THE SYNTHESES AND STRUCTURAL CHARACTERIZATIONS, ANTIMICROBIAL ACTIVITY AND IN VITRO DNA BINDING OF 4-FLUOROBENZYLSPIRO(N/O)CYCLOTRIPHOSPHAZENES AND THEIR PHOSPHAZENIUM SALTS

Gamze Elmas; Aytuğ Okumuş; Zeynel Kılıç; L. Yasemin Gönder; Leyla Açık; Tuncer Hökelek

doi:10.18596/jotcsa.04055

THE SYNTHESES AND STRUCTURAL CHARACTERIZATIONS, ANTIMICROBIAL ACTIVITY AND IN VITRO DNA BINDING OF 4-FLUOROBENZYLSPIRO(N/O)CYCLOTRIPHOSPHAZENES AND THEIR PHOSPHAZENIUM SALTS

Year 2016, Volume: 3 Issue: 3, 25 - 46, 08.01.2017

Gamze Elmas , Aytuğ Okumuş , Zeynel Kılıç , L. Yasemin Gönder Leyla Açık , Tuncer Hökelek

https://doi.org/10.18596/jotcsa.04055

Cited By: 14

Abstract

In the present study, the condensation reaction of N₃P₃Cl₆ (1) with sodium 3-(4-fluorobenzylamino)-1-propanoxide gave partly substituted 4-fluorobenzylspiro cyclotriphosphazene (2). The Cl replacement reactions of 2 with excess benzylamine, n-hexylamine, n-buthylamine and n-propylamine led to the formation of the corresponding 4-fluorobenzylspiro(N/O)tetrabenzylamino (3a), tetrahexylamino (3b), tetrabuthylamino (3c) and tetrapropylamino (3d) cyclotriphosphazenes. The protic ionic liquids (PILs), phosphazenium salts (4a-4d), were obtained from the reactions of the corresponding phosphazene bases (3a-3d) with gentisic acid in dry THF. The structures of all the isolated cyclotriphosphazene derivatives were determined by elemental analyses, FTIR and ¹H, ¹³C{¹H}, ³¹P{¹H} NMR techniques. The crystal structure of 4d was verified by X-ray diffraction analysis. All the compounds were screened for antibacterial and antifungal activities against bacteria and yeast strains. The interactions of the compounds with supercoiled pUC18 plasmid DNA were investigated.

References

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Allen W.C. Regio- and stereochemical control in substitution reactions of cyclophosphazenes. Chem. Rev. 1991 Mar;91:119-35. DOI: 10.1021/cr00002a002.
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Asmaﬁliz N, Kılıç Z, Hayvalı Z, Açık L, Hökelek T, Dal H, Öner Y. Phosphorus-nitrogen compounds. Part 23: syntheses, structural investigations, biological activities, and DNA interactions of new N/O spirocyclotriphosphazenes. Spectrochimica Acta Part A. 2012 Feb;86:214-23. DOI: 10.1016/j.saa.2011.10.027.
İlter E.E, Asmafiliz N, Kılıç Z, Işıklan M, Hökelek T, Çaylak N, Şahin E. Phosphorus−nitrogen compounds. 14. synthesis, stereogenism, and structural ınvestigations of novel N/O spirocyclic phosphazene derivatives. Inorg. Chem. 2007 Oct; 46:9931-44.
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Jimenez J, Pintre I, Gascon E, Sanchez-Somolinos C, Alcala R, Cavero E, Serrano J.L, Oriol L. Photoresponsive liquid-crystalline dendrimers based on a cyclotriphosphazene core. Macromol. Chem. Phys. 2014 Jun;215:1551-62. DOI: 10.1002/macp.201400190.
Ahn S, Kim H.S, Yang S, Do J.Y, Kim B.H, Kim K. Thermal stability and performance studies of LiCo1/3Ni1/3Mn1/3O2 with phosphazene additives for Li-ion batteries. J. Electroceram. 2009;23:289-94. DOI: 10.1007/s10832-008-9437-y.
Harrup M.K, Gering K.L, Rollins H.W, Sazhin S.V, Benson M.T, Jamison D.K, Michelbacher C.J, Luther T.A. Phosphazene based additives for ımprovement of safety and battery lifetimes in lithium-ıon batteries. ESC Trans. 2012 May;41(39):13-25. DOI: 10.1149/1.3703065.
Nishimoto T, Yasuda T, Lee S.Y, Kondo R, Adachi C. A six-carbazole-decorated cyclophosphazene as a host with high triplet energy to realize efficient delayed-fluorescence OLEDs. Mater. Horiz. 2014 Sep;1:264-69. DOI: 10.1039/C3MH00079F.
Schrogel P, Hoping M, Kowalsky W, Hunze A, Wagenblast G, Lennartz C, Strohriegl P. Phosphazene-based host materials for the use in blue phosphorescent organic light-emitting diodes. Chem. Mater. 2011 Oct;23:4947-53. DOI: 10.1021/cm201940f.
Zhu J, Liu W, Chu R, Meng X. Tribological properties of linear phosphazene oligomers as lubricants. Tribology Int. 2007 Mar;40:10-14. DOI: 10.1016/j.triboint.2006.01.014.
Wang X, Tan A.Y.X, Cho C.M, Ye Q, He C, Ji R, Xie H.Q, Tsai J.W.H, Xu J. Highly thermally stable cyclotriphosphazene based perfluoropolyether lubricant oil. Tribology Int. 2015 Apr;90:257–62. DOI: 0.1016/j.triboint.2015.04.018.
Tümer Y, Koç L.Y, Asmafliz N, Kılıç Z, Hökelek T, Soltanzade H, Açık L, Yola M.L, Solak A.O. Phosphorus–nitrogen compounds: part 30. syntheses and structural investigations, antimicrobial and cytotoxic activities and DNA interactions of vanillinato-substituted NN or NO spirocyclic monoferrocenyl cyclotriphosphazenes. J. Biol. Inorg. Chem. 2015 Dec;20:165-78. DOI: 10.1007/s00775-014-1223-5.
Başterzi N.S, Bilge Koçak S, Okumuş A, Kılıç Z, Hökelek T, Çelik Ö, Türk M, Koç L. Y, Açık L, Aydın B, Dal H. Syntheses, structural characterization and biological activities of spiro-ansa-spiro-cyclotriphosphazenes. New J. Chem. 2015 Sep;39:8825-39. DOI: 10.1039/C5NJ01530H.
Mutlu G, Elmas G, Kılıç Z, Hökelek T, Koç L.Y, Türk M, Açık L, Aydın B, Dal H. Phosphorus-nitrogen compounds: part 31. syntheses, structural and stereogenic properties, in vitro cytotoxic and antimicrobial activities, DNA interactions of novel bicyclotetraphosphazenes containing bulky side group. Inorganica Chimica Acta. 2015 July;436:69-81. DOI: 10.1016/j.ica.2015.07.027.
Akbaş H, Okumuş A, Kılıç Z, Hökelek T, Süzen Y, Koç L.Y, Açık L, Çelik Z.B. Phosphorus-nitrogen compounds: part 27. syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing secondary amino and pendant (4-fluorobenzyl)spiro groups. European Journal of Medicinal Chemistry. 2013 Dec;70:294-307. DOI: 10.1016/j.ejmech.2013.09.046.
Okumuş A, Elmas G, Cemaloğlu R, Aydın B, Binici A, Şimşek H, Açık L, Türk M, Güzel R, Kılıç Z, Hökelek T. Phosphorus-nitrogen compounds. part 35. syntheses, spectroscopic and electrochemical properties, antituberculosis, antimicrobial and cytotoxic activities of mono-ferrocenyl-spirocyclotetraphosphazenes. New J. Chem. 2016 Apr;40:5588-603. DOI: 10.1039/C6NJ00204H.
Greaves T.L, Drummond C.J. Protic ionic liquids: properties and applications. Chem. Rev. 2008 Dec;108:206-37. DOI: 10.1021/cr068040u.
Bicak N. A new ionic liquid: 2-hydroxy ethylammonium formate. Journal of Molecular Liquids. 2005 Jan;116:15-8. DOI: 10.1016/j.molliq.2004.03.006.
Karadağ A, Destegül A. N-(2-hydroxyethyl)-ethylenediamine-based ionic liquids: synthesis, structural characterization, thermal, dielectric and catalytic properties. Journal of Molecular Liquids. 2013;177:369-75. DOI: 10.1016/j.molliq.2012.10.040.
Akbaş H, Okumuş A, Karadağ A, Kılıç Z, Hökelek T, Süzen Y, Koç L.Y, Açık L, Aydın B, Türk M. Phosphorus–nitrogen compounds: part 32. structural and thermal characterizations, antimicrobial and cytotoxic activities, and in vitro DNA binding of the phosphazenium salts. J. Therm. Anal. Calorim. 2016 Sep;123:1627-41. DOI: 10.1007/s10973-015-5001-6.
Bruker program 1D WIN-NMR (release 6.0) and 2D WIN-NMR (release 6.1).
Bruker, SADABS, Bruker AXS Inc., Madison, Wisconsin, USA, (2005).
Sheldrick G.M. SHELXS-97, SHELXL-97 University of Gottingen, Gottingen, Germany, (1997).
Sheldrick G.M. A short history of SHELXL. Acta Crystallogr. Sect. A. 2008 Jan;64: 112-22. DOI: 10.1107/S0108767307043930.
Clinical and Laboratory Standards Institute, Performance Standards for Antimicrobial Susceptibility Testing Sixteenth Informational Supplement, CLSI document M100eS16, Pennsylvania, (2006).
Elmas G, Okumuş A, Koç L.Y, Soltanzade H, Kılıç Z, Hökelek T, Dal H, Açık L, Üstündağ Z, Dündar D, Yavuz M. Phosphorus-nitrogen compounds. part 29. syntheses, crystal structures, spectroscopic and stereogenic properties, electrochemical investigations, antituberculosis, antimicrobial and cytotoxic activities and DNA interactions of ansa-spiro-ansa cyclotetraphosphazenes. European Journal of Medicinal Chemistry. 2014 Oct;87:662-76. DOI: 10.1016/j.ejmech.2014.10.005.
Elmas (nee Egemen) G, Okumuş A, Kılıç Z, Hökelek T, Açık L, Dal H, Ramazanoğlu N, Koç L.Y. Phosphorus−nitrogen compounds. part 24. syntheses, crystal structures, spectroscopic and stereogenic properties, biological activities, and dna ınteractions of novel spiro-ansa-spiro- and ansa-spiro-ansa-cyclotetraphosphazenes. Inorg. Chem. 2012 Nov;51:12841-56. DOI: 10.1021/ic3017134.
Seto S, Tanioka A, Ikeda M, Izawa S. European Patent Office, Bulletin, 2004, EP 1 473 295 A 1 [0100].
Koçak S.B, Koçoğlu S, Okumuş A, Kılıç Z, Öztürk A, Hökelek T, Öner Y, Açık L. Syntheses, spectroscopic properties, crystal structures, biological activities, and dna interactions of heterocyclic amine substituted spiro-ansa-spiro- and spiro-bino-spiro-phosphazenes. Inorganica Chimica Acta. 2013 Sep;406:160-70. DOI: 10.1016/j.ica.2013.07.023.
Carriedo G.A, Alonso F.G, Gonzalez P.A, Menendez J.R. Infrared and Raman spectra of the phosphazene high polymer [NP(O2C12H8)]n. J. Raman Spectrosc. 1998 Dec;29:327-30. DOI: 10.1002/(SICI)1097-4555(199804)29:4.
Egemen G, Hayvalı M, Kılıç Z, Solak A.O, Üstündağ Z. Phosphorus-nitrogen compounds. part 17. the synthesis, spectral and electrochemical investigations of porphyrinophosphazenes. J. Porphyrins Phthalocyanines. 2010;14:1-8. DOI: 10.1142/.
Cremer D, Pople J.A, General definition of ring puckering coordinates. J. Am. Chem. Soc. 1975 Mar;97:1354-8. DOI: 10.1021/ja00839a011.
Okumuş A, Bilge S, Kılıç Z, Öztürk A, Hökelek T, Yılmaz F. Phosphorus–nitrogen compounds. part 20: fully substituted spiro-cyclotriphosphazenic lariat (PNP-pivot) ether derivatives. Spectrochimica Acta Part A. 2010 Apr;76:401-9. DOI: 10.1016/j.saa.2010.04.007.
Farrugia L.J. ORTEP-3 for Windows- a version of ORTEP-III with a Graphical User Interface (GUI). J. Appl. Crystallogr. 1997 Feb;30:565-6. DOI: 10.1107/S0021889897003117.
Haapasalo M, Ranta H, Ranta K.T. Facultative gram-negative enteric rods in persistent periapical infections. Acta Odontol Scand. 1983;41:19-22. DOI: 10.3109/00016358309162299.

Year 2016, Volume: 3 Issue: 3, 25 - 46, 08.01.2017

Gamze Elmas , Aytuğ Okumuş , Zeynel Kılıç , L. Yasemin Gönder Leyla Açık , Tuncer Hökelek

https://doi.org/10.18596/jotcsa.04055

Cited By: 14

Abstract

References

Chandrasekhar V, Thilagar P, Pandian B.M. Cyclophosphazene-based multi-site coordination ligands. Coord. Chem. Rev. 2007;251:1045-74. DOI: 10.1016/j.ccr.2006.07.005.
Allen W.C. Regio- and stereochemical control in substitution reactions of cyclophosphazenes. Chem. Rev. 1991 Mar;91:119-35. DOI: 10.1021/cr00002a002.
Okumuş A, Kılıç Z, Hökelek T, Dal H, Açık L, Öner Y, Koç L.Y. Phosphorus–nitrogen compounds part 22. syntheses, structural investigations, biological activities and DNA interactions of new mono and bis (4-fluorobenzyl)spirocyclophosphazenes. Polyhedron. 2011 Nov;30:2896-2907. DOI: 10.1016/j.poly.2011.08.035.
Işıklan M, Asmafiliz N, Özalp E.E, İlter E.E, Kılıç Z, Çoşut B, Yeşilot S, Kılıç A, Öztürk A, Hökelek T, Koç L.Y, Açık L, Akyüz E. Phosphorus−nitrogen compounds. 21. syntheses, structural investigations, biological activities, and DNA interactions of new N/O spirocyclic phosphazene derivatives. The NMR behaviors of chiral phosphazenes with stereogenic centers upon the addition of chiral solvating agents. Inorg. Chem. 2010 Jun;49:7057-71. DOI: 10.1021/ic100781v.
Asmaﬁliz N, Kılıç Z, Hayvalı Z, Açık L, Hökelek T, Dal H, Öner Y. Phosphorus-nitrogen compounds. Part 23: syntheses, structural investigations, biological activities, and DNA interactions of new N/O spirocyclotriphosphazenes. Spectrochimica Acta Part A. 2012 Feb;86:214-23. DOI: 10.1016/j.saa.2011.10.027.
İlter E.E, Asmafiliz N, Kılıç Z, Işıklan M, Hökelek T, Çaylak N, Şahin E. Phosphorus−nitrogen compounds. 14. synthesis, stereogenism, and structural ınvestigations of novel N/O spirocyclic phosphazene derivatives. Inorg. Chem. 2007 Oct; 46:9931-44.
Jimenez J, Laguna A, Gascon E, Sanz J.A, Serrano J.L, Barbera J, Oriol L. New liquid crystalline materials based on two generations of dendronised cyclophosphazenes. Chem. Eur. J. 2012 Nov;18:16801-14. DOI: 10.1002/chem.201202748.
Jimenez J, Pintre I, Gascon E, Sanchez-Somolinos C, Alcala R, Cavero E, Serrano J.L, Oriol L. Photoresponsive liquid-crystalline dendrimers based on a cyclotriphosphazene core. Macromol. Chem. Phys. 2014 Jun;215:1551-62. DOI: 10.1002/macp.201400190.
Ahn S, Kim H.S, Yang S, Do J.Y, Kim B.H, Kim K. Thermal stability and performance studies of LiCo1/3Ni1/3Mn1/3O2 with phosphazene additives for Li-ion batteries. J. Electroceram. 2009;23:289-94. DOI: 10.1007/s10832-008-9437-y.
Harrup M.K, Gering K.L, Rollins H.W, Sazhin S.V, Benson M.T, Jamison D.K, Michelbacher C.J, Luther T.A. Phosphazene based additives for ımprovement of safety and battery lifetimes in lithium-ıon batteries. ESC Trans. 2012 May;41(39):13-25. DOI: 10.1149/1.3703065.
Nishimoto T, Yasuda T, Lee S.Y, Kondo R, Adachi C. A six-carbazole-decorated cyclophosphazene as a host with high triplet energy to realize efficient delayed-fluorescence OLEDs. Mater. Horiz. 2014 Sep;1:264-69. DOI: 10.1039/C3MH00079F.
Schrogel P, Hoping M, Kowalsky W, Hunze A, Wagenblast G, Lennartz C, Strohriegl P. Phosphazene-based host materials for the use in blue phosphorescent organic light-emitting diodes. Chem. Mater. 2011 Oct;23:4947-53. DOI: 10.1021/cm201940f.
Zhu J, Liu W, Chu R, Meng X. Tribological properties of linear phosphazene oligomers as lubricants. Tribology Int. 2007 Mar;40:10-14. DOI: 10.1016/j.triboint.2006.01.014.
Wang X, Tan A.Y.X, Cho C.M, Ye Q, He C, Ji R, Xie H.Q, Tsai J.W.H, Xu J. Highly thermally stable cyclotriphosphazene based perfluoropolyether lubricant oil. Tribology Int. 2015 Apr;90:257–62. DOI: 0.1016/j.triboint.2015.04.018.
Tümer Y, Koç L.Y, Asmafliz N, Kılıç Z, Hökelek T, Soltanzade H, Açık L, Yola M.L, Solak A.O. Phosphorus–nitrogen compounds: part 30. syntheses and structural investigations, antimicrobial and cytotoxic activities and DNA interactions of vanillinato-substituted NN or NO spirocyclic monoferrocenyl cyclotriphosphazenes. J. Biol. Inorg. Chem. 2015 Dec;20:165-78. DOI: 10.1007/s00775-014-1223-5.
Başterzi N.S, Bilge Koçak S, Okumuş A, Kılıç Z, Hökelek T, Çelik Ö, Türk M, Koç L. Y, Açık L, Aydın B, Dal H. Syntheses, structural characterization and biological activities of spiro-ansa-spiro-cyclotriphosphazenes. New J. Chem. 2015 Sep;39:8825-39. DOI: 10.1039/C5NJ01530H.
Mutlu G, Elmas G, Kılıç Z, Hökelek T, Koç L.Y, Türk M, Açık L, Aydın B, Dal H. Phosphorus-nitrogen compounds: part 31. syntheses, structural and stereogenic properties, in vitro cytotoxic and antimicrobial activities, DNA interactions of novel bicyclotetraphosphazenes containing bulky side group. Inorganica Chimica Acta. 2015 July;436:69-81. DOI: 10.1016/j.ica.2015.07.027.
Akbaş H, Okumuş A, Kılıç Z, Hökelek T, Süzen Y, Koç L.Y, Açık L, Çelik Z.B. Phosphorus-nitrogen compounds: part 27. syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing secondary amino and pendant (4-fluorobenzyl)spiro groups. European Journal of Medicinal Chemistry. 2013 Dec;70:294-307. DOI: 10.1016/j.ejmech.2013.09.046.
Okumuş A, Elmas G, Cemaloğlu R, Aydın B, Binici A, Şimşek H, Açık L, Türk M, Güzel R, Kılıç Z, Hökelek T. Phosphorus-nitrogen compounds. part 35. syntheses, spectroscopic and electrochemical properties, antituberculosis, antimicrobial and cytotoxic activities of mono-ferrocenyl-spirocyclotetraphosphazenes. New J. Chem. 2016 Apr;40:5588-603. DOI: 10.1039/C6NJ00204H.
Greaves T.L, Drummond C.J. Protic ionic liquids: properties and applications. Chem. Rev. 2008 Dec;108:206-37. DOI: 10.1021/cr068040u.
Bicak N. A new ionic liquid: 2-hydroxy ethylammonium formate. Journal of Molecular Liquids. 2005 Jan;116:15-8. DOI: 10.1016/j.molliq.2004.03.006.
Karadağ A, Destegül A. N-(2-hydroxyethyl)-ethylenediamine-based ionic liquids: synthesis, structural characterization, thermal, dielectric and catalytic properties. Journal of Molecular Liquids. 2013;177:369-75. DOI: 10.1016/j.molliq.2012.10.040.
Akbaş H, Okumuş A, Karadağ A, Kılıç Z, Hökelek T, Süzen Y, Koç L.Y, Açık L, Aydın B, Türk M. Phosphorus–nitrogen compounds: part 32. structural and thermal characterizations, antimicrobial and cytotoxic activities, and in vitro DNA binding of the phosphazenium salts. J. Therm. Anal. Calorim. 2016 Sep;123:1627-41. DOI: 10.1007/s10973-015-5001-6.
Bruker program 1D WIN-NMR (release 6.0) and 2D WIN-NMR (release 6.1).
Bruker, SADABS, Bruker AXS Inc., Madison, Wisconsin, USA, (2005).
Sheldrick G.M. SHELXS-97, SHELXL-97 University of Gottingen, Gottingen, Germany, (1997).
Sheldrick G.M. A short history of SHELXL. Acta Crystallogr. Sect. A. 2008 Jan;64: 112-22. DOI: 10.1107/S0108767307043930.
Clinical and Laboratory Standards Institute, Performance Standards for Antimicrobial Susceptibility Testing Sixteenth Informational Supplement, CLSI document M100eS16, Pennsylvania, (2006).
Elmas G, Okumuş A, Koç L.Y, Soltanzade H, Kılıç Z, Hökelek T, Dal H, Açık L, Üstündağ Z, Dündar D, Yavuz M. Phosphorus-nitrogen compounds. part 29. syntheses, crystal structures, spectroscopic and stereogenic properties, electrochemical investigations, antituberculosis, antimicrobial and cytotoxic activities and DNA interactions of ansa-spiro-ansa cyclotetraphosphazenes. European Journal of Medicinal Chemistry. 2014 Oct;87:662-76. DOI: 10.1016/j.ejmech.2014.10.005.
Elmas (nee Egemen) G, Okumuş A, Kılıç Z, Hökelek T, Açık L, Dal H, Ramazanoğlu N, Koç L.Y. Phosphorus−nitrogen compounds. part 24. syntheses, crystal structures, spectroscopic and stereogenic properties, biological activities, and dna ınteractions of novel spiro-ansa-spiro- and ansa-spiro-ansa-cyclotetraphosphazenes. Inorg. Chem. 2012 Nov;51:12841-56. DOI: 10.1021/ic3017134.
Seto S, Tanioka A, Ikeda M, Izawa S. European Patent Office, Bulletin, 2004, EP 1 473 295 A 1 [0100].
Koçak S.B, Koçoğlu S, Okumuş A, Kılıç Z, Öztürk A, Hökelek T, Öner Y, Açık L. Syntheses, spectroscopic properties, crystal structures, biological activities, and dna interactions of heterocyclic amine substituted spiro-ansa-spiro- and spiro-bino-spiro-phosphazenes. Inorganica Chimica Acta. 2013 Sep;406:160-70. DOI: 10.1016/j.ica.2013.07.023.
Carriedo G.A, Alonso F.G, Gonzalez P.A, Menendez J.R. Infrared and Raman spectra of the phosphazene high polymer [NP(O2C12H8)]n. J. Raman Spectrosc. 1998 Dec;29:327-30. DOI: 10.1002/(SICI)1097-4555(199804)29:4.
Egemen G, Hayvalı M, Kılıç Z, Solak A.O, Üstündağ Z. Phosphorus-nitrogen compounds. part 17. the synthesis, spectral and electrochemical investigations of porphyrinophosphazenes. J. Porphyrins Phthalocyanines. 2010;14:1-8. DOI: 10.1142/.
Cremer D, Pople J.A, General definition of ring puckering coordinates. J. Am. Chem. Soc. 1975 Mar;97:1354-8. DOI: 10.1021/ja00839a011.
Okumuş A, Bilge S, Kılıç Z, Öztürk A, Hökelek T, Yılmaz F. Phosphorus–nitrogen compounds. part 20: fully substituted spiro-cyclotriphosphazenic lariat (PNP-pivot) ether derivatives. Spectrochimica Acta Part A. 2010 Apr;76:401-9. DOI: 10.1016/j.saa.2010.04.007.
Farrugia L.J. ORTEP-3 for Windows- a version of ORTEP-III with a Graphical User Interface (GUI). J. Appl. Crystallogr. 1997 Feb;30:565-6. DOI: 10.1107/S0021889897003117.
Haapasalo M, Ranta H, Ranta K.T. Facultative gram-negative enteric rods in persistent periapical infections. Acta Odontol Scand. 1983;41:19-22. DOI: 10.3109/00016358309162299.

There are 38 citations in total.

Details

Journal Section	Articles
Authors	Gamze Elmas Aytuğ Okumuş Zeynel Kılıç L. Yasemin Gönder This is me Leyla Açık Tuncer Hökelek
Publication Date	January 8, 2017
Submission Date	June 30, 2016
Published in Issue	Year 2016 Volume: 3 Issue: 3

Cite

Vancouver	Elmas G, Okumuş A, Kılıç Z, Gönder LY, Açık L, Hökelek T. THE SYNTHESES AND STRUCTURAL CHARACTERIZATIONS, ANTIMICROBIAL ACTIVITY AND IN VITRO DNA BINDING OF 4-FLUOROBENZYLSPIRO(N/O)CYCLOTRIPHOSPHAZENES AND THEIR PHOSPHAZENIUM SALTS. JOTCSA. 2017;3(3):25-46.