Synthesis of β-Cyclodextrin-Decorated Dendritic Compounds Based on EDTA Core: A New Class of PAMAM Dendrimer Analogs

被引：3

作者：

Gonzalez-Mendez, Israel ^{[1
]}

Loera-Loera, Esteban ^{[1
,2
]}

Sorroza-Martinez, Kendra ^{[3
]}

Vonlanthen, Mireille ^{[3
]}

Cuetara-Guadarrama, Fabian ^{[3
]}

Bernad-Bernad, Maria Josefa ^{[4
]}

Rivera, Ernesto ^{[3
]}

Gracia-Mora, Jesus ^{[1
]}

机构：

[1] Univ Nacl Autonoma Mexico, Fac Quim, Dept Quim Inorgan & Nucl, Ciudad Univ, Mexico City 04510, DF, Mexico

[2] Univ Valle Mexico, Escuela Ciencias Salud, Campus Coyoacan,Calzada Tlalpan 3000, Mexico City 04910, DF, Mexico

[3] Univ Nacl Autonoma Mexico, Inst Invest Mat, Ciudad Univ, Mexico City 04510, DF, Mexico

[4] Univ Nacl Autonoma Mexico, Fac Quim, Dept Farm, Ciudad Univ, Mexico City 04510, DF, Mexico

来源：

PHARMACEUTICS | 2022年 / 14卷 / 11期

关键词：

EDTA dendrimer; beta-cyclodextrin; click chemistry; PAMAM dendrimer; microwave assisted synthesis; SURFACE-ENGINEERED DENDRIMERS; POLY(AMIDOAMINE) DENDRIMERS; DRUG; DERIVATIVES; SOLUBILITY; TOXICITY;

D O I：

10.3390/pharmaceutics14112363

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

In this work, two dendritic molecules containing an ethylenediaminetetraacetic acid (EDTA) core decorated with two and four beta-cyclodextrin (beta CD) units were synthesized and fully characterized. Copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) click chemistry under microwave irradiation was used to obtain the target compounds with yields up to 99%. The classical ethylenediamine (EDA) core present in PAMAM dendrimers was replaced by an EDTA core, obtaining platforms that increase the water solubility at least 80 times compared with native beta CD. The synthetic methodology presented here represents a convenient alternative for the rapid and efficient construction of PAMAM analogs. These molecules are envisaged for future applications as drug carriers.

引用

页数：15

共 59 条

[1] Dendrimers: synthesis, applications, and properties [J].

Abbasi, Elham ;

Aval, Sedigheh Fekri ;

Akbarzadeh, Abolfazl ;

Milani, Morteza ;

Nasrabadi, Hamid Tayefi ;

Joo, Sang Woo ;

Hanifehpour, Younes ;

Nejati-Koshki, Kazem ;

Pashaei-Asl, Roghiyeh .

NANOSCALE RESEARCH LETTERS, 2014, 9 :1-10

[2] Formation of host-guest and sandwich complexes by a β-cyclodextrin derivative [J].

Antelo, Alvaro ;

Jover, Aida ;

Galantini, Luciano ;

Meijide, Francisco ;

Alvarez Alcalde, Mercedes ;

Pavel, Nicolae Viorel ;

Vazquez Tato, Jose .

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2011, 69 (1-2) :245-253

[3] Twenty Years of Research on Cyclodextrin Conjugates with PAMAM Dendrimers [J].

Arima, Hidetoshi .

PHARMACEUTICS, 2021, 13 (05)

[4] Dendrimers in Medical Nanotechnology Application of Dendrimer Molecules in Bioimaging and Cancer Treatment [J].

Barrett, Tristan ;

Ravizzini, Gregory ;

Choyke, Peter L. ;

Kobayashi, Hisataka .

IEEE ENGINEERING IN MEDICINE AND BIOLOGY MAGAZINE, 2009, 28 (01) :12-22

[5] Dendrimers in drug research [J].

Boas, U ;

Heegaard, PMH .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (01) :43-63

[6] Metal-induced chiral folding of depsipeptide dendrimers [J].

Buschhaus, B ;

Hampel, F ;

Grimme, S ;

Hirsch, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (12) :3530-3540

[7] Phosphorus dendrimers: from synthesis to applications [J].

Caminade, AM ;

Maraval, V ;

Laurent, R ;

Turrin, CO ;

Sutra, P ;

Leclaire, J ;

Griffe, L ;

Marchand, P ;

Baudoin-Dehoux, C ;

Rebout, C ;

Majoral, JP .

COMPTES RENDUS CHIMIE, 2003, 6 (8-10) :791-801

[8] Synthesis and characterization of fluorescent PAMAM dendrimer modified with 1,8-naphthalimide units and its Cu(II) complex designed for specific biomedical application [J].

Cangiotti, Michela ;

Staneva, Desislava ;

Ottaviani, M. Francesca ;

Vasileva-Tonkova, Evgenia ;

Grabchev, Ivo .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2021, 415

[9] A convenient method for multicolour labelling of proteins with BODIPY fluorophores via tyrosine residues [J].

Cheng, Miffy. H. Y. ;

Savoie, Huguette ;

Bryden, Francesca ;

Boyle, Ross. W. .

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2017, 16 (08) :1260-1267

[10] Applications and Limitations of Dendrimers in Biomedicine [J].

Chis, Adriana Aurelia ;

Dobrea, Carmen ;

Morgovan, Claudiu ;

Arseniu, Anca Maria ;

Rus, Luca Liviu ;

Butuca, Anca ;

Juncan, Anca Maria ;

Totan, Maria ;

Vonica-Tincu, Andreea Loredana ;

Cormos, Gabriela ;

Muntean, Andrei Catalin ;

Muresan, Maria Lucia ;

Gligor, Felicia Gabriela ;

Frum, Adina .

MOLECULES, 2020, 25 (17)

← 1 2 3 4 5 6 →