The synthesis and targeting of PPP-type copolymers to breast cancer cells: Multifunctional platforms for imaging and diagnosis

Colak, Demet Goen; Cianga, Ioan; Demirkol, Dilek Odaci; Kozgus, Ozge; Medine, E. Ilker; Sakarya, Serhan; Ünak, Perıhan; Timur, Suna; Yaǧcı, Yusuf

doi:10.1039/c2jm30692a

Cited by 33 publications

(45 citation statements)

References 54 publications

(57 reference statements)

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“…In the 1 H-NMR spectrum, characteristic benzyl amine protons appear at 1.96 ppm as a broad peak which shifts to 4.71 ppm after D 2 O exchange ( Figure 2S, Supplementary Information). 34 In our approach, the solubility is achieved without considerable negative effect on the fluorescence properties of PPP backbone. This value should be taken as the minimum estimation 63-64 since the polymer has hydrophilic side chain and comb-like structure and the GPC system was calibrated with linear polystyrene standards.…”

Section: Synthesis Of Ppp With Primary Amine Groups and Peg Side Chainsmentioning

confidence: 98%

Synthesis, characterization and targeted cell imaging applications of poly(p-phenylene)s with amino and poly(ethylene glycol) substituents

et al. 2015

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A novel approach for bioconjugation associated with fluorescent conjugated polymer is demonstrated. For this purpose, a conjugated polymer, poly(p-phenylene) (PPP), with lateral substituents, namely primary amino groups and poly(ethylene glycol) (PEG) chains, as potential building block for polymer bioconjugates was synthesized and characterized. The synthesis was achieved through Suzuki polycondensation reaction in the presence of Pd(PPh3)4 catalyst by using independently prepared PEG and amino functional dibromo benzenes in conjunction with benzene diboronic acid. For the evaluation of the bioactive PPP labeled with folic acid (FA) as a potential targeted cell imaging probe, HeLa and A549 cancer cells were used. Cytotoxicity assay showed that the polymer was not toxic to the both cells. Additionally, the fluorescence images showed that, depending on the level of the FA receptors on the cell surfaces, the fluorescent intensity in HeLa cells was obviously higher than A549 cells when treated with FA conjugated PPP-NH2-g-PEG polymer. The resulting FA/PPP-NH2-g-PEG conjugate was successfully used as bioconjugate for targeting and specifically imaging of FA receptor positive HeLa human cervices cancer cells.

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Section: Synthesis Of Ppp With Primary Amine Groups and Peg Side Chainsmentioning

confidence: 98%

Synthesis, characterization and targeted cell imaging applications of poly(p-phenylene)s with amino and poly(ethylene glycol) substituents

et al. 2015

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“…For example, Yagci et al . synthesized 2 by copolymerizing dibromo‐functionalized PEGylated monomer and carboxylated monomer with 1,4‐phenylenediboronic acid using Pd(PPh 3 ) 4 as the catalyst 28 . 2 was conjugated with antibody or protein for targeted cell imaging.…”

Section: Synthesis Of Functionalized Cpesmentioning

confidence: 99%

“…To reduce nonspecific interactions and to enhance water solubility, Yagci et al . also synthesized a PEGylated CPE 2 , but via a macromonomer approach, in which the monomer carrying a PEG 550 side chain was synthesized first 28. Anti‐Metadherin (Anti‐MTDH), an antibody that selectively binds with the antigen MTDH, and phaseolus vulgaris leukoagglutinin (PHA‐L), a lectin that selectively binds with β‐1,6 branched oligosaccharides, were chosen as recognition elements, and were further bioconjugated with 2 to yield three probes: 2 ‐Anti‐MTDH, 2 ‐PHA‐L, and Anti‐MTDH‐ 2 ‐PHA‐L.…”

Section: Imagingmentioning

confidence: 99%

Functionalized Conjugated Polyelectrolytes for Biological Sensing and Imaging

Zhan

Liu

2016

The Chemical Record

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Conjugated polyelectrolytes (CPEs) are macromolecules with highly delocalized π-conjugated backbones and charged side chains, which are unique types of active materials, with wide applications in optoelectronics, sensing, imaging, and therapy. By attaching specific groups (e.g., recognition elements, magnetic resonance (MR) contrast agents, gene carriers, and drugs) to the side chain or backbone of CPEs, functionalized CPEs have been developed and used for specific biological applications. In this account, we summarize the recent progress of functionalized CPEs with respect to their synthesis and biomedical applications. Future perspectives are also discussed at the end.

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“…Ever‐expanding research activity has focused on the development of fluorescence‐based water soluble organic conjugated polymers relying on π‐electron delocalization features. Among the vast number of π‐conjugated polymers, poly(p‐phenylene) (PPP) and its derivatives are the most appealing polymers in terms of their relatively good electrochemical, electrochromic, luminescent, and shielding properties …”

Section: Introductionmentioning

confidence: 99%

“…Polymers and co‐polymers such as PPP, polyethylene glycol (PEG), N ‐(2‐hydroxypropyl)‐methacrylamide copolymer (HPMA), poly‐ l ‐glutamic acid (PGA), poly(methyl methacrylate) (PMMA), and poly(2‐hydroxyethyl methacrylate) (PHEMA) are widely used as drug carrier scaffolds . Owing to various synthesis strategies, it is possible to introduce functional groups which enable further modification of the polymers with targeting and/or imaging agents . One of the main strategies used is carbodiimide‐mediated coupling reaction between primary amino groups and carboxyl groups between polymer and molecule of interest to be conjugated.…”

Section: Introductionmentioning

confidence: 99%

Poly(p‐phenylene) with Poly(ethylene glycol) Chains and Amino Groups as a Functional Platform for Controlled Drug Release and Radiotherapy

Guler

Akbulut

Barlas

et al. 2016

Macromolecular Bioscience

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Conventional cancer treatments such as chemotherapy, radiotherapy, or combination of these two result in side effects, which lower the quality of life of the patients. To overcome problems with these methods, altering the drug properties by conjugating them to carrier polymers has emerged. Such polymeric carriers also hold the potential to make tumor cells more sensitive to radiation therapy. Herein, poly(p-phenylene) (PPP) polymer with poly(ethylene glycol) (PEG) chains and primary amino groups (PPP-NH2 -g-PEG) is synthesized and conjugated with anticancer drug Doxorubicin (DOX). pH dependent drug release experiments are performed at pH 5.3 and pH 7.4, respectively. Cell viability studies on human cervix adenocarcinoma cells show that lower doses of DOX inhibit cell proliferation when conjugated with nontoxic doses of PPP-NH2 -g-PEG polymer. Additionally, PPP-NH2 -g-PEG/Cys/DOX bioconjugate significantly increases radiosensitive properties of DOX. It is possible to use lower doses of DOX when conjugated to PPP-NH2 -g-PEG in combination with radiotherapy.

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The synthesis and targeting of PPP-type copolymers to breast cancer cells: Multifunctional platforms for imaging and diagnosis

Cited by 33 publications

References 54 publications

Synthesis, characterization and targeted cell imaging applications of poly(p-phenylene)s with amino and poly(ethylene glycol) substituents

Synthesis, characterization and targeted cell imaging applications of poly(p-phenylene)s with amino and poly(ethylene glycol) substituents

Functionalized Conjugated Polyelectrolytes for Biological Sensing and Imaging

Poly(p‐phenylene) with Poly(ethylene glycol) Chains and Amino Groups as a Functional Platform for Controlled Drug Release and Radiotherapy

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