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Review Article

Photochemical stability of lipoic acid and its impact on skin ageing

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Pages 918-924 | Received 24 Feb 2011, Accepted 06 May 2011, Published online: 09 Jun 2011

References

  • Scott BC, Aruoma OI, Evans PJ, O'Neil C, Van der Viet A, Cross CE, Tritschler H, Halliwell B. Lipoic and dihydrolipoic acids as antioxidants. A critical evaluation. Free Rad Res Commun 1994; 20:119–133.
  • Moini H, Packer L, Sans HE. Antioxidant and prooxidant activities of alpha-lipoic acid and dihydrolipoic acid. Toxicol Appl Pharmacol 2002;182:84–90.
  • Packer L, Cadenas E. Lipoc acid energy metabolism and redox regulation and cell signaling. J Clin Biochem Nutr 2011;48:26–32.
  • Brown PR, Edwards JO. Effect of solvent on the photolysis of α-lipoic acid. J Org Chem 1969;34:3131–3135.
  • Brown PR, Edwards JO. The use of thin-layer chromatography in following product formation in the photolysis of α-lipoic acid. J Chromatography 1969;43:515–518.
  • Kondo S. The roles of cytokines in photoaging. J Dermatol Sci 2000;23(Suppl 1):30–36.
  • Stary FE, Jindai SL, Murray RW. Oxidation of α-lipoic acid. J Org Chem 1975;40:58–62.
  • Tierney EP, Hanke CW. Recent advances in combination treatments for photoaging: review of the literature. Dermatol Surg 2010;36:829–840.
  • Gonzalo S. Epigenetic alterations in aging. J Appl Physiol 2010;109:586–597.
  • Uitto J, Fazio MJ, Olsen DR. Molecular mechanisms of cutaneous aging. Age-associated connective tissue alterations in the dermis. J Am Acad Dermatol 1989;21:614–622.
  • Rabe JH, Mamelak AJ, McElgunn PJ, Morison WL, Sauder DN. Photoaging: mechanisms and repair. J Am Acad Dermatol 2006;55:1–19.
  • Yaar M, Gilchrest BA. Photoageing: mechanism, prevention and therapy. Br J Dermatol 2007;157:874–887.
  • Mitchell DL, Jen J, Cleaver JE. Sequence specificity of cyclobutane pyrimidine dimers in DNA treated with solar (ultraviolet B) radiation. Nucleic Acids Res 1992;20:225–229.
  • Beehler BC, Przybyszewski J, Box HB, Kulesz-Martin MF. Formation of 8-hydroxydeoxyguanosine within DNA of mouse keratinocytes exposed in culture to UVB and H2O2. Carcinogenesis 1992;13:2003–2007.
  • Applegate LA, Scaletta C, Panizzon R, Niggli H, Frenk E. In vivo induction of pyrimidine dimers in human skin by UVA radiation: initiation of cell damage and/or intercellular communication? Int J Mol Med 1999;3:467–472.
  • Bernstein EF, Brown DB, Schwartz MD, Kaidbey K, Ksenzenko SM. The polyhydroxy acid gluconolactone protects against ultraviolet radiation in an in vitro model of cutaneous photoaging. Dermatol Surg 2004;30:189–195; discussion 196.
  • Zhang X, Rosenstein BS, Wang Y, Lebwohl M, Wei H. Identification of possible reactive oxygen species involved in ultraviolet radiation-induced oxidative DNA damage. Free Radic Biol Med 1997;23:980–985.
  • Herrling T, Fuchs J, Rehberg J, Groth N. UV-induced free radicals in the skin detected by ESR spectroscopy and imaging using nitroxides. Free Radic Biol Med 2003;35:59–67.
  • Yamamoto Y. Role of active oxygen species and active oxygen species and antioxidants in photoaging. J Dermatol Sci 2001; 27(Suppl 1):1–4.
  • Shindo Y, Witt E, Han D, Packer L. Dose-response effects of acute ultraviolet irradiation on antioxidants and molecular markers of oxidation in murine epidermis and dermis. J Invest Dermatol 1994;102:470–475.
  • Hanada K, Sawamura D, Tamai K, Hashimoto I, Kobayashi S. Photoprotective effect of esterified glutathione against ultraviolet B-induced sunburn cell formation in the hairless mice. J Invest Dermatol 1997;108:727–730.
  • Podda M, Rallis M, Traber MG, Packer L, Maibach HI. Kinetic study of cutaneous and subcutaneous distribution following topical application of [7,8-14C] rac-alpha-lipoic acid onto hairless. Biochem Pharmacol 1996;52:627–633.
  • Han D, Tritschler HJ, Packer L. Alpha-lipoic acid increases intracellular glutathione in a human T-lymphocyte Jurkat cell line. Biochem Biophys Res Commun 1995;207:258–264.
  • Han D, Handelman G, Marcocci L, Sen CK, Roy S, Kobuchi H, Tritschler HJ, Floh L, Packer L. Lipoic acid increases de novo synthesis of cellular glutathione by improving cystine utilization. Biofactors 1997; 6:321–338.
  • Sen CK, Roy S, Han D, Packer L. Regulation of cellular thiols in human lymphocytes by alpha-lipoic acid: a flow cytometric analysis. Free Radic Biol Med 1997;22:1241–1257.
  • Packer L, Witt EH, Tritschler HJ. Alpha-lipoic acid as a biological antioxidant. Free Rad Biol Med 1995;19:227–250.
  • Manda K, Ueno M, Moritake T, Anzai K. Alpha-lipoic acid attenuates x-radiation induced oxidative stress in mice. Cell Biol Toxicol 2006;23:29–37.
  • Manda K, Ueno M, Moritake T, Anzai K. Radiation-induced cognitive dysfunction and cerebellar oxidative stress in mice: protective effect of alpha lipoic acid. Behav Brain Res 2007; 177:7–14.
  • Fuchs J, Milbradt R. Antioxidant inhibition of skin inflammation induced by reactive oxidants: evaluation of the redox couple dihydrolipoate/lipoate. Skin Pharmacol 1994;7: 278–284.
  • Venkatraman MS, Chittiboyina A, Meingassner J, Ho CI, Varani J, Ellis CN, Avery MA, Pershadsingh HA, Kurtz TW, Benson SC. Alpha-Lipoic acid-based PPARgamma agonists for treating inflammatory skin diseases. Arch Dermatol Res 2004; 296:97–104.
  • Beitner H. Randomized, placebo-controlled, double blind study on the clinical efficacy of a cream containing 5% alpha-lipoic acid related to photoageing of facial skin. Br J Dermatol 2003;149:841–849.
  • Thom E. A randomized double-blind, placebo-controlled study on the clinical efficacy of oral treatment with Dermavite on ageing symptoms of the skin. J Int Med Res 2005;33: 267–272.
  • Rijnkels JM, Moison RM, Podda E, van Henegouwen GM. Photoprotection by antioxidants against UVB-radiation-induced damage in pig skin organ culture. Radiat Res 2003; 159:210–217.
  • Lin JY, Lin FH, Burch JA, Selim MA, Monteiro-Riviere NA, Grichnik JM, Pinnell SR. Alpha-lipoic acid is ineffective as a topical antioxidant for photoprotection of skin. J Invest Dermatol 2004;123:996–998.
  • Seaton TA, Jenner P, Marsden CD. The isomers of thioctic acid alter C-deoxyglucose incorporation in rat basal ganglia. Biochem Pharmacol 1996;51:983–998.
  • Barltrop JA, Hayes PM, Calvin M. The chemistry of 1,2- dithiane (trimethylene disulfide) as a model for the primary quantum conversion act in photosynthesis. J Am Chem Soc 1954;76:4348–4367.
  • Wagmer AF, Walton E, Boxer GE, Pauss MP, Holly FW, Folkers K. Properties and derivatives of a-lipoic acid. J Am Chem Soc 1956;78:5079–5081.
  • Ohishi N. Photochemical reaction product of hydroxylethylamine with lipoic acid. J Vitaminol 1967;13:80–88.
  • Lu CX, Bucher G, Sander W. Photoinduced interactions between oxidized and reduced lipoic acid and riboflavin. ChemPhysChem 2004;5:47–56.
  • Takagi M, Goto S, Matsuda T. Photoreaction of lipoic acid and related organic disulfides: reductive acylation with aldehydes. J Chem Soc Chem Commun 1976;92–93.
  • Takagi M. Photochemical preparation of acyl lipoic acid. Meth Enzymol 1979;62:145–146.
  • Matsugo S, Han D, Tritschler HJ, Packer L. Decomposition of α-lipoic acid derivatives by photoirradaition – Formation of dihydrolipoic acid from α-lipoic acid. Biochem Mol Biol Int 1996;38:51–59.
  • Bucher G, Lu C, Sander W. The photochemistry of lipoic acid: photoionization and observation of a triplet excited states of disulfide. ChemPhysChem 2006;6:2607–2618.
  • Wada N, Wakami H, Konishi T, Matsugo S. The degradation and regeneration of α-lipoic acid under the irradiation of UV light in the existence of homocysteine. J Clin Biochem Nutr 2009;44:218–222.
  • Wada N, Wakami H, Konishi T, Matsugo S. The effect of biothiol on UV irradiated α-lipoic acid. Biofactors 2008;34: 285–292.
  • Kisanuki A, Kimpara Y, Oikado Y, Kado N, Matsumoto M, Endo K. Ring-opening polymerization of lipoic acid and characterization of the polymer. J Poly Sci Part A Polym Chem 2008;48:5247–5253.
  • Endo K, Yamanaka T. Copolymerization of lipoic acid with 1,2-dithiane and characterization of the copolymer as an interlocked cyclic polymer. Macromolecules 2006;39: 4038–4043.
  • Schmidt KN, Amstad P, Cerutti P, Baeuerle PA. The roles of hydrogen peroxide and superoxide as messengers in the activation of transcription factor NF-kappa B. Chem Biol 1995; 2:13–22.
  • Huang C, Li J, Ding M, Leonard SS, Wang L, Castranova V, Vallyathan V, Shi X. UV Induces phosphorylation of protein kinase B (Akt) at Ser-473 and Thr-308 in mouse epidermal Cl 41 cells through hydrogen peroxide. J Biol Chem 2001;276: 40234–40240.
  • Saliou C, Kitazawa M, McLaughlin L, Yang JP, Lodge JK, Tetsuka T, Iwasaki K, Cillard J, Okamoto T, Packer L. Antioxidants modulate acute solar ultraviolet radiation-induced NF-kappa-B activation in a human keratinocyte cell line. Free Radic Biol Med 1999;26:174–183.
  • Shi SS, Day RM, Halpner AD, Blumberg JB, Suzuki YJ. Homocysteine and alpha-lipoic acid regulate p44/42 MAP kinase phosphorylation in NIH/3T3 cells. Antioxid Redox Signal 1999;1:123–128.
  • Cho KJ, Moon HE, Moini H, Packer L, Yoon DY, Chung AS. Alpha-lipoic acid inhibits adipocyte differentiation by regulating pro-adipogenic transcription factors via mitogen-activated protein kinase pathways. J Biol Chem 2003;278: 34823–34833.
  • Bito T, Sumita N, Masaki T, Shirakawa T, Ueda M, Yoshiki R, Tokura Y, Nishigori C. Ultraviolet light induces Stat3 activation in human keratinocytes and fibroblasts through reactive oxygen species and DNA damage. Exp Dermatol 2010;19:654–660.
  • Kofuji K, Nakamura M, Isobe T, Murata Y, Kawashima S. Stabilization of α-lipoic acid by complex formation with chitosan. Food Chem 2008;109:167–171.

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