Acetylation of Poly(amidoamine) Dendrimers

Majoros, István J.; Keszler, B.; Woehler, Scott; Bull, Tricia; Baker, James R.

doi:10.1021/ma021540e

Cited by 174 publications

(220 citation statements)

References 10 publications

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“…The JCPDs were synthesized via divergent approach (Scheme 1) and characterized with 1 H NMR, 13 C NMR, FTIR-ATR, and GPC, and the results were in good agreement with the literature [11,12]. The prepared dendrimers were stored in methanolic solution and stored at ±4ºC.…”

Section: Preparation and Characterization Of Jcpdssupporting

confidence: 74%

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Characterization of Co(II)-PAMAM dendrimer complexes with polypropylene oxide core by using UV-VIS spectroscopy

Ertürk

Gürbüz

Tülü

et al. 2016

Maced. J. Chem. Chem. Eng.

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The aim of this study was to characterize poly(amidoamine) (PAMAM) dendrimer complexes of Co(II) ions by using UV-Vis spectroscopy. For this aim, a generation-4 polypropylene oxide (Jeffamine ® T-403) cored and amine-terminated PAMAM dendrimer (P4) was used as a model complexation agent. Optimum complexation condition for P4 was determined by potentiometric and spectroscopic titration studies. Extent of protonation (EOP) of the amino groups of P4 was determined from the potentiometric titration data and validated with spectroscopic titration data. The results indicated that pH 8 was the optimum dendrimer aqueous solution media, where the available number of tertiary amines present in P4 was the highest for possible metal complexation. At the optimized conditions, UV-Vis characterization of the Co(II)-P4 complexes was performed and 585-635 nm d-d transition bands were observed as the characteristic complexation bands of the tertiary amine groups of P4 with Co(II) ions. Obtained Co(II)-P4 complexes might be considered for the development of magnetic resonance image (MRI) improvers or MRI contrast agents.Keywords: PAMAM dendrimer; Jeffamine; complexation; UV-Vis spectroscopy; MRI contrast agents КАРАКТЕРИЗАЦИЈА НА PAMAM-ДЕНДРИМЕРНИ КОМПЛЕКСИ НА Co(II) СО ПРОПИЛЕН-ОКСИДЕН КОСТУР СО КОРИСТЕЊЕ НА UV-VIS СПЕКТРОСКОПИЈАЦелта на ова истражување е да се карактеризираат поли(амидоамински) (PAMAM) дендримерни комплекси на јоните на Co(II) со помош на UV-Vis спектроскопија. За таа цел беа користени полипропилено оксиден костур од генерацијата-4 (Jeffamine ® T-403) и амински терминиран PAMAM дендример (P4) како модел за средство за комплексирање. Оптималните услови за P4 беа определени со помош на потенциометриски и спектроскопски титрациски испитувања. Степенот на протонирање (EOP) на аминогрупите на P4 беше определен со потенциометриски титрации, кои потоа беа валидирани со спектроскопски титрации. Резултатите укажуваат дека оптимален медиум се водни раствори со рН 8 кога достапниот број на терцијарни амини присутни во P4 беше највисок за можно комплексирање на металот. Во оптимизираните услови беше извршена UV-Vis карактеризација на комплексите на Co(II)-P4. Беа регистрирани 585-635 nm d-d транзициски ленти како карактеристични комплексирачки ленти на терцијарните амински групи на P4 со јоните на Co(II). Добиените комплекси на Co(II)-P4 можат да се земат предвид за развивање на подобрувачи на магнетно резонатни слики (MRI) и како контрастни средства за MRI.Клучни зборови: PAMAM дендримери; комплексирање; UV-Vis спектроскопија; контрастни средства за MRI A. Serol Ertürk, M. Ulvi Gürbüz, M. Tülü, A. Emin Bozdoğan Maced.

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Section: Preparation and Characterization Of Jcpdssupporting

confidence: 74%

“…Acid base titrations were conducted according to the literature [13,14]. Here, 56.10 mg P4 was weighted and diluted to 60.0 ml with 0.10 M NaCl solution.…”

Section: Potentiometric Titrationsmentioning

confidence: 99%

Characterization of Co(II)-PAMAM dendrimer complexes with polypropylene oxide core by using UV-VIS spectroscopy

Ertürk

Gürbüz

Tülü

et al. 2016

Maced. J. Chem. Chem. Eng.

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“…A G5 PAMAM dendrimer was synthesized and purified from low molar mass contaminants as well as higher molar mass dimers or oligomers (22). The number average molar mass of the dendrimer was determined to be 26,530 g/mol by size exclusion chromatography using multiangle laser light scattering, UV, and refractive index detectors.…”

Section: Methodsmentioning

confidence: 99%

Nanoparticle Targeting of Anticancer Drug Improves Therapeutic Response in Animal Model of Human Epithelial Cancer

Kukowska-Latallo¹,

Candido²,

Cao³

et al. 2005

Cancer Research

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832

688

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Prior studies suggested that nanoparticle drug delivery might improve the therapeutic response to anticancer drugs and allow the simultaneous monitoring of drug uptake by tumors. We employed modified PAMAM dendritic polymers <5 nm in diameter as carriers. Acetylated dendrimers were conjugated to folic acid as a targeting agent and then coupled to either methotrexate or tritium and either fluorescein or 6-carboxytetramethylrhodamine. These conjugates were injected i.v. into immunodeficient mice bearing human KB tumors that overexpress the folic acid receptor. In contrast to nontargeted polymer, folate-conjugated nanoparticles concentrated in the tumor and liver tissue over 4 days after administration. The tumor tissue localization of the folate-targeted polymer could be attenuated by prior i.v. injection of free folic acid. Confocal microscopy confirmed the internalization of the drug conjugates into the tumor cells. Targeting methotrexate increased its antitumor activity and markedly decreased its toxicity, allowing therapeutic responses not possible with a free drug. (Cancer Res 2005; 65(12): 5317-24 )

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“…Literature survey disclosed that remarkably few methods are reported for the acetylation of PAMAM dendrimers 9 Solubility enhancements of poorly soluble compounds is facilitated by acetylated conjugates 8 . Acetic anhydride is popularly used for acetylation of amine terminated PAMAM dendrimers.…”

Section: Introductionmentioning

confidence: 99%

An Alternative Approach for Acetylation of Amine Terminated Polyamidoamine (PAMAM) Dendrimer

Gautam¹,

Keservani

Gautam³

et al. 2015

Ars Pharm

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RESUMENObjetivos. Las propiedades inherentes de la poliamidoamina (PAMAM) la han convertido en el nanotransportador de elección en la era actual de la innovación. A pesar de que sufren de toxicidad hemolítica que podría ser reducido mediante la protección del grupo amino libre. En el presente trabajo se discutió el método alternativo de acetilación para los dendrímeros PAMAM. Material y Métodos.El enlazador 1-Etill-3-(3-dimetilaminopropil) carbodiimida (EDC) se utilizó para la acetilación. El conjugado acetilado se evaluó mediante la reacción de color, mediante espectroscopia Ultravioleta visible, espectroscopia infrarroja con transformado de Fourrier, Calorimetría Diferencial de barrido y los estudios de los espectros de Resonancia magnetica nuclear.. Resultados.Los dendrímeros PAMAM se sintetizaron utilizando el método divergente y más acetilado. Cambio en los valores λmax 282,0 a 282,5 nm se observó para dendrímeros acetilados. El pico característico del NH de amina primaria a 3284,16 cm-1, desapareció debido a la conversión de amina primaria a amina secundaria. Un nuevo pico de -(CO) -NH se obtuvo a 1640,28 cm-1 (medianas), que muestra la unión de grupo de superficie de ácido acético. Se observaron los cambios en el pico endotérmico de 120,56 a 110.40 ºC que muestra las modificaciones superficiales de dendrímeros PAMAM. El pico de -NH 2 en 2,99 ppm fue sustituido por (-NHCOCH 3 ) a 2,42 ppm apoya aun más la prueba de acetilación.Conclusión. Los datos espectrales revelaron claramente que este enfoque para la acetilación da considerable cantidad de acetilación en menos tiempo de duración con la eliminación de disolvente orgánico.Este método podría ser empleado para regular la acetilación de las aminas terminales de nanovehículos.El enlazador EDC de grupos amino abre una nueva vía para la acetilación de amina terminales de proteínas / péptidos.Palabras clave: dendrímeros, poliamidoamina (PAMAM), Etylenediamine, acetilación, vinculador, Propiedades de la superficie. ABSTRACTAim. Polyamidoamine (PAMAM) dendrimers inherent properties have made it the nanocarrier of choice in the current era of innovation. Dendrimer based products are growing and mushrooming like anything in the current time. Although it suffer from hemolytic toxicity which could be reduced by protecting free amino group.Methods. In the present work alternate acetylated method for PAMAM dendrimers was discussed. 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide Linker was used for acetylation. The acetylated conjugate was evaluated for color reaction, Ultraviolet-visible spectroscopy, Fourier Transform infrared spectroscopy, Differential scanning calorimetric, Nuclear magnetic resonance spectra studies.Results. The PAMAM dendrimers were synthesized using divergent approach and further acetylated. Change in λ max values from 282.0 to 282.5 nm was observed for acetylated dendrimers. Characteristic peak of N-H stretch of primary amine at 3284.16 cm-1 was disappeared due to conversion of primary Financiación FundingsNo funding agency for the research wor...

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Acetylation of Poly(amidoamine) Dendrimers

Cited by 174 publications

References 10 publications

Characterization of Co(II)-PAMAM dendrimer complexes with polypropylene oxide core by using UV-VIS spectroscopy

Characterization of Co(II)-PAMAM dendrimer complexes with polypropylene oxide core by using UV-VIS spectroscopy

Nanoparticle Targeting of Anticancer Drug Improves Therapeutic Response in Animal Model of Human Epithelial Cancer

An Alternative Approach for Acetylation of Amine Terminated Polyamidoamine (PAMAM) Dendrimer

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