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Now in Photochem Photobiol: Phototoxicity of Lamotrigine

Quantum yield of singlet oxygen production by LTG (ordinate, 0-0.12) as a function of solvent composition in deuterated acetonitrile (abscissa, 0-100%) See: [1]

Lamotrigine (LTG), an anti-convulsant drug that blocks voltage-gated sodium channels, is widely given to treat epilepsy. More recently, it has been approved for treatment of bipolar I disorder and is also given off-label to treat various other conditions. Unfortunately, patients taking LTG often experience exaggerated sunburn and other phototoxic skin problems.

In the current issue of Photochemistry and Photobiology, a research article by Bilski and colleagues characterizes the photochemical properties of LTG in order to better understand the phototoxic skin reactions associated with its use. In particular they examined LTG singlet oxygen photosensitization and LTG photodegradation. Their results confirm that LTG is a photochemically active drug.

[1] Bilski PJ, Wolak MA, Zhang V, Moore DE, Chignell, CF (2009) Photochemical reactions involved in the phototoxicity of the anticonvulsant and antidepressant drug lamotrigine (lamictal). Photochem Photobiol 85:1327-1335.

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1: Zhang Y, Kubicki J, Platz MS. Ultrafast UV-visible and infrared spectroscopic observation of a singlet vinylcarbene and the intramolecular cyclopropenation reaction. J Am Chem Soc. 2009 Sep 30;131(38):13602-3. PubMed PMID: 19787856.

2: Teng Y, Liu R, Yan S, Pan X, Zhang P, Wang M. Spectroscopic Investigation on the Toxicological Interactions of 4-aminoantipyrine with Bovine Hemoglobin. J Fluoresc. 2009 Sep 29. [Epub ahead of print] PubMed PMID: 19787443.

3: Moon YH, Kwon SM, Kim HJ, Jung KY, Park JH, Kim SA, Kim YC, Ahn SG, Yoon JH. Efficient preparation of highly pure chlorin e6 and its photodynamic anti-cancer activity in a rat tumor model. Oncol Rep. 2009 Nov;22(5):1085-91. PubMed PMID: 19787225.

4: Ohtsuki A, Hasegawa T, Hirasawa Y, Tsuchihashi H, Ikeda S. Photodynamic therapy using light-emitting diodes for the treatment of viral warts. J Dermatol. 2009 Oct;36(10):525-8. PubMed PMID: 19785705.

5: Mikolajewska P, Iani V, Juzeniene A, Moan J. Topical aminolaevulinic acid- and aminolaevulinic acid methyl ester-based photodynamic therapy with red and violet light: influence of wavelength on pain and erythema. Br J Dermatol. 2009 Aug 8. [Epub ahead of print] PubMed PMID: 19785604.

6: Yarasi S, Ng S, Loppnow GR. Initial excited-state structural dynamics of uracil from resonance Raman spectroscopy are different from those of thymine (5-methyluracil). J Phys Chem B. 2009 Oct 29;113(43):14336-42. PubMed PMID: 19785434.

7: Trian T, Ge Q, Moir LM, Burgess JK, Kuo C, King NJ, Reddel HK, Black JL, Oliver BG, McParland BE. Rhinovirus-induced Exacerbations of Asthma - How is the {beta}2-adrenoceptor Implicated? Am J Respir Cell Mol Biol. 2009 Sep 25. [Epub ahead of print] PubMed PMID: 19783788.

8: Bonnecarrère L, Templier I, Carron PL, Maurizi J, Salameire D, Beani JC, Blaise S. [Two cases of iatrogenic cutis and subcutis calcinosis after calcium-containing heparin injection.]. J Mal Vasc. 2009 Sep 24. [Epub ahead of print] French. PubMed PMID: 19782485.

9: Nagao R, Tomo T, Noguchi E, Nakajima S, Suzuki T, Okumura A, Kashino Y, Mimuro M, Ikeuchi M, Enami I. Purification and characterization of a stable oxygen-evolving Photosystem II complex from a marine centric diatom, Chaetoceros gracilis. Biochim Biophys Acta. 2009 Sep 23. [Epub ahead of print] PubMed PMID: 19781519.

10: Kaushik M, Prasad M, Kaushik S, Singh A, Kukreti S. Structural transition from dimeric to tetrameric i-motif, caused by the presence of TAA at the 3'-end of human telomeric C-rich sequence. Biopolymers. 2009 Sep 24. [Epub ahead of print] PubMed PMID: 19780129.

11: Kim TW, Oh EJ, Jee AY, Lim ST, Park DH, Lee M, Hyun SH, Choy JH, Hwang SJ. Soft-chemical exfoliation route to layered cobalt oxide monolayers and its application for film deposition and nanoparticle synthesis. Chemistry. 2009 Oct 19;15(41):10752-61. PubMed PMID: 19780114.

12: Kim Y, Choi Y, Kim S, Park J, Chung M, Song KB, Hwang I, Kwon K, Park J. Disinfection of iceberg lettuce by titanium dioxide-UV photocatalytic reaction. J Food Prot. 2009 Sep;72(9):1916-22. PubMed PMID: 19777894.

13: Ye JY, Huang ZY, Min C, Pan SR, Chen DH. Structure and haemocompatibility of ZnO films deposited by radio frequency sputtering. Biomed Mater. 2009 Oct;4(5):55004. Epub 2009 Sep 23. PubMed PMID: 19776492.

14: Sepulveda R, Pe'er J, Midena E, Seregard S, Dua H, Singh AD. Topical Chemotherapy for OSSN : Current Status. Br J Ophthalmol. 2009 Sep 23. [Epub ahead of print] PubMed PMID: 19776089.

15: Trakatelli M, Charalampidis S, Novakovic LB, Patsatsi A, Kalabalikis D, Sotiriadis D. Photodermatoses with onset in the elderly. Br J Dermatol. 2009 Nov;161 Suppl 3:69-77. PubMed PMID: 19775360.

16: James KA, Burkhart CN, Morrell DS. Emerging drugs for acne. Expert Opin Emerg Drugs. 2009 Sep 22. [Epub ahead of print] PubMed PMID: 19772370.

17: Dandler J, Scheer H. Inhibition of aggregation of [pd]-bacteriochlorophyllides in mesoporous silica. Langmuir. 2009 Oct 20;25(20):11988-92. PubMed PMID: 19772311.

18: Chen J, Louis E, Lee CJ, Wormeester H, Kunze R, Schmidt H, Schneider D, Moors R, van Schaik W, Lubomska M, Bijkerk F. Detection and characterization of carbon contamination on EUV multilayer mirrors. Opt Express. 2009 Sep 14;17(19):16969-79. doi: 10.1364/OE.17.016969. PubMed PMID: 19770915.

19: Ito A, Hosokawa S, Miyoshi S, Soejima K, Ogawa S, Arai T. The Myocardial Electrical Blockade Induced By Photosensitization Reaction. IEEE Trans Biomed Eng. 2009 Sep 18. [Epub ahead of print] PubMed PMID: 19770088.

20: Verma SB, Wollina U. Ultraviolet light-induced leukoderma of the scalp associated with androgenetic alopecia: senescent actinic depigmentation of the scalp. J Cutan Med Surg. 2009 Sep-Oct;13(5):262-5. PubMed PMID: 19769835.

21: Tzaneva S, Kittler H, Holzer G, Reljic D, Weber M, Hönigsmann H, Tanew A. 5-methoxypsoralen plus UVA is superior to medium-dose UVA1 in the treatment of severe atopic dermatitis. A randomized crossover trial. Br J Dermatol. 2009 Sep 21. [Epub ahead of print] PubMed PMID: 19769631.

22: Han SK, Sik RH, Motten AG, Chignell CF, Bilski PJ. Photosensitized Oxidation of Tetrabromobisphenol A by Humic Acid in Aqueous Solution. Photochem Photobiol. 2009 Sep 21. [Epub ahead of print] PubMed PMID: 19769581.

23: Mimuro M, Yokono M, Akimoto S. Variations in Photosystem I Properties in the Primordial Cyanobacterium Gloeobacter violaceus PCC 7421. Photochem Photobiol. 2009 Sep 21. [Epub ahead of print] PubMed PMID: 19769578.

24: Yang YL, Liao WY, Liu WY, Liaw CC, Shen CN, Huang ZY, Wu SH. Discovery of New Natural Products by Intact-Cell Mass Spectrometry and LC-SPE-NMR: Malbranpyrroles, Novel Polyketides from Thermophilic Fungus Malbranchea sulfurea. Chemistry. 2009 Sep 18. [Epub ahead of print] PubMed PMID: 19768713.

25: Nagano T, Kakegawa A, Yamakoshi Y, Tsuchiya S, Hu JC, Gomi K, Arai T, Bartlett JD, Simmer JP. Mmp-20 and Klk4 cleavage site preferences for amelogenin sequences. J Dent Res. 2009 Sep;88(9):823-8. PubMed PMID: 19767579; PubMed Central PMCID: PMC2751868.

26: Häder DP, Lebert M. Photoorientation in photosynthetic flagellates. Methods Mol Biol. 2009;571:51-65. PubMed PMID: 19763958.

27: Gollnick SO, Brackett CM. Enhancement of anti-tumor immunity by photodynamic therapy. Immunol Res. 2009 Sep 10. [Epub ahead of print] PubMed PMID: 19763892.

28: Has C, Herz C, Zimina E, Qu HY, He Y, Zhang ZG, Wen TT, Gache Y, Aumailley M, Bruckner-Tuderman L. Kindlin-1 Is required for RhoGTPase-mediated lamellipodia formation in keratinocytes. Am J Pathol. 2009 Oct;175(4):1442-52. Epub 2009 Sep 17. PubMed PMID: 19762715; PubMed Central PMCID: PMC2751541.

29: Luo P, Niu H, Zheng G, Bai X, Zhang M, Wang W. From salmon pink to blue natural sensitizers for solar cells: Canna indica L., Salvia splendens, cowberry and Solanum nigrum L. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Nov;74(4):936-42. Epub 2009 Aug 25. PubMed PMID: 19762275.

30: Kawanami Y, Pace TC, Mizoguchi J, Yanagi T, Nishijima M, Mori T, Wada T, Bohne C, Inoue Y. Supramolecular complexation and enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid with 4-aminoprolinol derivatives as chiral hydrogen-bonding templates. J Org Chem. 2009 Oct 16;74(20):7908-21. PubMed PMID: 19761230.

31: Bell TD, Yap S, Jani CH, Bhosale SV, Hofkens J, De Schryver FC, Langford SJ, Ghiggino KP. Synthesis and photophysics of core-substituted naphthalene diimides: fluorophores for single molecule applications. Chem Asian J. 2009 Oct 5;4(10):1542-50. PubMed PMID: 19760701.

32: Tsai HL, Lue WL, Lu KJ, Hsieh MH, Wang SM, Chen J. Starch Synthesis in Arabidopsis is Achieved by Spatial Co-transcription of Core Starch Metabolism Genes. Plant Physiol. 2009 Sep 16. [Epub ahead of print] PubMed PMID: 19759345.

33: Singh AK, Bhattacharyya-Pakrasi M, Elvitigala T, Ghosh B, Aurora R, Pakrasi HB. A systems level analysis of the effects of light quality on the metabolism of a cyanobacterium. Plant Physiol. 2009 Sep 16. [Epub ahead of print] PubMed PMID: 19759342.

34: Sharma SD, Meeran SM, Katiyar N, Tisdale B, Yusuf N, Xu H, Elmets CA, Katiyar SK. IL-12-deficiency suppresses 12-O-tetradecanoylphorbol-13-acetate-induced skin tumor development in 7, 12-dimethylbenz(a)anthracene-initiated mouse skin through inhibition of inflammation. Carcinogenesis. 2009 Sep 16. [Epub ahead of print] PubMed PMID: 19759192.

35: Damian DL, Kim YJ, Dixon KM, Halliday GM, Javeri A, Mason RS. Topical calcitriol protects from UV-induced genetic damage but suppresses cutaneous immunity in humans. Exp Dermatol. 2009 Sep 16. [Epub ahead of print] PubMed PMID: 19758324.

36: De Vijlder HC, Middelburg T, De Bruijn HS, Martino Neumann HA, Sterenborg HC, Robinson DJ, De Haas ER. Optimizing ALA-PDT in the management of non-melanoma skin cancer by fractionated illumination. G Ital Dermatol Venereol. 2009 Aug;144(4):433-9. PubMed PMID: 19755946.

37: Do TT, Bailey EC, Wang F, Smith N, Lee W, Fisher GJ, Voorhees JJ, Kang S. Targeted broadband ultraviolet B phototherapy improves disorders characterized by increased dermal matrix. Br J Dermatol. 2009 Sep 15. [Epub ahead of print] PubMed PMID: 19754865.

38: Clemente-Leo�?n M, Coronado E, Lo�?pez-Muñoz A, Repetto D, Ito T, Konya T, Yamase T, Constable EC, Housecroft CE, Doyle K, Graber S. Dual-Emissive Photoluminescent Langmuir-Blodgett Films of Decatungstoeuropate and an Amphiphilic Iridium Complex. Langmuir. 2009 Sep 15. [Epub ahead of print] PubMed PMID: 19754063.

39: Kubota H, Sakurai I, Katayama K, Mizusawa N, Ohashi S, Kobayashi M, Zhang P, Aro EM, Wada H. Purification and characterization of photosystem I complex from Synechocystis sp. PCC 6803 by expressing histidine-tagged subunits. Biochim Biophys Acta. 2009 Sep 12. [Epub ahead of print] PubMed PMID: 19751700.

40: Lim YC, Yoo JO, Park D, Kang G, Hwang BM, Kim YM, Ha KS. Antitumor effect of photodynamic therapy with chlorin-based photosensitizer DH-II-24 in colorectal carcinoma. Cancer Sci. 2009 Aug 25. [Epub ahead of print] PubMed PMID: 19751236.

41: Yamada H, Kitauchi Y, Tanabe K, Ito T, Nishimoto S. Efficient photooxidative strand cleavage at 5-methylcytosine in DNA by sensitization with 9,10-anthraquinone-tethered oligonucleotides. Nucleic Acids Symp Ser (Oxf). 2009;(53):209-10. PubMed PMID: 19749334.

42: Tanabe K, Yamada H, Ito T, Nishimoto S. Photoelectrochemical identification of 5-methylcytosine modification in DNA: combination of photosensitization and enzymatic cleavage. Nucleic Acids Symp Ser (Oxf). 2009;(53):205-6. PubMed PMID: 19749332.

43: Whitaker MJ, Bordowitz JR, Montgomery BL. CpcF-dependent regulation of pigmentation and development in Fremyella diplosiphon. Biochem Biophys Res Commun. 2009 Nov 27;389(4):602-6. Epub 2009 Sep 11. PubMed PMID: 19748483.

44: Branchini BR, Ablamsky DM, Davis AL, Southworth TL, Butler B, Fan F, Jathoul AP, Pule MA. Red-emitting luciferases for bioluminescence reporter and imaging applications. Anal Biochem. 2009 Sep 11. [Epub ahead of print] PubMed PMID: 19748472.

45: Meeran SM, Singh T, Nagy TR, Katiyar SK. High-fat diet exacerbates inflammation and cell survival signals in the skin of ultraviolet B-irradiated C57BL/6 mice. Toxicol Appl Pharmacol. 2009 Sep 9. [Epub ahead of print] PubMed PMID: 19747500.

46: Steinbauer J, Schreml S, Karrer S, Ackermann G, Babilas P, Landthaler M, Szeimies RM. Phototoxic reactions in healthy volunteers following photodynamic therapy with methylaminolevulinate cream or with cream containing 5-aminolevulinic acid: a phase II, randomized study. Photodermatol Photoimmunol Photomed. 2009 Oct;25(5):270-5. PubMed PMID: 19747247.

47: Murakami H, Kohno E, Kohmura Y, Ozawa H, Ito H, Sugihara K, Horiuchi K, Hirano T, Kanayama N. Antitumor effect of photodynamic therapy in mice using direct application of Photofrin dissolved in lidocaine jelly. Photodermatol Photoimmunol Photomed. 2009 Oct;25(5):259-63. PubMed PMID: 19747245.

48: Yang HP, Chen K, Ju M, Chang BZ, Wang LY, Gu H. A study of the way in which dermatologists and photosensitive patients apply sunscreen in China. Photodermatol Photoimmunol Photomed. 2009 Oct;25(5):245-9. PubMed PMID: 19747243.

49: Liu R, Zhang Y, Feng P. Multiresponsive Supramolecular Nanogated Ensembles. J Am Chem Soc. 2009 Sep 11. [Epub ahead of print] PubMed PMID: 19746981.

50: Hirano T, Kitagawa S, Ohtani H. Methacrylate-ester-based reversed phase monolithic columns for high speed separation prepared by low temperature UV photo-polymerization. Anal Sci. 2009 Sep;25(9):1107-13. PubMed PMID: 19745538.

51: Yao SS, Li YY, Xue LH, Yan YW, You Y. Luminescence studies on Ba(2)ZnSi(2)O(7) : Eu(2+) phosphors crystals. Luminescence. 2009 Sep 10. [Epub ahead of print] PubMed PMID: 19743524.

52: Zhao Q, Wang QE, Ray A, Wani G, Han C, Milum K, Wani AA. Modulation of nucleotide excision repair by mammalian SWI/SNF chromatin-remodeling complex. J Biol Chem. 2009 Sep 8. [Epub ahead of print] PubMed PMID: 19740755.

53: Frommholz D, Kusch P, Blavid R, Scheer H, Tu JM, Marcus K, Zhao KH, Atemnkeng V, Marciniak J, Kaiser AE. Completing the hypusine pathway in Plasmodium. FEBS J. 2009 Oct;276(20):5881-91. Epub 2009 Sep 9. PubMed PMID: 19740108.

54: Theodossiou TA, Hothersall JS, De Witte PA, Pantos A, Agostinis P. The Multifaceted Photocytotoxic Profile of Hypericin. Mol Pharm. 2009 Sep 24. [Epub ahead of print] PubMed PMID: 19739671.

55: Zhang Y, Burdzinski G, Kubicki J, Vyas S, Hadad CM, Sliwa M, Poizat O, Buntinx G, Platz MS. Study of the S1 excited state of para-methoxy-3-phenyl-3-methyl diazirine by ultrafast time resolved UV-Vis and IR spectroscopies and theory. J Am Chem Soc. 2009 Sep 30;131(38):13784-90. PubMed PMID: 19736936.

56: Key T, McCarthy A, Campbell DA, Six C, Roy S, Finkel ZV. Cell size trade-offs govern light exploitation strategies in marine phytoplankton. Environ Microbiol. 2009 Sep 4. [Epub ahead of print] PubMed PMID: 19735282.

57: Ferrario A, Gomer CJ. Targeting the 90kDa heat shock protein improves photodynamic therapy. Cancer Lett. 2009 Sep 2. [Epub ahead of print] PubMed PMID: 19733005.

58: Terasaki N, Yamamoto N, Hattori M, Tanigaki N, Hiraga T, Ito K, Konno M, Iwai M, Inoue Y, Uno S, Nakazato K. Photosensor based on an FET utilizing a biocomponent of photosystem i for use in imaging devices. Langmuir. 2009 Oct 6;25(19):11969-74. PubMed PMID: 19731941.

59: Li Q, Lin S, Wang X, Lian G, Lu Z, Guo H, Ruan K, Wang Y, Ye Z, Han J, Lin SC. Axin determines cell fate by controlling the p53 activation threshold after DNA damage. Nat Cell Biol. 2009 Sep;11(9):1128-34. PubMed PMID: 19731416.

60: Schreml S, Gantner S, Steinbauer J, Babilas P, Landthaler M, Szeimies RM. Melanoma promotion after photodynamic therapy of a suspected Bowen's disease lesion. Dermatology. 2009;219(3):279-81. Epub 2009 Sep 2. PubMed PMID: 19729877.

61: Sanovic R, Krammer B, Grumboeck S, Verwanger T. Time-resolved gene expression profiling of human squamous cell carcinoma cells during the apoptosis process induced by photodynamic treatment with hypericin. Int J Oncol. 2009 Oct;35(4):921-39. PubMed PMID: 19724930.

62: Kim SG, Hong JW, Boo SH, Kim MG, Lee KD, Ahn JC, Hwang HJ, Shin JI, Lee SJ, Oh JK, Chung PS. Combination treatment of Cetuximab and photodynamic therapy in SNU-1041 squamous cancer cell line. Oncol Rep. 2009 Oct;22(4):701-8. PubMed PMID: 19724846.

63: Meeran SM, Katiyar N, Singh T, Katiyar SK. Loss of endogenous interleukin-12 activates survival signals in ultraviolet-exposed mouse skin and skin tumors. Neoplasia. 2009 Sep;11(9):846-55. PubMed PMID: 19724678; PubMed Central PMCID: PMC2735800.

64: Tan J, Liu R, Wang W, Liu W, Tian Y, Wu M, Huang Y. Controllable Aggregation and Reversible pH Sensitivity of AuNPs Regulated by Carboxymethyl Cellulose. Langmuir. 2009 Sep 1. [Epub ahead of print] PubMed PMID: 19722539.

65: Lu YG, Wu JJ, Yang YD, He Y. Photodynamic therapy of port-wine stains. J Dermatolog Treat. 2009 Jan 1:1-5. [Epub ahead of print] PubMed PMID: 19722122.

66: Hunt DM, Carvalho LS, Cowing JA, Davies WL. Evolution and spectral tuning of visual pigments in birds and mammals. Philos Trans R Soc Lond B Biol Sci. 2009 Oct 12;364(1531):2941-55. PubMed PMID: 19720655.

67: Song P, Sun SG, Liu JY, Xu YQ, Han KL, Peng XJ. Theoretical and experimental study on the intramolecular charge transfer excited state of the new highly fluorescent terpyridine compound. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Oct 15;74(3):753-7. Epub 2009 Aug 12. PubMed PMID: 19720560.

68: Lin SW, Hsu JH, Chang CH, Lin CH. Objective-type dark-field system applied to multi-wavelength capillary electrophoresis for fluorescent detection and analysis. Biosens Bioelectron. 2009 Oct 15;25(2):450-5. Epub 2009 Aug 11. PubMed PMID: 19720517.

69: Chen J, Dvornikov AS, Rentzepis PM. Comment on "New insight into photochemistry of ferrioxalate". J Phys Chem A. 2009 Jul 30;113(30):8818-9; discussion 8820-2. PubMed PMID: 19719321.

70: Pace TC, Nishijima M, Wada T, Inoue Y, Bohne C. Photophysical studies on the supramolecular photochirogenesis for the photocyclodimerization of 2-anthracenecarboxylate within human serum albumin. J Phys Chem B. 2009 Jul 30;113(30):10445-53. PubMed PMID: 19719288.

71: Roy S, Saha S, Majumdar R, Dighe RR, Chakravarty AR. Photocytotoxic 3d-metal scorpionates with a 1,8-naphthalimide chromophore showing photoinduced DNA and protein cleavage activity. Inorg Chem. 2009 Oct 5;48(19):9501-9. PubMed PMID: 19719144.

72: Wang L, Zhu L, Yin P, Fu W, Chen J, Hao J, Xiao F, Lv C, Zhang J, Shi L, Li Q, Wei Y. From 0D dimer to 2D network-supramolecular assembly of organic derivatized polyoxometalates with remote hydroxyl via hydrogen bonding. Inorg Chem. 2009 Oct 5;48(19):9222-35. PubMed PMID: 19719087.

73: Komori K, Miyajima S, Tsuru T, Fujii T, Mohri S, Ono Y, Sakai Y. A rapid and simple evaluation system for gas toxicity using luminous bacteria entrapped by a polyion complex membrane. Chemosphere. 2009 Aug 27. [Epub ahead of print] PubMed PMID: 19716582.

74: Lee CT, Smith KA, Hatton TA. Small-Angle Neutron Scattering Study of the Micellization of Photosensitive Surfactants in Solution and in the Presence of a Hydrophobically Modified Polyelectrolyte (dagger). Langmuir. 2009 Aug 28. [Epub ahead of print] PubMed PMID: 19715336.