New-generation Jeffamine (R) D230 core amine, TRIS and carboxyl-terminated PAMAM dendrimers: Synthesis, characterization and the solubility application for a model NSAID drug Ibuprofen

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Erturk A. S., GÜRBÜZ M. U., TÜLÜ M.

MARMARA PHARMACEUTICAL JOURNAL, vol.21, no.2, pp.385-399, 2017 (ESCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 21 Issue: 2
  • Publication Date: 2017
  • Doi Number: 10.12991/marupj.300924
  • Journal Name: MARMARA PHARMACEUTICAL JOURNAL
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.385-399
  • Keywords: Dendrimers, poly (amidoamine) PAMAM, Jeffamine, drug carrier, NSAID, ibuprofen, MICROWAVE-ASSISTED SYNTHESIS, POLY(AMIDOAMINE) DENDRIMERS, POLYAMIDOAMINE DENDRIMERS, IN-VITRO, DELIVERY, CARRIERS, BIOCOMPATIBILITY, NANOPARTICLES, COMPLEXATION, ENHANCEMENT
  • Yıldız Technical University Affiliated: Yes

Abstract

Many therapeutically active drugs are poor water soluble and, therefore, bioavailability of these molecules in the living cells is low and a major problem. In this study, new-generation Jeffamine (R) D230 core, amine (NH2), Tris(hydroxymethyl) aminomethane (TRIS), and carboxyl (COOH) terminated poly(amidoamine) PAMAM dendrimers (PAMAMs) were synthesized. Synthesized new-generation PAMAMs were characterized by H-1 NMR, C-13 NMR, ATR-FTIR, and investigated as solubility enhancer of a sample non-steroidal anti-inflammatory drug (NSAID) Ibuprofen (IBU). The effect of generation size (D2-D4), concentration (0-2.0 mM), and surface functional group (NH2, COOH, TRIS) of the synthesized new-generation PAMAMs on the aqueous solubility of IBU was also investigated. The observed solubility enhancement of IBU was in the order of D4.COOH (18.21 mg/mL)> D3.COOH (13.21 mg/mL)> D4.TRIS (10.30 mg/mL)> D2.COOH (8.55 mg/mL)> D3.TRIS (6.04 mg/mL)> D4.NH2 (4.56 mg/mL)> D3.NH2 (3.36 mg/mL)> D2.TRIS (2.42 mg/mL)> D2.NH2 (1.86 mg/mL). Results showed that synthesized PAMAMs improved the solubility of IBU significantly (30 to 247-fold) with an increasing generation size, and concentration.