Synthesis and Analytical Characterization of Ester and Amine Terminated PAMAM Dendrimers

Surya Prakash Gautam; Arun Kumar Gupta; Anupama Sharma; Tapsya Gautam; Unknown Madhu

Authors

Surya Prakash Gautam
Arun Kumar Gupta
Anupama Sharma
Tapsya Gautam
Unknown Madhu

Keywords:

poly (amido) amine; PAMAM dendrimers; divergent approach; polydispersity

Abstract

PAMAM dendrimers containing ethylene diamine core and methyal acrylate as repeating unit were synthesized by divergent approach. Analytical characterization of PAMAM dendrimers amine terminated full generation 4.0 G and ester terminated half generation 3.5 G were performed using UV-Vis spectroscopy, FT-IR spectroscopy, differential scanning calorimetry, NMR spectroscopy and MASS spectroscopy. The half generation dendrimers have the methyl ester terminating groups, which have the characteristic IR peaks for carbonyl at 1730-1750 cm-1. For the full generation dendrimers, when the methyl ester groups were converted to amide groups, the corresponding carbonyl shifted to 1660 cm-1.The characteristic methyl ester peak, which appeared in all the 1 H-NMR spectra of the ester terminating dendrimers, whereas it is absent in all the amine terminating dendrimers. The molecular weight was determined by ESI mass spectroscopy which further confirms the preparation of PAMAM dendrimers and provides information about the structural defects, polydispersity and purity.

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Synthesis and Analytical Characterization of Ester and Amine Terminated PAMAM Dendrimers. (2013). Global Journal of Medical Research, 13(9), 7-15. https://medicalresearchjournal.org/index.php/GJMR/article/view/

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References

Tomalia DA, Naylor AM, Goddard WA (1990) Starburst dendrimers: molecular-level control of size, shape, surface chemistry, topology, and flexibility from atoms to macroscopic matter. 29, 138-175.

D. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, P. Smith (1985) A new class of polymers: starburst-dendritic macromolecules. 17, 117-132.

Roseita Esfand, Donald Tomalia (2001) Poly (amidoamine) (PAMAM) dendrimers: from biomimicry to drug delivery and biomedical applications Drug Discovery Today. 6(8), 427-436. https://doi.org/10.1016/s1359-6446(01)01757-3

Konda SD, Aref M, Wang S, Brechbiel M, Wiener EC (2001) Specific targeting of folate-dendrimer MRI contrast agents to the high affinity folate receptor expressed in ovarian tumor xenografts. 12, 104-113.

H. Namazi, M. Adeli (2005) Dendrimers of citric acid and poly (ethyleneglycol) as the new drugdelivery agents Biomaterials. 26(10), 1175-1183. https://doi.org/10.1016/j.biomaterials.2004.04.014

A. Patri, J. Kukowskalatallo, J. Bakerjr (2005) Targeted drug delivery with dendrimers: Comparison of the release kinetics of covalently conjugated drug and non-covalent drug inclusion complex. 57, 2203-2214.

Zeng F, Zimmerman SC (1997) Dendrimers in supramolecular chemistry: from molecular recognition to self-assembly. 97, 1681-1712.

Gaurang Purohit, Thiagarajan Sakthivel, Alexander Florence (2001) Purohit G, Sakthivel T, Florence AT.Interaction of cationic partial dendrimers with charged and neutral liposomes. 214(1-2), 71-76. https://doi.org/10.1016/s0378-5173(00)00635-9

R. Duncan, N. Malik (1996) Dendrimers: biocompatibility and potential for delivery of anticancer agents. 23, 105-106.

Tomalia DA (2004) Dendrimer as quantized building blocks for nanoscale synthetic organic chemistry. 37, 39-57.

A. Bielinska, J. Kukowska-Latallo, J. Johnson, D. Tomalia, J. Baker (1996) Regulation of in vitro gene expression using antisense oligonucleotides or antisense expression plasmids transfected using starburst pamam dendrimers. 24, 2176-2182.

Mary Tang, Carl Redemann, Francis Szoka (1996) In vitro gene delivery by degraded polyamidoamine dendrimers Bioconjugate Chem. 7(6), 703-714. https://doi.org/10.1021/bc9600630

Pratap Singh (1998) Terminal groups in starburst dendrimers: activation and reactions with proteins Bioconjugate Chem. 9(1), 54-63. https://doi.org/10.1021/bc970048a

Wiener EC, Brechbiel MW, Brothers H, Magin RL, Gansow OA, Tomalia DA, Lauterbur PC (1994) Dendrimerbased metal chelates: a new class of magnetic resonance imaging contrast agents. 31, 1-8.

Rao C, Tam JP (1994) Synthesis of peptide dendrimer. 116.

Shi X, Majoros IJ, Patri AK, Bi X, Islam MT, Desai A, Ganser TR, Baker JR (2006) Molecular heterogeneity analysis of poly(amidoamine) dendrimer-based mono- and multifunctional nanodevices by capillary electrophoresis. 131, 374-381.

Bauer Hedden RC, Grohn Smith AP (2002) Templating of inorganic nanoparticles by PAMAM/PEG dendrimer-star polymers. 43, 5473-5481.

Balogh LP, Ganser TR, Shi X (2005) Characterization of dendrimer-gold nanocomposite materials. 847, 13.33.1-EE13.33.6.

L. Guoping, L. Yunjun, T. Huimin (2005) PVP and G1.5 PAMAM dendrimer co-mediated synthesis of silver nanoparticles J Solid State Chem. 178, 1038-1043.

Neddersen J, Chumanov G, Cotton TM (1993) Laser ablation of metals: a new method for preparing SERS active colloids. 47.

Anil Patri, István Majoros, James Baker (2002) Dendritic polymer macromolecular carriers for drug delivery Curr Opin Chem Biol. 6(4), 466-471. https://doi.org/10.1016/s1367-5931(02)00347-2

Kojima C, Kono K, Maruyama K, Tkagishi T (2000) Synthesis of polyamidoamine dendrimers having poly-(ethylene glycol) grafts and their ability to encapsulate anticancer drugs. 11, 910-917.

Moreno KX (2008) Conformational Analysis of Triazine Dendrimers: Using NMR Spectroscopy To Probe the Choreography of a Dendrimer's Dance. 41, 4108-4114.

Laurent Caminade AM, Rebout Turrin CO, Ouali Nicot BD, Zablocka M, characterization (2010) Phosphorus dendrimers as viewed by 31P NMR spectroscopy; synthesis and characterization. 13, 1006-1027.

Wijmenga SS, Hallenga K, Hilberts CW (1989) A threedimensional heteronuclear multiple-quantum coherence homonuclear Hartman-Hahn experiment. 84, 634-642.

Chai M, Niu Y, Youngs WJ, Rinaldi PL (2001) Structure and conformation of DAB dendrimers in solution via multidimensional NMR techniques. 123, 4670-4678.

Farrington PJ, Hawker CJ, Frechet JMJ, Mackay ME (1998) The melt viscosity of dendritic poly(benzyl ether) macromolecules Macromolecules. 31(15), 5043-5050. https://doi.org/10.1021/ma970198g

Elsasser R, Mehl GH, Goodby JW, Veith M (2001) Nematic dendrimers based on carbosilazane cores. 40, 2688-2690.

Pesak DJ, Moore JS (1997) Columnar liquid crystals from shapepersistent dendritic molecules. 36, 1636-1639.

Felder T, Schalley CA, Fakhrnabavi H, Lukin O (2005) A combined ESI- and MALDI-MS(/MS) study of peripherally persulfonylated dendrimers: false negative results by MALDI-MS and analysis of defects. 11, 5625-5636.

Hummelen JC, Dongen JLJ, Meijer EW (1997) Chirality in dendritic architectures. 3, 1489-1493.