- DIPEPTIDE MIMETICS OF NGF AND BDNF NEUROTROPHINS
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The invention relates to compounds having either agonist or antagonist activities for the neurotrophins NGF and BDNF and represented by monomeric or dimeric substituted dipeptides that are analogs of the exposed portions of loop 1 or loop 4 regions of these neurotrophins near or at a beta-turn of the respective loop. N-acylated substituents of these dipeptides are biostereoisomers of the amino acid residues preceding these dipeptide sequences in the neurotrophin primary structure. The dimeric structure is produced advantageously by using hexatnethylenediaanine to which dipeptides are attached via their carboxyl groups. The claimed compounds displayed neuroprotective and differentiation-inducing activities in cellular models and enhanced the amount of phosphorylated tyrosine kinase A and the heat shock proteins Hsp32 and Hsp70 in the concentration range of 10 -9 to 10 -5 M. They also displayed neuroprotective, anti-parkinsonian, anti-stroke, anti-ischemic, anti-depressant and anti-amnestic activities in animal models and were active in experimental models of Alzheimer's disease. These in vivo effects of the claimed compounds are displayed in the dose range of 0.01 to 10 mg/kg when administered intraperitoneally.
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Paragraph 0168; 0169
(2019/04/16)
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- Tumor intelligent targeting and environmental double responsiveness siRNA delivery system and its preparation method and application
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The invention particularly discloses an intelligent targeting and environmental dual-responsibility siRNA [short interfering RNA (ribonucleic acid)] delivery system for tumor, a preparation method and application. The siRNA delivery system is characterized in that siRNA is concentrated and compounded in nanometer particle nucleuses by the aid of acid-sensitive amphiphilic three-block polymers, and intermolecular disulfide bonds are formed by PAsp(MEA) on sub-surfaces, so that the siRNA can be protected, and the intelligent targeting and environmental dual-responsibility siRNA delivery system can respond to release of the siRNA in reductive cytoplasm. The acid-sensitive amphiphilic three-block polymers comprise polyethylene glycol block-intermediate block-acid-sensitive block three-block copolymers, intermediate blocks comprise polyaspartate acyl mercaptoethylamine, and acid-sensitive blocks comprise poly (diisopropyl amine) ethyl methacrylate. The intelligent targeting and environmental dual-responsibility siRNA delivery system, the preparation method and the application have the advantages that the siRNA delivery system can be applied to preparing intelligent targeting siRNA nanometer medicines for the tumor and is low in N/P ratio dependence degree, and the siRNA can be quickly and completely released at targets; a novel idea can be provided for gene delivery systems, and the intelligent targeting and environmental dual-responsibility siRNA delivery system, the preparation method and the application have important significance on preparing clinical diagnosis and treatment medicines for the tumor.
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Paragraph 0039; 0040; 0041; 0042
(2019/02/19)
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- Photo-thermal chemotherapy and treatment combined microenvironment responsive drug-loading nano micelle preparation method and application
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The invention discloses a photo-thermal chemotherapy and treatment combined microenvironment responsive drug-loading nano micelle preparation method and application. A nano micelle comprises TIID-BT,a medicine active component and an amphiphilic block polymer, and the amphiphilic block polymer refers to polyethylene glycol-polyaspartic acid. By synthesis, a near infrared TIID-BT dye and a DOX chemotherapy drug are loaded on the specific nano micelle at the same time to obtain the nano micelle which is capable of giving play to photo-thermal treatment and chemotherapy at the same time. The nano micelle enables DOX to avoid a combination effect of opsonin and a capturing effect of an MPS system to form a stable and long-acting drug delivery system with high drug loading capacity, and accordingly an antitumor effect of DOX is improved while DOX resistance of tumors is changed. In addition, due to loading of the TIID-BT dye in the nano micelle, in-vivo application effects of the TIID-BT dye are improved, combination of hoto-thermal treatment and chemotherapy is realized, and in-vivo tumor treatment effects are improved due to synergistic effects of DOX and TIID-BT.
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Paragraph 0046; 0052-0054
(2019/06/27)
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- Preparation method of drug-loaded nano-micelle capable of releasing anti-cancer drug in tumor matrix as well as product and application of drug-loaded nano-micelle
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The invention relates to a preparation method of a drug-loaded nano-micelle capable of releasing an anti-cancer drug in a tumor matrix as well as a product and an application of the drug-loaded nano-micelle, which belongs to the technical field of drug carriers. The preparation method comprises the following steps: the beta-benzyl aspartate is prepared, benzyloxycarbonyl aspartic anhydride is prepared, a polyaspartic acid benzyl ester polymer is prepared, a carboxylation-polyaspartic acid benzyl ester polymer is prepared, a carboxyl-polyaspartic acid dimethylethylenediamine polymer is prepared, a polyaspartic acid dimethylethylenediamine-polyaspartic acid benzyl ester polymer is prepared, a poly(aspartic acid-dimethylethylenediamine)-poly (aspartic acid-mercaptoethylamine) polymer is prepared, and drug-loaded nano-micelle for releasing an anti-cancer drug in a tumor matrix is prepared. The drug-loaded nano-micelle prepared by the preparation method has double sensitivities of pH sensitivity and reduction sensitivity, can accurately release drugs, and effectively improves the tumor treatment effect.
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Paragraph 0055-0057
(2019/12/25)
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- Thermoresponsive Alignment Media in NMR Spectroscopy: Helix Reversal of a Copolyaspartate at Ambient Temperatures
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Poly(aspartic acid esters) are known to form either right-or left-handed α-helices depending on the ester group in the side chain, on solvent and/or on temperature. Polyphenethyl-l-aspartates (PPLA) exhibit a helix reversal from the right- to the left-handed form with increasing temperature. We have recently reported the application of polyphenethylaspartates as helically chiral alignment media. The thermoresponsivity observed for these polymers offers the possibility to measure different orientations of analytes before and after helix reversal of the alignment medium at 373 K. Herein we present a synthesized copolymer of phenethyl- and benzylaspartate as a new alignment medium undergoing this helix reversal at 303–313 K. Thus, the measurement of residual dipolar couplings (RDC) before and after the helix reversal is allowed for at ambient temperatures. A complete sign change of all 1H–13C RDCs was observed, which is close to the highest possible difference in NMR spectra.
- Schwab, Mira,Schmidts, Volker,Thiele, Christina M.
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supporting information
p. 14373 - 14377
(2018/09/20)
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- Activity of (+)-Discadenine as a Plant Cytokinin
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Discadenine (1), a self-spore germination inhibitor from the cellular slim mold Dictyostelium discoideum, is structurally related to the plant hormone cytokinin. This compound was synthesized from l-aspartic acid, and its activities were confirmed by three classical cytokinin bioassays as well as by using binding and activation assays with the Arabidopsis cytokinin receptors AHK3 and CRE1/AHK4.
- Mik, Václav,Mi?ková, Zuzana,Dole?al, Karel,Frébort, Ivo,Pospí?il, Tomá?
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p. 2136 - 2140
(2017/08/04)
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- Novel preparation method for anti-type-II-diabetes drug sitagliptin
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The invention discloses a novel preparation method for an anti-type-II-diabetes drug sitagliptin. According to the invention, trifluorobenzene with a cheaper price is used as a fluorization reagent and a starting raw material and a basic skeleton of sitagliptin is successfully synthesized through effective acylation of trifluorobenzene and L-aspartic acid; a synthesis route in the invention, from starting raw material and final product, is completely different from schemes disclosed in the prior art; the route is optimized, and easily-available natural L-aspartic acid is used as a chiral source for successful synthesis of an optically pure sitagliptin product; the problems of asymmetric catalysis and complex splitting in the prior art are overcome; the method also effectively overcomes the problem of low yield of the basic skeleton of sitagliptin synthesized via Friedel-Crafts acylation of trifluorobenzene and improves yield; the method is lower in cost, more convenient to operate and more suitable for industrial production; and compared with the prior art, the method is simpler in the synthesis route and better in operability.
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Paragraph 0009; 0010; 0011
(2017/09/13)
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- A transmission for a total of medicine and liquid fluorocarbon polymer nano vesicle and its preparation method and application
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The invention relates to an acid-sensitive amphipathic tri-block polymer. The polymer is composed of a polyethylene glycol-acid sensitive segment 1-acid sensitive segment 2 tri-block copolymer, wherein the acid sensitive segment 1 is poly(acrylamidophenylboronic acid); the acid sensitive segment 2 is poly(aminoacyl dimethyl-ethylenediamine); the molecular weight of the polyethylene glycol is 2000-5000, the molecular weight of the acid sensitive segment is 2000-6000, and the molecular weight of the acid sensitive segment is 1000-2000. The invention further relates to application of the acid sensitive amphipathic tri-block polymer in preparation of polymer nano-vesicle for co-delivering drug and perfluorooctylbromide. The nano-vesicle has a uniform nano-diameter, can stably circulate in a body and can be enriched in a tumor position, has excellent capability of reinforcing ultrasonic development to realize application of ultrasonic development under diagnostic ultrasound, and has ultrasonic sensitivity to stimulate the cavitation effect under a condition of low-frequency high-energy ultrasonic-radiation so as to realize controllable release of drugs.
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Paragraph 0040-0043
(2018/01/11)
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- Photo-induced reduction of Cr6+ by the hybrid systems “CuII complex with Schiff base and TiO2”: dependence on irradiation wavelength
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The synthesis of novel CuII complexes with a Schiff base obtained by condensation of salicylaldehyde and an l-aspartic acid ester are described. The physicochemical properties of the complexes were compared with those of related CuII complexes obtained earlier. All the complexes studied were characterized by elemental analysis as well as by IR, UV-Vis, and EPR spectroscopies. The activity of the complexes and their hybrid systems (HS) with TiO2 in visible-light-driven photocatalysis in organic solvents was investigated. After irradiation with visible light, the complexes and corresponding HS reduce Cr6+ to Cr3+ more efficiently than bare TiO2. To determine the molecular orbital compositions and energies and to explain the electronic spectra and redox properties of the systems studied, density functional calculations of the optimized structures of representative model complexes were performed.
- Yoshida,Tsaturyan,Akitsu,Tsunoda,Shcherbakov
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p. 2057 - 2065
(2018/03/22)
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- N-Pyrrolidine-based α/β-peptides incorporating ABOC, a constrained bicyclic β-amino acid, for asymmetric aldol reaction catalysis
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A series of N-pyrrolidine-based α,β-peptide catalysts incorporating a constrained 2-aminobicyclo[2.2.2]octane carboxylic acid (ABOC) residue were synthesized and evaluated in the asymmetric aldol reaction from acetone and some p-substituted benzaldehydes. Their catalytic properties were shown to be highly dependent on the amino acid sequences and on the absolute configuration of the ABOC residue that played a determinant role. Among the peptides tested, the heterochiral tripeptide H-Pro-(R)-ABOC-Asp-OCH3 13, that adopts a turn conformation in the solid state, proved to be the most efficient catalyst affording β-hydroxy ketones in high yields and good enantioselectivities (up to 87%).
- Milbeo, Pierre,Maurent, Kelly,Moulat, Laure,Lebrun, Aurélien,Didierjean, Claude,Aubert, Emmanuel,Martinez, Jean,Calmès, Monique
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p. 1706 - 1715
(2016/03/08)
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- Heating reactions of N-t-Butyloxycarbonyl-Asparagine and related compounds
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N-t-Butyloxycarbonyl-amino acids (Boc-) are labile on heating to afford free amino acids, but Boc-aspartic acid gives a kind of polypeptide. This chemical feature of Boc-aspartic acid may be caused by dehydration between two carboxyl groups as well as the formation of a free amino group. Boc-Asparagine may have a similar reactivity to Boc-aspartic acid. This research describes polypeptide formation by heating Boc-asparagine and its isomer Boc-aspartic acid amide.
- Munegumi,Akao,Kawatu,Yamada,Harada
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p. 6541 - 6548
(2015/02/19)
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- Microwave assisted synthesis and antimicrobial study of Schiff base vanadium(IV) complexes of phenyl esters of amino acids
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Schiff base vanadium(IV) complexes of phenyl esters of the two acidic amino acids, i.e., aspartic and glutamic acid, were synthesized. The phenyl esters of these amino acids were synthesized by conventional method whereas the Schiff base vanadium(IV) complexes were synthesized using microwave irradiation. The complexes were characterized by spectroscopic tools such as IR, 1H NMR, mass (ES), ESR, and UV visible spectroscopy. All the complexes were studied for antibacterial and antifungal activity and found to be moderately active. Copyright Taylor & Francis Group, LLC.
- Wazalwar, Sachin S.,Bhave, Narayan S.,Dikundwar, Amol G.,Ali, Parvez
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experimental part
p. 459 - 464
(2011/06/28)
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- Degradation-promoters of cellular inhibitor of apoptosis protein 1 based on bestatin and actinonin
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A series of hybrid compounds of bestatin (1) and actinonin (3), which promote degradation of cellular inhibitor of apoptosis protein 1 (cIAP1), were designed and synthesized. Structure-activity relationship studies indicated that absolute configuration, hydrophobicity at the α-position of the internal amide carbonyl group, and the presence of a small substituent at the α-position of the ester group are important factors for the expression of potent cIAP1 degradation-promoting activity. HAB-5A (30b) showed the most potent activity (IC50 = 0.53 μM) among the compounds prepared.
- Sato, Shinichi,Tetsuhashi, Masashi,Sekine, Keiko,Miyachi, Hiroyuki,Naito, Mikihiko,Hashimoto, Yuichi,Aoyama, Hiroshi
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p. 4685 - 4698
(2008/12/20)
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- Decomposition of copper-amino acid complexes by sodium sulfide
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Sodium sulfide very efficiently removes copper from protected amino acid-copper complexes. The copper in the amino acid complex was reduced to insoluble cuprous sulfide and the free amino acid was released in pure form. This method is very convenient and rapid, requiring only 5-10 min and 0.55-0.75 equiv of sodium sulfide.
- Nowshuddin, Shaik,Reddy, A. Ram
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p. 5159 - 5161
(2007/10/03)
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- Potential tuberculostatic agent: Micelle-forming pyrazinamide prodrug
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Pyrazinamide was condensed with the poly(ethylene glycol)-poly(aspartic acid) copolymer (PEG-PASP), a micelle-forming derivative was obtained that was characterized in terms of its critical micelle concentration (CMC) and micelle diameter. The CMC was found by observing the solubility of Sudan III in Poly(ethylene glycol)-poly(pyrazinamidomethyl aspartate) copolymer (PEG-PASP-PZA) solutions. The mean diameter of PEG-PASP-PZA micelles, obtained by analyzing the dynamic light-scattering data, was 78.2 nm. The PEG-PASP-PZA derivative, when assayed for anti-Mycobacterium activity, exhibited stronger activity than the simple drug.
- Silva, Marcia,Ricelli, Nara L.,Seoud, Omar El,Valentim, Celso S.,Ferreira, Antonio G.,Sato, Daisy N.,Leite, Clarice Q. F.,Ferreira, Elizabeth I.
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p. 283 - 290
(2007/10/03)
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- Process for the preparation of omega-benzyl esters of amino diacids and of alkanesulphonates of these esters, and these alkanesulphonates
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The invention relates to a process for the preparation of an ?-benzyl ester of an amino diacid, characterized in that the amino diacid is reacted with a benzyl alcohol derivative of formula (I) 1 in which the R1 substituent or substituents, which are identical or different, represent a hydrogen atom, a C1 to C4 alkyl group, a C1 to C4 alkoxy group or a halogen atom and n is equal to 1, 2 or 3, in the presence of at least one mol per mole of the amino diacid of an alkanesulphonic acid, optionally in the presence of a solvent. The intermediate alkanesulphonates of the ?-benzyl esters of amino diacids and the ?-benzyl esters of amino diacids are obtained with a good yield and an excellent purity by virtue of this process.
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- Potential tuberculostatic agents: Micelle-forming copolymer poly(ethylene glycol)-poly(aspartic acid) prodrug with isoniazid
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With the objective of obtaining slow-acting isoniazid derivatives, of potential use as chemoprophylactics or chemotherapeutics in tuberculosis, the micelle-forming copolymer of poly(ethylene glycol)-poly(aspartic acid) prodrug with isoniazid was synthesized. The derivative obtained was found to be active in Mycobacterium tuberculosis culture, with a minimal inhibitory concentration (MIC) 5.6 times lower than that of the tuberculostatic drug.
- Silva,Lara,Leite,Ferreira
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p. 189 - 193
(2007/10/03)
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- Novel ester linked glycosyl amino acids: Convenient building blocks for the synthesis of glycopeptide libraries
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The completely orthogonally protected aspartic acid derivative FmocAsp(OBn)O'Bu is readily synthesized on a large scale. Deprotection of the β-carboxylic acid allows coupling to various sugar derivatives via free hydroxyl groups to produce novel glycosyl amino acids. Subsequent deprotection of either the α-acid or nitrogen is achieved cleanly to allow elaboration into an oligopeptide, whilst selective deprotection of PMB protected sugar hydroxyls is also readily achievable. Such novel glycosyl amino acid building blocks may be useful for the combinatorial synthesis of novel glycopeptide libraries.
- Tennant-Eyles, Richard J.,Fairbanks, Antony J.
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p. 391 - 401
(2007/10/03)
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- The synthesis of pyrimidin-4-yI substituted a-amino acids. a versatile approach from alkynyl ketones
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The reaction of amidines with a-amino acid alkynyl ketones is shown to be a versatile route to pyrimidin-4-yl substituted a-amino acids. This route is also applicable to a parallel synthesis approach and has allowed the formation of a range of pyrimidin-4-yl substituted a-amino acids, including the naturally occurring a-amino acid L-lathyrine 4.
- Adlington, Robert M.,Baldwin, Jack E.,Catterick, David,Pritchard, Garcth J.
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p. 855 - 866
(2007/10/03)
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- Cross-linked crystals of subtilisin: Versatile catalyst for organic synthesis
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Cross-linked enzyme crystals (CLECs) of subtilisin exhibit excellent activity in aqueous and various organic solvents. This catalyst is more stable than the native enzyme in both aqueous and mixed aqueous/organic solutions. Subtilisin-CLEC was shown to be a versatile catalyst. It was used for the syntheses of peptides and peptidomimetics, mild hydrolysis of amino acid and peptide amides, enantio- and regioselective reactions, and transesterifications.
- Wang, Yi-Fong,Yakovlevsky, Kirill,Zhang, Bailing,Margolin, Alexey L.
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p. 3488 - 3495
(2007/10/03)
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- SYNTHESE DE DERIVES PHOSPHONYLES DE L'ACIDE ASPARTIQUE INHIBITEURS POTENTIELS DE L'ATCase
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New derivatives and analogues of N-phosphonoacetyl-L-aspartate (PALA) were synthesized starting from the aspartic acid and evaluated for the enzymatic inhibition of the ATCase.Key words: ATCase inhibitors, PALA, aspartic acid, Arbuzov reaction, Wittig reaction.
- Ben-Bari, Mohamed,Dewynter, Georges,Aymand, Christian,Jei, Taib,Montero, Jean-Louis
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p. 129 - 144
(2007/10/03)
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- Acceleration of the N(α)-deprotection rate by the addition of m-cresol to diluted methanesulfonic acid and its application to the Z(OMe)-based solid-phase syntheses of human pancreastatin-29 and magainin 1
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In solid-phase peptide synthesis, the addition of m-cresol to diluted methanesulfonic acid (MSA) in dichloromethane accelerated the deprotection rate of the acid-labile α-amino protecting group, the p-methoxybenzyloxycarbonyl (Z(OMe)) group. Further, 0.1 M MSA, 20% m-cresol/CH2Cl2 was found to be a practically useful N(α)-deprotecting reagent system, since the deprotection of the Z(OMe) group occurred selectively within 30 min at room temperature, leaving intact the other side chain protecting groups, such as benzyloxycarbonyl, benzyl ester, S-p-methoxybenzyl and N(G)-mesitylene-2-sulfonyl groups. This reagent system was applied to the Z(OMe)-based solid phase syntheses of human pancreastatin-29 and magainin 1.
- Tamamura,Nakamura,Noguchi,Funakoshi,Fujii
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p. 954 - 957
(2007/10/02)
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- Enzymatic Synthesis of Side Chain Benzyl Esters of L-α-Amino Dicarboxylic Acids
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Diesters of L-α-amino dicarboxylic acids were specifically hydrolyzed by pronase at their α carboxylic group while the corresponding D-enantiomers remained unchanged.This enabled easy obtention of side chain benzyl esters of L-α-amino dicarboxylic acids starting from both optically active and racemic dibenzyl ester derivatives. Key Words: Enzymatic Synthesis: Pronase: L-α-amino suberic acid-ω-benzyl ester; Regioselectivity; Optical Resolution.
- Pugniere, Martine,Castro, Bertrand,Domergue, Nicole,Previero, Aldo
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p. 1015 - 1018
(2007/10/02)
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- A NEW TYPE OF ANTAGONIST OF ANGIOTENSIN II
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AngII has been resynthesized utilizing of the chemically homogeneous L-β-homophenylalanine (βHph) obtained in the Arndt-Eistert synthesis.The syntheses of AngII, AngII and AngII have also been described.The agonistic/antagonistic properties of the analogs have been studied in the tests on rabbit aorta strips (r.a.s.).
- Plucinska, Krystyna,Gumulka, Witold,Wisniewska, Elzbieta I.
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p. 1251 - 1257
(2007/10/02)
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- A Simple and Convenient Synthesis of β-Aspartates and γ-Glutamates
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A simple and convenient, high yield synthesis of ω-esters of aspartic as well as glutamic acid has been developed, using tetrafluoroboric acid as catalyst. (13)C-NMR data of the products are given.
- Albert, Rainer,Danklmaier, Johann,Hoenig, Helmut,Kandolf, Harald
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p. 635 - 637
(2007/10/02)
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- Process for the preparation of 4-benzyl aspartate
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In the process for the preparation of 4-benzyl aspartate starting from dibenzyl aspartate and/or its salts only one benzyl group is selectively removed by catalytic hydrogenation. By setting up appropriate reaction conditions elimination takes place mainly of the benzyl group on the C1 atom of the compound. The desired product can be isolated from the reaction mixture by precipitation.
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- The Synthesis of β-Benzyl L-Aspartate and γ-Benzyl L-Glutamate by Enzyme-Catalyzed Hydrolysis
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The enzyme-catalyzed hydrolysis of dibenzyl ester of aspartic acid and glutamic acid in α-position to give better yield of β-benzyl aspartate and γ-benzyl glutamate than the chemical method is reported.
- Chen, Shui-Tein,Wang, Kung-Tsung
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p. 581 - 582
(2007/10/02)
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- IMMOBILIZED PENICILLINACYLASE: APPLICATION TO THE SYNTHESIS OF THE DIPEPTIDE ASPARTAME
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Immobilized penicillinacylase efficently catalyzes the conversion at pH 7.5 of N-phenacetyl aspartame (4) into aspartame (2) and phenylacetic acid.
- Fuganti, Claudio,Grasselli, Piero,Casati, Paolo
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p. 3191 - 3194
(2007/10/02)
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- BOROXAZOLIDONES AS SIMULTANEOUS PROTECTION OF THE AMINO AND CARBOXYL GROUP IN α-AMINO ACIDS
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The synthesis of boroxazolidones 1 from a variety of α-amino acids is given.These compounds 1 show a strong intramolecular coordination between B and the amino group.These heterocycles can serve as protected α-amino acids in which the α-amino and the carboxyl function are simultaneously blocked, while the side chain remains free for further reactions.The boroxazolidines were reconverted into α-amino acids under mild acid conditions.Using this methodology aspartic acid was converted into β-benzyl aspartate and glutamic acid into γ-benzyl glutamate.
- Nefkens, G. H. L.,Zwanenburg, B.
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p. 2995 - 2998
(2007/10/02)
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- Novel immunological adjuvant compounds and methods of preparation thereof
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This application relates to novel immunological adjuvant compounds of the formula: STR1 wherein each of R and R1 are the same or different and are hydrogen or an acyl radical; R2 is an unsubstituted or substituted alkyl radical, or an unsubstituted or substituted aryl radical; R6 is an alkyl radical X is an aminoacyl moiety; and Y is D-isoasparagine or D-isoglutamine.
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- Novel immunological adjuvant compounds and methods of preparation thereof
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This application relates to novel immunological adjuvant compounds of the formula: STR1 wherein each of R and R1 are the same or different and are hydrogen or an acyl radical; R2 is an unsubstituted or substituted alkyl radical, or an unsubstituted or substituted aryl radical; X is an aminoacyl moiety; and Y is D-isoasparagine or D-isoglutamine.
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