International Journal of Bioorganic Chemistry

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Design, Synthesis of New Amino Acid Derivatives and Evaluate DNA Binding Activity, Anticancer and Antimicrobial Activity

Received: 23 December 2016    Accepted: 10 January 2017    Published: 2 March 2017
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Abstract

The present review covers the recent synthetic amino acid derivatives with chemical transformations to peptide derivatives. The amino acids were used as starting keys for synthesis peptides and pseudopeptides derived from pyridinine, coumarine, imaddizole, pyrazole phthalyl, qunolinine and sulfonamide rings. these biomolecules have diverse biological and pharmacological actions, as antimicrobial, anti-cancer targeting human carbonic anhydrase (CA) and DNA binding activities.

DOI 10.11648/j.ijbc.20170202.11
Published in International Journal of Bioorganic Chemistry (Volume 2, Issue 2, June 2017)
Page(s) 36-50
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Amino Acid, DNA Binding, Anticancer, Antimicrobial

References
[1] Tripathi, R., Tewari N., Dwivedi, N., Tiwari V. K., Med. Res. Rev., 2005,25, 93,.
[2] Pathak, A., Pathak, V., Seitz, L. E., Suling, W. J., Reynolds, R. C., Bio. Org. Med. Chem., 2013,21, 1685.
[3] Voynikov, Y.; Stavrakov, G.; Tencheva, J.; Peikov, P. Compt. Rend. Acad. Bulg. Sci. 2013, 66, 1399.
[4] Y. Voynikov, V. Valcheva, G. Momekov, P. Peikov, G. Stavrakov, Bio. Org. Med. Chem. Lett., 2014, 24, 3043.
[5] A. Hughes, Carboxy Protection, Amino Acids, Peptides and Proteins in Organic Chemistry; Wiley: Victoria, p 34, 2011.
[6] Nielsen, P. E. Pseudo-peptides in drug discovery; Wiley-VCH: New York, 2004. Pp 1.
[7] Leader, B.; Baca, Q. J.; Golan, D. E. Nat. Rev. Drug Disc. 2008, 7, 21.
[8] Kim, M. K.; Wang-su, P. K.; Woon-seok, Y.; Choob, H.; Chong, Y. BioOrg. Med. Chem. 2009, 17, 1164.
[9] Ibrahim, M. A.; Panda, S. S.; Birs, A. S.; Serrano, J. C.; Gonzalez, C. F.; Alamry, K. A.; Katritzky, A. R.; Bioorg. Med. Chem. Lett., 2014, 24, 1856.
[10] EI-Kerdawy, M. M.; Eisa, M.; Barghash, A., and Marouf, A.; Sulfur Lett. (1989), 10, 57-70.
[11] Abd EI-Fattah, M. E, Arch. Pharm. Res. 1998, 21 (6), 723-728.
[12] Hofmann, K.; Johi, A.; Furlemeier, A. E. and Kappeler, H.; J. Am. Chem. Soc.; 1957, 79, 1636.
[13] Charitos, C.; KoKtos,G.; Tzougraki, C.; j. Heterocyclic Chem. 2001,38, 153.
[14] Besson, T.; Joseph, B.; Moreau.; P.; Viaeud, G.; Coudert, G. and Guillaumet, G.; Heterocycles. 1992, 34, 273.
[15] Bajaj, K.; Panda, S. S.; El-Nachef, C.; Katritzky, Chem. Biol. Drug. Des. 2012, 80, 17.
[16] Abdelmajeid, A.; Tala, S. R.; Amine, M. S.; Katritzky, A. R. Synthesis, 2011,18, 2995.
[17] Tsuji K and Ishikawa H.; Bio. Org. Med. Chem. Lett.;1994, 4, 1606.
[18] Peter, W.; Aslan, DC.; Southwick, EC.; and Lazob, JS.; Bio. Org. Med. Chem. Lett, 2001, 11, 313.
[19] Helal, CJ.; Sanner, MA; and Cooper, CB.;Bioorg. Med. Chem. Lett t, 2004; 14: 5521.
[20] Deliwala, CV.; Modi, JD.; and Sabnis, S. S.; J. Med. Chem, 1979, 14 (3), 887.
[21] PRAKASHA, K. C.; Raghavendra, G. M.; Harisha, R.; and Gowd, D. C.; Int. J. Pharm. Pharm. Sci.; 2011, 3, 120.
[22] Leite, A. C. L.; Santos, L. M. F.;Nascimento, D. D. S.; Sena, K. X. F. R.;Brondani, D. J. Acta farm. Bonaer.2004, 23, 117.
[23] Leite, A. C.; Santos, L. M. F.; Anjos, J. V.; Farias, M. P. A.; Souza, I. A.; Brondani, D. J. Heterocycl. Commun. 2003, 9, 73–76.
[24] Leite, A. C.; Renata, S. L.; Moreira, D. R. M.; V. C.; Marcos, C. G. B.; Ana, M. F. S.; Luciene, Z. H.; Marcelo, C. K.; Alice, S. de Ricardo L.; and Milena.; B. P. S., Bioorg. Med. Chem.. 2006, 14, 3749.
[25] Schmidt, A.;Krauth-Siegel, R. L. Curr. Top. Med. Chem.2002, 2, 1239.
[26] K. P.; VINOD, U. MRIDULA, MRINALINI U.; VISHNU D. G.; MEENAL T.; Acta Pharm. 2005, 55, 47.
[27] Fathalla, O. A.; Zaki, M. E. A.; Indian J. Chem., 1998, 37B, 484.
[28] Schnabel, E.; Herzog, H.; Hoffman, P.; Klauke, E.; and Ugi.; I.; Angew. Chem. 1968, 7, 380.
[29] Shalaby, A. M.;Fathalla, O. A.;Kassem, E. M. M.; and ZakiActa, M. E. A.; Chim. Slov., 2000, 47, 187.
[30] McKennon, M. J.; Meyers, A. I.; Drauz, K.; Schwarm, M. J. Org. Chem. 1993, 58, 3568.
[31] Humljan, J.; Kotnik, M.; Boniface, A.; Solmajer, T.; Urleb, U.; Blanot, D.; and Gobec, S.; Tetrahedron Lett, 2006, 62, 10980.
[32] Kienzle, F.; Kaiser,A.;and Minder, R. E.; Helv. Chim. Acta, 66, 148 (1983).
[33] Heiba, H. I.; Ghorab, M. M.; El-gawish,M. A. Phosphorus Sulfur Silicon Relat Elem, 1997, 131, 197.
[34] Hassan, H. M.; Abdelall, M. M.; El-Naggar, A. M.; Tamer, M. E.; and Bayoumi, R. A.; J. of American Science, 2011, 7(2), 378.
[35] Al-Amin, M.; and Rabiul, M. I.; Bangladesh J. Pharmacol.; 2006, 1, 21-6.
[36] El-henawy, A. A.; J. of American Science 2010,6,240.
[37] El-Sayed, R. A.; Phosphorus Sulfur Silicon Relat Elem,, 1997, 131, 207.
[38] Pintilie, O.; Profire, L.; Sunel, V., Popa, M., and Pui. A.; Molecules 2007, 12, 103.
[39] Letai.; A.; Cancer Cell 2006,10, 343.
[40] Zhai, D.; Jin, C.; Satterthwait, A. C.; Reed. J. C.; Cell Death Differ. 2006, 13, 1419.
[41] Goldsmith, K. C.; Hogarty, M. D.; Cancer Lett. 2005, 228, 133.
[42] Lessene, G.; Czabotar, P. E.; Colman.; P. M.; Nat. Rev. Drug Discov.; 2008,7, 989.
[43] Del Gaizo Moore, V.; Brown, J. R.; Certo, M.; Love, T. M.; Novina, C. D.; Letai. A.; J. Clin. Invest. 2007, 117, 112.
[44] Oltersdorf, T.; Elmore, S. W.; Shoemaker, A. R.; Armstrong, R. C.; Augeri, D. J.; Belli, B. A.; Bruncko, M.; Deckwerth, T. L.; Dinges, J.; Hajduk, P. J.; Joseph, M. K. Kitada, S.; Korsmeyer, S. J.; Kunzer, A. R.; Letai, A.; Li, C.; Mitten, M. J.; Nettesheim, D. G.; Ng, S. C.; Nimmer, P. M.; O’Connor, J. M.; Oleksijew, A.; Petros, A. M.; Reed, J. C.; Shen, W.; Tahir, S. K.; Thompson, C. B.; Tomaselli, K. J. m, Wang, B.; Wendt, M. D.; Zhang, H.; Fesik, S. W.; Rosenberg.; S. H.; Nature, 2005,435, 677.
[45] Kazi, A.; Smith, D. M.; Zhong, Q.; Dou. Q. P.; Mol. Pharmacol. 2002, 62, 765.
[46] Zhao, Y.; Yang, L.-F.; Ye, M.; Gu, H.-H.; Cao. Y.; Prev. Med. 2004,39, 1172.
[47] Nishikawa, T.; Nakajima, T.; Moriguchi, M.; Jo, M.; Sekoguchi, S.; Ishii, M.; Takashima, H.; Katagishi, T.; Kimura, H.; Minami, M.; Itoh, Y.; Kagawa, K.; Okanoue, T.; J. Hepatol. 2006, 44, 1074.
[48] Qin, J.; Xie, L.-P.; Zheng, X.-Y.; Wang, Y.-B.; Bai, Y.; Shen, H.-F.; Li, L.-C.; Dahiya. R.; Biochem. Biophys. Res. Commun., 2007,354, 852.
[49] Hao, M. J.-H. Y.; Liu, F.-T.; Newland, A. C.; Jia, L.; Cancer Res. 2004, 64, 3607.
[50] Sing, W. T.; Lee, C. L.; Yeo, S. L.; Lim, S. P.; Sim, M. M.;Bioorg. Med. Chem. Lett. 2001, 11, 91.
[51] Handy, S. T.; Wilson, T.; Muth.; A. J. Org. Chem. 2007, 72, 8496.
[52] Bernardo, P. H.; Sivaraman, T.; Wan, K-F, Xu, J.; Krishnamoorthy, J.; Song, C. M.; Tian, L.; Chin, J. S. F.; Lim, D. S. W.; Mok, H. Y. K.; Yu, V. C.; Tong, J. C.; and Chai, C. L. L.; Pure Appl. Chem. 2011,83 (3),723.
[53] Nathalie, L.; Cynthia, M. C.; Emmanuel, R.; Ann, B.; Bernard, P. R.; Marie-Claude,F. Z., Biochemistry, 1998, 37, 686.
[54] Florence, N.; Nathalie, L.; Sophie, D. N.; René, L. K.; Laurent, B.; Hui, X. C.; Marie-Claude, F. Z.; Bernard, P. R. FEBS Lett,. 2000, 467, 81.
[55] Xu, W. F.; Li, Q. B, Curr. Med. Chem. Anti-Cancer Agents, 2005, 5, 281.
[56] Testa, M. L.; Ciriminna, R.; Hajji, C.; Garcia, E. Z.; Ciclosi, M.; Arques, J. S.; Pagliaroa, M. Adv. Synth. Catal. 2004, 346, 655.
[57] Yang, K.; Wang, Q.; Su, L.; Fang, H.; Wang, X.; Gong, Wang, J. B.; Xu, W.; Bioorg Med Chem., 2009,17, 3810.
[58] Wang, Q.; Chen, M. Y.; Zhu, H. W.; Zhang, J.; Fang, H.; Wang, H. B.; Xu, W. F Bioorg Med Chem., 2008, 16, 5473.
[59] Addlagatta, A.; Gay, L.; Matthews, B. W. Biochemistry 2008, 47, 5303.
[60] Hashimoto, S.; Okada, K.; Sakakibara, R.; Fujii, S. U.S. Patent [11] 3, 799, 988, 1974.
[61] Jordis, U.; Sauter, F.; Siddiqi, S. M. Indian J. Chem. Sec. B 1989, 294.
[62] Mou, J.; Fang, H.; Jing, F.; Wang, Q.; Liu, Y.; Zhu, H.; Shang, L.; Wang, X.; Xu., Bioorg Med Chem.., 2009, 17,4666.
[63] Mou, J.; Fang, H.; Liu, Y.; Shang, L.; Wang, Q.; Zhu, L.; Xu, W.; Bioorg Med Chem.. 2010, 18,887.
[64] Xun L.; Yazhou W.; Jifeng W.; Yonggang L.; Qiang W.; Wenfang X.; Bioorg Med Chem., 2009, 7, 3061.
[65] Tsai, J.; Takaoka, L.; Powell, N.; Nowick, J. Org. Synth. 2002, 78, 220.
[66] Su, L.; Jia, Y.; Zhang, L.; Xu, Y.; Fang, H.; Xu, W.;., Bioorg Med Chem. 2012, 20,3807.
[67] Fournié-Zaluski, M.; Coric, P.; Turcaud, S.; Bruetschy, L.; Lucas, E.; Noble, F.; Roques, B. P.; J. Med. Chem. 1992, 35, 1259.
[68] Shang, L.; Fang, H.; Zhu, H.; Wang, X.; Wang, Q.; Mu, J.; Wang, B.; Kishioka, S.; Xu, W.; Bioorg Med Chem, 2009,17, 2775.
[69] Li, X.; Wang, D. H.; Wu, J. F.; Xu, W. F.; Synth. Commun. 2005, 35, 1.
[70] Li, Y.; Zhang, J.; Xu, W.; Zhu, H.; Li, X.; Bioorg Med Chem, 2010, 18, 1516.
[71] Li, Q.; Fang, H.; Wang, X.; Xu, W. Eur. J. Med. Chem. 2010, 45, 1618.
[72] Li, Q.; Fang, H.; Wang, X.; Hu, G.; Wang, Q.; Xu, W.; Bioorg Med Chem. Lett., 2012, 22, 850.
[73] Foroumadi, A.; Daneshtalab, M.; Shafiee, A.; Arzneimitt. Forsch. 1999, 49, 1035.
[74] Levy, M.; Palmer, A. H.; J. Biol. Chem. 1942, 146, 493.
[75] Song, K. S.; Ishikawa, Y.; Kobayashi, S.; Sankawa, U.; Ebizuka, Y. Phytochemistry,1992, 31, 823.
[76] Tu, G.; Li, S.; Huang, H.; Li, G.; Xiong, F.; Mai, X.; Zhu, H.; Kuang, B.; Xu, W. F.; Bio. Org.. Med. Chem. 2008,16,6663.
[77] Kivela, A. J.; Kivela, J.; Saarnio, J.; Parkkila, S.; World J. Gastroenterol.; 2005;11, 155.
[78] Supuran, C. T.; Nat. Rev. Drug Discov. 2008,7, 168.
[79] Supuran, v; and Scozzafava A.; Supuran; Bio. Org.. Med. Chem.; 2007, 15, 4336.
[80] Supuran, C. T.; Scozzafava, A; and Casini, A.; Med. Res. Rev.; 2003, 23, 146.
[81] Casini, A.; Scozzafava, A.; Mastrolorenzo; and. Supuran, L. T; Curr. Cancer Drug Targets.; 2002, 2, 55.
[82] Maresca, A.; Temperini, C.; Vu, H.; Pham, N. B.; Poulsen, S. A.; Scozzafava, A.; Quinn, R. J.; Supuran, C. T. J. Am. Chem. Soc. 2009, 131, 3057
[83] Vu, H.; Pham, N. B.; Quinn, R. J.; J. Biomol. Screen. 2008, 13, 265.
[84] Maresca, A.; Temperini, C.; Pochet, L.; Masereel, B.; Scozzafava, A.; Supuran, C. T.; J. Med. Chem. 2010, 53, 335.
[85] Innocenti, A.; Durdagi, S.; Doostdar, N.; Strom, T. A.; Barron, A. R.; Supuran, C. T. Bio. Org.. Med. Chem. 2010, 18, 2822.
[86] El-Henawy, A. A.; Kadah, M. S.; Nassar, H. S.; Egypt. J. Chem., 2010, 53 (2), 279.
[87] Supuran, C. T., Scozzafava, A., Casini A., Med Res Rev.; 2003, 23, 146.
[88] Thiry, A.; Ledecq, M.;Cecchi, A.;Dogne, J. M.; Wouters, J.; Supuran, C. T.; Masereel, B.; J. Med. Chem.; 2006, 49,2743.
[89] El-Henawy, A. A.; Mohamed, Sh. I.; Ibrahim, T. M. A.; El-Hag Ali, G. A. M.; N. Y. Sci. J., 2011,4 (12), 20.
[90] Hanafy, A. I.; El-Bahyab, Z. M.; El-Henawy, A. A, Faheima, A. A., J. Mol. Catal. A: Chem. 2012, 355, 192.
Cite This Article
  • APA Style

    Ahmed A. Elhenawy. (2017). Design, Synthesis of New Amino Acid Derivatives and Evaluate DNA Binding Activity, Anticancer and Antimicrobial Activity. International Journal of Bioorganic Chemistry, 2(2), 36-50. https://doi.org/10.11648/j.ijbc.20170202.11

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    ACS Style

    Ahmed A. Elhenawy. Design, Synthesis of New Amino Acid Derivatives and Evaluate DNA Binding Activity, Anticancer and Antimicrobial Activity. Int. J. Bioorg. Chem. 2017, 2(2), 36-50. doi: 10.11648/j.ijbc.20170202.11

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    AMA Style

    Ahmed A. Elhenawy. Design, Synthesis of New Amino Acid Derivatives and Evaluate DNA Binding Activity, Anticancer and Antimicrobial Activity. Int J Bioorg Chem. 2017;2(2):36-50. doi: 10.11648/j.ijbc.20170202.11

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  • @article{10.11648/j.ijbc.20170202.11,
      author = {Ahmed A. Elhenawy},
      title = {Design, Synthesis of New Amino Acid Derivatives and Evaluate DNA Binding Activity, Anticancer and Antimicrobial Activity},
      journal = {International Journal of Bioorganic Chemistry},
      volume = {2},
      number = {2},
      pages = {36-50},
      doi = {10.11648/j.ijbc.20170202.11},
      url = {https://doi.org/10.11648/j.ijbc.20170202.11},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijbc.20170202.11},
      abstract = {The present review covers the recent synthetic amino acid derivatives with chemical transformations to peptide derivatives. The amino acids were used as starting keys for synthesis peptides and pseudopeptides derived from pyridinine, coumarine, imaddizole, pyrazole phthalyl, qunolinine and sulfonamide rings. these biomolecules have diverse biological and pharmacological actions, as antimicrobial, anti-cancer targeting human carbonic anhydrase (CA) and DNA binding activities.},
     year = {2017}
    }
    

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  • TY  - JOUR
    T1  - Design, Synthesis of New Amino Acid Derivatives and Evaluate DNA Binding Activity, Anticancer and Antimicrobial Activity
    AU  - Ahmed A. Elhenawy
    Y1  - 2017/03/02
    PY  - 2017
    N1  - https://doi.org/10.11648/j.ijbc.20170202.11
    DO  - 10.11648/j.ijbc.20170202.11
    T2  - International Journal of Bioorganic Chemistry
    JF  - International Journal of Bioorganic Chemistry
    JO  - International Journal of Bioorganic Chemistry
    SP  - 36
    EP  - 50
    PB  - Science Publishing Group
    SN  - 2578-9392
    UR  - https://doi.org/10.11648/j.ijbc.20170202.11
    AB  - The present review covers the recent synthetic amino acid derivatives with chemical transformations to peptide derivatives. The amino acids were used as starting keys for synthesis peptides and pseudopeptides derived from pyridinine, coumarine, imaddizole, pyrazole phthalyl, qunolinine and sulfonamide rings. these biomolecules have diverse biological and pharmacological actions, as antimicrobial, anti-cancer targeting human carbonic anhydrase (CA) and DNA binding activities.
    VL  - 2
    IS  - 2
    ER  - 

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Author Information
  • Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt; Chemistry Department, Faculty of Science and Art, Al-Baha University, Al-Baha, Saudi Arabia

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