Infrared spectroscopic study of Inclusion Complex Of aziridine with amphiphiphilic Cyclodextrin

Assia Keniche

Abstract


In this work, interactions between components of solid amphiphilic b-cyclodextrin - aziridine (ACD –AZ) nclusion complex were confirmed by the IR spectroscopy data. It was established that the vibrations and bends of the guest molecule are restricted and shifted through it encapsulation into the amphiphilic-b-cyclodextrin (ACD) cavity. The inclusion complex with 1:1 molar ratio was prepared by a kneading method. Fourier transform infrared spectroscopy (FTIR), confirmed the formation of the inclusion complex.


Keywords


Aziridines, ampiphilic cyclodextrin, host-guest system, IR spectroscopy, Job’s method.

Full Text:

PDF PDF

References


Lowden, P. A. S. Aziridine Natural Products Discovery, Biological Acitvity and Biosynthesis. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley VCH: Weinheim, Germany, pp 399–442 (2006). doi:10.1002/3527607862.

Fahey, K.; Aldabbagh, F.; Tetrahedron Lett., 49, 5235–5237 (2008).

Fahey, K.; O’Donovan, L.; Carr, M.; Carty, M.P.; Aldabbagh, F; Eur. J. Med. Chem., 45, 1873–1879 (2010).

Prosser, G.A.; Copp. J. N.; Syddall, S.P.; Williams, E. M.; Smaill, J. B.; Wolson, W.R.; Patterson, A.V.; Ackerley, D.F.; Biochem. Pharmacol., 79, 678-687 (2010).

Sucre, A.P.; Vicik, R.; Schultheis, M.; Schirmeister,T.; Moll, H.; Agents Chemother., 50, 2439-2447 (2006).

Hanessian, S.; Moitessier, N.; Cantin, L.D. ; Tetrahedron., 57, 6885-6900 (2001).

Schirmeier, T.; Peric, M., Bioorg. Med. Chem., 8, 1281-1291 (2000).

Ismail, M.D.; Levitsky, D.O.; Dembitsky, V.M. ; Eur. J. Med. Chem. 44, 3373- 3387 (2009).

(a) Filigheddu, S. N.; Taddei, M.; Tetrahedron Lett., 39, 3857-3860 (1998); (b) Sharma, P.; Kumar, A.; Upadhyay, S.; Sahu, V.; Singh, J.; Eur. J. Med. Chem., 44, 251-259 (2009).

Baba Ahmed, F. Z.; Bouanane, S.; Merzouk, S. A.; Merzouk, H.; Medjahed, W.; Kajima Mulengi,J.; Prost,J.; Pathol. Biol., 56, 137–142 (2008).

Baba Ahmed, F.Z.; Merzouk, H.; Bouanane, S.; Benkalfat, N. B.;,Merzouk, S.A.; Kajima Mulengi, J.; Narce, M. Evaluation de la toxicité aiguë de la 2-hydroxyméthyl-1(Nphtaloyltryptophyl) aziridine chez le rat Wistar. Ann Toxicol Anal. 2010, DOI: 10.1051/ata/2010017. www.ata-journal.org

Keniche, A.; Drici, W.; Slimani, M.Z.; Mezrai, A.; Kajima Mulengi, J.; Mediter. J. Chem., 2, 583-594 (2013).

Keniche A., Mezrai A., Kajima Mulengi J.,Novel class of phosphonoaziridines as antibacterial agents, The Open Conference Proceedings Journal, Dubai, 2, 28-36 (2011).

J.Kajima Mulengi, A. Keniche, A. Mezrai, F.Djedaini Pillard, V.Bonnet, Asian Journal of Materials Chemistry, 1, 38-49 (2016).

Keniche, A.; Bellifa, S.; Hassaine, H.; Simani, M. Z.; Kajima Mulengi, J.; Algerian. J. Nat. Products, 4, 226-232 (2016).

Van der Schoot, S.C.; Vainchtein, L.D.; Beijnen, J.H.; Gore, A.; Mirejovsky, D.; Lenaz, L.; Nuijen, B.; Int.J.Pharm, 329, 135 (2007).

Surendra, K. ; S.Krishnaveni, N. ; Mahesh, A. ; Rao, K.R. ; J.Org.Chem, 71, 2532 (2006).

Surendra, K. ; S.Krishnaveni, N. ; Rao, K.R. ; Synlett, 42, 506 (2005).

Surendra, K. ; S.Krishnaveni, N. ; Nageswar, Y.V.D. ; Rao, K.R. ; J.Org. Chem, 68, 4994 (2003).

Surendra, K. ; S.Krishnaveni, N. ; Reddy, M.A. ; Nageswar, Y.V.D. ; K.R.Rao, J.Org.Chem, 68, 2058 (2003).

Surendra, K. ; S.Krishnaveni, N. ; Sridhar, R. ; Rao, K.R. ; J Org.Chem, 71, 5819 (2006).

Reddy, M.S. ; Narender, M. ;Rao, K.R. ; Tetrahedron Letters, 46, 1299 (2005).

Sierpe,R.; Lang,E; Jara, P.; Guerrero,A.R.; Chornik,B; Kogan,M.J.; Yutronic.N.; ACS Appl. Mater. Interfaces, 7, 15177–15188 (2015).

Bilensoy, E.; Cyclodextrin nanoparticles for drug delivery. In: Ravi Kumar, M.N.V., Ed., Handbook of Particulate Drug Delivery, Vol. 1, American Scientific, Valencia, CA, pp. 187–204 (2008).

Bin Li, Zhang,W.; Ma, H.; , Tropical Journal of Pharmaceutical Research January, 15, 167-172 (2016).

Kfoury, M.; Landy, D.; Ruellan, S.; Auezova, L. ; Greige-Gerges, H. ; Fourmentin.S ; Beilstein J. Org. Chem. 12, 29–42 (2016).

Nath Roy, M.; Saha, S.; Barman, S.; Ekka, D.; , RSC Adv., 6, 8881-889 (2016).

Ling, C.C.; Darcy, R.; Risse, W.; J.Chem. Soc. Chem. Commun., 5, 438–440 (1993).

Munoz, M. ; Deschenaux, R.; Coleman, A.W. ; J. Phys. Org.Chem., 12, 364–369 (1999).

Lombardo, M. ; Longo, A. ; Darcy, R.; Mazzaglia, A. ; Langmuir, 20, 1057–1064 (2004).

Keniche , A.; Slimani, M. Z.; José Miranda, I.; Jesus Azipura, M.; Kajima Mulengi, J.; Mediterr. J. Chem., 2, 620-631 (2014).

Kajima Mulengi, J.; Slimani-Keniche, A.; A Bit of Chemistry with Aziridines and Applications,LAP LAMBERT Academic Publishing, p.80 (2016).

Auzély-Velty, R.; Perly, B.; Taché, O.; Zemb, T.; Jéhan, P.; Guenot, P.; Dalbiez, J.-P.; Djedaı̈ni-Pilard, F., Carbohydr. Res., 318, 82–90(1999).

Gervaise, C.; Bonnet, V.; Wattraint, O.; Aubry, F.; Sarazin, C.; Jaffrès, P.-A.; Djedaïni-Pilard, F., Biochimie, 94, 66–74 (2012).

Choisnard, L.; Gèze, A.; Vanhaverbeke, C.; Yaméogo, J.B.G.; Putaux, J.-L.; Brasme, B.; Jullien, L.; Boullanger, S.; Elfakir, C.; Wouessidjewe, D. , Biomacromolecules 12, 3031–3038 (2011).

Yaméogo, J.B.G.; Gèze, A.; Choisnard, L.; Putaux, J.-L.; Gansané, A.; Sirima, S.B.; Semdé, R.; Wouessidjewe, D.,Eur. J. Pharm.Biopharm.80, 508–517 (2012).

Mazzaglia, A.; Bondì, M.L.; Scala, A.; Zito, F.; Barbieri, G.; Crea, F.; Vianelli, G.; Mineo, P.; Fiore, T.; Pellerito, C.; Biomacromolecules, 14, 3820–3829 (2013).

Perret, F.; Marminon, C.; Zeinyeh, W.; Nebois, P.; Bollacke, A.; Jose, J.; Parrot-Lopez, H.; Le Borgne, M.,Int. J. Pharm, 441, 491–498 (2013).

Martínez, Ã.; Bienvenu, C.; Jiménez Blanco, J.L.; Vierling, P.; Mellet, C.O.; García Fernández, J.M.; Di Giorgio, C., J. Org. Chem., 78, 8143–8148 (2013).

Perret, F.; Marminon, C.; Zeinyeh, W.; Nebois, P.; Bollacke, A.; Jose, J.; Parrot-Lopez, H.; Le Borgne, M., Int. J. Pharm., 441, 491–498 (2013).

Angelova, A.; Fajolles, C.; Hocquelet, C.; Djedaïni-Pilard, F.; Lesieur, S.; Bonnet, V.; Perly, B.; Lebas, G.; Mauclaire, L.,J. Colloid Interface Sci., 322, 304–314 (2008).

Aranda, C.; Urbiola, K.; Méndez Ardoy, A.; García Fernández, J.M.; Ortiz Mellet, C.; Eur. J. Pharm. Biopharm., 85, 390–397 (2013).

Kemelbekov, U.; Luo, Y.; Orynbekova, Z.; Rustembekov, Z.; Haag, R.; Saenger, W.; Pralivey, K.; J. Incl. Phenom. Macrocycl. Chem., 69, 181-190 (2011).

Cwiertnia, B.; Hladon, T.; Stobiecki, M., J. Pharm. Pharmacol., 51, 1213–1218 (1999).

Gopalan, R.; Selvi, A.; Subramaniam, A.G.; International Journal of Agriculture and Food Science, 3, 90 94 (2013).

Kemelbekov, U.; Luo, Y.; Orynbekova, Z.; Rustembekov, Z.; Haag, R.; Saenger, W.; Pralivey, R.; , J. Incl. Phenom. Macrocycl. Chem., 69, 181-190 (2011) .

. Choi, S. H.; Kim, S.Y.; Ryoo, J.J.; Park , J.Y. ; Lee, K.P. ; Anal. Sci., 17, 785-787 (2002).

J. Szejtli. Introduction and general overview of cyclodextrin chemistry // Chem. Rev., 98(5), pp. 1743-1753 (1998).

Choi, S.H.; Kim S.Y.; Ryoo, J.J.; Park, J.Y.; Lee, K.P.; Anal. Sci., 17, 1785 (2001)

Patil Dipak R.; Ingole Pravin G.; Kripal S.; Dalal Dipak S.; Res.J.Chem. Sci., 2, 60-63 (2012).

Li, N.; Liu, J.; Zhao, X.; Gao, Y.; Zhang, L.; Zhang, J.; Yu, L. ; Colloids Surf. A, 292, 196–201 (2007).

Li, W.; Lu, B.; Sheng, A.; Yang, F.; Wang, Z. ; J. Mol. Struct., 981, 194–203 (2010).

Li, J.; Ni, X.; Zhou, Z.; Leong, K.W.; J. Am. Chem. Soc., 125, 1788–1795 (2003).

Rusa, C.C.; Luca, C.; Tonelli, A.E.; Macromolecules, 34, 1318–1322 (2001).

Celebioglu ,A., Uyar , T., J. Agric. Food Chem., 2017, 65, 5404–5412.




DOI: http://dx.doi.org/10.5281/zenodo.2561091

Refbacks

  • There are currently no refbacks.




Copyright (c) 2019 Assia Keniche

_________________________________________________________________________________________________________________________

 All open access articles published in AJNP are distributed under the terms of the  Creative Commons Attribution-  4.0 International License

The research works published in this journal are free to be accessed. They can be shared (copied and redistributed in any medium or format) and\or adapted (remixed, transformed, and built upon the material for any purpose, commercially and\or not commercially) under the following terms: attribution (appropriate credit must be given indicating original authors, research work name and publication name mentioning if changes were made) and without adding additional restrictions (without restricting others from doing anything the actual license permits). Authors retain the full copyright of their published research works and cannot revoke these freedoms as long as the license terms are followed.

 

 Flag Counter