- A reactive oxygen species (ROS)-responsive polymer for safe, efficient, and targeted gene delivery in cancer cells
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Stimuli-responsive release: The high levels of reactive oxygen species (ROS) in prostate cancer cells can be exploited to trigger cancer-targeted gene delivery. A ROS-responsive thioketal-based cationic polymer was synthesized and functionalization with a cancer-targeting peptide led to selective and enhanced gene transfection in prostate cancer cells (see scheme). Copyright
- Shim, Min Suk,Xia, Younan
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- A reactive oxygen species-responsive dendrimer with low cytotoxicity for efficient and targeted gene delivery
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Nonviral vectors have been attracting more attention for several advantages in gene delivery and the development of nonviral gene carriers with high delivery efficiency and low cytotoxicity has long been a key project. Starburst polyamidoamine dendrimers are a class of synthetic polymers with unique structural and physical characteristics. However, when they are used as gene carrier, the gene transfection efficiency is not satisfactory. Herein, a novel thioketal-core polyamidoamine dendrimer (i.e., ROS-PAMAM) was synthesized and characterized. Compared to ethylenediamine-core dendrimers or widely used cationic polymers of polyetherimide, ROS-PAMAM showed lower cytotoxicity. Moreover, ROS-PAMAM demonstrated reactive oxygen species responsive characteristics, which can facilitate the release of siRNA in the tumor microenvironment. In vitro gene transfection experiments based on A549 cells confirmed that siRNA/ROS-PAMAM exhibits high gene transfection efficiency. It is concluded that ROS-PAMAM shows great potential as a generalizable vehicle for gene therapy applications.
- Wang, Yueqi,Li, Changjian,Du, Libo,Liu, Yang
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- Synthesis of a reactive oxygen species-responsive doxorubicin derivative
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A heterobifunctional reactive oxygen species (ROS)-responsive linker for directed drug assembly onto and delivery from a quantum dot (QD) nanoparticle carrier was synthesized and coupled to doxorubicin using N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC)/sulfo–NHS coupling. The doxorubicin conjugate was characterized using 1H NMR and LC-MS and subsequently reacted under conditions of ROS formation (Cu2+/H2O2) resulting in successful and rapid thioacetal oxidative cleavage, which was monitored using 1H NMR.
- Delehanty, James B.,Das, Shivani,Goldberg, Efram,Sangtani, Ajmeeta,Knight, D. Andrew
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- Synthesis of thioketal connecting unit and application thereof in DNA sequencing
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The invention discloses synthesis of a thioketal connecting unit and application thereof in DNA sequencing. The connecting unit has a structural formula shown as the specification, wherein R=OH or COOH; R1=R2=methyl, or R1=phenyl, p-methoxyphenyl, 2, 4, 6
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Paragraph 0050-0055
(2017/05/23)
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- Thioketal connection unit, synthetic method and purpose thereof
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The invention discloses a thioketal connection unit, a synthetic method and a purpose thereof. The thioketal connection unit has a structure shown as a formula (I) in the specification, wherein, R=-OH or -COOH; R1 and R2 can satisfy one of the following c
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Paragraph 0065; 0066; 0067
(2017/01/02)
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- Synthesis method of reactive oxygen type sensitive molecules
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The invention discloses a synthesis method of reactive oxygen type sensitive molecules. Mercaptoethylamine is added to methanol and stirred, a solution with the concentration being 1-2 mol/L is prepared, and triethylamine and ethyl trifluoroacetate are added to the solution; the mixture is stirred for 5-10 h at the room temperature; the reacted mixed solution is extracted through ethyl acetate; an organic phase of the ethyl acetate is obtained; anhydrous magnesium sulfate is added to the organic phase until no bubbles are generated and water is sufficiently removed, a filtered liquid is subjected to separation and purification with a silica gel column chromatography method, an intermediate product is obtained, a solution with the concentration being 0.5-1 mol/L is prepared, p-toluene sulfonic acid is added to the solution, 4A or 5A molecular sieves are added during stirring at the room temperature until no bubbles are generated, and the mixture is stirred at the room temperature; 2-methoxypropene is added and reacts for 12-24 h at the room temperature; the molecular sieves are removed through filtration, and a liquid is obtained; the filtered liquid is subjected to separation and purification with the silica gel column chromatography method, and the white solid reactive oxygen type sensitive molecules are obtained.
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Paragraph 0028; 0029; 0030; 0031
(2016/12/07)
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- Synthesis of a reactive oxygen species responsive heterobifunctional thioketal linker
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A new heterobifunctional reactive oxygen species (ROS) responsive thioketal linker and its synthesis are described. This linker allows for developing new ROS-responsive agents with two distinct functionalities using universal bioconjugation methods. The reaction kinetics of the thioketal cleavage in the presence of ROS is also described.
- Ling, Xiaoxi,Zhang, Shaojuan,Shao, Pin,Wang, Pengcheng,Ma, Xiaochao,Bai, Mingfeng
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supporting information
p. 5242 - 5244
(2015/08/19)
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- Improved syntheses of 5′- S -(2-Aminoethyl)-6- N -(4-nitrobenzyl)- 5′-thioadenosine (SAENTA), analogues, and fluorescent probe conjugates: Analysis of cell-surface human equilibrative nucleoside transporter 1 (hENT1) levels for prediction of the antitumor
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5′-S-(2-Aminoethyl)-6-N-(4-nitrobenzyl)-5′-thioadenosine (SAENTA), 5′-S-(2-acetamidoethyl)-6-N-[(4-substituted)benzyl]-5′- thioadenosine analogues, 5′-S-[2-(6-aminohexanamido)]ethyl-6-N-(4- nitrobenzyl)-5′-thioadenosine (SAHENTA), and related compounds we
- Robins, Morris J.,Peng, Yunshan,Damaraju, Vijaya L.,Mowles, Delores,Barron, Geraldine,Tackaberry, Tracey,Young, James D.,Cass, Carol E.
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experimental part
p. 6040 - 6053
(2010/11/02)
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- Pattern-based recognition of heparin contaminants by an array of self-assembling fluorescent receptors
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(Figure Presented) Tracking down potential killers: Strong host-guest interactions enable the facile combination of polycationic cyclodextrin binding motifs (blue) with fluorescent reporters (orange) tethered to a hydrophobic guest molecule (dark green). An array of supramolecular fluorescent receptors prepared by this modular approach was used for the pattern-based recognition of negatively charged contaminants in the anticoagulant drug heparin.
- Jagt, Richard B. C.,Gomez-Biagi, Rodolfo F.,Nitz, Mark
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supporting information; experimental part
p. 1995 - 1997
(2009/07/25)
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