Evaluation of poly(amidoamine) dendrimers as potential carriers of iminodiacetic derivatives using solubility studies and 2D-NOESY NMR spectroscopy

Journal of Biological Physics

Volumn 38, Issue 4, 2012, Pages 637-656

  Markowicz, Magdalena ^a   Szymański, Paweł ^a   Ciszewski, Marcin ^a   Kłys, Arkadiusz ^b   Mikiciuk Olasik, Elzbieta ^a  

^a MEDICAL UNIVERSITY OF LODZ   (Poland)

^b UNIVERSITY OF LODZ   (Poland)

Author keywords

Electrostatic interactions; Iminodiacetic acid; MRI contrast agents; PAMAM dendrimers; Solubility studies

Indexed keywords

AMINE; CARBOXYL GROUP; DENDRIMER; DICLOFENAC; DIFLUNISAL; DIGLYCINE; DRUG CARRIER; FLURBIPROFEN; IBUPROFEN; IMINOADIACETIC ACID DERIVATIVE; INDOMETACIN; KETOPROFEN; MEBROFENIN; MEFENAMIC ACID; METHOTREXATE; MYCOPHENOLIC ACID; N (2,4 DIMETHYLACETANILIDE)IMINODIACETIC ACID; N (2,4,6 TRIMETHYLACETANILIDE)IMINODIACETIC ACID; N (3 BROMO 2,4,6 TRIMETHYLACETANILIDE)IMINODIACETIC ACID; N (4 METHYLACETANILIDE)IMINODIACETIC ACID; NAPROXEN; NICOTINIC ACID; NIFEDIPINE; PACLITAXEL; PHENYLBUTAZONE; PIROXICAM; POLYAMIDOAMINE; POLYAMIDOAMINE DENDRIMER; SALICYLIC ACID; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; COMPLEX FORMATION; CONJUGATION; DRUG SOLUBILITY; DRUG STRUCTURE; ENCAPSULATION; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STATIC ELECTRICITY; STRUCTURE ANALYSIS; TWO DIMENSIONAL NUCLEAR OVERHAUSER EFFECT SPECTROSCOPY;

EID: 84867874062     PISSN: 00920606     EISSN: 15730689     Source Type: Journal    
DOI: 10.1007/s10867-012-9277-5     Document Type: Article

References (55)

1. Jang, W.D.; Kamruzzaman Selim K.M.; Lee, C.H.; Kang, I.K.: Bioinspired application of dendrimers: from bio-mimicry to biomedical applications. Prog. Polym. Sci. 34, 1-23 (2009)
2. Duncan, R.; Izzo, L.: Dendrimer biocompatibility and toxicity. Adv. Drug Delivery Rev. 57, 2215-2237 (2005)
3. Naylor, A.M.; Goddard, W.A.: Starburst dendrimers. 5. Molecular shape control. J. Am. Chem. Soc. 111, 2339-2341 (1989)
4. Caminati, G.; Turro, N.J.; Tomalia, D.A.: Photophysical investigation of starburst dendrimers and their interactions with anionic and cationic surfactants. J. Am. Chem. Soc. 112, 8515-8522 (1999)
5. Fischer, M.; Vögtle, F.: Dendrimers: from design to applicationa progress report. Angew. Chem. Int. Edn. 38, 884-905 (1999)
6. Khang, D.; Carpenter, J.; Wook Chun, Y.; Pareta, R.; Webster, T.J.: Nanotechnology for regenerative medicine. Biomed. Microdevices 12, 575-587 (2010)
7. Lin, L.N.; Liu, Q.; Song, L.; Liu, F.F.; Sha, J.X.: Recent advances in nanotechnology based drug delivery to the brain. Cytotechnology. 62, 377-380 (2010)
8. Szymański, P.; Markowicz, M.; Mikiciuk-Olasik, E.: Nanotechnology in pharmaceutical and biomedical applications. Dendrimers. NANO: Brief Rep. Rev. 6, 509-539 (2011)
9. Maciejewski, M.: Concepts of trapping topologically by shell molecules. J. Macromol. Sci. Chem. A. 17, 689-703 (1982)
10. Santo, M.; Fox, M.: Starburst dendrimers and several molecules of biological interest. J. Phys. Org. Chem. 12, 293-307 (1999)
11. Bawarski, W.E.; Chidlowsky, E.; Bharali, D.J.; Mousa, S.A.: Emerging nanopharmaceuticals. Nanomed. Nanotechnol. Biol. Med. 4, 273-282 (2008)
12. Hu, J.J.; Cheng, Y.Y.; Ma, Y.R.; Wu, Q.L.; Xu, T.: Host-guest chemistry and physico-chemical properties of dendrimer-mycophenolic acid complexes. J. Phys. Chem. B 113, 64-74 (2009)
13. Najlah, M.; Freeman, S.; Attwood, D.; D'Emanuele, A.: Synthesis, characterization and stability studies of PAMAM dendrimer prodrugs. Int. J. Pharm. 308, 175-182 (2006)
14. Cheng, Y.; Xu, T.: Dendrimers as versatile platform in drug delivery applications. Eur. J. Med. Chem. 43, 2291-2297 (2008)
15. Potluri, S.; Ramulu, A.R.; Pardhasaradhi, M.: Synthesis of new unsymmetrical optically active (s)-(+)-naproxen. Tetrahedron 60, 10915-10920 (2004)
16. Gupta, U.; Agashe, H.B.; Jain, N.K.: Polypropylene imine dendrimer mediated solubility enhancement: effect of pH and functional groups of hydrophobes. J. Pharm. Pharmaceut. Sci. 10, 358-367 (2007)
17. Wolinsky, J.B.; Grinstaff, M.W.: Therapeutic and diagnostic applications of dendrimers for cancer treatment. Adv. Drug Deliv. Rev. 60, 1037-1055 (2008)
18. Reynolds, C.H.; Annan, N.; Beshah, K.; Huber, J.H.; Shaber, S.H.; Lenkinski, R.E.; Wortman, J.: Gadolinium-loaded nanoparticles: new contrast agents for magnetic resonance imaging. J. Am. Chem. Soc. 122, 8940-8945 (2000)
19. Lu, Z.R.; Wang, X.; Parker, D.; Goodrich, K.C.; Buswell, H.R.: Poly(l-glutamic acid) Gd(III)-DOTA conjugate with a degradable spacer for magnetic resonance imaging. Bioconjugate Chem. 14, 715-719 (2003)
20. Rudovsky, J.; Botta, M.; Hermann, P.; Hardcastle, K.I.; Lukes, I.; Aime, S.: PAMAM dendrimeric conjugates with a Gd-DOTA phosphinate derivative and their adducts with polyaminoacids: the interplay of global motion, internal rotation, and fast water exchange. Bioconjugate Chem. 17, 975-987 (2006)
21. Kim, J.H.; Park, K.; Nam, H.Y.; Lee, S.; Kim, K.; Kwon, I.C.: Biopolymers for molecular imaging. Prog. Polym. Sci. 32, 1031-1053 (2007)
22. Duarte, M.G.; Gil, M.H.; Peters, J.A.; Colet, J.M.; Vander Elst, L.; Muller, R.N.; Geraldes, C.F.: Synthesis, characterization, and relaxivity of two linear Gd(DTPA)-polymer conjugates. Bioconjugate Chem. 12, 170-177 (2001)
23. Kobayashi, H.; Brechbiel, M.W.: Dendrimer-based macromolecular MRI contrast agents: characteristic and application. Mol. Imaging 2, 1-10 (2003)
24. Karwowski, B.; Witczak, M.; Mikiciuk-Olasik, E.; Studniarek, M.: Gadolinium Gd(III) complexes with derivatives of nitriloacetic acid: synthesis and biological properties. Acta Poloniae Pharm. Drug Res. 5, 535-541 (2008)
25. Loberg, M.D.; Cooper, M.; Harvey, E.; Callery, P.; Faith, W.: Development of new radiopharmaceuticals based on N-substitution of iminodiacetic acid. J. Nucl. Med. 17, 633-638 (1976)
26. Brboriú, J.S.; Jovanoviú, M.S.; Popoviú, G.; Kapetanoviú, V.; Vladimirov, S.: Acid-base equilibria of 2,4-diiodo-6-methylphenylcarbamoylmethyl iminodiacetic acid and its labeling with technetium-99m. J. Serb. Chem. Soc. 71, 55-65 (2006)
27. Nunn, A.; Loberg, M.: N-substituted iminodiacetic acids. United States Patent, 4,418,208 (23 Nov 1983)
28. Burns D.; Sowa D.; Marzilli L.: Improved synthesis of N-(2,-6 dimethylphenylcarbamoylmethyl)iminodiacetic acid and analogs. J. Pharm. Sci. 67, 1434-1436 (1978)
29. Esfand, R.; Tomalia, D.A.: Poly(amidoamine) (PAMAM) dendrimers: from biomimicry to drug delivery and biomedical applications. Drug Discov. Today 6, 427-436 (2001)
30. Beezer, A.E.; King, A.S.H.; Martin, I.K.; Mitchel, J.C.; Twyman, L.J.; Wain, C.F.: Dendrimers as potential drug carriers; encapsulation of acidic hydrophobes within water soluble PAMAM derivatives. Tetrahedron 59, 3873-3880 (2003)
31. Kim, S.Y.; Shin, I.L.G.; Lee, Y.M.; Cho, C.S.; Sung, Y.K.: Methoxy poly(ethylene glycol) and ε-caprolactone amphiphilic block copolymeric micelle containing indomethacin: II. Micelle formation and drug release behaviours. J. Control. Release 51, 13-21 (1998)
32. Chauhan, A.S.; Sridevi, S.; Chalasani, K.B.; Jain, A.K.; Jain, S.K.; Jain, N.K.; Diwan, P.V.: Dendrimer-mediated transdermal delivery: enhanced bioavailability of indomethacin. J. Control. Release 90, 335-343 (2003)
33. Ooya, T.; Lee, J.; Park, K.: Effects of ethylene glycol-based graft, star-shaped, and dendritic polymers on solubilization and controlled release of paclitaxe l. J. Control. Release 93, 121-127 (2003)
34. Khopade, A.J.; Caruso, F.; Tripathi, P.; Nagaich, S.; Jain, N.K.: Effect of dendrimer on entrapment and release of bioactive from liposomes. Int. J. Pharm. 232, 157-162 (2002)
35. Asthana, A.; Chauhan, A.S.; Diwan, P.V.; Jain, N.K.: Poly(amidoamine) (PAMAM) Dendritic nanostructures for controlled site-specific delivery of acidic anti-inflammatory active ingredient. AAPS Pharm. Sci. Technol. 27, 536-542 (2005)
36. Namazi, H.; Adeli, M.: Dendrimers of citric acid and poly(ethylene glycol) as the new drug delivery agents. Biomaterials 26, 1175-1183 (2005)
37. Wiwattanapatapee, R.; Jee, R.D.; Duncan, R.: PAMAM dendrimers as a potential oral drug delivery system: dendrimer complexes with piroxicam. Proc. Int. Symp. Control. Release. Bioact. Mater. 26, 241 (1999)
38. Cheng, Y.; Xu, T.: Polyamidoamine dendrimers used as solubility enhancers of ketoprofen. Eur. J. Med. Chem. 40, 1188-1192 (2005)
39. Cheng, Y.; Xu, T.: Solubility of nicotinic acid in polyamidoamine dendrimer solutions. Eur. J. Med. Chem. 40, 1384-1389 (2005)
40. Yang, W. Li, Y.; Cheng, Y.; Wu, Q.; Wen, L.; Xu, T.: Evaluation of phenylbutazone and poly(amidoamine) dendrimers interactions by a combination of solubility, 2D-NOESY NMR, and isothermal titration calorimetry studies. J. Pharm. Sci. 98, 1075-1085 (2009)
41. Cheng, Y.; Xu, T.: Polyamidoamine dendrimers used as solubility enhancers of ketoprofen. Eur. J. Med. Chem. 40(12), 1390-1393 (2005)
42. D'Emanuele, A.; Attwood, D.: Dendrimer-drug interactions. Adv. Drug Deliv. Rev. 57, 2147-2162 (2005)
43. Gupta, U.; Agashe, H.B.; Asthana, A.; Jain, N.K.: Dendrimers: novel polymeric nanoarchitectures for solubility enhancement. Biomacromolecules 7, 649-658 (2006)
44. Chauhan, A.S.; Jain, N.K.; Diwan, P.V.; Khopade, A.J.: Solubility enhancement of indomethacin with poly(amidoamine) dendrimers and targeting to inflammatory regions of arthritic rats. J. Drug Target. 12, 575-583 (2004)
45. Kolhe, P.; Misra, E.; Kannan, R.M.; Kannan, S.; Lieh-Lai, M.: Drug complexation, in vitro release and cellular entry of dendrimers and hyperbranched polymers. Int. J. Pharm. 259, 143-160 (2003)
46. Devarakonda, B.; Hill, R.A.; de Villiers, M.M.: The effect of PAMAM dendrimer generation size and surface functional group on the aqueous solubility of nifedipine. Int. J. Pharm. 248, 133-140 (2004)
47. Cheng, Y.; Wu, Q.; Li, Y.; Xu, T.: External electrostatic interaction versus internal encapsulation between cationic dendrimers and negatively charged drugs: which contributes more to solubility enhancement of the drugs? J. Phys. Chem. B 112, 8884-8890 (2008)
48. Cheng, Y.; Li, Y.; Wu, Q.; Zhang, J.; Xu, T.: Generation-dependent encapsulation/electrostatic attachment of phenobarbital molecules by poly(amidoamine) dendrimers: evidence from 2D-NOESY investigations. Eur. J. Med. Chem. 44, 2219-2223 (2009)
49. Tomalia, D.A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P.: A new class of polymers: starburst-dendritic macromolecules. Polym. J. 17, 117-132 (1985)
50. Devarakonda, B.; Otto, D.; Judefeind, A.; Hill, R.A.; de Villiers, M.M.: Effect of pH on the solubility and release of furosemide from polyamidoamine (PAMAM) dendrimer complexes. Int. J. Pharm. 345, 142-153 (2007)
51. Broeren, M.A.C.; de Waal, B.F.M.; van Genderen, M.H.P.; Sanders, H.M.H.F.; Fytas, G.; Meijer, E.W.: Multicomponent host-guest chemistry of carboxylic acid and phosphonic acid based guests with dendritic hosts: an NMR study. J. Am. Chem. Soc. 127, 10334-10343 (2005)
52. Hu, J.; Cheng, Y.; Wu, Q.; Zhao, L.; Xu, T.: Host-guest chemistry of dendrimer-drug complexes. 2. Effects of molecular properties of guests and surface functionalities of dendrimers. J. Phys. Chem. B 113, 10650-10659 (2009)
53. Zhao, L.; Cheng, Y.; Hu, J.; Wu, Q.; Xu, T.: Host-guest chemistry of dendrimer-drug complexes. 3. Competitive binding of multiple drugs by a single dendrimer for combination therapy. J. Phys. Chem. B 113, 14172-14179 (2009)
54. Fang, M.; Zhang, J.; Wu, Q.; Xu, T.; Cheng, Y.: Host-guest chemistry of dendrimer-drug complexes: 7. Formation of stable inclusions between acetylated dendrimers and drugs bearing multiple charges. J. Phys. Chem. B 116, 3075-2082 (2012)
55. Chai, M.H.; Holley, A.K.; Kruskamp, M.: Encapsulating fluorescein using adipic acid self-assembly on the surface of PPI-3 dendrimer. Chem. Commun. 2, 168-170 (2007)