1609-40-1Relevant academic research and scientific papers
Co-delivery of doxorubicin and P-glycoprotein siRNA by multifunctional triblock copolymers for enhanced anticancer efficacy in breast cancer cells
Xu, Minghui,Qian, Junmin,Suo, Aili,Cui, Ning,Yao, Yu,Xu, Weijun,Liu, Ting,Wang, Hongjie
, p. 2215 - 2228 (2015)
Combined treatment of chemotherapeutics and small interfering RNAs (siRNAs) is a promising therapy strategy for breast carcinoma via their synergetic effects. In this study, to improve the therapeutic effect of doxorubicin (DOX), novel triblock copolymers, folate/methoxy-poly(ethylene glycol)-block-poly(l-glutamate-hydrazide)-block-poly(N,N-dimethylaminopropyl methacrylamide) (FA/m-PEG-b-P(LG-Hyd)-b-PDMAPMA), were synthesized and used as a vehicle for the co-delivery of DOX and P-glycoprotein (P-gp) siRNA into breast cancer cells. The triblock copolymers were synthesized by a combination of ring-opening polymerization of γ-benzyl-l-glutamate-N-carboxyanhydride using cystamine-terminated heterotelechelic PEG derivatives possessing folate or methoxy end groups (FA/m-PEG-Cys) as initiators and reversible addition-fragmentation chain transfer polymerization of N,N-dimethylaminopropyl methacrylamide followed by hydrazinolysis. The successful synthesis of the copolymers was confirmed by 1H NMR and gel permeation chromatography. DOX was covalently conjugated onto the poly(l-glutamate-hydrazide) blocks via a pH-labile hydrazone linkage, and the DOX-conjugated triblock copolymers could self-assemble into nanoparticles in aqueous solutions. P-glycoprotein (P-gp) siRNA was then bound to the cationic poly(N,N-dimethylaminopropyl methacrylamide) (PDMAPMA) blocks through an electrostatic interaction, resulting in the formation of spherical nanocomplexes with an average diameter of 196.8 nm and a zeta potential of +28.3 mV. The in vitro release behaviors of DOX and siRNA from the nanocomplexes were pH- and reduction-dependent, and the release rates were much faster under a reductive acidic condition (pH 5.0, glutathione: 10 mM) simulating the intracellular endo-lysosomal environment of cancer cells compared to physiological conditions. The fast payload release rates were closely related to both the glutathione-triggered detachment of PEG blocks from the nanocomplex surface and the pH-sensitive cleavage of hydrazone linkages. FA-decorated nanocomplexes showed higher cellular uptake efficiency and cytotoxicity against MCF-7 cells than FA-free nanocomplexes, as confirmed by confocal laser scanning microscopy, transmission electron microscopy, MTT and flow cytometry analyses. Our results demonstrated that the multifunctional triblock copolymer-mediated co-delivery of DOX and P-gp siRNA might be a new promising therapeutic strategy for breast cancer treatment. This journal is
Preparation, characterization, and biocompatibility evaluation of poly(Nε-acryloyl-l-lysine)/hyaluronic acid interpenetrating network hydrogels
Cui, Ning,Qian, Junmin,Xu, Weijun,Xu, Minghui,Zhao, Na,Liu, Ting,Wang, Hongjie
, p. 1017 - 1026 (2016)
In the present study, poly(Nε-acryloyl-l-lysine)/hyaluronic acid (pLysAAm/HA) interpenetrating network (IPN) hydrogels were successfully fabricated through the combination of hydrazone bond crosslinking and photo-crosslinking reactions. The HA hydrogel network was first synthesized from 3,3′-dithiodipropionate hydrazide-modified HA and polyethylene glycol dilevulinate by hydrazone bond crosslinking. The pLysAAm hydrogel network was prepared from Nε-acryloyl-l-lysine and N,N′-bis(acryloyl)-(l)-cystine by photo-crosslinking. The resultant pLysAAm/HA hydrogels had a good shape recovery property after loading and unloading for 1.5 cycles (up to 90%) and displayed a highly porous microstructure. Their compressive moduli were at least 5 times higher than that of HA hydrogels. The pLysAAm/HA hydrogels had an equilibrium swelling ratio of up to 37.9 and displayed a glutathione-responsive degradation behavior. The results from in vitro biocompatibility evaluation with pre-osteoblasts MC3T3-E1 cells revealed that the pLysAAm/HA hydrogels could support cell viability and proliferation. Hematoxylin and eosin staining indicated that the pLysAAm/HA hydrogels allowed cell and tissue infiltration, confirming their good in vivo biocompatibility. Therefore, the novel pLysAAm/HA IPN hydrogels have great potential for bone tissue engineering applications.
Method and device for continuously producing thiopropionate series compounds through pipeline type
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Paragraph 0100; 0102; 0110; 0112-0114, (2021/11/27)
The invention discloses a method and a device for continuously producing thiopropionate series compounds through pipeline type, and can simultaneously or separately prepare thiodipropionate compounds. Dithionate type compounds and mercapto ester compounds. The method is simple to operate, low in cost and high in yield, and is suitable for industrial production.
Photochemical metal-free aerobic oxidation of thiols to disulfides
Spiliopoulou, Nikoleta,Kokotos, Christoforos G.
supporting information, p. 546 - 551 (2021/01/28)
Thiol oxidation to disulfides is an area of great importance in organic synthesis, both for synthetic and biological purposes. Herein, we report a mild, inexpensive and green photochemical approach for the synthesis of both symmetrical and non-symmetrical disulfides, using metal-free and environmentally friendly conditions. Utilizing phenylglyoxylic acid as the photoinitiator, common household bulbs as the light source and a simple inorganic salt as the additive, a versatile oxidation of thiols leading to products in excellent yields is described. This journal is
Ca2+-mediated thiolysis of peptide-resin linkage as an option for preparing protected peptide thioesters
Proti, Patrícia B.,Miranda, M. Terêsa M.
, p. 3853 - 3857 (2008/09/21)
A mild new procedure for preparing protected peptide thioesters, based on Ca2+-assisted thiolysis of peptide-Kaiser oxime resin (KOR) linkage, is described. Ac-Ile-Ser(Bzl)-Asp(OcHx)-SR (Ac: acetyl; Bzl: benzyl; cHx: cyclohexyl), model peptide, was readily released from the resin by incubating the peptide-KOR at 60 °C in mixtures of DMF with n-butanethiol [R = (CH2)3CH3] or ethyl 3-mercaptopropionate [R = (CH2)2COOCH2CH3] containing Ca(CH3COO)2. After serine and aspartic acid side-chain deprotection under acid conditions, Ac-Ile-Ser-Asp-S(CH2)2COOCH2CH3 was successfully obtained with good quality and high yield. This type of C-terminal modified peptide may act as an excellent acyl donor in peptide segment condensation by the thioester method, native chemical ligation and enzymatic methods.
Phthalimidomethyl Group. A New Protecting Group of Thiols
Gong, Young-Dae,Iwasawa, Nobuharu
, p. 2139 - 2142 (2007/10/02)
Phthalimidomethyl group is employed as a protecting group of thiols.This group can be introduced to thiols under mild reaction conditions and be removed by treatment with hydrazine hydrate followed by mercuric acetate or cupric acetate.
N-Ethyldiisopropylamine and Sulfur Dioxide Solutions. 2. Reactions with Conjugate Acceptors
Eugene, Fabrice,Langlois, Bernard,Laurent, Eliane
, p. 2599 - 2603 (2007/10/02)
Solutions of sulfur dioxide and N-ethyldiisopropylamine (EDIA) are able to reduce α,β-unsaturated-γ-dicarbonyl compounds (esters or ketones) into α-dicarbonyl alkanes.In contrast, monoactivated Michael acceptors, such as acrylates, give symmetrical sulfones.These processes involve the conjugate addition of HSO2(-), formed from a charge-transfer complex between EDIA and SO2.Secondary amines are formed as byproducts.Triethylamine, which forms a more stable complex with sulfur dioxide than EDIA, is far less reactive toward the same substrates.
REDUCTION AND SULFONYLATION OF OLEFINS BY SOLUTIONS OF DIISOPROPYLETHYLAMINE AND SULFUR DIOXIDE
Eugene, Fabrice,Langlois, Bernard,Laurent, Eliane
, p. 377 - 378 (2007/10/02)
Solutions of diisopropylethylamine and SO2 deliver sulfones from acrylates and reduce olefins substituted by two carbonyl moieties in α and β positions.
Use of carbon-sulfur cathodes in electro-organic chemistry - Part 2 - Reactions with activated alkenes; evidence for a vicarious substitution specific of this type of electrode.
Guillanton, G. Le,Do, Q. T.,Simonet, J.
, p. 427 - 439 (2007/10/02)
The sulfur-carbon electrode, used as a cathode, appears to be an excellent source of nucleophiles which are good sulfuration reagents towards alkenes not substituted by leaving groups.However, the electrochemical reactions are often complex.It should be w
