喹诺酮金属配合物的研究进展
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摘要
喹诺酮类是人工合成的广谱抗生素,具有良好的口服吸收和生物利用度。喹诺酮衍生物是世界上最常用的处方抗菌药物,许多喹诺酮金属配合物具有与母体类似或更强的抗菌活性。设计具有潜在药理活性的金属配合物已经引起广泛关注,是日后开发此类药物的重要方向。本文总结了喹诺酮金属配合物的研究进展。
Quinolones are synthetic broad-spectrum antibiotics with good oral absorption and excellent bioavailability,quinolone derivatives are among the most commonly prescribed antibacterials in the world. Many metal complexes were obtained with equal or enhanced antimicrobial activity compared to the parent quinolones. The design of metal complexes with potential pharmacological activity had attracted broad interest,would be an important direction for the development of such drugs in the future. This paper summarizes the research progress of quinolone metal.
Quinolones are synthetic broad-spectrum antibiotics with good oral absorption and excellent bioavailability,quinolone derivatives are among the most commonly prescribed antibacterials in the world. Many metal complexes were obtained with equal or enhanced antimicrobial activity compared to the parent quinolones. The design of metal complexes with potential pharmacological activity had attracted broad interest,would be an important direction for the development of such drugs in the future. This paper summarizes the research progress of quinolone metal.
引文
[1]Appelbaum P C,Hunter P A.The fluoroquinolone antibacterials:past,present and future perspectives[J].International journal of antimicrobial agents,2000,16(1):5-15.
[2]Hooper D C.Clinical applications of quinolones[J].Biochimica et Biophysica Acta(BBA)-Gene Structure and Expression,1998,1400(1-3):45-61.
[3]Buchbinder M,Webb J C,Anderson L V,et al.Laboratory studies and clinical pharmacology of nalidixic acid(WIN 18,320)[J].Antimicrob Agents Chemother,1962,2:308-317.
[4]Oliphant C M,Green G M.Quinolones:a comprehensive review[J].American family physician,2002,65(3):455-464.
[5]King D E,Malone R,Lilley S H.New classification and update on the quinolone antibiotics[J].American family physician,2000,61(9):2741-2748.
[6]Zhanel G G,Walkty A,Vercaigne L,et al.The new fluoroquinolones:a critical review[J].Canadian Journal of Infectious Diseases and Medical Microbiology,1999,10(3):207-238.
[7]刘惠清.氟喹诺酮类药物[J].中国医院药学杂志,1999,19(3):181-182.
[8]成好文.喹诺酮类抗菌药的研究进展[J].中国抗生素杂志,1999,24(B12):41-45.
[9]Cozzarelli,N.R.DNA gyrase and the supercoiling of DNA.Science 1980,207,953-960.
[10]Mitscher L A.Bacterial topoisomerase inhibitors:quinolone and pyridone antibacterial agents[J].Chemical reviews,2005,105(2):559-592.
[11]Blondeau J M.Fluoroquinolones:mechanism of action,classification,and development of resistance[J].Survey of ophthalmology,2004,49(2):S73-S78.
[12]Drlica K,Zhao X.DNA gyrase,topoisomerase IV,and the 4-quinolones[J].Microbiology and molecular biology reviews,1997,61(3):377-392.
[13]Hooper D C.Mechanisms of action and resistance of older and newer fluoroquinolones[J].Clinical Infectious Diseases,2000,31(Supplement_2):S24-S28.
[14]MAXWELL A.The molecular basis of quinolone action[J].Journal of Antimicrobial Chemotherapy,1992,30(4):409-414.
[15]Schaumann R,Rodloff A C.Activities of quinolones against obligately anaerobic bacteria[J].Anti-Infective Agents in Medicinal Chemistry(Formerly Current Medicinal Chemistry-Anti-Infective Agents),2007,6(1):49-56.
[16]Shen L L,Chu D T W.Type II DNA topoisomerases as antibacterial targets[J].Current Pharmaceutical Design,1996,2(2):195-208.
[17]Peterson L R.Quinolone molecular structure-activity relationships:what we have learned about improving antimicrobial activity[J].Clinical Infectious Diseases,2001,33(Supplement_3):S180-S186.
[18]Ross D L,Riley C M.Physicochemical properties of the fluoroquinolone antimicrobials.II.Acid ionization constants and their relationship to structure[J].International journal of pharmaceutics,1992,83(1-3):267-272.
[19]Takács‐Novák K,Noszál B,Hermecz I,et al.Protonation equilibria of quinolone antibacterials[J].Journal of pharmaceutical sciences,1990,79(11):1023-1028.
[20]Turel I.The interactions of metal ions with quinolone antibacterial agents[J].Coordination Chemistry Reviews,2002,232(1-2):27-47.
[21]Zupancic M,Cerc Korosec R,Bukovec P.The thermal stability of ciprofloxacin complexes with magnesium(II),zinc(II)and cobalt(II)[J].Journal of thermal analysis and calorimetry,2001,63(3):787-795.
[22]Uivarosi V.Metal complexes of quinolone antibiotics and their applications:an update[J].Molecules,2013,18(9):11153-11197.
[23]Efthimiadou E K,Sanakis Y,Katsaros N,et al.Transition metal complexes with the quinolone antibacterial agent pipemidic acid:synthesis,characterization and biological activity[J].Polyhedron,2007,26(5):1148-1158.
[24]Sha J Q,Li X,Qiu H B,et al.Nickel complexes of the different quinolone antibacterial drugs:Synthesis,structure and interaction with DNA[J].Inorganica Chimica Acta,2012,383:178-184.
[25]Al-Mustafa J.Magnesium,calcium,and barium perchlorate complexes of ciprofloxacin and norfloxacin[J].Acta Chimica Slovenica,2002,49(3):457-466.
[26]Breda S A,Jimenez-Kairuz A F,Manzo R H,et al.Solubility behavior and biopharmaceutical classification of novel highsolubility ciprofloxacin and norfloxacin pharmaceutical derivatives[J].International journal of pharmaceutics,2009,371(1-2):106-113.
[27]Shaikh A R,Giridhar R,Yadav M R.Bismuth-norfloxacin complex:Synthesis,physicochemical and antimicrobial evaluation[J].International journal of pharmaceutics,2007,332(1-2):24-30.
[28]Shaikh A,Giridhar R,Megraud F,et al.Metalloantibiotics:Synthesis,characterization and antimicrobial evaluation of bismuth-fluoroquinolone complexes against Helicobacter pylori[J].Acta Pharmaceutica,2009,59(3):259-271.
[29]Sadeek S A.Synthesis,thermogravimetric analysis,infrared,electronic and mass spectra of Mn(II),Co(II)and Fe(III)norfloxacin complexes[J].Journal of molecular structure,2005,753(1-3):1-12.
[30]Golovnev N N,Kirik S D,Golovneva I I.Synthesis of norfloxacin compounds with cobalt(II),zinc(II),cadmium(II),and mercury(II)[J].Russian Journal of Inorganic Chemistry,2009,54(2):223-225.
[31]da G J Batista D,da Silva P B,Stivanin L,et al.Co(II),Mn(II)and Cu(II)complexes of fluoroquinolones:synthesis,spectroscopical studies and biological evaluation against Trypanosoma cruzi[J].Polyhedron,2011,30(10):1718-1725.
[32]Ruiz P,Ortiz R,PerellóL,et al.Synthesis,structure,and nuclease properties of several binary and ternary complexes of copper(II)with norfloxacin and 1,10 phenantroline[J].Journal of inorganic biochemistry,2007,101(5):831-840.
[33]Zivec P,Perdih F,Turel I,et al.Different types of copper complexes with the quinolone antimicrobial drugs ofloxacin and norfloxacin:Structure,DNA-and albumin-binding[J].Journal of inorganic biochemistry,2012,117:35-47.
[34]Zhang J,Ge L,Zhang X,et al.Thermal decomposition kinetics of the Zn(II)complex with norfloxacin in static air atmosphere[J].Journal of thermal analysis and calorimetry,1999,58(2):269-278.
[35]Refat M S,Mohamed G G,de Farias R F,et al.Spectroscopic,thermal and kinetic studies of coordination compounds of Zn(II),Cd(II)and Hg(II)with norfloxacin[J].Journal of thermal analysis and calorimetry,2010,102(1):225-232.
[36]Sadeek S A,El-Did Amony A M,El-Shwiniy W H,et al.Uranium(VI)and zirconium(IV)of the secondgeneration quinolone antimicrobial drug norfloxacin:Structure and biological activity[J].J.Argent.Chem.Soc,2009,97:51-76.
[37]Uivarosi V,Badea M,Olar R,et al.Thermal degradation behavior of some ruthenium complexes with fluoroquinolone derivatives as potential antitumor agents[J].Journal of thermal analysis and calorimetry,2011,105(2):645-650.
[38]Patel M N,Gandhi D S,Parmar P A.DNA interaction and in-vitro antibacterial studies of fluoroquinolone based platinum(II)complexes[J].Inorganic Chemistry Communications,2012,15:248-251.
[39]Gouvea L R,Garcia L S,Lachter D R,et al.Atypical fluoroquinolone gold(III)chelates as potential anticancer agents:relevance of DNA and protein interactions for their mechanism of action[J].European journal of medicinal chemistry,2012,55:67-73.
[40]Sadeek S A,El-Shwiniy W H,Zordok W A,et al.Synthesis,spectroscopic,thermal and biological activity investigation of new Y(ΙΙΙ)and Pd(ΙΙ)norfloxacin complexes[J].J.Argent.Chem.Soc,2009,97:128-148.
[41]Refat M S,El-Hawary W F,Mohamed M A.Study of the chemical chelates and anti-microbial effect of some metal ions in nanostructural form on the efficiency of antibiotic therapy"norfloxacin drug"[J].Journal of Molecular Structure,2012,1013:45-54.
[42]Shaikh A,Giridhar R,Megraud F,et al.Metalloantibiotics:Synthesis,characterization and antimicrobial evaluation of bismuth-fluoroquinolone complexes against Helicobacter pylori[J].Acta Pharmaceutica,2009,59(3):259-271.
[43]da GJ Batista D,da Silva P B,Stivanin L,et al.Co(II),Mn(II)and Cu(II)complexes of fluoroquinolones:synthesis,spectroscopical studies and biological evaluation against Trypanosoma cruzi[J].Polyhedron,2011,30(10):1718-1725.
[44]Patel M N,Gandhi D S,Parmar P A.DNA interaction and in-vitro antibacterial studies of fluoroquinolone based platinum(II)complexes[J].Inorganic Chemistry Communications,2012,15:248-251.
[45]Gouvea L R,Garcia L S,Lachter D R,et al.Atypical fluoroquinolone gold(III)chelates as potential anticancer agents:relevance of DNA and protein interactions for their mechanism of action[J].European journal of medicinal chemistry,2012,55:67-73.
[46]Vieira L M M,de Almeida M V,Lourenco M C S,et al.Synthesis and antitubercular activity of palladium and platinum complexes with fluoroquinolones[J].European journal of medicinal chemistry,2009,44(10):4107-4111.
[47]Efthimiadou E K,Karaliota A,Psomas G.Mononuclear dioxomolybdenum(VI)complexes with the quinolones enrofloxacin and sparfloxacin:Synthesis,structure,antibacterial activity and interaction with DNA[J].Polyhedron,2008,27(1):349-356.
[48]Efthimiadou E K,Karaliota A,Psomas G.Metal complexes of the third-generation quinolone antimicrobial drug sparfloxacin:Structure and biological evaluation[J].Journal of inorganic biochemistry,2010,104(4):455-466.
[49]Sadeek S A,El-Shwiniy W H,El-Attar M S.Synthesis,characterization and antimicrobial investigation of some moxifloxacin metal complexes[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2011,84(1):99-110.
[50]Sadeek S A,El-Shwiniy W H,Zordok W A,et al.Spectroscopic studies,thermal analyses and biological evaluation of new V(IV),Zr(IV)and U(VI)moxifloxacin complexes[J].Journal of Molecular Structure,2011,1006(1-3):192-209.
[51]Elshafie H S,Sakr S H,Sadeek S A,et al.Biological investigations and spectroscopic studies of new Moxifloxacin/Glycine‐Metal complexes[J].Chemistry&Biodiversity,2019.
[2]Hooper D C.Clinical applications of quinolones[J].Biochimica et Biophysica Acta(BBA)-Gene Structure and Expression,1998,1400(1-3):45-61.
[3]Buchbinder M,Webb J C,Anderson L V,et al.Laboratory studies and clinical pharmacology of nalidixic acid(WIN 18,320)[J].Antimicrob Agents Chemother,1962,2:308-317.
[4]Oliphant C M,Green G M.Quinolones:a comprehensive review[J].American family physician,2002,65(3):455-464.
[5]King D E,Malone R,Lilley S H.New classification and update on the quinolone antibiotics[J].American family physician,2000,61(9):2741-2748.
[6]Zhanel G G,Walkty A,Vercaigne L,et al.The new fluoroquinolones:a critical review[J].Canadian Journal of Infectious Diseases and Medical Microbiology,1999,10(3):207-238.
[7]刘惠清.氟喹诺酮类药物[J].中国医院药学杂志,1999,19(3):181-182.
[8]成好文.喹诺酮类抗菌药的研究进展[J].中国抗生素杂志,1999,24(B12):41-45.
[9]Cozzarelli,N.R.DNA gyrase and the supercoiling of DNA.Science 1980,207,953-960.
[10]Mitscher L A.Bacterial topoisomerase inhibitors:quinolone and pyridone antibacterial agents[J].Chemical reviews,2005,105(2):559-592.
[11]Blondeau J M.Fluoroquinolones:mechanism of action,classification,and development of resistance[J].Survey of ophthalmology,2004,49(2):S73-S78.
[12]Drlica K,Zhao X.DNA gyrase,topoisomerase IV,and the 4-quinolones[J].Microbiology and molecular biology reviews,1997,61(3):377-392.
[13]Hooper D C.Mechanisms of action and resistance of older and newer fluoroquinolones[J].Clinical Infectious Diseases,2000,31(Supplement_2):S24-S28.
[14]MAXWELL A.The molecular basis of quinolone action[J].Journal of Antimicrobial Chemotherapy,1992,30(4):409-414.
[15]Schaumann R,Rodloff A C.Activities of quinolones against obligately anaerobic bacteria[J].Anti-Infective Agents in Medicinal Chemistry(Formerly Current Medicinal Chemistry-Anti-Infective Agents),2007,6(1):49-56.
[16]Shen L L,Chu D T W.Type II DNA topoisomerases as antibacterial targets[J].Current Pharmaceutical Design,1996,2(2):195-208.
[17]Peterson L R.Quinolone molecular structure-activity relationships:what we have learned about improving antimicrobial activity[J].Clinical Infectious Diseases,2001,33(Supplement_3):S180-S186.
[18]Ross D L,Riley C M.Physicochemical properties of the fluoroquinolone antimicrobials.II.Acid ionization constants and their relationship to structure[J].International journal of pharmaceutics,1992,83(1-3):267-272.
[19]Takács‐Novák K,Noszál B,Hermecz I,et al.Protonation equilibria of quinolone antibacterials[J].Journal of pharmaceutical sciences,1990,79(11):1023-1028.
[20]Turel I.The interactions of metal ions with quinolone antibacterial agents[J].Coordination Chemistry Reviews,2002,232(1-2):27-47.
[21]Zupancic M,Cerc Korosec R,Bukovec P.The thermal stability of ciprofloxacin complexes with magnesium(II),zinc(II)and cobalt(II)[J].Journal of thermal analysis and calorimetry,2001,63(3):787-795.
[22]Uivarosi V.Metal complexes of quinolone antibiotics and their applications:an update[J].Molecules,2013,18(9):11153-11197.
[23]Efthimiadou E K,Sanakis Y,Katsaros N,et al.Transition metal complexes with the quinolone antibacterial agent pipemidic acid:synthesis,characterization and biological activity[J].Polyhedron,2007,26(5):1148-1158.
[24]Sha J Q,Li X,Qiu H B,et al.Nickel complexes of the different quinolone antibacterial drugs:Synthesis,structure and interaction with DNA[J].Inorganica Chimica Acta,2012,383:178-184.
[25]Al-Mustafa J.Magnesium,calcium,and barium perchlorate complexes of ciprofloxacin and norfloxacin[J].Acta Chimica Slovenica,2002,49(3):457-466.
[26]Breda S A,Jimenez-Kairuz A F,Manzo R H,et al.Solubility behavior and biopharmaceutical classification of novel highsolubility ciprofloxacin and norfloxacin pharmaceutical derivatives[J].International journal of pharmaceutics,2009,371(1-2):106-113.
[27]Shaikh A R,Giridhar R,Yadav M R.Bismuth-norfloxacin complex:Synthesis,physicochemical and antimicrobial evaluation[J].International journal of pharmaceutics,2007,332(1-2):24-30.
[28]Shaikh A,Giridhar R,Megraud F,et al.Metalloantibiotics:Synthesis,characterization and antimicrobial evaluation of bismuth-fluoroquinolone complexes against Helicobacter pylori[J].Acta Pharmaceutica,2009,59(3):259-271.
[29]Sadeek S A.Synthesis,thermogravimetric analysis,infrared,electronic and mass spectra of Mn(II),Co(II)and Fe(III)norfloxacin complexes[J].Journal of molecular structure,2005,753(1-3):1-12.
[30]Golovnev N N,Kirik S D,Golovneva I I.Synthesis of norfloxacin compounds with cobalt(II),zinc(II),cadmium(II),and mercury(II)[J].Russian Journal of Inorganic Chemistry,2009,54(2):223-225.
[31]da G J Batista D,da Silva P B,Stivanin L,et al.Co(II),Mn(II)and Cu(II)complexes of fluoroquinolones:synthesis,spectroscopical studies and biological evaluation against Trypanosoma cruzi[J].Polyhedron,2011,30(10):1718-1725.
[32]Ruiz P,Ortiz R,PerellóL,et al.Synthesis,structure,and nuclease properties of several binary and ternary complexes of copper(II)with norfloxacin and 1,10 phenantroline[J].Journal of inorganic biochemistry,2007,101(5):831-840.
[33]Zivec P,Perdih F,Turel I,et al.Different types of copper complexes with the quinolone antimicrobial drugs ofloxacin and norfloxacin:Structure,DNA-and albumin-binding[J].Journal of inorganic biochemistry,2012,117:35-47.
[34]Zhang J,Ge L,Zhang X,et al.Thermal decomposition kinetics of the Zn(II)complex with norfloxacin in static air atmosphere[J].Journal of thermal analysis and calorimetry,1999,58(2):269-278.
[35]Refat M S,Mohamed G G,de Farias R F,et al.Spectroscopic,thermal and kinetic studies of coordination compounds of Zn(II),Cd(II)and Hg(II)with norfloxacin[J].Journal of thermal analysis and calorimetry,2010,102(1):225-232.
[36]Sadeek S A,El-Did Amony A M,El-Shwiniy W H,et al.Uranium(VI)and zirconium(IV)of the secondgeneration quinolone antimicrobial drug norfloxacin:Structure and biological activity[J].J.Argent.Chem.Soc,2009,97:51-76.
[37]Uivarosi V,Badea M,Olar R,et al.Thermal degradation behavior of some ruthenium complexes with fluoroquinolone derivatives as potential antitumor agents[J].Journal of thermal analysis and calorimetry,2011,105(2):645-650.
[38]Patel M N,Gandhi D S,Parmar P A.DNA interaction and in-vitro antibacterial studies of fluoroquinolone based platinum(II)complexes[J].Inorganic Chemistry Communications,2012,15:248-251.
[39]Gouvea L R,Garcia L S,Lachter D R,et al.Atypical fluoroquinolone gold(III)chelates as potential anticancer agents:relevance of DNA and protein interactions for their mechanism of action[J].European journal of medicinal chemistry,2012,55:67-73.
[40]Sadeek S A,El-Shwiniy W H,Zordok W A,et al.Synthesis,spectroscopic,thermal and biological activity investigation of new Y(ΙΙΙ)and Pd(ΙΙ)norfloxacin complexes[J].J.Argent.Chem.Soc,2009,97:128-148.
[41]Refat M S,El-Hawary W F,Mohamed M A.Study of the chemical chelates and anti-microbial effect of some metal ions in nanostructural form on the efficiency of antibiotic therapy"norfloxacin drug"[J].Journal of Molecular Structure,2012,1013:45-54.
[42]Shaikh A,Giridhar R,Megraud F,et al.Metalloantibiotics:Synthesis,characterization and antimicrobial evaluation of bismuth-fluoroquinolone complexes against Helicobacter pylori[J].Acta Pharmaceutica,2009,59(3):259-271.
[43]da GJ Batista D,da Silva P B,Stivanin L,et al.Co(II),Mn(II)and Cu(II)complexes of fluoroquinolones:synthesis,spectroscopical studies and biological evaluation against Trypanosoma cruzi[J].Polyhedron,2011,30(10):1718-1725.
[44]Patel M N,Gandhi D S,Parmar P A.DNA interaction and in-vitro antibacterial studies of fluoroquinolone based platinum(II)complexes[J].Inorganic Chemistry Communications,2012,15:248-251.
[45]Gouvea L R,Garcia L S,Lachter D R,et al.Atypical fluoroquinolone gold(III)chelates as potential anticancer agents:relevance of DNA and protein interactions for their mechanism of action[J].European journal of medicinal chemistry,2012,55:67-73.
[46]Vieira L M M,de Almeida M V,Lourenco M C S,et al.Synthesis and antitubercular activity of palladium and platinum complexes with fluoroquinolones[J].European journal of medicinal chemistry,2009,44(10):4107-4111.
[47]Efthimiadou E K,Karaliota A,Psomas G.Mononuclear dioxomolybdenum(VI)complexes with the quinolones enrofloxacin and sparfloxacin:Synthesis,structure,antibacterial activity and interaction with DNA[J].Polyhedron,2008,27(1):349-356.
[48]Efthimiadou E K,Karaliota A,Psomas G.Metal complexes of the third-generation quinolone antimicrobial drug sparfloxacin:Structure and biological evaluation[J].Journal of inorganic biochemistry,2010,104(4):455-466.
[49]Sadeek S A,El-Shwiniy W H,El-Attar M S.Synthesis,characterization and antimicrobial investigation of some moxifloxacin metal complexes[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2011,84(1):99-110.
[50]Sadeek S A,El-Shwiniy W H,Zordok W A,et al.Spectroscopic studies,thermal analyses and biological evaluation of new V(IV),Zr(IV)and U(VI)moxifloxacin complexes[J].Journal of Molecular Structure,2011,1006(1-3):192-209.
[51]Elshafie H S,Sakr S H,Sadeek S A,et al.Biological investigations and spectroscopic studies of new Moxifloxacin/Glycine‐Metal complexes[J].Chemistry&Biodiversity,2019.