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Synthesis and voltammetric detection of 1H-benzimidazole derivatives on the interaction with DNA

Year 2012, Volume: 16 Issue: 1, 48 - 55, 07.03.2014

Ayşe Alpan Övgü Yılmaz Ozan Kılıçkaya Pınar Kara Hasan Güneş Mehmet Özsöz

Abstract

References

  • Göker H, Özden S, Yıldız S, Boykin DW. Synthesis and potent antibacterial activity against MRSA of some novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5-car- boxamidines. Eur J Med Chem 2005;40: 1062-9.
  • Coburn RA, Clark MT, Evans RT, Genco RJ. Substituted 2-(2-hydroxyphenyl)benzimidazoles as potential agents for the control of periodontal diseases. J Med Chem 1987;30: 205-8.
  • Göker H, Kus C, Boykin DW, Yıldız S, Altanlar N. Syn- thesis of some new 2-substituted-phenyl-1H-benzimi- dazole-5-carbonitriles and their potent activity against candida species. Bioorg Med Chem 2002;10: 2589-96.
  • Garcia-Domenech R, Rios-Santamarina I, Catala A, Cal- abuig C, Del Castillo L, Galvez J. Application of molecu- lar topology to the prediction of antifungal activity for a set of dication-substituted carbazoles, furans and benz- imidazoles. J Mol Struct (Theochem)2003;624: 97-107.
  • Güven OO, Erdoğan T, Göker H, Yildiz S. Synthesis and antimicrobial activity of some novel phenyl and benz- imidazole substituted benzyl ethers. Bioorg Med Chem Lett 2007;17: 2233-6.
  • Ates-Alagoz Z, Yıldız S, Buyukbingol E. Antimicrobial activities of some tetrahydronaphthalene-benzimidazole derivatives. Chemotherapy 2007;53: 110-3.
  • Ramla MM, Omar MA, El-Khamry AM, El-Diwani HI. Synthesis and antitumor activity of 1-substituted-2-me- thyl-5-nitrobenzimidazoles. Bioorg Med Chem 2006;14: 7324-32.
  • Taniguchi K, Shigenaga S, Ogahara T, Fujitsu T, Matsuo M. Synthesis and antiinflammatory and analgesic prop- erties of 2-amino-1H-benzimidazole and 1,2-dihydro-2- iminocycloheptimidazole derivatives. Chem Pharm Bull 1993;41: 301-9.
  • Estrada-Soto S, Villalobos-Molina R, Aguirre-Crespo F, Vergara-Galicia J, Oreno-Diaz H, Torres-Piedra M, Navarrete-Vazquez G. Relaxant activity of 2-(substi- tuted phenyl)-1H-benzimidazoles on isolated rat aortic rings: design and synthesis of 5-nitro derivatives. Life Sci 2006;79: 430-5.
  • Shimai T, Islam MT, Fukushi Y, Hashidoko Y, Yokosawa R, Tahara SZ. Nicotinamide and structurally related compounds show halting activity against zoospores of the phytopathogenic fungus aphanomyces cochlioides. Naturforsch C 2002;57: 323-31.
  • Ray SD, Balasubramanian G, Bagchi D, Reddy CS. Ca2+- calmodulin antagonist chlorpromazine and poly(ADP- ribose) polymerase modulators 4-aminobenzamide and nicotinamide influence hepatic expression of BCL-XL and P53 and protect against acetaminophen-induced programmed and unprogrammed cell death in mice. Free Radic Biol Med 2001;31: 277-91.
  • Alpan AS, Günes HS, Topcu Z. 1H-Benzimidazole deriv- atives as mammalian DNA topoisomerase I inhibitors. Acta Biochim Pol 2007;54: 561-5.
  • Alpan AS, Zencir S, Zupkó I, Coban G, Réthy B, Gunes HS, Topcu Z. Biological activity of bis-benzimidazole de- rivatives on DNA topoisomerase I and HeLa, MCF7 and A431 cells. J Enzym Inhib Med Ch 2009;24: 844-9.
  • Jin S, Kim JS, Sim S, Liu A, Pilch DS, Liu LF, La Voie EJ. Heterocyclic bibenzimidazole derivatives as topoisomer- ase I inhibitors. Bioorg Med Chem Lett 2000;10: 719-23.
  • Seaton A, Higgins C, Mann J, Baron A, Bailly C, Neidle S, Van den Berg H. Mechanistic and anti-proliferative stud- ies of two novel, biologically active bis-benzimidazoles. Eur J Cancer 2003;39: 2548-55.
  • Bagni G, Osella D, Sturchio E, Mascini M. Deoxyribonucleic acid (DNA) biosensors for environmental risk assessment and drug studies. Anal Chim Acta 2006;573-574: 81-9.
  • Rauf S, Gooding JJ, Akhtar K, Ghauri MA, Rahman M, Anwar MA, Khalid AM. Electrochemical approach of anticancer drugs-DNA interaction. J Pharmaceut Bi- omed 2005;37: 205-17.
  • Kara P, Kerman K, Ozkan D, Meric B, Erdem A, Ozkan Z, Ozsoz M. Electrochemical genosensor for the detec- tion of interaction between methylene blue and DNA Electrochem Commun 2002;4: 705-9.
  • Haq I. Thermodynamics of drug-DNA interactions. Arch Biochem Biophys 2002;403: 1-15.
  • Shaikh SA, Ahmed SR, Jayaram B. A molecular thermo- dynamic view of DNA-drug interactions: a case study of 25 minor-groove binders. Arch Biochem Biophys 2004;429: 81-99.
  • Richards AD, Rodger A. Synthetic Metallomolecules as Agents for the Control of DNA Structure. Chem Soc Rev 2007;36: 471-83.
  • Eichhorn GL, Shin YA. Interaction of metal ions with polynucleotides and related compounds. XII. The rela- tive effect of various metal ions on DNA helicity. J Am Chem Soc 1968;90: 7323-8.
  • Snow GA. The molecular basis of antibiotic action. Edi- tors: Gale EF, Cundliffe E, Reynolds PE, Richmond MH, Waring Wiley MJ. London, New York, Sydney, Toronto 1982, pp.152.
  • Campbell PN. Nucleic acid biochemistry and molecular biology. Editors: Mainwaring WIP, Parish JH, Pickering JD, Mann NH. Blackwell Scientific Publications, Oxford, London 1982, pp. 57.
  • Wang J. Electrochemical biosensors: Towards point-of- care cancer diagnostics. Biosens Bioelectron 2006;21: 1887-92.
  • Bogdanovskaya VA, Tarasevich MR. Electrochemical bi- osensors for medicine and ecology. Biosens Bioelectron 1996;11: 853-61.
  • Meric B, Kerman K, Ozkan D, Kara P, Erdem A, Kucu- koglu O, Erciyas E, Ozsoz M. Electrochemical biosen- sor for the interaction of DNA with the alkylating agent 4,4’-dihydroxy chalcone based on guanine and adenine signals. J Pharmaceut Biomed 2002;30: 1339-46.
  • Kerman K, Meric B, Ozkan D, Kara P, Erdem A, Ozsoz M. Electrochemical DNA biosensor for the determina- tion of benzo[a]pyrene-DNA adducts. Anal Chim Acta 2001;450: 45-52.
  • Li N, Guo L, Jiang J, Yang X. Interaction of echinomycin with guanine: Electrochemistry and spectroscopy stud- ies. Biophys Chem 2004; 111: 259-65.
  • Preaston PN. The Chemistry of Heretocyclic Compounds of Benzimidazoles and Congeneric Tricyclic Compounds. John Wiley & Sons, New York 198, pp 63-4.
  • Silverstein RM, Bassler GC, Morrill TC. Spectrometric Identification of Organic Compounds. John Wiley & Sons, New York 1981, chapter 3.
  • Sridharan V, Saravanan S, Muthusubramanian S, Sivas- ubramanian S. NMR investigation of hydrogen bonding and 1,3-tautomerism in 2-(2-hydroxy-5-substituted-aryl) benzimidazoles. Magn Reson Chem 2005;43: 551-6.
  • Kerman K, Ozkan D, Kara P, Karadeniz H, Ozkan Z, Er- dem A, Jelen F, Ozsoz M. Electrochemical detection of specific DNA sequences from PCR amplicons on carbon and mercury electrodes using Meldola’s Blue as an inter- calator. Turk J Chem 2004;28: 523-33.
  • Ariksoysal DO, Karadeniz H, Erdem A, Sengonul A, Sayiner AA, Ozsoz M. Label-free electrochemical hy- bridization genosensor for the detection of hepatitis B virus genotype on the development of lamivudine resist- ance. Anal Chem 2005;77: 4908-17.

Synthesis and voltammetric detection of 1H-benzimidazole derivatives on the interaction with DNA

Year 2012, Volume: 16 Issue: 1, 48 - 55, 07.03.2014

Ayşe Alpan Övgü Yılmaz Ozan Kılıçkaya Pınar Kara Hasan Güneş Mehmet Özsöz

Abstract

Keywords

1H-benzimidazole electrochemical genosensor DNA-drug interaction synthesis

References

  • Göker H, Özden S, Yıldız S, Boykin DW. Synthesis and potent antibacterial activity against MRSA of some novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5-car- boxamidines. Eur J Med Chem 2005;40: 1062-9.
  • Coburn RA, Clark MT, Evans RT, Genco RJ. Substituted 2-(2-hydroxyphenyl)benzimidazoles as potential agents for the control of periodontal diseases. J Med Chem 1987;30: 205-8.
  • Göker H, Kus C, Boykin DW, Yıldız S, Altanlar N. Syn- thesis of some new 2-substituted-phenyl-1H-benzimi- dazole-5-carbonitriles and their potent activity against candida species. Bioorg Med Chem 2002;10: 2589-96.
  • Garcia-Domenech R, Rios-Santamarina I, Catala A, Cal- abuig C, Del Castillo L, Galvez J. Application of molecu- lar topology to the prediction of antifungal activity for a set of dication-substituted carbazoles, furans and benz- imidazoles. J Mol Struct (Theochem)2003;624: 97-107.
  • Güven OO, Erdoğan T, Göker H, Yildiz S. Synthesis and antimicrobial activity of some novel phenyl and benz- imidazole substituted benzyl ethers. Bioorg Med Chem Lett 2007;17: 2233-6.
  • Ates-Alagoz Z, Yıldız S, Buyukbingol E. Antimicrobial activities of some tetrahydronaphthalene-benzimidazole derivatives. Chemotherapy 2007;53: 110-3.
  • Ramla MM, Omar MA, El-Khamry AM, El-Diwani HI. Synthesis and antitumor activity of 1-substituted-2-me- thyl-5-nitrobenzimidazoles. Bioorg Med Chem 2006;14: 7324-32.
  • Taniguchi K, Shigenaga S, Ogahara T, Fujitsu T, Matsuo M. Synthesis and antiinflammatory and analgesic prop- erties of 2-amino-1H-benzimidazole and 1,2-dihydro-2- iminocycloheptimidazole derivatives. Chem Pharm Bull 1993;41: 301-9.
  • Estrada-Soto S, Villalobos-Molina R, Aguirre-Crespo F, Vergara-Galicia J, Oreno-Diaz H, Torres-Piedra M, Navarrete-Vazquez G. Relaxant activity of 2-(substi- tuted phenyl)-1H-benzimidazoles on isolated rat aortic rings: design and synthesis of 5-nitro derivatives. Life Sci 2006;79: 430-5.
  • Shimai T, Islam MT, Fukushi Y, Hashidoko Y, Yokosawa R, Tahara SZ. Nicotinamide and structurally related compounds show halting activity against zoospores of the phytopathogenic fungus aphanomyces cochlioides. Naturforsch C 2002;57: 323-31.
  • Ray SD, Balasubramanian G, Bagchi D, Reddy CS. Ca2+- calmodulin antagonist chlorpromazine and poly(ADP- ribose) polymerase modulators 4-aminobenzamide and nicotinamide influence hepatic expression of BCL-XL and P53 and protect against acetaminophen-induced programmed and unprogrammed cell death in mice. Free Radic Biol Med 2001;31: 277-91.
  • Alpan AS, Günes HS, Topcu Z. 1H-Benzimidazole deriv- atives as mammalian DNA topoisomerase I inhibitors. Acta Biochim Pol 2007;54: 561-5.
  • Alpan AS, Zencir S, Zupkó I, Coban G, Réthy B, Gunes HS, Topcu Z. Biological activity of bis-benzimidazole de- rivatives on DNA topoisomerase I and HeLa, MCF7 and A431 cells. J Enzym Inhib Med Ch 2009;24: 844-9.
  • Jin S, Kim JS, Sim S, Liu A, Pilch DS, Liu LF, La Voie EJ. Heterocyclic bibenzimidazole derivatives as topoisomer- ase I inhibitors. Bioorg Med Chem Lett 2000;10: 719-23.
  • Seaton A, Higgins C, Mann J, Baron A, Bailly C, Neidle S, Van den Berg H. Mechanistic and anti-proliferative stud- ies of two novel, biologically active bis-benzimidazoles. Eur J Cancer 2003;39: 2548-55.
  • Bagni G, Osella D, Sturchio E, Mascini M. Deoxyribonucleic acid (DNA) biosensors for environmental risk assessment and drug studies. Anal Chim Acta 2006;573-574: 81-9.
  • Rauf S, Gooding JJ, Akhtar K, Ghauri MA, Rahman M, Anwar MA, Khalid AM. Electrochemical approach of anticancer drugs-DNA interaction. J Pharmaceut Bi- omed 2005;37: 205-17.
  • Kara P, Kerman K, Ozkan D, Meric B, Erdem A, Ozkan Z, Ozsoz M. Electrochemical genosensor for the detec- tion of interaction between methylene blue and DNA Electrochem Commun 2002;4: 705-9.
  • Haq I. Thermodynamics of drug-DNA interactions. Arch Biochem Biophys 2002;403: 1-15.
  • Shaikh SA, Ahmed SR, Jayaram B. A molecular thermo- dynamic view of DNA-drug interactions: a case study of 25 minor-groove binders. Arch Biochem Biophys 2004;429: 81-99.
  • Richards AD, Rodger A. Synthetic Metallomolecules as Agents for the Control of DNA Structure. Chem Soc Rev 2007;36: 471-83.
  • Eichhorn GL, Shin YA. Interaction of metal ions with polynucleotides and related compounds. XII. The rela- tive effect of various metal ions on DNA helicity. J Am Chem Soc 1968;90: 7323-8.
  • Snow GA. The molecular basis of antibiotic action. Edi- tors: Gale EF, Cundliffe E, Reynolds PE, Richmond MH, Waring Wiley MJ. London, New York, Sydney, Toronto 1982, pp.152.
  • Campbell PN. Nucleic acid biochemistry and molecular biology. Editors: Mainwaring WIP, Parish JH, Pickering JD, Mann NH. Blackwell Scientific Publications, Oxford, London 1982, pp. 57.
  • Wang J. Electrochemical biosensors: Towards point-of- care cancer diagnostics. Biosens Bioelectron 2006;21: 1887-92.
  • Bogdanovskaya VA, Tarasevich MR. Electrochemical bi- osensors for medicine and ecology. Biosens Bioelectron 1996;11: 853-61.
  • Meric B, Kerman K, Ozkan D, Kara P, Erdem A, Kucu- koglu O, Erciyas E, Ozsoz M. Electrochemical biosen- sor for the interaction of DNA with the alkylating agent 4,4’-dihydroxy chalcone based on guanine and adenine signals. J Pharmaceut Biomed 2002;30: 1339-46.
  • Kerman K, Meric B, Ozkan D, Kara P, Erdem A, Ozsoz M. Electrochemical DNA biosensor for the determina- tion of benzo[a]pyrene-DNA adducts. Anal Chim Acta 2001;450: 45-52.
  • Li N, Guo L, Jiang J, Yang X. Interaction of echinomycin with guanine: Electrochemistry and spectroscopy stud- ies. Biophys Chem 2004; 111: 259-65.
  • Preaston PN. The Chemistry of Heretocyclic Compounds of Benzimidazoles and Congeneric Tricyclic Compounds. John Wiley & Sons, New York 198, pp 63-4.
  • Silverstein RM, Bassler GC, Morrill TC. Spectrometric Identification of Organic Compounds. John Wiley & Sons, New York 1981, chapter 3.
  • Sridharan V, Saravanan S, Muthusubramanian S, Sivas- ubramanian S. NMR investigation of hydrogen bonding and 1,3-tautomerism in 2-(2-hydroxy-5-substituted-aryl) benzimidazoles. Magn Reson Chem 2005;43: 551-6.
  • Kerman K, Ozkan D, Kara P, Karadeniz H, Ozkan Z, Er- dem A, Jelen F, Ozsoz M. Electrochemical detection of specific DNA sequences from PCR amplicons on carbon and mercury electrodes using Meldola’s Blue as an inter- calator. Turk J Chem 2004;28: 523-33.
  • Ariksoysal DO, Karadeniz H, Erdem A, Sengonul A, Sayiner AA, Ozsoz M. Label-free electrochemical hy- bridization genosensor for the detection of hepatitis B virus genotype on the development of lamivudine resist- ance. Anal Chem 2005;77: 4908-17.
There are 34 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Ayşe Alpan This is me

Övgü Yılmaz This is me

Ozan Kılıçkaya This is me

Pınar Kara This is me

Hasan Güneş This is me

Mehmet Özsöz This is me

Publication Date March 7, 2014
Published in Issue Year 2012 Volume: 16 Issue: 1

Cite

APA Alpan, A., Yılmaz, Ö., Kılıçkaya, O., Kara, P., et al. (2014). Synthesis and voltammetric detection of 1H-benzimidazole derivatives on the interaction with DNA. Marmara Pharmaceutical Journal, 16(1), 48-55. https://doi.org/10.12991/mpj.31520
AMA Alpan A, Yılmaz Ö, Kılıçkaya O, Kara P, Güneş H, Özsöz M. Synthesis and voltammetric detection of 1H-benzimidazole derivatives on the interaction with DNA. Marmara Pharm J. March 2014;16(1):48-55. doi:10.12991/mpj.31520
Chicago Alpan, Ayşe, Övgü Yılmaz, Ozan Kılıçkaya, Pınar Kara, Hasan Güneş, and Mehmet Özsöz. “Synthesis and Voltammetric Detection of 1H-Benzimidazole Derivatives on the Interaction With DNA”. Marmara Pharmaceutical Journal 16, no. 1 (March 2014): 48-55. https://doi.org/10.12991/mpj.31520.
EndNote Alpan A, Yılmaz Ö, Kılıçkaya O, Kara P, Güneş H, Özsöz M (March 1, 2014) Synthesis and voltammetric detection of 1H-benzimidazole derivatives on the interaction with DNA. Marmara Pharmaceutical Journal 16 1 48–55.
IEEE A. Alpan, Ö. Yılmaz, O. Kılıçkaya, P. Kara, H. Güneş, and M. Özsöz, “Synthesis and voltammetric detection of 1H-benzimidazole derivatives on the interaction with DNA”, Marmara Pharm J, vol. 16, no. 1, pp. 48–55, 2014, doi: 10.12991/mpj.31520.
ISNAD Alpan, Ayşe et al. “Synthesis and Voltammetric Detection of 1H-Benzimidazole Derivatives on the Interaction With DNA”. Marmara Pharmaceutical Journal 16/1 (March 2014), 48-55. https://doi.org/10.12991/mpj.31520.
JAMA Alpan A, Yılmaz Ö, Kılıçkaya O, Kara P, Güneş H, Özsöz M. Synthesis and voltammetric detection of 1H-benzimidazole derivatives on the interaction with DNA. Marmara Pharm J. 2014;16:48–55.
MLA Alpan, Ayşe et al. “Synthesis and Voltammetric Detection of 1H-Benzimidazole Derivatives on the Interaction With DNA”. Marmara Pharmaceutical Journal, vol. 16, no. 1, 2014, pp. 48-55, doi:10.12991/mpj.31520.
Vancouver Alpan A, Yılmaz Ö, Kılıçkaya O, Kara P, Güneş H, Özsöz M. Synthesis and voltammetric detection of 1H-benzimidazole derivatives on the interaction with DNA. Marmara Pharm J. 2014;16(1):48-55.