16975-62-5Relevant academic research and scientific papers
Synthesis of Phosphatidylserine and Its Stereoisomers: Their Role in Activation of Blood Coagulation
Mallik, Suman,Prasad, Ramesh,Bhattacharya, Anindita,Sen, Prosenjit
supporting information, p. 434 - 439 (2018/05/23)
Natural phosphatidylserine (PS), which contains two chiral centers, enhances blood coagulation. However, the process by which PS enhanced blood coagulation is not completely understood. An efficient and flexible synthetic route has been developed to synthesize all of the possible stereoisomers of PS. In this study, we examined the role of PS chiral centers in modulating the activity of the tissue factor (TF)-factor VIIa coagulation initiation complex. Full length TF was relipidated with phosphatidylcholine, and the synthesized PS isomers were individually used to estimate the procoagulant activity of the TF-FVIIa complex via a FXa generation assay. The results revealed that the initiation complex activity was stereoselective and had increased sensitivity to the configuration of the PS glycerol backbone due to optimal protein-lipid interactions.
Nucleic acid medicine delivery system and application thereof
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Paragraph 0053; 0057; 0078, (2018/09/21)
The invention discloses a nucleic acid medicine delivery system and application thereof. The system consists of a neutral base lipid carrier and metal salt, wherein the structure of the neutral base lipid carrier is shown as a formula I. In addition, the delivery system provided by the invention also comprises metal salt. The experiment proves that through the existence of metal ion, the silent activity of the nucleic acid medicine can be effectively improved; the effective transportation of the nucleic acid medicine in the cells and in the body can be realized. The chemical modification methods such as D,L-isonucleoside modification, deoxyinosine modification, peptide conjugation modification and phosphorylation modification are jointly used for nucleic acid delivery system study; the advantages and rules of the nucleic acid delivery in a composite modification mode are sufficiently explored; the modification strategies are used in the nucleic acid medicine study. Study proves that the products obtained through chemical modification are more applicable to the system; in addition, the advantages of stable physicochemical properties, good bioactivity and good membrane permeability and the like are realized. The nucleic acid medicine delivery system provided by the invention has wide application prospects in the gene treatment field. The formula is shown in the description.
Lipid-modified oligonucleotide conjugates: Insights into gene silencing, interaction with model membranes and cellular uptake mechanisms
Ugarte-Uribe, Bego?a,Grijalvo, Santiago,Pertí?ez, Samuel Nú?ez,Busto, Jon V.,Martín, César,Alagia, Adele,Go?i, Félix M.,Eritja, Ramón,Alkorta, Itziar
supporting information, p. 175 - 186 (2016/12/23)
The ability of oligonucleotides to silence specific genes or inhibit the biological activity of specific proteins has generated great interest in their use as research tools and therapeutic agents. Unfortunately, their biological applications meet the limitation of their poor cellular accessibility. Developing an appropriate delivery system for oligonucleotides is essential to achieve their efficient cellular uptake. In the present work a series of phosphorothioate lipid–oligonucleotide hybrids were synthesized introducing covalently single or double lipid tails at both 3′- and 5′-termini of an antisense oligonucleotide. Gene transfections in cultured cells showed antisense luciferase inhibition without the use of a transfecting agent for conjugates modified with the double-lipid tail at 5′-termini. The effect of the double lipid-tailed modification was further studied in detail in several model membrane systems as well as in cellular uptake experiments. During these studies the spontaneous formation of self-assembled microstructures is clearly observed. Lipidation allowed the efficient incorporation of the oligonucleotide in HeLa cells by a macropinocytosis mechanism without causing cytotoxicity in cells or altering the binding properties of the oligonucleotide conjugates. In addition, both single- and double-tailed compounds showed a similar behavior in lipid model membranes, making them useful in nucleotide-based technologies.
Cooperative Activation of Cobalt–Salen Complexes for Epoxide Hydration Promoted on Flexible Porous Organic Frameworks
Zhong, Mingmei,Li, He,Chen, Jian,Tao, Lin,Li, Can,Yang, Qihua
supporting information, p. 11504 - 11508 (2017/08/30)
Developing solid catalysts with multiple active sites working cooperatively is desirable for efficient chemical transformations. However, most solid catalysts are rigid and impede the cooperation between their spatially isolated active sites. Two flexible porous organic frameworks (POFs) with integrated Co(salen) as active sites have been successfully synthesized for mimicking the cooperative modes of enzymes. The POFs exhibit second-order rate dependence on Co(salen) concentration in the network and afford much higher TOF (3300 versus 2670 h?1) than the homogeneous counterpart in the hydration of propylene epoxide. POFs with a flexible network thus not only facilitate but also enhance the cooperation of nearby Co(salen). Moreover, POFs could catalyze oversized substrates, have a wide substrate scope, and exhibit high stability.
Total Synthesis of the Bis-silyl Ether of (+)-15-epi-Aetheramide A
Revu, Omkar,Prasad, Kavirayani R.
, p. 438 - 460 (2017/04/26)
Synthesis of the macrolactone depsipeptide aetheramide A was attempted by three different approaches. The first approach to form the macrolactone involving macrolactonization to form the C1-C21 bond and the second approach using a ring-closing metathesis (RCM) strategy to form the C10-C11 olefinic bond failed. The third approach starting from R-mandelic acid, involving the RCM reaction to install the C18-C19 ring junction, was successful in assembling the macrolactone.
Supramolecular assemblies of novel aminonucleoside phospholipids and their bonding to nucleic acids
Pan, Delin,Sun, Jing,Jin, Hongwei,Li, Yating,Li, Liyu,Wu, Yun,Zhang, Lihe,Yang, Zhenjun
supporting information, p. 469 - 472 (2015/02/19)
A novel class of aminonucleoside phospholipids has been developed. These molecules could spontaneously assemble into supramolecular structures including multilamellar organization, hydrogels, superhelical strands, and vesicles. Their ability to bind to DNA by hydrogen bonding and π-π stacking interactions was investigated by many means. This journal is
MELANIN PRODUCTION INHIBITOR
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Paragraph 0331 - 0334, (2015/12/17)
Disclosed is a melanin production inhibitor which has an excellent inhibitory activity on the production of melanin and is highly safe. The melanin production inhibitor is represented by general formula (1) (excluding clotrimazole) and/or a pharmacologically acceptable salt thereof. In the formula, A1, A2 and A3 are independently selected from a hydrogen atom, an aryl group which may have a substituent, and an aromatic heterocyclic group which may have a substituent. At least one of A1, A2 and A3 is selected from the aryl group and the aromatic heterocyclic group, the total number of carbon atoms contained in A1, A2 and A3 is 6 to 50 and, when at least two of A1, A2 and A3 represent the aryl groups or the aromatic heterocyclic groups, the adjacent two aryl or aromatic heterocyclic groups may be bound to each other via an alkyl chain or an alkenyl chain to form a ring; m represents an integer of 0 to 2; X represents a hetero atom, a hydrogen atom, or a carbon atom; R1 and R2 are independently selected from a hydrogen atom and an oxo group. When one of R1 and R2 is an oxo group, the other is not present. R3 is selected from a hydrogen atom, and a C1-8 hydrocarbon group in which one or some of hydrogen atoms or carbon atoms may be substituted by a hetero atom or hetero atoms. The number of R3's present in the compound corresponds to X and, when two or more R3's are present, the R3's are independently present and the adjacent two R3's may be bound to each other to form, together with X, a ring, and the terminal of R3 may be bound to a carbon atom to which A1, A2 and A3 are bound, thereby forming a ring.
Smart tools and orthogonal click-like reactions onto small unilamellar vesicles
Salomé, Christophe,Spanedda, Maria Vittoria,Hilbold, Benoit,Berner, Etienne,Heurtault, Béatrice,Fournel, Sylvie,Frisch, Benoit,Bourel-Bonnet, Line
, p. 27 - 36 (2015/04/14)
Abstract Click-based reactions were conducted at the surface of small unilamellar vesicles (SUVs) to provide onto-vesicle chemistry with efficient innovative ready-for-use tools. For that purpose, four amphiphilic molecules were designed to insert into bi
Total synthesis of bafilomycin A1
Kleinbeck, Florian,Fettes, Gabriela J.,Fader, Lee D.,Carreira, Erick M.
supporting information; experimental part, p. 3598 - 3610 (2012/05/04)
A convergent synthesis of bafilomycin A1, a potent inhibitor of V-type ATPases, is presented. The synthesis relies on the zinc triflate mediated diastereoselective addition of a complex enyne to a sensitive aldehyde as the key fragment coupling. A ruthenium-catalyzed trans-reduction of the resulting propargylic enyne efficiently installs the required C10-C13 trans,trans-diene subunit, implementing an alternative strategy to traditional palladium-catalyzed cross-coupling strategies. A highly selective oxidation of a secondary hydroxyl group in a triol sets the stage for the completion of the synthesis. Copyright
Chiral nanoporous metal-metallosalen frameworks for hydrolytic kinetic resolution of epoxides
Zhu, Chengfeng,Yuan, Guozan,Chen, Xu,Yang, Zhiwei,Cui, Yong
supporting information; experimental part, p. 8058 - 8061 (2012/07/14)
Chiral nanoporous metal-organic frameworks are constructed by using dicarboxyl-functionalized chiral Ni(salen) and Co(salen) ligands. The Co(salen)-based framework is shown to be an efficient and recyclable heterogeneous catalyst for hydrolytic kinetic resolution (HKR) of racemic epoxides with up to 99.5% ee. The MOF structure brings Co(salen) units into a highly dense arrangement and close proximity that enhances bimetallic cooperative interactions, leading to improved catalytic activity and enantioselectivity in HKR compared with its homogeneous analogues, especially at low catalyst/substrate ratios.
