胍丁胺的柱前衍生方法及评价
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摘要
胍丁胺是精氨酸脱羧基生成的内源性代谢产物,生物学作用丰富,广泛存在于植物、细菌及哺乳类动物的各种组织中。胍丁胺极性强,相对分子质量小,其结构中无紫外和荧光吸收基团,难以气化,加之内源性胍丁胺含量低,生物样品中干扰成分较多,一般方法难以检测。胍丁胺与荧光试剂进行柱前衍生化,不仅可以增加胍丁胺的相对分子质量,还可以使其带上荧光,大大提高检测灵敏度,使内源性胍丁胺得到很好的分离,是目前测定胍丁胺含量的重要方法。该文对胍丁胺近年来常用的柱前衍生化试剂进行了总结,并对各种衍生试剂的优缺点、最佳衍生条件及检测方法做了比较全面的分析,旨在为后期测定胍丁胺的含量及生物学研究提供方法与思路。
Agmatine is an endogenous amine synthesized from the decarboxylation of arginine.It has a rich biological effects and presents in plants,bacteria and mammalian tissues.Agmatine is highly polar and has a low molecular weight.There are no UV and fluorescent absorption groups in agmatine structure,so it is difficult to gasify.In addition,the content of endogenous agmatine is low,and there are many interference components in biological samples,and the general method is difficult to detect.The pre-column derivatization of agmatine with fluorescence reagents not only increase the molecular weight of agmatine,but also make them with fluorescence,which greatly improve the detection sensitivity and enable the endogenous agmatine to be well separated.It is an important method to determine the content of agmatine.In this paper,several kinds of precolumn derivatives are summarized,and the advantages and disadvantages of various derivatives,the best derivation conditions and detection methods were also analyzed comprehensively.The aim is to determine the content of agmatine and to provide methods and ideas for its biological research.
Agmatine is an endogenous amine synthesized from the decarboxylation of arginine.It has a rich biological effects and presents in plants,bacteria and mammalian tissues.Agmatine is highly polar and has a low molecular weight.There are no UV and fluorescent absorption groups in agmatine structure,so it is difficult to gasify.In addition,the content of endogenous agmatine is low,and there are many interference components in biological samples,and the general method is difficult to detect.The pre-column derivatization of agmatine with fluorescence reagents not only increase the molecular weight of agmatine,but also make them with fluorescence,which greatly improve the detection sensitivity and enable the endogenous agmatine to be well separated.It is an important method to determine the content of agmatine.In this paper,several kinds of precolumn derivatives are summarized,and the advantages and disadvantages of various derivatives,the best derivation conditions and detection methods were also analyzed comprehensively.The aim is to determine the content of agmatine and to provide methods and ideas for its biological research.
引文
[1] UZBAY T I.The pharmacological importance of agmatine in the brain[J].Neurosci Biobehav Rev,2012,36(1):502-519.
[2]兰忠平,顾楠,熊利泽,等.胍丁胺对鞘内吗啡镇痛作用的影响[J].第二军医大学学报,2014,35(8):842-846.
[3]李锦,曹丹旎,吴宁,等.抗阿片成瘾性药物研究历史与现状[J].中国药理学与毒理学杂志,2012,26(3):255-261.
[4] LI F,WU N,SU R B,et al.Imidazoline receptor antiseraselected/Nischarin regulates the effect of agmatine on the development of morphine dependence[J].Addict Biol,2012,17(2):392-408.
[5] NANDKISHOR R K,SUNIL J T,MANISH M A,et al.Evidences for the agmatine involvement in antidepressant like effect of bupropion in mouse forced swim test[J].Pharmacol Biochem Behav,2013,107(1):42-47.
[6] HANS-GERT B,CLAUDIA S,KRISTIN J,et al.Agmatinase,an inactivator of the putative endogenous antidepressant agmatine,is strongly upregulated in hippocampal interneurons of subjects with mood disorders[J].Neuropharmacology,2012,62(1):237-246.
[7] BRIJESH G T,NANDKISHOR R K,MITAL R P,et al.Agmatine,an endogenous imidazoline receptor ligand modulates ethanol anxiolysis and withdrawal anxiety in rats[J].Eur J Pharmacol,2010,637(1/2/3):89-101.
[8]李冲,陈涛.胍丁胺器官保护作用的研究进展[J].重庆医学,2016,45(22):3143-3145.
[9]刘辰麒,丁卓平,王锡昌.生物胺的检测方法评价[J].现代科学仪器,2006(4):87-89.
[10]尹雪梅,杨柳,施超欧,等.离子色谱法测定硫酸胍丁胺含量[J].理化检验(化学分册),2014,50(2):260-261.
[11]FENG Y Z,ANGELOS E H,JOHN E P,et al.Determination of agmatine in brain and plasma using high performance liquid chromatography with fluorescence detection[J].J Chromatogr,1997,691(2):277-286.
[12]MARKOWSKI P,BARANOWSKA I,BARANOWSKI J.Simultaneous determination of L-arginine and 12 molecules participating in its metabolic cycle by gradient RPHPLC method,application to human urine samples[J].Anal Chim Acta,2007,605(2):205-217.
[13]DAI Z L,WU Z L,WANG J J,et al.Analysis of polyamines in biological samples by HPLC involving pre-column derivatization with o-phthalaldehyde and N-acetyl-Lcysteine[J].Amino Acids,2014,46(6):1557-1564.
[14]ROBERTS J C,GROCHOLSKI B M,KITTO K F,et al.Pharmacodynamic and pharmacokinetic studies of agmatine after spinal administration in the mouse[J].J Pharmacol Exp Ther,2005,314(3):1226-1233.
[15]ZHAO S L,FENG Y Z,MICHAEL H L,et al.Quantitation of agmatine by liquid chromatography with laser-induced fluorescence detection[J].Analytica Chimica Acta,2002,470(2):155-161.
[16]BAUZA T,BLAISE A,DAUMAS F,et al.Determination of biogenic amines and their precursor amino acids in wines of the Vallee du Rhone,by HPLC with precolumn derivatization and luorimetric detection[J].J Chromatogr A,1995,707(3):373-379.
[17]丘忠丽,林缨,熊志立,等.同位素稀释-气相色谱-质谱法检测大鼠血浆中的内源性胍丁胺[J].色谱,2014,32(7):779-783.
[18]苏瑞斌,李锦,高凯,等.高效液相色谱法测定大鼠脑和NG108-15细胞内胍丁胺含量[J].中国药理学与毒理学杂志,2002,16(6):459-463.
[19]宋滇文,邢旺兴,贾连顺.脊髓组织胍丁胺含量的测定及其脊髓损伤后内源性胍丁胺的含量的变化[J].中华医学杂志,2007,87(37):2649-2652.
[20]张玉瑶,姜国华,班涛.生物样品中胍丁胺的定量分析方法及评价[J].神经药理学报,2015,5(2):9-16.
[21]CHEN C K,LIU K T,CHIU T C,et al.Separation of amino acids and amines by capillary electrophoresis using poly(ethylene oxide)solution containing cetyltrimethylammonium bromide[J].J Chromatogr A,2009,1216:7576-7581.
[22]PAULSON N B,GILBERTSEN A J,DALLUGE J J,et al.The arginine decarboxylase pathways of host and pathogen interact to impact inflammatory pathways in the lung[J].PLoS One,2014,9(10):e111441.
[23]KIRSCHBAUM J,LUCKAS B,BEINERT W D.HPLC analysis of biogenic amines and amino acids in food[J].J Chromatogr A,1994,661(1/2):193-199.
[24]DOUGLAS S,ALAN B,RICHARD B,et al.Quantitation of the putative neurotramsmitter agmatine as the hexafluoroacetylacetonate derivative by stable isotope dilution gas chromatograph and negative:ion chemical ionization mass spectrometry[J].Anal Biochem,1996,238(2):129-136.
[25]阮志鹏.胍丁胺的衍生化GC-NPD测定及大鼠药动学研究[J].中国现代医用药学,2012,29(1):63-66.
[2]兰忠平,顾楠,熊利泽,等.胍丁胺对鞘内吗啡镇痛作用的影响[J].第二军医大学学报,2014,35(8):842-846.
[3]李锦,曹丹旎,吴宁,等.抗阿片成瘾性药物研究历史与现状[J].中国药理学与毒理学杂志,2012,26(3):255-261.
[4] LI F,WU N,SU R B,et al.Imidazoline receptor antiseraselected/Nischarin regulates the effect of agmatine on the development of morphine dependence[J].Addict Biol,2012,17(2):392-408.
[5] NANDKISHOR R K,SUNIL J T,MANISH M A,et al.Evidences for the agmatine involvement in antidepressant like effect of bupropion in mouse forced swim test[J].Pharmacol Biochem Behav,2013,107(1):42-47.
[6] HANS-GERT B,CLAUDIA S,KRISTIN J,et al.Agmatinase,an inactivator of the putative endogenous antidepressant agmatine,is strongly upregulated in hippocampal interneurons of subjects with mood disorders[J].Neuropharmacology,2012,62(1):237-246.
[7] BRIJESH G T,NANDKISHOR R K,MITAL R P,et al.Agmatine,an endogenous imidazoline receptor ligand modulates ethanol anxiolysis and withdrawal anxiety in rats[J].Eur J Pharmacol,2010,637(1/2/3):89-101.
[8]李冲,陈涛.胍丁胺器官保护作用的研究进展[J].重庆医学,2016,45(22):3143-3145.
[9]刘辰麒,丁卓平,王锡昌.生物胺的检测方法评价[J].现代科学仪器,2006(4):87-89.
[10]尹雪梅,杨柳,施超欧,等.离子色谱法测定硫酸胍丁胺含量[J].理化检验(化学分册),2014,50(2):260-261.
[11]FENG Y Z,ANGELOS E H,JOHN E P,et al.Determination of agmatine in brain and plasma using high performance liquid chromatography with fluorescence detection[J].J Chromatogr,1997,691(2):277-286.
[12]MARKOWSKI P,BARANOWSKA I,BARANOWSKI J.Simultaneous determination of L-arginine and 12 molecules participating in its metabolic cycle by gradient RPHPLC method,application to human urine samples[J].Anal Chim Acta,2007,605(2):205-217.
[13]DAI Z L,WU Z L,WANG J J,et al.Analysis of polyamines in biological samples by HPLC involving pre-column derivatization with o-phthalaldehyde and N-acetyl-Lcysteine[J].Amino Acids,2014,46(6):1557-1564.
[14]ROBERTS J C,GROCHOLSKI B M,KITTO K F,et al.Pharmacodynamic and pharmacokinetic studies of agmatine after spinal administration in the mouse[J].J Pharmacol Exp Ther,2005,314(3):1226-1233.
[15]ZHAO S L,FENG Y Z,MICHAEL H L,et al.Quantitation of agmatine by liquid chromatography with laser-induced fluorescence detection[J].Analytica Chimica Acta,2002,470(2):155-161.
[16]BAUZA T,BLAISE A,DAUMAS F,et al.Determination of biogenic amines and their precursor amino acids in wines of the Vallee du Rhone,by HPLC with precolumn derivatization and luorimetric detection[J].J Chromatogr A,1995,707(3):373-379.
[17]丘忠丽,林缨,熊志立,等.同位素稀释-气相色谱-质谱法检测大鼠血浆中的内源性胍丁胺[J].色谱,2014,32(7):779-783.
[18]苏瑞斌,李锦,高凯,等.高效液相色谱法测定大鼠脑和NG108-15细胞内胍丁胺含量[J].中国药理学与毒理学杂志,2002,16(6):459-463.
[19]宋滇文,邢旺兴,贾连顺.脊髓组织胍丁胺含量的测定及其脊髓损伤后内源性胍丁胺的含量的变化[J].中华医学杂志,2007,87(37):2649-2652.
[20]张玉瑶,姜国华,班涛.生物样品中胍丁胺的定量分析方法及评价[J].神经药理学报,2015,5(2):9-16.
[21]CHEN C K,LIU K T,CHIU T C,et al.Separation of amino acids and amines by capillary electrophoresis using poly(ethylene oxide)solution containing cetyltrimethylammonium bromide[J].J Chromatogr A,2009,1216:7576-7581.
[22]PAULSON N B,GILBERTSEN A J,DALLUGE J J,et al.The arginine decarboxylase pathways of host and pathogen interact to impact inflammatory pathways in the lung[J].PLoS One,2014,9(10):e111441.
[23]KIRSCHBAUM J,LUCKAS B,BEINERT W D.HPLC analysis of biogenic amines and amino acids in food[J].J Chromatogr A,1994,661(1/2):193-199.
[24]DOUGLAS S,ALAN B,RICHARD B,et al.Quantitation of the putative neurotramsmitter agmatine as the hexafluoroacetylacetonate derivative by stable isotope dilution gas chromatograph and negative:ion chemical ionization mass spectrometry[J].Anal Biochem,1996,238(2):129-136.
[25]阮志鹏.胍丁胺的衍生化GC-NPD测定及大鼠药动学研究[J].中国现代医用药学,2012,29(1):63-66.