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Quinolone photoallergy: Photosensitivity dermatitis induced by systemic administration of photohaptenic drugs

      Abstract

      Quinolone antibacterial agents are well known to elicit photosensitivity as a side effect. The photoallergenicity of fluoroquinolones, the representative quinolone derivatives, is mainly derived from their photohaptenic moiety. When epidermal cells are irradiated with ultraviolet A light in the presence of fluoroquinolones, quinolone photoadducts are formed in the treated cells. This photomodification is thought to be an initial step for sensitization and elicitation of this photoallergy, and quinolone-photoderivatized Langerhans cells are capable of stimulating immune T cells in mice. In the murine model, fluoroquinolone photoallergy is mediated by Th1 cells bearing T cell receptor Vβ13. There is a broad photoantigenic cross-reactivity among fluoroquinolones in recognition by T cells and immunoglobulins. Therefore, it is most likely that fluoroquinolones carry the same photoantigenic epitope, which is recognized by Vβ13+ T cells, leading to fluoroquinolone photosensitivity and cross-reactivity.

      Keywords

      Abbreviations:

      CPFX, ciprofloxacin (), ELISA, enzyme-linked immunosorbent assay (), ENX, enoxacin (), FLRX, fleroxacin (), Ig, immunoglobulin (), IL, interleukin (), LC, Langerhans cells (), LFLX, lomefloxacin (), LVLX, levofloxacin (), mAb, monoclonal antibody (), MHC, major histocompatibility complex (), NFLX, norfloxacin (), OFLX, ofloxacin (), PBMC, peripheral blood mononuclear cells (), SPFX, sparfloxacin (), TCSA, 3,3′,4′,5-tetrachlorosalicylanilide (), TFLX, tosufloxacin (), UVA, ultraviolet A light (), UVB, ultraviolet B light ()
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      References

        • Domagala JM
        Structure-activity and structure-side-effect relationship for the quinolone antibacterials.
        J Antimicrob Chemother. 1994; 33: 685-706
      1. Harber LC, Bickers DR. Drug induced photosensitivity (Phototoxic and photoallergic drug reactions). In: Harber LC, Bickers DR, editors. Photosensitivity Diseases: Principles of Diagnosis and Treatment, 2nd edn. Philadelphia: B.C. Decker, 1989:160–202.

      2. Fukuda E. Informations on drug eruptions (registered in the International Drug Benefit/Risk Assessment Data Resource Handbook). Fukuoka: Fukuda Dermatologic Clinic, 1997.

        • Ferguson J
        Fluoroquinolone photosensitization: A review of clinical and laboratory studies.
        Photochem Photobiol. 1995; 62: 954-958
        • Tokura Y
        • Iwamoto Y
        • Mizutani K
        • Takigawa M
        Sparfloxacin phototoxicity: potential photoaugmentation by ultraviolet A and B sources.
        Arch Dermatol Res. 1996; 288: 45-50
        • Przybila B
        • Georgii A
        • Berner T
        • Ring J
        Demonstration of quinolone phototoxicity in vitro.
        Dermatologica. 1990; 181: 98-103
        • Iwamoto Y
        • Kurita K
        • Shimizu T
        • Masuzawa T
        • Uno K
        • Yagi M
        • Oku T
        • Yanagihara Y
        DNA strand-breaking activities of quinolone antimicrobial agents under visible light irradiation.
        Biol Pharm Bull. 1994; 17: 654-657
        • Wagai N
        • Tawara K
        Quinolone antibacterial-agent-induced cutaneous phototoxicity: ear swelling reactions in Balb/c mice.
        Toxicol Lett. 1991; 58: 215-223
        • Horio T
        • Miyauchi H
        • Asada Y
        • Aoki Y
        • Harada M
        Phototoxicity and photoallergenicity of quinolones in guinea pigs.
        J Dermatol Sci. 1994; 7: 130-135
        • Fujita H
        • Matsuo I
        In vitro phototoxic activities of new quinolone antibacterial agents: lipid peroxidative potentials.
        Photodermatol Photoimmunol Photomed. 1994; 10: 202-205
        • Kawabe Y
        • Mizuno N
        • Sakakibara S
        Photoallergic reaction induced by enoxacin.
        Photodermatology. 1989; 6: 57-60
        • Kurumaji Y
        • Shono M
        Scartified photopatch testing in lomefloxacin photosensitivity.
        Contact Dermatitis. 1992; 26: 5-10
        • Yoshizawa M
        • Hashimoto A
        • Asai T
        Photosensitivity induced by lomefloxacin.
        Hifubyou-Shinryou. 1992; 14: 1085-1088
        • Correia O
        Bullous photodermatosis after lomefloxacin.
        Arch Dermatol. 1994; 130: 808-809
        • Tokura Y
        • Nishijima T
        • Yagi H
        • Furukawa F
        • Takigawa M
        Photohaptenic properties of fluoroquinolones.
        Photochem Photobiol. 1996; 64: 838-844
        • Izu R
        • Gardeazabal J
        • Gonzalez M
        • Landa N
        • Raton JA
        • Diaz-Perez JL
        Enoxacin-induced photosensitivity: study of two cases.
        Photodermatol Photoimmunol Photomed. 1992; 9: 86-88
        • Kang JS
        • Kim TH
        • Park KB
        • Chung BH
        • Youn JI
        Enoxacin photosensitivity.
        Photodermatol Photoimmunol Photomed. 1993; 9: 159-161
        • Takigawa M
        • Miyachi Y
        Mechanisms of contact photosensitivity in mice. I. T cell regulation of contact photosensitivity to tetrachlorosalicylanilide under the genetic restrictions of the major histocompatibility complex.
        J Invest Dermatol. 1982; 79: 108-115
        • Tokura Y
        • Takigawa M
        Immunological mechanisms of contact photosensitivity.
        Eur J Dermatol. 1993; 3: 87-91
        • Kochevar IE
        • Harber LC
        Photoreactions of 3,3′,4′,5-tetrachlorosalicylanilide with proteins.
        J Invest Dermatol. 1977; 68: 151-156
        • Tokura Y
        • Satoh T
        • Yamada M
        • Takigawa M
        Genetic control of contact photosensitivity to tetrachlorosalicylanilide. II. Igh complex controls the sensitivity induced by photohapten-modified spleen cells but not epidermal cells.
        Cell Immunol. 1991; 135: 195-207
        • Tokura Y
        • Yagi H
        • Satoh T
        • Takigawa M
        Effect of melanin pigment on the sensitization and elicitation of murine contact photosensitivity to tetrachlorosalicyanilide: mechanism of low responsiveness in C57BL/10 mice.
        J Invest Dermatol. 1993; 101: 673-678
        • Tokura Y
        • Satoh T
        • Takigawa M
        • Yamada M
        Genetic control of contact photosensitivity to tetrachlorosalicylanilide. I. Preferential activation of suppressor T cells in low responder H-2k mice.
        J Invest Dermatol. 1990; 94: 471-476
        • Yagi H
        • Tokura Y
        • Wakita H
        • Furukawa F
        • Takigawa M
        TCR Vβ7+ Th2 cells mediate ultraviolet B-induced suppression of murine contact photosensitivity by releasing IL-10.
        J Immunol. 1996; 156: 1824-1831
        • Tokura Y
        • Wakita H
        • Yagi H
        • Nishimura K
        • Furukawa F
        • Takigawa M
        Th2 suppressor cells are more susceptible to sphingosine than Th1 cells in murine contact photosensitivity.
        J Invest Dermatol. 1996; 107: 34-40
        • Mauri-Hellweg DM
        • Zanni M
        • Frei E
        • Bettens F
        • Brader C
        • Mauri D
        • Padovan E
        • Welzien H-U
        • Pichler WJ
        Cross-reactivity of T cell lines and clones to β-lactam antibiotics.
        J Immunol. 1996; 157: 1071-1079
        • Padovan E
        • Mauri-Hellweg D
        • Pichler WJ
        • Weltzien HU
        T cell recognition of penicillin G: structural features determining antigenic specificity.
        Eur J Immunol. 1996; 26: 42-48
        • Padovan E
        • Bauer T
        • Tongio MM
        • Kalbacher H
        • Weltzien HU
        Penicilloyl peptides are recognized as T cell antigenic determinants in penicillin allergy.
        Eur J Immunol. 1997; 27: 1303-1307
        • Weltzien HU
        • Padovan E
        Molecular features of penicillin allergy.
        J Invest Dermatol. 1998; 110: 203-206
        • Tokura Y
        • Ogai M
        • Yagi H
        • Takigawa M
        Afloqualone photosensitivity: immunogenicity of afloqualone-photomodified epidermal cells.
        Photochem Photobiol. 1994; 60: 262-267
      3. Tokura Y, Seo N, Yagi H, Furukawa F, Takigawa M. Cross-reactivity in murine fluoroquinolone photoallergy: exclusive usage of TCR Vβ13 by immune T cells that recognize fluoroquinolone-photomodified cells. J Immunol 1998;160:3719–28.

        • Miyachi Y
        • Takigawa M
        Mechanisms of contact photosensitivity in mice. II. Langerhans cells are required for successful induction of contact photosensitivity to TCSA.
        J Invest Dermatol. 1982; 78: 363-365
        • Nishijima T
        • Tokura Y
        • Imokawa G
        • Seo N
        • Furukawa F
        • Takigawa M
        Altered permeability and disordered cutaneous immunoregulatory function in mice with acute barrier disruption.
        J Invest Dermatol. 1997; 109: 175-182
        • Katayama I
        • Matsunaga T
        • Yokozeki H
        • Nishioka K
        Blockade of costimulatory molecules B7-1 (CD80) and B7-2 (CD86) down-regulates induction of contact photosensitivity by haptenated epidermal cells.
        Br J Dermatol. 1997; 136: 846-852
        • Martin S
        • Weltzien HU
        T cell recognition of haptens, a molecular view.
        Int Arch Allergy Immunol. 1994; 104: 10-16
        • Brander C
        • Mauri-Hellweg D
        • Bettens F
        • Rolli H
        • Goldman M
        • Pichler WJ
        Heterogeneous T cells responses to lactam-modified self-structures are observed in penicillin-allergic individuals.
        J Immunol. 1995; 155: 2670-2678
        • Luescher IF
        • Anjuere F
        • Peitsch MC
        • Jongeneel CV
        • Cerottini JC
        • Romero P
        Structural analysis of TCR-ligand interactions studied on H-2Kd-restricted cloned CTL specific for a photoreactive peptide derivative.
        Immunity. 1995; 3: 51-63
        • Alonso MD
        • Martin JA
        • Quirce S
        • Davila I
        • Lezaun A
        • Sanchez Cano M
        Fixed eruption caused by ciprofloxacin with cross-sensitivity to norfloxacin.
        Allergy. 1993; 48: 296-297
        • Kumagai Y
        • Okumura K
        • Tada T
        Photoaffinity-labeled hapten-binding T-cell receptor on a suppressor T-cell hybridoma.
        Mol Immunol. 1984; 21: 545-559
        • Hansburg D
        • Fairwell T
        • Schwartz RH
        • Appella E
        The T lymphocyte response to cytochrome c. IV. Distinguishable sites on a peptide antigen which affect antigenic strength and memory.
        J Immunol. 1983; 131: 319-324
        • Matsumoto M
        • Kajima K
        • Nagano H
        • Matsubara S
        • Yokota T
        Photostability and biological activity of fluoroquinolones substituted at the 8-position after UV irradiation.
        Antimicrob Agents Chemother. 1992; 37: 1715-1719
        • Yoshida Y
        • Moroi R
        Photodegradation products of levofloxacin in aqueous solution.
        Drug Res. 1993; 43: 601-606
        • Tiefenbacher E-M
        • Haen E
        • Przybilla B
        • Kurz H
        Photodegradation of some quinolones used as antimicrobial therapeutics.
        J Pharm Sci. 1994; 83: 463-467