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Drug Delivery

The importance of drug delivery to chemists, medicinal and otherwise, has increased since the advent of integrated drug discovery processes. Physicochemical and biological barriers, pathways for drug delivery, formulation, pharmacokinetic and pharmacodynamic issues, metabolism, and cell culture models used in studying drug delivery are just some of the topics that make drug delivery an exciting field for researchers.

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Gd-Hybridized Plasmonic Au-Nanocomposites Enhanced Tumor-Interior Drug Permeability in Multimodal Imaging-Guided Therapy

Gd‐Hybridized Plasmonic Au‐Nanocomposites Enhanced Tumor‐Interior Drug Permeability in Multimodal Imaging‐Guided Therapy

An original gadolinium-hybridized plasmonic gold nanocomposite is fabricated to provide an insightful and attractive strategy to overcome both the physiological and pathological barriers of tumor, and increase the transportation and permeability of imaging agents and drugs in tumor interior for achieving high-sensitive multimodal imaging and simultaneously improving the therapeutic efficacy of cancer.

[Communication]
Jing Wang, Jing Liu, Ying Liu, Liming Wang, Mingjing Cao, Yinglu Ji, Xiaochun Wu, Yingying Xu, Bing Bai, Qing Miao, Chunying Chen, Yuliang Zhao
Adv. Mater., August 26, 2016, DOI: 10.1002/adma.201603114. Read article

Macrophages as Active Nanocarriers for Targeted Early and Adjuvant Cancer Chemotherapy

Macrophages as Active Nanocarriers for Targeted Early and Adjuvant Cancer Chemotherapy

The critical considerations and recent advancements in using macrophages as carriers for nanomedicines are reviewed. Key factors determining the efficacy of macrophage-based nanomedicines are highlighted. The goal of this review is to contribute to the rational design of EPR-independent tumor-targeting active nanomedicines for targeted early and adjuvant cancer chemotherapy.

[Review]
Jingxing Si, Shiqun Shao, Youqing Shen, Kai Wang
Small, August 25, 2016, DOI: 10.1002/smll.201601282. Read article

Multifunctional Mixed Micelles for Efficient Docetaxol Delivery for Cancer Therapy

Multifunctional Mixed Micelles for Efficient Docetaxol Delivery for Cancer Therapy

Critical micelles concentrate on cancer: Mixed micelles made of a disulfide-linked drug–polymer conjugate and a polymer–folate conjugate were tested as a targeted, redox-sensitive delivery system (PEG–PBLG-SS-DTX/PEG–FA) for the anticancer drug docetaxel (DTX). The results showed improved anticancer efficiency of DTX delivered by these micelles to folate-receptor-expressing MCF-7 cancer cells.

[Full Paper]
Pei Zhang, Wenxiu He, Huiyuan Zhang, Chunzhi Huang, Dujuan Zhao, Yuxia Luan
ChemPlusChem, August 25, 2016, DOI: 10.1002/cplu.201600363. Read article

Inflammation-Triggered Cancer Immunotherapy by Programmed Delivery of CpG and Anti-PD1 Antibody

Inflammation‐Triggered Cancer Immunotherapy by Programmed Delivery of CpG and Anti‐PD1 Antibody

Inflammation-triggered combination delivery of anti-PD-1 antibody and CpG oligodeoxynucleotides (CpG ODNs) has been demonstrated to prevent cancer relapse utilizing postsurgical inflammatory response. The controlled release of anti-PD1 and CpG ODN by CpG DNA-based "nano-cocoons" can induce considerable immune response, which in turn significantly prolongs the survival time of mice.

[Communication]
Chao Wang, Wujin Sun, Grace Wright, Andrew Z. Wang, Zhen Gu
Adv. Mater., August 25, 2016, DOI: 10.1002/adma.201506312. Read article

Exploiting Noncovalent Interactions in an Imine-Based Covalent Organic Framework for Quercetin Delivery

Exploiting Noncovalent Interactions in an Imine‐Based Covalent Organic Framework for Quercetin Delivery

Covalent organic frameworks (COFs) are a new class of nanoporous polymeric vector showing promise as drug-delivery vehicles with high loading capacity and biocompatibility. The interaction between the carrier and the cargo is specifically tailored on a molecular level by H-bonding. Cell-proliferation studies indicate higher efficacy of the drug in cancer cells by nanocarrier delivery mediated by the COF.

[Communication]
Vijay S. Vyas, Medhavi Vishwakarma, Igor Moudrakovski, Frederik Haase, Gökcen Savasci, Christian Ochsenfeld, Joachim P. Spatz, Bettina V. Lotsch
Adv. Mater., August 22, 2016, DOI: 10.1002/adma.201603006. Read article

Quantum Dot - Based Nanotools for Bioimaging, Diagnostics, and Drug Delivery

Quantum dots (QDs) are highly fluorescent nanocrystals that exhibit advanced photophysical and spectral properties: high brightness and stability against photobleaching accompanied by broad excitation and narrow emission spectra. Commonly, water-soluble QDs functionalized with biomolecules, such as proteins, peptides, antibodies, and drugs are used for biomedical applications. Advantages of QD-based approaches to immunohistochemical analysis, single-molecule tracking, and in vivo imaging, over traditional methods employing organic dyes and fluorescent proteins have been demonstrated. Unique spectral properties of QDs offer opportunities for designing systems for multiplexed analysis using multicolor imaging for simultaneous detection of multiple targets. Conjugation of drug molecules with QDs or their incorporation into QD-based drug-delivery particles makes it possible to perform real-time drug tracking and carry out image-guided therapy. Due to tunability of their photophysical properties, QDs emitting in the near-infrared spectral region have become an attractive tool for deep-tissue mono- and multiphoton in vivo imaging. Here, we review recent achievements in QD applications for bioimaging, targeting, and drug delivery, as well as challenges related to their toxicity and non-biodegradability. The key issues related to the perspectives of further development of advanced QD-based nanotools are addressed in the Summary and Outlook Section.

[Review]
Regina Bilan, Alyona Sukhanova, Igor Nabiev
ChemBioChem, August 18, 2016, DOI: 10.1002/cbic.201600357. Read article

Benzoic-Imine-Based Physiological-pH-Responsive Materials for Biomedical Applications

Benzoic‐Imine‐Based Physiological‐pH‐Responsive Materials for Biomedical Applications

Block party: A dynamic covalent benzoic imine bond has been developed as a highly pH-sensitive building block for the construction of polymeric biomedical systems.

[Focus Review]
Xiaozhong Qu, Zhenzhong Yang
Chem. Asian J., August 18, 2016, DOI: 10.1002/asia.201600452. Read article

A pH-Sensitive Phospholipid Polymeric Prodrug Based on Branched Polyethylenimine for Intracellular Drug Delivery

A pH‐Sensitive Phospholipid Polymeric Prodrug Based on Branched Polyethylenimine for Intracellular Drug Delivery

A biomimic pH-sensitive polymeric prodrug based on branched polyethylenimine-graft-12-acryloyloxy dodecyl phosphorylcholine and 6-maleimidocaproyl-doxorubicin is developed successfully. This polymeric prodrug can assemble into micelles with phosphorylcholine shells in aqueous solution and is stable in the physiological environment. Moreover, doxorubicin can be released from the prodrug micelles upon cancer cell intracellular acidic stimulus, which inhibits the proliferation of cancer cells efficiently.

[Full Paper]
Haibo Wang, Junjie Xiong, Gongyan Liu, Yunbing Wang
Macromol. Chem. Phys., August 16, 2016, DOI: 10.1002/macp.201600261. Read article

Acid-Labile Copolymer Micelles Cross-Linked by a Twin Ortho Ester Cross-Linking Agent: Synthesis, Characterization, and Evaluation

Acid‐Labile Copolymer Micelles Cross‐Linked by a Twin Ortho Ester Cross‐Linking Agent: Synthesis, Characterization, and Evaluation

In this paper, a series of poly(ethylene glycol)-block-poly(N-succinimidyl methacrylate) (PEG-b-PNSM) with different length of PNSM is synthesized and self-assembled to give non-cross-linked micelles. The cross-linked micelles (CLM) are obtained by adding a pH-sensitive cross-linker, 2-{4-[2-(2-amino-ethoxy)-[1,3] dioxolan-4-ylmethoxymethyl]-[1,3]dioxolan-2-yloxy}-ethylamine. PTX is incorporated into CLM, and released at accelerated rate under mildly acidic pH (pH = 5), resulting in an appropriate cytotoxicity against MCF-7 cells.

[Full Paper]
Xin Wang, Xiaojing Zhou, Jun Wang, Zhipeng Cao, Lei Zhang, Rupei Tang
Macromol. Chem. Phys., August 11, 2016, DOI: 10.1002/macp.201600234. Read article

Recent Advances of Using Hybrid Nanocarriers in Remotely Controlled Therapeutic Delivery

Recent Advances of Using Hybrid Nanocarriers in Remotely Controlled Therapeutic Delivery

The development of hybrid biomaterials has been attracting great attention in the design of materials for biomedicine. The most recent advances of using hybrid nanovehicles as remotely controlled therapeutic delivery system are summarized.

[Review]
Zibiao Li, Enyi Ye, David, Rajamani Lakshminarayanan, Xian Jun Loh
Small, August 02, 2016, DOI: 10.1002/smll.201601129. Read article

Cationic DOPC–Detergent Conjugates for Safe and Efficient in Vitro and in Vivo Nucleic Acid Delivery

Cationic DOPC–Detergent Conjugates for Safe and Efficient in Vitro and in Vivo Nucleic Acid Delivery

Pulmonary delivery: Biolabile DOPC–C12E4 conjugates were developed as nucleic acid carriers for in vitro and in vivo gene delivery. Their transfection efficiency and safety profile in mouse lung reflect their biodegradability and the surface active properties of the detergent released in situ. Thus, they might act as DNA carriers for gene therapy local administration through the airways.

[Full Paper]
Philippe Pierrat, Anne Casset, Pascal Didier, Dimitri Kereselidze, Marie Lux, Françoise Pons, Luc Lebeau
ChemBioChem, August 02, 2016, DOI: 10.1002/cbic.201600302. Read article

Synthesis of Degradable Poly[(Ethylene Glycol)-co-(Glycolic Acid)] via the Post-Polymerization Oxyfunctionalization of Poly(Ethylene Glycol)

Synthesis of Degradable Poly[(Ethylene Glycol)‐co‐(Glycolic Acid)] via the Post‐Polymerization Oxyfunctionalization of Poly(Ethylene Glycol)

To enhance the limited degradability of poly(ethylene glycol) (PEG), a straightforward method of synthesizing poly[(ethylene glycol)-co-(glycolic acid)] is described. Hydrolytically labile ester groups are directly incorporated into the polymer backbone via a ruthenium catalyzed C–H oxyfunctionalization reaction with minimal molecular-weight reduction under some conditions. The method should facilitate access to a variety of degradable PEG platforms.

[Communication]
Di Liu, Christopher W. Bielawski
Macromol. Rapid Commun., July 27, 2016, DOI: 10.1002/marc.201600336. Read article

Simultaneously Photo-Cleavable and Activatable Prodrug-Backboned Block Copolymer Micelles for Precise Anticancer Drug Delivery

Simultaneously Photo‐Cleavable and Activatable Prodrug‐Backboned Block Copolymer Micelles for Precise Anticancer Drug Delivery

A simultaneously photo-cleavable and activatable prodrug-backboned block copolymer (BCP) micelle strategy is demonstrated. Without light treatment, the micelles stay silent and inactivated, being biocompatible to normal tissues. Concurrent chain cleavage of BCP micelles and the activation of Pt(IV) prodrug could be temporally and spatially triggered by UV or even visible light for precise anticancer drug delivery.

[Communication]
Dongfang Zhou, Jinshan Guo, Gloria B. Kim, Jizhen Li, Xuesi Chen, Jian Yang, Yubin Huang
Adv. Healthcare Mater., July 27, 2016, DOI: 10.1002/adhm.201600470. Read article

pH-Triggered Sustained Drug Delivery from a Polymer Micelle having the β-Thiopropionate Linkage

pH‐Triggered Sustained Drug Delivery from a Polymer Micelle having the β‐Thiopropionate Linkage

An effective design for pH-responsive polymeric micelle is demonstrated and utilized as a nanocontainer for intracellular sustained drug delivery in cancer cells. The strategy relies on slow hydrolysis of the as yet unexplored β-thiopropionate linkage connecting the hydrophobic chains to the polymer backbone.

[Communication]
Prithankar Pramanik, Debdatta Halder, Siddhartha Sankar Jana, Suhrit Ghosh
Macromol. Rapid Commun., July 22, 2016, DOI: 10.1002/marc.201600260. Read article

A Biodegradable and Amphiphilic Linear-Dendritic Copolymer as a Drug Carrier Platform for Intracellular Drug Delivery

A Biodegradable and Amphiphilic Linear‐Dendritic Copolymer as a Drug Carrier Platform for Intracellular Drug Delivery

A biodegradable linear-dendritic copolymer as a drug delivery platform is synthesized successfully. The polymer drug delivery system is internalized effectively by cancer cells and releases DOX rapidly at endosomal pH.

[Full Paper]
Haibo Wang, Yan Wu, Gongyan Liu, Zongliang Du, Xu Cheng
Macromol. Chem. Phys., July 21, 2016, DOI: 10.1002/macp.201600269. Read article

MicroRNA-Responsive Drug Release System for Selective Fluorescence Imaging and Photodynamic Therapy In Vivo

MicroRNA‐Responsive Drug Release System for Selective Fluorescence Imaging and Photodynamic Therapy In Vivo

MicroRNA-responsive drug release system based on the chlorin e6 conjugated peptide nucleic acid (Ce6-PNA) and the dextran coated reduced graphene oxide nanocolloid (Dex-RGON) is developed exploiting oncogenic microRNA-21 as an internal stimulus for initiating drug release in cancer treatment. The platform shows sequence-specific fluorescence in response to overexpressed microRNA-21 in cancer cells and selective cytotoxic effect for tumor growth inhibition in vivo.

[Full Paper]
Ji-Seon Lee, Seongchan Kim, Hee-Kyung Na, Dal-Hee Min
Adv. Healthcare Mater., July 07, 2016, DOI: 10.1002/adhm.201600328. Read article

Endocytosis Mechanism of Nano Metal-Organic Frameworks for Drug Delivery

Endocytosis Mechanism of Nano Metal‐Organic Frameworks for Drug Delivery

The study of the uptake mechanisms and final fate of a promising metal-organic framework (MOF) is a crucial step for optimizing these materials for drug delivery applications. UiO-66 particles of 260 nm are able to partially bypass the acidic degradation in the lysosomes whereas particles of 150 nm are destroyed in this compartment.

[Full Paper]
Claudia Orellana-Tavra, Sergio A. Mercado, David Fairen-Jimenez
Adv. Healthcare Mater., July 06, 2016, DOI: 10.1002/adhm.201600296. Read article

Preparation of a Noncytotoxic Hemocompatible Ion Gel by Self-Polymerization of HEMA in a Green Deep Eutectic Solvent

Preparation of a Noncytotoxic Hemocompatible Ion Gel by Self‐Polymerization of HEMA in a Green Deep Eutectic Solvent

Self-polymerization of 2-hydroxyethylmethacrylate in a natural deep eutectic solvent in the presence of indomethacin resulted the formation of a drug-immobilized ion gel. The ion gel thus obtained is found to be stable in gastrointestinal fluid pH and sustained release in simulated lower intestinal fluid at physiological human body temperature of the drug is recorded.

[Full Paper]
Chandrakant Mukesh, Kapil K. Upadhyay, Ranjitsinh V. Devkar, Nishith A. Chudasama, Gopalkumar G. Raol, Kamalesh Prasad
Macromol. Chem. Phys., June 20, 2016, DOI: 10.1002/macp.201600122. Read article

Molecular Polymer Brushes in Nanomedicine

Molecular Polymer Brushes in Nanomedicine

Molecular polymer brushes present an emerging class of polymer nanostructures with the potential to address persevering problems in nanomedicine. Recent improvements in the synthesis of these polymeric architectures allowed the tailoring of sophisticated nanomaterials for applications in drug and gene delivery, as well as the design of new imaging probes and prototype nanomaterials.

[Talent]
Markus Müllner
Macromol. Chem. Phys., May 06, 2016, DOI: 10.1002/macp.201600086. Read article

Evaluation of New Palladium Cages as Potential Delivery Systems for the Anticancer Drug Cisplatin

Evaluation of New Palladium Cages as Potential Delivery Systems for the Anticancer Drug Cisplatin

Self-assembled metallocages of the type Pd2L4 are promising delivery vehicles for the anticancer drug cisplatin. Drug encapsulation was proven by different methods, and the biological properties were investigated in cancer cells also with the aid of fluorescence microscopy. The host–guest systems possess improved toxic effects in ovarian cancer cells compared to cisplatin while having limited toxicity in liver tissues (see scheme).

[Communication]
Andrea Schmidt, Viviana Molano, Manuela Hollering, Alexander Pöthig, Angela Casini, Fritz E. Kühn
Chem. Eur. J., January 12, 2016, DOI: 10.1002/chem.201504930. Read article.

Targeting Innate Immunity with dsRNA-Conjugated Mesoporous Silica Nanoparticles Promotes Antitumor Effects on Breast Cancer Cells

Targeting Innate Immunity with dsRNA-Conjugated Mesoporous Silica Nanoparticles Promotes Antitumor Effects on Breast Cancer Cells

Messenger of death: A new drug-delivery system based in mesoporous silica nanoparticles capped with the synthetic double stranded RNA polyinosinic–polycytidylic acid (poly(I:C)) for targeting breast carcinoma cells is reported (see figure).

[Communication]
Amelia Ultimo, Cristina Giménez, Pavel Bartovsky, Elena Aznar, Félix Sancenón, M. Dolores Marcos, Pedro Amorós, Ana R. Bernardo, Ramón Martínez-Máñez, Ana M. Jiménez-Lara, José R. Murguía
Chem. Eur. J., January 7, 2016, DOI: 10.1002/chem.201504629. Read article.

A Divalent PAMAM-Based Matrix Metalloproteinase/Carbonic Anhydrase Inhibitor for the Treatment of Dry Eye Syndrome

A Divalent PAMAM-Based Matrix Metalloproteinase/Carbonic Anhydrase Inhibitor for the Treatment of Dry Eye Syndrome

It’s all in the delivery: The inhibitor shown here is a nanomolar, dendron-based divalent sulfonamide that can bind gelatinase (MMP-9), the most important MMP on the ocular surface, and the transmembrane human carbonic anhydrase XII, present in eyes and considered an antiglaucoma target. In an animal model of a dry eye, no evidence of corneal desiccation was observed in eyes treated with our inhibitor.

[Full Paper]
B. Richichi, V. Baldoneschi, S. Burgalassi, M. Fragai, D. Vullo, A. Akdemir, E. Dragoni, A. Louka, M. Mamusa, D. Monti, D. Berti, E. Novellino, G. De Rosa, C. T. Supuran, C. Nativi
Chem. Eur. J., December 22, 2015, DOI: 10.1002/chem.201504355. Read article.

Controlled Multi-functionalization Facilitates Targeted Delivery of Nanoparticles to Cancer Cells

Controlled Multi-functionalization Facilitates Targeted Delivery of Nanoparticles to Cancer Cells

Through the barricades: Controlled multi-functionalization of nanoparticles with a cytotoxic drug, a glycan ligand for the cell surface receptor CD22, and an imaging moiety led to a remarkable 60-fold enhancement in cytotoxicity of CD22 (+) lymphoma cells compared to non-targeted nanoparticles.

[Full Paper]
Manish S. Hudlikar, Xiuru Li, Ivan A. Gagarinov, Nagesh Kolishetti, Margreet A. Wolfert, Geert-Jan Boons
Chem. Eur. J., December 18, 2015, DOI: 10.1002/chem.201503999. Read article.

Coordination Polymers Derived from Non-Steroidal Anti-Inflammatory Drugs for Cell Imaging and Drug Delivery

Coordination Polymers Derived from Non-Steroidal Anti-Inflammatory Drugs for Cell Imaging and Drug Delivery

Coordinated functions: A series of MnII-based coordination polymers were derived from different non-steroidal anti-inflammatory drugs (NSAIDs), which showed excellent cell imaging, in vitro anti-inflammatory and drug delivery properties (see figure).

[Full Paper]
Mithun Paul, Parthasarathi Dastidar
Chem. Eur. J., December 11, 2015, DOI: 10.1002/chem.201503706. Read article.

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