Synthesis of polypeptide conjugated with near infrared fluorescence probe and doxorubicin for pH-responsive and image-guided drug delivery

Xing, Tao; Yang, Xianzhu; Wang, Rui; Lai, Bin; Liu, Yan

doi:10.1039/c2jm35627a

Cited by 26 publications

(28 citation statements)

References 48 publications

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“…Thus, PTX conjugated to P(L‐Glu) is inactive and needs to be degraded within the cell to provide its therapeutic effect . Polymer conjugates of Doxorubicin (Dox), also require in‐cell degradation, as the anti‐tumorigenic effect requires Dox interaction with the DNA and the polymer conjugate cannot penetrate the nuclear membrane . However, polymer conjugation prevents Dox‐related cardiotoxic effects .…”

Section: Key Design Features Of Polypeptide Conjugatesmentioning

confidence: 99%

“…Applicability of synthetic polypeptide‐based conjugate development has reached multiple areas of medicine, including the elaboration of anti‐microbial, anti‐virus, anti‐cancer, anti‐diabetic, anti‐apoptotic, and anti‐tuberculosis drugs, magnetic resonance imaging (MRI) agents, and theranostic agents . The great advantage of polypeptides is their structural versatility which allows the generation of a myriad of architectures with differential physico‐chemical features, allowing high loading rates and the possibility to conjugate drugs of different origin, polarity, and hydrophilicity.…”

Section: Introductionmentioning

confidence: 99%

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Polypeptide‐Based Conjugates as Therapeutics: Opportunities and Challenges

Zagorodko

Arroyo‐Crespo

Nebot

et al. 2016

Macromolecular Bioscience

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Synthetic polypeptides or polyamino acids have become a useful and multifunctional platform in advanced drug delivery studies. Nonetheless, the full potential of these systems has yet to be achieved. The final structure of polypeptide conjugates and their in vivo behavior are dependent on an extraordinarily complex pattern of interconnected physico-chemical and structural parameters, making sophisticated directional design of such systems difficult and often unachievable. In this review, the authors aim to discuss the role of these parameters in the successful design of different drug delivery architectures and to delineate some basic correlations between structure, properties, and the biological behavior of polypeptide-based conjugates.

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Section: Key Design Features Of Polypeptide Conjugatesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Polypeptide‐Based Conjugates as Therapeutics: Opportunities and Challenges

Zagorodko

Arroyo‐Crespo

Nebot

et al. 2016

Macromolecular Bioscience

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“…24 The specific synthesis route is shown in Scheme S1. 24 The specific synthesis route is shown in Scheme S1.…”

Section: Synthesis Of the Near Infrared Aminocyanine Dyementioning

confidence: 99%

“…24 The final polymer was characterized by means of NMR, FTIR, GPC, DLS, UV-vis and fluorescence spectrophotometers. After the triblock polymer was synthesized, a NIR dye aminocyanine was attached to the chain end by esterifaction using EDC as the dehydrant.…”

Section: Introductionmentioning

confidence: 99%

An amphiphilic block copolymer conjugated with carborane and a NIR fluorescent probe for potential imaging-guided BNCT therapy

Ruan

Liu

et al. 2016

Polym. Chem.

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A carborane-containing triblock copolymer conjugated with a near infrared (NIR) fluorescence probe has been synthesized via reversible addition fragmentation chain transfer (RAFT), ring open polymerization (ROP), and conjugations of a cyanine NIR dye. Reactions were traced by means of 1 H-NMR, GPC and FT-IR. The NIR amphiphilic copolymer with polycaprolactone and polycarborane as hydrophobic segments and poly(ethylene glycol)methyl ether methacrylate as the hydrophilic segment could self-assemble into micelles in aqueous solution, and was characterized by means of DLS and TEM. In the copolymer, carborane works as a boron neutron capture therapy (BNCT) agent while the aminocyanine (Cy) dye works as a NIR bioimaging agent, and the nanoparticles of the copolymers are a potential theranostic BNCT system for cancer therapy, which was supported by MTT experiments and in vitro fluorescence microscopy studies.Scheme 1 Internalization of the carborane-containing NIR polymeric nanoparticles followed by imaging guided BNCT therapy. † Electronic supplementary information (ESI) available. See

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“…Fluorescent polymeric amphiphilic materials acts as a superior probe for live cell imaging compared to the small molecular probe because of their longer blood circulation time and their ability to preferentially accumulate in tumors . Thus, polymeric amphiphiles were used for detecting live cells and plays an important role for their subsequent treatment . Besides this, the polymer could serve as a protection layer for the fluorescent group inside the nanoprobe, eliminating the interaction between fluorescent group and solvent or even blood components, thus prolonging its fluorescent lifetime in vitro.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Amphiphilic PEG‐Peptide‐PEG Triblock Conjugate Micelles for Cell Imaging

Paira

Saha

Banerjee

et al. 2014

Macromolecular Bioscience

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A fluorescent amphiphilic poly(ethylene glycol)-peptide-fluorophore-peptide-poly(ethylene glycol) (PEG-Pep-F-Pep-PEG) triblock conjugate with a hydrophobic fluorophore moiety at the centre of the chain is synthesized by "grafting to" technique based on Schiff-base coupling chemistry. The conjugate is characterized by nuclear magnetic resonance (NMR), circular dichroism (CD), and fluorescence spectroscopy techniques. The aqueous solution of the triblock conjugate emits blue light and exhibits a fluorescence emission band at 430 nm. The amphiphilic conjugate molecules undergo self-assembly into micelles (D ≈ 15-20 nm) in aqueous solution as confirmed from transmission electron microscopy (TEM) and dynamic light scattering (DLS). The critical aggregation concentration is determined by pyrene fluorescence assay and is found to be 0.051 mg mL(-1) . The highly stable and low toxic fluorescent PEG-Pep-F-Pep-PEG conjugate micelles are used for imaging of HeLa cells.

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Synthesis of polypeptide conjugated with near infrared fluorescence probe and doxorubicin for pH-responsive and image-guided drug delivery

Cited by 26 publications

References 48 publications

Polypeptide‐Based Conjugates as Therapeutics: Opportunities and Challenges

Polypeptide‐Based Conjugates as Therapeutics: Opportunities and Challenges

An amphiphilic block copolymer conjugated with carborane and a NIR fluorescent probe for potential imaging-guided BNCT therapy

Fluorescent Amphiphilic PEG‐Peptide‐PEG Triblock Conjugate Micelles for Cell Imaging

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