cited by 35 · see citing works
Self-citationHelaly, M. N., El-Hoseiny, H. M., Elsheery, N. I., Kalaji, H. M., Santos‐Villalobos, S. D. L., Wróbel, J., Hassan, I. F. Z., Gaballah, M. S., Abdelrhman, L. A., Mira, A. M., et al. (2022) · Plants · doi:10.3390/plants11060743 · Cited by 35 · see citing works
Carbon dot-protoporphyrin IX conjugates for improved drug delivery and bioimaging
Cosme, J. R. A., Bryant, H. E., & Claeyssens, F. (2019) · PLoS ONE · doi:10.1371/journal.pone.0220210 · Cited by 34 · see citing works
Yu, T.-H., Yi, Y.-C., Shih, I.-T., & Ng, I. (2019) · Applied Biochemistry and Biotechnology · doi:10.1007/s12010-019-03178-9 · Cited by 34 · see citing works
Xiang, W., Weingandt, H., Ließmann, F., Klein, S., Stepp, H. G., Baumgartner, R., & Hillemanns, P. (2001) · Photochemistry and Photobiology · doi:10.1562/0031-8655(2001)0740617peibaa2.0.co2 · Cited by 33 · see citing works
5-Aminolevulinic Acid as a Theranostic Agent for Tumor Fluorescence Imaging and Photodynamic Therapy
Howley, R., Chandratre, S., & Chen, B. (2023) · Bioengineering · doi:10.3390/bioengineering10040496 · Cited by 33 · see citing works
Hydroxypyridinone and 5-Aminolaevulinic Acid Conjugates for Photodynamic Therapy
Battah, S., Hider, R. C., MacRobert, A. J., Dobbin, P. S., & Zhou, T. (2017) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.7b00346 · Cited by 33 · see citing works
Pharmacological Treatments for Basal Cell Carcinoma
Lee, S., Selva, D. N., Huilgol, S. C., Goldberg, R. A., & Leibovitch, I. (2007) · Drugs · doi:10.2165/00003495-200767060-00007 · Cited by 33 · see citing works
Schmitz, L., Novak, B., Hoeh, A.-K., Luebbert, H., & Dirschka, T. (2015) · Photodiagnosis and Photodynamic Therapy · doi:10.1016/j.pdpdt.2015.11.004 · Cited by 33 · see citing works
Cosserat-Gérardin, I., Bezdetnaya, L., Notter, D., Vigneron, C., & Guillemin, F. H. (2000) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/s1011-1344(00)00142-1 · Cited by 34 · see citing works
Akens, M. K., Yee, A., Wilson, B. C., Burch, S., Johnson, C. L., Lilge, L. D., & Bisland, S. K. (2007) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2007.00172.x · Cited by 32 · see citing works
Thermosetting Gel for the Delivery of 5-Aminolevulinic Acid Esters to the Cervix
Basset, S. C., Peng, Q., Gurny, R., & Lange, N. (2007) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.21181 · Cited by 32 · see citing works
Self-citationMorrow, D. I. J., McCarron, P. A., Woolfson, A. D., Juzenas, P., Juzeniene, A., Iani, V., Moan, J. E., & Donnelly, R. F. (2010) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.22116 · Cited by 32 · see citing works
Lee, J. B., Choi, J. Y., Chun, J. S., Yun, S. J., Lee, S. C., Oh, J., & Park, H. R. (2008) · British Journal of Dermatology · doi:10.1111/j.1365-2133.2008.08611.x · Cited by 32 · see citing works
Niu, C. J., Fisher, C., Scheffler, K., Wan, R., Maleki, H., Liu, H., Sun, Y., Simmons, C. A., Birngruber, R., & Lilge, L. D. (2015) · Journal of Biomedical Optics · doi:10.1117/1.jbo.20.9.098002 · Cited by 31 · see citing works
Collaud, S., Warloe, T., Jordan, O., Gurny, R., & Lange, N. (2007) · Journal of Controlled Release · doi:10.1016/j.jconrel.2007.08.015 · Cited by 30 · see citing works
Self-citationComparison of the uptake of 5-aminolevulinic acid and its methyl ester in keratinocytes and skin
Schulten, R., Novak, B., Schmitz, B., & Lübbert, H. (2012) · Naunyn-Schmiedeberg s Archives of Pharmacology · doi:10.1007/s00210-012-0777-4 · Cited by 29 · see citing works
Li, K., Dong, W., Qiu, L., Liu, Q., Lv, G., Peng, Y. H., Xie, M., & Lin, J. (2019) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2019.111582 · Cited by 30 · see citing works
Togsverd‐Bo, K., Idorn, L. W., Philipsen, P. A., Wulf, H. C., & Hædersdal, M. (2012) · Experimental Dermatology · doi:10.1111/j.1600-0625.2012.01557.x · Cited by 31 · see citing works
WINKLER, A., & Müller-Goymann, C. C. (2005) · European Journal of Pharmaceutics and Biopharmaceutics · doi:10.1016/j.ejpb.2005.01.014 · Cited by 30 · see citing works
Adigbli, D. K., Wilson, D. G. G., Farooqui, N., Sousi, E., Risley, P., Taylor, I., MacRobert, A. J., & Loizidou, M. (2007) · British Journal of Cancer · doi:10.1038/sj.bjc.6603895 · Cited by 29 · see citing works
The Dark Side: Photosensitizer Prodrugs
Sansaloni-Pastor, S., Bouilloux, J., & Lange, N. (2019) · Pharmaceuticals · doi:10.3390/ph12040148 · Cited by 28 · see citing works
Self-citationDonnelly, R. F., Morrow, D. I. J., McCarron, P. A., Garland, M. J., & Woolfson, A. D. (2007) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/j.jphotobiol.2007.09.009 · Cited by 28 · see citing works
Activity of phosphatase-sensitive 5-aminolevulinic acid prodrugs in cancer cell lines
Herceg, V., Lange, N., Allémann, É., & Babič, A. (2017) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/j.jphotobiol.2017.04.029 · Cited by 27 · see citing works
Self-citationPhotodynamische Diagnostik im Harntrakt
Stenzl, A., Jocham, D., Jichlinski, P., Junker, K., König, F., van den Bergh, H., Volkmer, B., Zaak, D., & Gschwend, J. E. (2008) · Der Urologe · doi:10.1007/s00120-008-1791-5 · Cited by 27 · see citing works
Gilmore, B., McCarron, P. A., Morrow, D. I. J., Murphy, D. J., Woolfson, A. D., & Donnelly, R. F. (2006) · European Journal of Pharmaceutics and Biopharmaceutics · doi:10.1016/j.ejpb.2006.03.002 · Cited by 27 · see citing works
Assessment of ALA‐induced PpIX production in porcine skin pretreated with microneedles
Rodrigues, P. G. S., de Menezes, P. F. C., Fujita, A. K. L., Escobar, A., Nardi, A. B. D., Kurachi, C., & Bagnato, V. S. (2014) · Journal of Biophotonics · doi:10.1002/jbio.201400081 · Cited by 26 · see citing works
- Authors
- Uehlinger, P., Zellweger, M., Wagnières, G., Juillerat-Jeanneret, L., van den Bergh, H., & Lange, N.
- Affiliations
- École Polytechnique Fédérale de Lausanne (CH)
- Venue
- Journal of Photochemistry and Photobiology B: Biology
- Publisher
- Elsevier BV
- Published
- 2000-01
- Volume
- 54
- Issue
- 1
- Pages
- 72-80
- ISSN
- 1011-1344 (ISSN-L)
- OpenAlex
- W1996290414
- Cited by
- 221
- References
- 39
- Citations by year
- 2026: 5 · 2025: 3 · 2024: 3 · 2023: 2 · 2022: 5 · 2021: 2 · 2020: 6 · 2019: 6 · 2018: 3 · 2017: 6 · 2016: 5 · 2015: 4 · 2014: 7 · 2013: 7 · 2012: 11
- FWCI
- 12.40
- Type
- journal article
- Language
- en
- Open access
- green
- infoscience.epfl.ch
- Locations
- Journal of Photochemistry and Photobiology B Biology (publishedVersion)
- PubMed (publishedVersion)
- Infoscience (Ecole Polytechnique Fédérale de Lausanne) (submittedVersion)
- Infoscience (Ecole Polytechnique Fédérale de Lausanne) (submittedVersion, cc-by-nc-nd)
- IRIS (submittedVersion)
- SERVAL (Université de Lausanne) (submittedVersion)
- Topics
- Health Sciences › Medicine › Pulmonary and Respiratory Medicine › 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
- 5-aminolevulinic acid, protoporphyrin IX, photodynamic therapy, photosensitizers, lipophilicity, octanol-water partition coefficient, pH dependence, cell viability, lung cancer cell lines, bladder cancer cell lines, mitochondrial activity
- MeSH terms
- Aminolevulinic Acid, Urinary Bladder Neoplasms, Bronchi, Cell Line, Humans, Hydrogen-Ion Concentration, Kinetics, Lung Neoplasms, Protoporphyrins, Structure-Activity Relationship, Tumor Cells, Cultured, Photosensitizing Agents, Respiratory Mucosa
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
