DFT/NBO study of Nanotube and Calixarene with anti-cancer drug

Journal of Nanostructure in Chemistry

Volumn 3, Issue 1, 2013, Pages

  Zare, Karim ^a,b   Shadmani, Nasim ^c   Pournamdari, Elham ^d  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b SHAHID BEHESHTI UNIVERSITY   (Iran)

^c ISLAMIC AZAD UNIVERSITY   (Iran)

^d ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Calix n arene; Capacity heat; DFT; Drug delivery; Fluorouracil; Formation energy; Nanotube; NBO

Indexed keywords

EID: 85130821232     PISSN: 20089244     EISSN: 21938865     Source Type: Journal    
DOI: 10.1186/2193-8865-3-75     Document Type: Article

References (42)

1. Wong Shi Kam N, Jessop TC, Wender PA, Dai H: Nanotube molecular transporters: Internalization of carbon nanotube-protein conjugates into mammalian cells. J. Am. Chem. Soc. 2004, 126: 6850–6851. DOI: 10.1021/ja0486059
2. Colomer JF, Henrard L, Lambin P, Van Tendelool G: 2001. Phys. Rev. B 2001, 64: 1–7. DOI: 10.1103/PhysRevB.64.125425
3. Moradi O, Zare K: Adsorption of Pb(II), Cd(II) and Cu(II) Ions in Aqueous Solution on SWCNTs and SWCNT–COOH Surfaces: Kinetics Studies. Fullerenes, Nanotubes, and Carbon Nanostructures 2011, 19: 628–652. DOI: 10.1080/1536383X.2010.504955
4. Pouton CW, Seymour L: Key issues in non-viral gene delivery. Adv. Drug. Deliv. Rev. 2001, 46: 187–203. DOI: 10.1016/S0169-409X(00)00133-2
5. Singh R, Pantarotto D, Lacerda L, Pastorin G, Klumpp C, Prato M, Bianco A, Kostarelos K: Tissue biodistribution and blood clearance rates of intravenously administered carbon nanotube radiotracers. Proc. Natl. Acad. Sci. U.S.A. 2006, 103: 3357–3362. DOI: 10.1073/pnas.0509009103
6. Iijima S: Helical microtubules of graphitic carbon. Nature 1991, 354: 56–58. DOI: 10.1038/354056a0
7. Yan CS, Mao HK, Li W, Qian J, Zhao Y, Hemley RJ: Ultrahard diamond single crystals from chemical vapor deposition. Physica Status Solidi (A) 2004,201(4):25–27. DOI: 10.1002/pssa.200409033
8. Kalele S, Gosavi SW, Urban J, Kulkarni SK: Nanoshell particles: synthesis, properties and applications. Curr. Sci. 2006, 91: 8.
9. Wong Shi Kam N, Jessop TC, Wender PA, Dai H: Nanotube molecular transporters: Internalization of carbon nanotube-protein conjugates into mammalian cells. J. Am. Chem. Soc. 2004, 126: 6850–6851. DOI: 10.1021/ja0486059
10. Pastorin G: Crucial Functionalizations of Carbon Nanotubes for Improved Drug Delivery: A Valuable Option? Pharmaceut. Res. 2009, 26: 746–769. DOI: 10.1007/s11095-008-9811-0
11. Taft BJ, Lazareck AD, Withey GD, Yin A, Xu JM, Kelley SO: Site-specific 258 assembly of DNA and appended cargo on arrayed carbon nanotubes. J. Am. Chem. Soc. 2004, 126: 12750–12751. DOI: 10.1021/ja045543d
12. Pantarotto D, Singh R, McCarthy D, Erhardt M, Briand JP, Prato M, Kostarelos K, Bianco A: Functionalized carbon nanotubes for plasmid DNA 262 gene delivery. Angew. Chem. Int. Ed. 2004, 43: 5242–5236. DOI: 10.1002/anie.200460437
13. Asfari Z, Böhmer V, Harrowfield J, Vicens J: Calixarenes 2001. Dordrecht: ED; Kluwer; 2001.
14. Gungor O, Memon S, Yilmaz M: Synthesis of Alkyl Nitrile and Alkyl Benzonitrile Derivatives of Calix[4]Arene and Their Polymer Supported Analogues: A Comparative Study in Two-Phase Extraction Systems. J. Funct. Polym. 2005, 63: 1–9. DOI: 10.1016/j.reactfunctpolym.2005.02.004
15. Gutsche CD, Bauer LJ: The conformational properties of calix[4]arenes, calix[6]arenes, calix[8]arenes, and oxacalixarenes. J. Am. Chem. Soc. 1985, 107: 6052–6059. DOI: 10.1021/ja00307a038
16. Faraji M, Zare K, Aghaei H, Farajtabar A, Asfari Z, Gharib F: Complexation of p-Sulphonato-calix[6]arene by Glycine, Glycyl-glycine, and Glycyl-glycyl-glycine in Aqueous Solution. J. Solution. Chem. 2012. 10.1007/s10953-012-9924-2
17. Gharib F, Zare K, Taghvaei S, Monajjemi M, Amiri A: Complexation of tri-o-propoyl-p-t-butyl calix[4]arene with alkali metal cations in carbon tetrachloride solvent. Main. Group. Met. Chem. 2003, 26: 255–258.
18. Gharib F, Zare K, Amiri A: Spectrophotometric studies of alkali metal ion complexes of p-tetrabutyl- calix[4]arenes. Russ. J. Inorg. Chem. 2004, 49: 1511–1514.
19. Gharib F, Osouleddini N, Zare K, Taghvaei-Ganjali S: Spectrophotometric studies of alkali and alkali earth metal ions complexes of mono amino derivative of calix[4]arene. Russ. J. Inorg. Chem. 2010, 55: 434–437. DOI: 10.1134/S003602361003023X
20. Brunink JAJ, Verboom W, Engbersen JFJ, Reinhoudt DN, Harkema S: Synthesis and cation complexation selectivity of bis (syn-proximally) functionalized calix[4]arenes. Recl. Trav. Chim. Pays-Bas 1992, 111: 511–516. DOI: 10.1002/recl.19921111203
21. Shirakawa S, Shimizu S: Dehydrative amination of alcohols in water using a water-soluble calix[4]resorcinarene sulfonic acid. Syn. Lett. 2008, 10: 1539–1542.
22. Liu YL, Liu L, Wang YL, Han YC, Wang D, Chen YJ: Calix[n]arene sulfonic acids bearing pendant aliphatic chains as recyclable surfactant-type Brønsted acid catalysts for allylic alkylation with allyl alcohols in water. Green. Chem. 2008, 10: 635–640. DOI: 10.1039/b719278a
23. Zhang YJ, Cao WX, Xu: Interaction of Sulfonated Calix[n]arenes with Rhodamine B and Its Application to Determine Acetylcholine in a Real Neutral Aqueous Medium J. Chin. Chem. 2002, 20: 322–326. DOI: 10.1002/cjoc.20020200406
24. Dolg M: Recent progress in understanding chemical shifts. J. Chem. Phys. 2009, 115: 7348–7355.
25. de Dios AC, Oldfield E: Antimalarial drugs and heme in detergent micelles: an NMR study. Solid State NMR 1996, 6: 101–125. DOI: 10.1016/0926-2040(95)01207-9
26. Whitehead RP, Benedetti JK, Abbruzzese JL, Ardalan B, Goodwin JW, Balcerzak SP, Samlowski WE, Lenz H-Z, Macdonald JS: A phase II study of high-dose 24 hour continuous infusion 5-FU and leucovorin and low-dose PALA for patients with advanced pancreatic adenocarcinoma: A Southwest Oncology Group Study. Inves. New. Drug. 2004, 22: 335–341. DOI: 10.1023/B:DRUG.0000026261.76197.54
27. Cornell GN, Cahow CE, Frey C, McSherry C, Beal JM: Clinical experience with 5-fluorouracil (NSC-19 893) in the treatment of malignant disease. Cancer Chemother. Rep. 1960, 9: 23–30.
28. Monajjemi M, Chahkandi B, Zare K, Amiri A: Study of the hydrogen bond in different orientations of adenine-thymine base pairs: an ab initio study. Biochem 2005, 70: 366–76.
29. Guo D, Liu Y: Calixarene-based supramolecular polymerization in solution. Chem. Soc. Rev. 2012, 41: 5907–5921. DOI: 10.1039/c2cs35075k
30. Tirado-Rives J, Jorgensen WL: Performance of B3LYP Density Functional Methods for a Large Set of Organic Molecules. J. Chem. Theory. Comput. 2008, 4: 297–306. DOI: 10.1021/ct700248k
31. Zeevaart JG, Wang L, Thakur VV, Leung CS, Tirado-Rives J, Bailey CM, Domaoal RA, Anderson KS, Jorgensen WL: Optimization of azoles as anti-human immunodeficiency virus agents guided by free-energy calculations. J. Am. Chem. Soc 2008, 130: 9492–9499. DOI: 10.1021/ja8019214
32. Casabianca LB, Kallgren JB, Natarajan JK, Alumasa JN, Roepe PD, Wolf C, de Dios AC: Antimalarial drugs and heme in detergent micelles: An NMR study. Inorg, J: Biochem. 2009, 103: 745–748. DOI: 10.1016/j.jinorgbio.2009.01.013
33. Abul Haider Shipar M: DFT Studies on Fructose and Glycine Maillard Reaction: Formation of the Heyns Rearrangement Products in the Initial Stage. J. Iran. Chem. Soc. 2011, 8: 433–448. DOI: 10.1007/BF03249077
34. Delchev VB: Computational (DFT and TD DFT) study of the electron structure of the tautomers/conformers of uridine and deoxyuridine and the processes of intramolecular proton transfers. J. Mol. Model 2010, 16: 749–757. DOI: 10.1007/s00894-009-0593-z
35. Ramachandran KI, Deepa G, Namboori K: Research on computational chemistry and molecular modeling. In Computational Chemistry and 344 Molecular Modeling: Principles and Applications. Heidelberg: Springer; 2008:297–310.
36. Miehlich B, Savin A, Stoll H, Preuss H: Results obtained with the correlation energy density functionals of Becke and Lee–Yang and Parr. Chem. Phys. Lett. 1989, 157: 200–206. DOI: 10.1016/0009-2614(89)87234-3
37. Dalili N, Zare K, Gharib F, Shadmani N: Calixarenes or Nanotubes: Which are better in drug delivery? JNSC 2011, 2: 213–217.
38. . Nanotube Modeler. version 1.2.4 (2004–2005) http://www.jcrystal.com/products/wincnt/Nanotube
39. Frisch A, Nielsen AB, Holder AJ: GaussView User Manual. Wallingford: Gaussian Inc.; 2000.
40. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head Gordon M, Replogle ES, Pople JA: GAUSSIAN 03, revision B.02. Pittsburgh, PA: Gaussian Inc; 2003.
41. Glendening ED, Reed AE, Carpenter JE, Weinhold F: NBO version 3.1. Pittsburg, PA: Gaussian Inc; 2003.
42. Fernandez L, Viruela-Martin P, Latorre J, Guillem C, Beltrán A, Amorós P: Molecular precursors of mesostructured silica materials in the atrane route: A DFT/GIAO/NBO theoretical study. J. Mol. Struc: THEOCHEM 2007, 822: 89–102. DOI: 10.1016/j.theochem.2007.07.022