New-generation Jeffamine® D230 core amine, TRIS and carboxylterminated PAMAM dendrimers: Synthesis, characterization and the solubility application for a model NSAID drug Ibuprofen

Year 2017, Volume: 21 Issue: 2, 385 - 399, 01.04.2017

Ali Serol Ertürk Mustafa Ulvi Gürbüz , Metin Tülü

https://doi.org/10.12991/marupj.300924

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® 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 1H NMR, 13C 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-

Keywords

Dendrimers, poly (amidoamine) PAMAM, Jeffamine, drug carrier, NSAID, ibuprofen

New-generation Jeffamine® D230 core amine, TRIS and carboxylterminated PAMAM dendrimers: Synthesis, characterization and the solubility application for a model NSAID drug Ibuprofen

Abstract

Birçok terapötik olarak aktif olan ilaçların sudaki çözünürlüğü

zayıf ve bundan dolayı canlı hücrelerde biyoyararlanımları

düşük ve büyük bir problem oluşturmaktadır. Bu çalışmada,

yeni nesil Jeffamine® D230 çekirdekli amin (NH2),

Tris(hidroksimetil)aminometan (TRIS) ve karboksil (COOH)

sonlu poli(amidoamine) PAMAM dendrimerler (PAMAMs)

sentezlendi. Sentezlenen yeni tip PAMAMs’lar 1H NMR, 13C

NMR, ATR-FTIR kullanılarak karakterize edildi ve örnek bir

non-steroidal anti-inflamatuar ilaç (NSAID) olan Ibuprofen

(IBU) için çözünürlük arttırıcı olarak araştırıldı. Sentezlenen

yeni nesil PAMAMs’ların, jenerasyon büyüklüğünün (D2-D4),

konsantrasyonun (0-2.0 mM) ve yüzey fonksiyonel gruplarının

(NH2, COOH, TRIS), IBU’nun çözünürlüğüne olan etkisi ayrıca

araştırıldı. IBU’nun gözlemlenen çözünürlük artışı, 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) sırasındadır. Sonuçlar

gösteriyor ki, sentezlenen PAMAMs’ların jenerasyon büyüklüğü

ve konsantrasyonun artmasıyla birlikte IBU’nu çözünürlüğü

önemli ölçüde artmıştır (30 ile 247 kat arası).

Keywords

Dendrimer, poly(amidoamin) PAMAM, Jeffamin, ilaç taşıyıcı, NSAID, ibuprofen

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