Evaluation of different PAMAM dendrimers as molecular vehicle of 1,2,4-triazine N-oxide derivative with potential antitumor activity

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 79, Issue 1-2, 2014, Pages 65-73

  Dib, Nahir ^a   Fernández, Luciana ^a   Gonzalez, Mercedes ^b   Cerecetto, Hugo ^b   Durantini, Edgardo ^a   Otero, Luis ^a   Santo, Marisa ^a  

^a DEPARTAMENTO DE QUÍMICA   (Argentina)

^b UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

Antitumor drug stability; Dendrimers; Host guest association; PAMAM; Triazine N oxide

Indexed keywords

EID: 84900797342     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-013-0324-z     Document Type: Article

References (39)

1. Sztanke, K., Pasternak, K., Rajtar, B., Sztanke, M., Majek, M., Polz-Dacewicz, M.: Identification of antibacterial and antiviral activities of novel fused 1,2,4-triazine esters. Bioorg. Med. Chem. 15, 5480-5486 (2007)
2. Diana, P., Barraja, P., Lauria, A., Montalbano, A., Almerico, A.M., Dattolo, G., Cirrincione, G.: Pyrrolo[2,1-c][1,2,4]triazines from 2-diazopyrroles: synthesis and antiproliferative activity. Eur. J. Med. Chem. 37, 267-272 (2002)
3. Hay, M.P., Hicks, K.O., Pchalek, K., Lee, H.H., Blaser, A., Pruijn, F.B., Anderson, R.F., Shinde, S.S., Wilson, W.R., Denny, W.A.: Tricyclic [1,2,4]triazine 1,4-dioxides as hypoxia selective cytotoxins. J. Med. Chem. 51, 6853-6865 (2008)
4. Patil, S.A., Otter, B.A., Klein, R.S.: 4-Aza-7,9-dideazaadenosine, a new cytotoxic synthetic C-nucleoside analog of adenosine. Tetrahedron Lett. 35, 5339-5342 (1994)
5. Hay, M.P., Pchalek, K., Pruijn, F.B., Hicks, K.O., Siim, B.G., Anderson, R.F., Shinde, S.S., Phillips, V., Denny, W.A., Wilson, W.R.: Hypoxia-selective 3-Alkyl 1,2,4-benzotriazine 1,4-dioxides: the influence of hydrogen bond donors on extravascular transport and antitumor activity. J. Med. Chem. 50, 6654-6664 (2007)
6. Imbaraj, J.J., Motten, A.G., Chignell, C.F.: Photochemical and photobiological studies of tirapazamine (SR 4233) and related quinoxaline 1,4-di-N-oxide analogues. Chem. Res. Toxicol. 16(2), 164-170 (2003)
7. Peer, D., Karp, J.M., Hong, S., Farokhzad, O.C., Margalit, R., Langer, R.: Nanocarriers as an emerging platform for cancer therapy. Nat. Nanotechnol. 2, 751-760 (2007)
8. Kaminskas, L.M., McLeod, V.M., Porter, C.J.H., Boyd, B.J.: Association of chemotherapeutic drugs with dendrimer nanocarriers: an assessment of the merits of covalent conjugation compared to noncovalent encapsulation. Mol. Pharmaceutics 9, 355-373 (2012)
9. Wang, Y., Grayson, S.M.: Approaches for the preparation of nonlinear amphiphilic polymers and their applications to drug delivery. Adv. Drug. Deliver. Rev. 64, 852-865 (2012)
10. Mintzer, M.A., Grinstaff, M.W.: Biomedical applications of dendrimers: a tutorial. Chem. Soc. Rev. 40, 173-190 (2011)
11. Ionov, M., Gardikis, G., Wróbel, D., Hatziantoniou, S., Mourelatou, H., Majoral, J.P., Klajnert, B., Bryszewska, M., Demetzos, C.: Interaction of cationic phosphorus dendrimers (CPD) with charged and neutral lipid membranes. Colloids. Surf. B 82, 8-12 (2011)
12. Quadir, M.A., Haag, R.: Biofunctional nanosystems based on dendritic polymers. J. Control Release 161, 484-495 (2012)
13. Ciolkowski, M., Petersen, J.F., Ficker, M., Janaszewska, A., Christensen, J.B., Klajnert, B., Bryszewska, M.: Surface modification of PAMAM dendrimer improves its biocompatibility Nanomed. Nanotechnology 8, 815-817 (2012)
14. Szymanski, P., Markowicz, M., Mikiciuk-Olasik, E.: Nanotechnology in pharmaceutical and biomedical applications. Dendrimers Brief Rep. Rev. 6, 509-539 (2011)
15. Fernández, L., Sigal, E., Otero, L.: Silber., J.J., Santo, M.: Solubility improvement of anthelmintic benzimidazole carbamate by association with dendrimers. Braz. J. Chem. Eng. 28(4), 679-689 (2011)
16. Davarakonda, B., Hill, R., Villiers, M.: The effect of PAMAM dendrimer generation size and surface functional group on the aqueous solubility of nifedipine. Int. J. Phar. 284, 133-140 (2004)
17. Yiyun, C., Tongwen, X.: Dendrimers as Potential Drug Carriers. Part I. Solubilization of Non-Steroidal Anti-Inflammatory Drugs in the Presence of Polyamidoamine Dendrimers. Eur. J. Med. Chem. 40, 1188-1192 (2005)
18. Hu, J., Su, Y., Zhang, H., Xu, T., Cheng, Y.: Design of interiorfunctionalized fully acetylated dendrimers for anticancer drug delivery. Biomaterials 32, 9950-9959 (2011)
19. Ouyan, L., Ma, L., Jiang, B., Li, Y., He, D., Guo, L.: Synthesis of novel dendrimers having aspartate grafts and their ability to enhance the aqueous solubility of model drugs. Eur. J. Med. Chem. 45, 2705-2711 (2010)
20. Cerecetto, H., González, M., Onetto, S., Saenz, P., Ezpeleta, O., De Ceráin, A.L., Monge, A.: 1, 2, 4-Triazine N-oxide derivatives: studies as potential hypoxic cytotoxins. Part II. Arch. Pharm. 337(5), 247-258 (2004)
21. Cerecetto, H., González, M., Risso, M., Saenz, P., Olea-Azar, C., Bruno, A.M., Azqueta, A., De Ceráin, A.L., Monge, A.: 1, 2, 4-Triazine N-oxide derivatives: studies as potential hypoxic cytotoxins. Part III. Arch. Pharm. 337(5), 271-280 (2004)
22. Kamlet, M.J., Abboud, J.L.M., Taft, R.W.: The Solvatochromic comparison method. 6. The p scale of solvent polarities. J. Am. Chem. Soc. 99, 6027-6038 (1977)
23. Dewar, M.J.S., Zoebisch, E.G., Healy, E.F., Stewart, J.J.P.: AM1: a new general purpose quantum mechanical. J. Am. Chem. Soc. 107, 3902-3909 (1985)
24. Kamlet, M.J., Abboud, J.L.M., Abraham, M.H., Taft, R.W.: Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, p, a, and b, and some methods for simplifying the generalized solvatochromic equation. J. Org. Chem. 48, 2877-2887 (1983)
25. Gupta, U., Agashe, H.B., Asthana, H., Jain, N.K.: Dendrimers: novel polymeric nanoarchitectures for solubility anhancement. Biomacromolecules 7(3), 649-658 (2006)
26. Avila-Salas, F., Sandoval, C., Caballero, J., Guinez-Molinos, S., Santos, L.S., Cachau, R.E., González-Nilo, F.D.: Study of interaction energies between the PAMAM dendrimer and nonsteroidal anti-inflammatory drug using a distributed computational strategy and experimental analysis by ESI-MS/MS. J. Phys. Chem. B 116, 2031-2039 (2012)
27. Maingi, V., Kumar, M.V.S., Maiti, P.K.: PAMAM dendrimer -drug interactions: effect of pH on the binding and release pattern. J. Phys. Chem. B 116, 4370-4376 (2012)
28. Reichardt, C.: Losungmittel-Effekte in der Organischen Chenie, 2nd edn. Verlang Chemie, Weiheim (1973)
29. Poole, J.S., Hadad, C.M., Platz, M.S., Fredin, Z.P., Pickard, L., Guerrero, E.L., Kessler, M., Chowdhury, G., Kotandeniya, D., Gates, K.S.: Photochemical Electron Transfer Reactions of Tirapazamine Photochem. Photobiology 75(4), 339-345 (2002)
30. Chupakhin, O.N., Kozhevnikov, V.N., Prokhorov, A.M., Kozhevnikov, D.N., Rusinov, V.L.: The amidine rearrangement in 5-Amino-6-Aryl-1,2,4-triazine-4- oxides initiated by hydroxylamine. Tetrahedron Lett. 41, 7379-7382 (2000)
31. Chelmecka, M.: Complexes of polyelectrolytes with defined charge distance and different dendrimer counterions. Dissertation pdf, Mainz (2004)
32. Kozhevnikov, D.N., Rusinov, V.L., Chupakhin, O.N.: 1,2,4-Triazine N-oxides and their annelated derivatives. Russ. Chem. Rev. 67, 633-648 (1948)
33. D'Emanuele, A., Attwood, D.: Dendrimer-drug interactions. Adv. Drug Delivery Rev. 57, 2147-2162 (2005)
34. Klajnert, B., Stanislawskaa, L., Bryszewska, M., Palecz, B.: Interactions between PAMAM dendrimers and bovine serum albumin. Biochim. Biophys. Acta. 1648, 115-126 (2003)
35. Ottaviani, M.F., Montalti, F., Romanelli, M., Turro, N.J., Tomalia, D.A.: Characterization of starburst dendrimers by EPR. 4. Mn(II) as probe of interphase properties. J. Phys. Chem. 100, 11033-11042 (1996)
36. Kleinman, M.H., Flory, J.H., Tomalia, D.A., Turro, N.J.: Effect of protonation and PAMAM dendrimer size on the complexation and dynamic mobility of 2-naphthol. J. Phys. Chem. B 104, 11472-11479 (2000)
37. Fernández, L., Santo, M., Silber, J.J., Cerecetto, H., Gonzalez, M.: Solubilization and release proper ties of dendrimer s. Evaluation as prospective drug delivery systems. Supramol. Chem. 18(8), 633-643 (2006)
38. Morgan, M.T., Carnahan, M.A., Immoos, C.E., Ribeiro, A.A., Finkelstein, S., Lee, S.J., Grinstaff, M.W.: Dendritic molecular capsules for hydrophobic compounds. J. Am. Chem. Soc. 125, 15485-15489 (2003)
39. Qiao, W., Wang, B., Wang, Y., Yang, L., Zhang, Y., Shao, P.: Cancer therapy based on nanomaterials and nanocarrier systems. J. Nanomater. (2010). doi:10.1155/2010/796303