Complex Structured Fluorescent Polythiophene Graft Copolymer as a Versatile Tool for Imaging, Targeted Delivery of Paclitaxel, and Radiotherapy

Guler, Emine; Akbulut, Hüseyin; Geyik, Caner; Yilmaz, Tülay; Gümüş, Zinar Pınar; Barlas, F. Baris; Ahan, Recep Erdem; Demirkol, Dilek Odaci; Yamada, Shuhei; Endō, Takeshi; Timur, Suna; Yaǧcı, Yusuf

doi:10.1021/acs.biomac.6b00491

Cited by 20 publications

(16 citation statements)

References 59 publications

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“…Using macromonomer B functionalized with the poly(ethylene glycol) chain as a comonomer, the resulting poly(p-phenylene) achieved the hydrophilicity that is necessary for the bioelectronic applications of the graft copolymer C. Poly(p-phenylene) is emissive upon the irradiation of UV light, and its applications in biosensors are investigated. A similar synthetic approach has been used for the preparation of a polymeric pro-drug for targeted drug delivery (Scheme 24) [32]. The graft copolymer E bearing the polythiophene main chain and poly(L-lysine) graft chains was synthesized by the palladium-catalyzed coupling polymerization of the macromonomer D bearing the 1,4-dibromothiophene moiety at the terminal, followed by the acid-catalyzed removal of the t-butoxycarbonyl group in the side chain.…”

Section: Applications In Macromolecular Architecturesmentioning

confidence: 99%

“…The polypeptide segment was prepared by the polymerization of L-lysine-derived urethane 2r using the amino-functionalized bis(3,4-ethylenedioxythiophene) F. The resulting macromonomer G and bis(thiophene) H bearing the ferrocene moieties were electrochemically copolymerized on a graphite electrode, leading to electrode-surface modification by the graft copolymer composed of a π-conjugated main chain, and thus, a conductive main chain, polypeptide graft chains, and redox-responsive ferrocene moieties. The amino group at the chain end of the A similar synthetic approach has been used for the preparation of a polymeric pro-drug for targeted drug delivery (Scheme 24) [32]. The graft copolymer E bearing the polythiophene main chain and poly(L-lysine) graft chains was synthesized by the palladium-catalyzed coupling polymerization of the macromonomer D bearing the 1,4-dibromothiophene moiety at the terminal, followed by the acid-catalyzed removal of the t-butoxycarbonyl group in the side chain.…”

Section: Applications In Macromolecular Architecturesmentioning

confidence: 99%

“…A similar synthetic approach has been used for the preparation of a polymeric pro-drug for targeted drug delivery ( Scheme 24 ) [ 32 ]. The graft copolymer E bearing the polythiophene main chain and poly(L-lysine) graft chains was synthesized by the palladium-catalyzed coupling polymerization of the macromonomer D bearing the 1,4-dibromothiophene moiety at the terminal, followed by the acid-catalyzed removal of the t -butoxycarbonyl group in the side chain.…”

Section: Applications In Macromolecular Architecturesmentioning

confidence: 99%

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Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid Urethanes

Endō

Sudo

2020

Biomedicines

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Polypeptide synthesis was accomplished using the urethane derivatives of amino acids as monomers, which can be easily prepared, purified, and stored at ambient temperature without the requirement for special precautions. The urethanes of amino acids are readily synthesized by the N-carbamoylation of onium salts of amino acids using diphenyl carbonate (DPC). The prepared urethanes are then efficiently cyclized to produce amino acid N-carboxyanhydrides (NCAs). Thereafter, in the presence of primary amines, the ring-opening polymerization (ROP) of NCAs is initiated using the amines, to yield polypeptides with controlled molecular weights. The polypeptides have propagating chains bearing reactive amino groups and initiating chain ends endowed with functional moieties that originate from the amines. Aiming to benefit from these interesting characteristics of the polypeptide synthesis using the urethanes of amino acids, various macromolecular architectures containing polypeptide components have been constructed and applied as biofunctional materials in highly efficient antifouling coatings against proteins and cells, as biosensors for specific molecules, and in targeted drug delivery.

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Section: Applications In Macromolecular Architecturesmentioning

confidence: 99%

Section: Applications In Macromolecular Architecturesmentioning

confidence: 99%

Section: Applications In Macromolecular Architecturesmentioning

confidence: 99%

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Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid Urethanes

Endō

Sudo

2020

Biomedicines

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“…[10][11][12][13] Polypeptides play a pivotal role in biological, medical, and pharmaceutical research. Therefore, the synthesis of such polypeptide structures has been a major focus of organic chemistry for over a century.…”

Section: Introductionmentioning

confidence: 99%

Phosgene‐Free Synthesis of Poly(l‐cysteine) Containing Styrene Moiety as a Reactive Function

Akbulut

Yamada

Endō

2017

Macro Chemistry & Physics

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for extreme impurity-free conditions to achieve the polymerization without side reactions, the sensitive nature of NCA for heating, and moisture are major drawbacks of its production toward practical use and chemical modifications. Thus, research on the development of alternative procedures [16][17][18][19][20][21][22] to obtain polypeptides from nontoxic materials with high purity and stability through the development of new synthetic strategies is of great interest in this research area.Quite recently, we have developed a newly synthetic route for the production of NCAs and polypeptides where the intramolecular cyclization of activated urethane derivatives of α-amino acids followed by the ring-opening polymerization of the in situ formed NCA led to the production of polypeptides without the use and production of any toxic compounds. [23][24][25] In this synthetic method, these activated urethane derivatives were readily synthesized by a twostep procedure: (i) the transformation of α-amino acids into the corresponding ammonium salts and (ii) the smooth reaction of N-carbamylation of the salts with diphenyl carbonate (DPC) to afford the corresponding urethane compound. Therefore, polypeptides synthesis using the urethane derivative, which are stable for moisture or heating and available for storing several months at room temperature, is more feasible than traditional ring opening polymerization of highly reactive NCAs in aspect of potential applicability for the convenient preparation of various kinds of functional polypeptides.The side-chain modification of polypeptides is an important tool for creating therapeutic conjugates, generating novel protein constructs and probing natural systems. Research on the combination of some reactive groups with amino acids and the discovery of different initiator systems for NCA-based peptide synthesis have emerged as one of the most popular topics in the synthesis of unique macromolecular architectures in recent years. [26][27][28] However, the sensitive nature of NCAs derivatives only allows two fundamental routes for the preparation of sidechain-modified polypeptides: (i) the prepolymerization modification route where the modified amino acid can be converted to NCA derivatives and then polymerized and (ii) the postpolymerization modification route where a chemically reactive moiety bearing polypeptide on the side chain can react with various functional reagents. [24,29] Polypeptides A novel approach toward the synthesis of N-carboxyanhydride precursor available for postpolymerization modification has been developed through a phosgene-free method offering a safer and green way to obtain peptide monomers under exceptionally mild reaction conditions. The homo and co-polypeptide bearing a reactive styrene moiety are prepared through the polycondensation of N-phenoxycarbonyl derivative of 4-vinylbenzyl-l-cysteine (NPC-Cys(VBn)) with the elimination of phenol and CO 2 while varying the feed ratio to the primary amine initiator to give the corresponding polypeptides without any d...

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“…Scientists focused on developments of targeting and bioimaging probes in improved properties [1][2][3]. Fluorophores, which are used in visualization of cells, can be divided some main groups such as organic dyes, conjugated polymers and inorganic-organic nanostructures [2][3][4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Preparation of Quantum Dot Bioconjugates as Fluorescence Probe for Targeting and Visualization of Cells

Demirkol¹,

Timur²

2017

HJBC

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Ö ZB urada, hedeflenmiş hücresel görüntüleme için suda çözünür kuantum noktaların (QD) biyokonjugasyonu ve uygulamaları gerçekleştirilmiştir. Kanser hücrelerine nanoyapıların hedeflenmesi için anti-c-ErbB2 antikoru QD'lara bağlanmıştır. QD'lar ve anti-c-ErbB2/QD biyokonjugatları floresans/UV-Görünür bölge spektroskopisi ve hidrodinamik boyut ölçümleri ile karakterize edilmiştir. Hücre canlılığına QD'lar ve antic-ErbB2/QD biyokonjugatlarının etkisi MTT denemeleri kullanılarak gerçekleştirilmiştir. Anti-c-ErbB2/QD biyokonjugatlarının hedefleme etkinliğini gözlemlemek için, floresans mikroskopi kullanılmıştır. Hücreleri görüntüleme ve iyi gerçekleştirilmiş hedeflemenin ispatı olarak anti-c-ErbB2 konjuge edilen QD'lar ile daha yüksek hücre afiniteleri elde edilmiştir. Anahtar KelimelerKuantum noktalar, biyokonjugasyon, anti-c-ErbB2, hücre hedefleme. A B S T R A C TH ere, the bioconjugation and application of water-soluble quantum dots (QDs) for targeted cellular imaging were investigated. Human anti-c-ErbB2 antibodies were bound to QDs for the targeting of these nanostructures towards the cancer cells. QDs and anti-c-ErbB2/QD bioconjugates were characterized by fluorescence and UV-Vis spectroscopy and hydrodynamic sizing. The effect of QDs and anti-c-ErbB2/QD bioconjugates on cell viability was evaluated using an MTT assay. To observe targeting efficiency of anti-c-ErbB2/QD bioconjugates, fluorescence microscopy and was performed. Higher cell affinities were obtained by anti-c-ErbB2-conjugated QDs which is an evidence that these are well-suited for targeting and imaging of cells.

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Complex Structured Fluorescent Polythiophene Graft Copolymer as a Versatile Tool for Imaging, Targeted Delivery of Paclitaxel, and Radiotherapy

Cited by 20 publications

References 59 publications

Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid Urethanes

Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid Urethanes

Phosgene‐Free Synthesis of Poly(l‐cysteine) Containing Styrene Moiety as a Reactive Function

Preparation of Quantum Dot Bioconjugates as Fluorescence Probe for Targeting and Visualization of Cells

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