中国临床药理学与治疗学 ›› 2014, Vol. 19 ›› Issue (10): 1177-1182.
杨倩1, 杨俭2
收稿日期:
2013-05-24
修回日期:
2014-06-20
出版日期:
2014-10-26
发布日期:
2014-10-29
通讯作者:
杨俭,女,博士,教授,博士生导师,研究方向:临床药理。E-mail: jianyang@njmu.edu.cn
作者简介:
杨倩,女,学士,副研究员,研究方向:药物化学。E-mail: 07105@njnu.edu.cn
基金资助:
YANG Jian1, YANG Qian2
Received:
2013-05-24
Revised:
2014-06-20
Online:
2014-10-26
Published:
2014-10-29
摘要: 8-甲氧补骨脂素(8-methoxypsoralen, 8-MOP) 主要存在于多种常见中草药如蛇床子、北沙参、白芷、枳实、羌活、芫荽等根茎或果实中,由于8-MOP结构简单、易与DNA发生相互作用,有较多的生物活性,目前已成为天然药物研究的热点。本文结合本实验室研究工作对近年8-MOP在抗微生物和抑制炎症反应、调节免疫功能、抗肿瘤作用、其他药理和毒副作用研究进展做一综述。
中图分类号:
杨倩, 杨俭. 8-甲氧补骨脂素药理作用研究进展[J]. 中国临床药理学与治疗学, 2014, 19(10): 1177-1182.
YANG Jian, YANG Qian. Advances in pharmacological research of 8-methoxypsoralen[J]. Chinese Journal of Clinical Pharmacology and Therapeutics, 2014, 19(10): 1177-1182.
[1] | Smith SI, Brodbelt JS.Rapid characterization of cross-links, mono-adducts, and non-covalent binding of psoralens to deoxyoligonucleotides by LC-UV/ESI-MS and IRMPD mass spectrometry[J]. Analyst, 2010, 135(5):943-952. |
[2] | Kanne D, Straub K, Rapoport H, et al.Psoralen-deoxyribonucleic acid photoreaction. Characterization of the monoaddition products from 8-methoxypsoralen and 4,5'8-trimethylpsoralen[J].Biochemistry, 1982,21(5):861-871. |
[3] | Hearst JE, Isaacs ST, Kanne D, et al.The reaction of the psoralens with deoxyribonucleic acid[J]. Q Rev Biophys, 1984, 17(1):1-44. |
[4] | Peckler S, Graves B, Kanne D, et al.Structure of a psoralen-thymine monoadduct formed in photoreaction with DNA[J]. J Mol Biol, 1982,162(1):157-172. |
[5] | Cimino GD, Gamper HB, Isaacs ST, et al.Psoralens as photoactive probes of nucleic acid structure and function: organic chemistry, photochemistry, and biochemistry[J]. Annu Rev Biochem, 1985,54:1151-1193. |
[6] | Esposito F, Brankamp RG, Sinden RR.DNA sequence specificity of 4,5',8-trimethylpsoralen cross-linking. Effect of neighboring bases on cross-linking the 5'-TA dinucleotide[J]. J Biol Chem, 1988,263(23):11466-11472. |
[7] | Thompson JF, Bachellerie JP, Hall K, et al.Dependence of 4'-(hydroxymethyl)-4,5',8-trimethylpsoralen photoaddition on the conformation of ribonucleic acid[J]. Biochemistry, 1982,21(6):1363-1368. |
[8] | Gamper H, Piette J, Hearst JE.Efficient formation of a crosslinkable HMT monoadduct at the Kpn I recognition site[J]. Photochem Photobiol, 1984,40(1):29-34. |
[9] | Zhen WP, Buchardt O, Nielsen H, et al.Site specificity of psoralen-DNA interstrand cross-linking determined by nuclease Bal31 digestion[J]. Biochemistry, 1986,25(21):6598-6603. |
[10] | Yeung AT, Jones BK, Capraro M, et al.The repair of psoralen monoadducts by the Escherichia coli UvrABC endonuclease[J]. Nucleic Acids Res, 1987,15(12):4957-4971. |
[11] | Miolo G, Dall'Acqua F, Moustacchi E, et al. Monofunctional angular furocoumarins: sequence specificity in DNA photobinding of 6,4,4'-trimethylangelicin and other angelicins[J]. Photochem Photobiol, 1989,50(1):75-84. |
[12] | Gia O, Magno SM, Garbesi A, et al.Sequence specificity of psoralen photobinding to DNA: a quantitative approach[J]. Biochemistry, 1992,31(47):11818-11822. |
[13] | Kuete V, Metuno R, Ngameni B,et al.Antimicrobial activity of the methanolic extracts and compounds from Treculia obovoidea (Moraceae)[J]. J Ethnopharmacol, 2007,112(3):531-536. |
[14] | Bose SK, Dewanjee S, Sahu R, et al.Effect of bergapten from Heracleum nepalense root on production of proinflammatory cytokines[J]. Nat Prod Res, 2011,25(15):1444-1449. |
[15] | Nicolis E, Lampronti I, Dechecchi MC, et al.Modulation of expression of IL-8 gene in bronchial epithelial cells by 5-methoxypsoralen[J]. Int Immunopharmacol, 2009,9(12):1411-1422. |
[16] | de Paulis A, Monfrecola G, Casula L, et al. 8-Methoxypsoralen and long-wave ultraviolet A inhibit the release of proinflammatory mediators and cytokines from human Fc epsilon RI+ cells: an in vitro study[J]. J Photochem Photobiol B, 2003,69(3):169-177. |
[17] | Stadler K, Frey B, Munoz LE, et al.Photopheresis with UV-A light and 8-methoxypsoralen leads to cell death and to release of blebs with anti-inflammatory phenotype in activated and non-activated lymphocytes[J]. Biochem Biophys Res Commun, 2009,386(1):71-76. |
[18] | Cox GW, Orosz CG, Lewis MG, et al.Evidence that 8-methoxypsoralen (8-MOP) is a T-lymphocyte immunomodulatory agent[J]. Int J Immunopharmacol, 1988,10(6):773-781. |
[19] | Roberts LK, Schmitt M, Daynes RA.Tumor-susceptibility generated in mice treated with subcarcinogenic doses of 8-methoxypsoralen and long-wave ultraviolet light[J]. J Invest Dermatol, 1979,72(6):306-309. |
[20] | Morhenn VB, Benike CJ, Engleman EG.Inhibition of cell mediated immune responses by 8-methoxypsoralen and long-wave ultraviolet light: a possible explanation for the clinical effects of photoactivated psoralen[J]. J Invest Dermatol, 1980,75(3):249-252. |
[21] | Laskin JD, Mermelstein FH, Heindel ND, et al.Selective inactivation of lymphocytes after psoralen/ultraviolet light (PUVA) treatment without affecting systemic immune responses[J]. J Leukoc Biol, 1993,54(2):138-144. |
[22] | Schön MP, Wallbrecht K, Wolf P.8-Methoxypsoralen plus UVA treatment increases C<inline-formula><mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" id="Mml1-1009-2501-19-10-1177"><mml:msup><mml:mrow><mml:msub><mml:mrow><mml:mi mathvariant="normal">D</mml:mi></mml:mrow><mml:mrow><mml:mn>4</mml:mn></mml:mrow></mml:msub></mml:mrow><mml:mrow><mml:mo>+</mml:mo></mml:mrow></mml:msup></mml:math></inline-formula> T cells in lymph nodes of K5. hTGFβ1 transgenSingh TP, ic?CD25+?the proportion of CLA+ mice[J]. Exp Dermatol, 2012,21(3):228-230. |
[23] | Jonson CO, Pihl M, Nyholm C, et al.Regulatory T cell-associated activity in photopheresis-induced immune tolerance in recent onset type 1 diabetes children[J]. Clin Exp Immunol, 2008,153(2):174-181. |
[24] | Zheng DH, Dou LP, Wei YX, et al.Uptake of donor lymphocytes treated with 8-methoxypsoralen and ultraviolet A light by recipient dendritic cells induces C<inline-formula><mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" id="Mml2-1009-2501-19-10-1177"><mml:msup><mml:mrow><mml:msub><mml:mrow><mml:mi mathvariant="normal">D</mml:mi></mml:mrow><mml:mrow><mml:mn>4</mml:mn></mml:mrow></mml:msub></mml:mrow><mml:mrow><mml:mo>+</mml:mo></mml:mrow></mml:msup></mml:math></inline-formula>C<inline-formula><mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" id="Mml3-1009-2501-19-10-1177"><mml:msup><mml:mrow><mml:msub><mml:mrow><mml:mi mathvariant="normal">D</mml:mi></mml:mrow><mml:mrow><mml:mn>25</mml:mn></mml:mrow></mml:msub></mml:mrow><mml:mrow><mml:mo>+</mml:mo></mml:mrow></mml:msup></mml:math></inline-formula>Foxp3+ regulatory T cells and down-regulates cardiac allograft rejection[J]. Biochem Biophys Res Commun, 2010,395(4):540-546. |
[25] | Legitimo A, Consolini R, Di Stefano R, et al.Psoralen and UVA light: an in vitro investigation of multiple immunological mechanisms underlying the immunosuppression induction in allograft rejection[J]. Blood Cells Mol Dis, 2002,29(1):24-34. |
[26] | Failli A, Legitimo A, Mazzoni A, et al.The combination of immunosuppressive drugs with 8-methoxypsoralen and ultraviolet a light modulates the myeloid-derived dendritic cell function[J]. Int J Immunopathol Pharmacol, 2011,24(1):89-99. |
[27] | R?mer R, Anders A. NMR study of the drug-base overlap geometry in the dark complex of 8-methoxypsoralen and d(pApT)4[J]. Biochemistry, 1985,24(25):7450-7456. |
[28] | Dalla Via L, Gia O, Marciani Magno S, et al.New tetracyclic analogues of photochemotherapeutic drugs 5-MOP and 8-MOP: synthesis, DNA interaction, and antiproliferative activity[J]. J Med Chem, 1999,42(21):4405-4413. |
[29] | Yokohira M, Takeuchi H, Saoo K, et al.Establishment of a bioassay model for lung cancer chemoprevention initiated with 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in female A/J mice[J]. Exp Toxicol Pathol, 2008,60(6):469-473. |
[30] | Wolnicka-Glubisz A, Fraczek J, Skrzeczynska-Moncznik J, et al.Effect of UVA and 8-methoxypsoralen, 4, 6, 4'-trimethylangelicin or chlorpromazine on apoptosis of lymphocytes and their recognition by monocytes[J]. J Physiol Pharmacol, 2010,61(1):107-114. |
[31] | Panno ML, Giordano F, Palma MG, et al.Evidence that bergapten, independently of its photoactivation, enhances p53 gene expression and induces apoptosis in human breast cancer cells[J]. Curr Cancer Drug Targets, 2009,9(4):469-481. |
[32] | Viola G, Fortunato E, Cecconet L, et al.Central role of mitochondria and p53 in PUVA-induced apoptosis in human keratinocytes cell line NCTC-2544[J]. Toxicol Appl Pharmacol, 2008,227(1):84-96. |
[33] | Kurita M, Shimauchi T, Kobayashi M, et al.Induction of keratinocyte apoptosis by photosensitizing chemicals plus UVA[J]. J Dermatol Sci, 2007,45(2):105-112. |
[34] | Peng Y, Liu W, Xiong J, et al.Down regulation of differentiated embryonic chondrocytes 1 (DEC1) is involved in 8-methoxypsoralen-induced apoptosis in HepG2 cells[J]. Toxicology, 2012,301(1/2/3):58-65. |
[35] | Shen M, Yoshida E, Yan W, et al.Basic helixloop-helix protein DEC1 promotes chondrocyte differentiationat the early and terminal stages[J]. J Biol Chem,2002,277(51):50112-50120. |
[36] | Sun H,Taneja R.Stra13 expression is associated with growth arrest and represses transcription through histone deacetylase (HDAC)-dependent and HDAC-independent mechanisms[J]. Proc Natl Acad Sci, 2000,97(8):4058-4063. |
[37] | Sun H, Lu B, Li RQ, et al.Defective T cell activation and autoimmune disorder in Stra13-deficient mice[J]. Nat Immunol,2001,2(11):1040-1047. |
[38] | Nakashima A, Kawamoto T, Honda KK, et al.DEC1 modulates the circadian phase of clock gene expression[J]. Mol Cell Biol, 2008,28(12):4080-4092. |
[39] | Currie MJ, Hanrahan V, Gunningham SP, et al.Expression of vascular endothelial growth factor D is associated with hypoxia inducible factor (HIF-1alpha) and the HIF-1alpha target gene DEC1, but not lymph node metastasis in primary human breast carcinomas[J]. J Clin Pathol, 2004,57(8):829-834. |
[40] | Qian Y, Jung YS, Chen X.DeltaNp63, a target of DEC1 and histone deacetylase 2, modulates the efficacy of histonedeacetylase inhibitors in growth suppression and keratinocyte differentiation[J]. J Biol Chem, 2011, 286(14):12033-12041. |
[41] | Wu Y, Sato F, Yamada T, et al.The BHLH transcription factor DEC1 plays an important role in the epithelial-mesenchymal transition of pancreatic cancer[J]. Int J Oncol, 2012,41(4):1337-1346. |
[42] | Sumpio BE, Phan SM, Gasparro FP, et al.Control of smooth muscle cell proliferation by psoralen photochemotherapy[J]. J Vasc Surg, 1993,17(6):1010-1016. |
[43] | Lee DM, Gasparro FP, Wang XJ, et al.Photochemotherapy of vascular cells with 8-methoxypsoralen and visible light: differential effects on endothelial and smooth muscle cells[J]. Photodermatol Photoimmunol Photomed, 2002,18(5):244-252. |
[44] | Bisaccia E, Palangio M, Gonzalez J, et al.Photopheresis. Therapeutic potential in preventing restenosis after percutaneous transluminal coronary angioplasty[J]. Am J Cardiovasc Drugs, 2003,3(1):43-51. |
[45] | Kim JK, Choi SJ, Bae H, et al.Effects of methoxsalen from Poncirus trifoliata on acetylcholinesterase and trimethyltin-induced learning and memory impairment[J]. Biosci Biotechnol Biochem, 2011,75(10):1984-1989. |
[46] | Hayashi S, Ikeda M, Kitamura Y, et al.UVA irradiation following treatment with topical 8-methoxypsoralen improves bleomycin-induced scleroderma in a mouse model, by reducing the collagen content and collagen gene expression levels in the skin[J]. J Dermatol Sci, 2012,67(1):20-25. |
[47] | Ye Y, Chou GX, Wang H, et al.Flavonoids, apigenin and icariin exert potent melanogenic activities in murine B16 melanoma cells[J]. Phytomedicine, 2010,18(1):32-35. |
[48] | Sehgal VN.Vitiligo and alopecia areata associated with subclinical/clinical hypothyroidism[J]. Skinmed, 2011,9(3):192-194. |
[49] | Kamel MM, Salem SA, Attia HH.Successful treatment of resistant alopecia areata with a phototoxic dose of ultraviolet A after topical 8-methoxypsoralen application[J]. Photodermatol Photoimmunol Photomed, 2011,27(1):45-50. |
[50] | Ehsani AH, Ghaninejad H, Kiani A, et al.Comparison of topical 8-methoxypsoralen and narrowband ultraviolet B with narrowband ultraviolet B alone in treatment-resistant sites in plaque-type psoriasis: a placebo-controlled study[J]. Photodermatol Photoimmunol Photomed, 2011,27(6):294-296. |
[51] | Ono S, Hatanaka T, Hotta H, et al.Specificity of substrate and inhibitor probes for cytochrome P450s: evaluation of in vitro metabolism using cDNA-expressed human P450s and human liver microsomes[J]. Xenobiotica, 1996,26(7):681-693. |
[52] | Zhang W, Kilicarslan T, Tyndale RF, et al.Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro[J]. Drug Metab Dispos,2001,29(6):897-902. |
[53] | Yang J, Yan B.Photochemotherapeutic agent 8-methoxypsoralen induces cytochrome P450 3A4 and carboxylesterase HCE2: evidence on an involvement of the pregnane X receptor[J]. Toxicol Sci, 2007,95(1):13-22. |
[14] | National toxicology program. toxicology and carcinogenesis studies of 8-methoxypsoralen (CAS No. 298-81-7) in F344/N rats[J]. Natl Toxicol Program Tech Rep Ser, 1989,359:1-130. |
[55] | Diawara MM, Williams DE, Oganesian A, et al.Dietary psoralens induce hepatotoxicity in C57 mice[J]. J Nat Toxins, 2000,9(2):179-195. |
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