- Determination of sulfated and nonsulfated bile acids in serum by mass fragmentography
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A Sep-Pak C18 cartridge was used for purification of bile acids from serum. Three kinds of deuterium labeled internal standards were required for accurate measurement of individual sulfated and nonsulfated bile acids. These internal standards were added to the serum before its application to the cartridge. Separation of sulfated and nonsulfated bile acids was performed on piperidinohydroxypropyl Sephadex LH-20 column chromatography. The nonsulfate fraction was submitted to alkaline hydrolysis, and the sulfate fraction to solvolysis followed by alkaline hydrolysis. Each fraction was converted to the hexafluoroisopropyl-trifluoroacetyl derivatives and quantitated by mass fragmentography. The recovery of each bile acid sulfate was quite satisfactory. In fasting healthy subjects the mean of total nonsulfated bile acids in serum was 1.324 μg/ml, and that of total sulfated bile acids was 0.450 μg/ml. Sulfated lithocholic aid comprised a large part of sulfated bile acids in healthy subjects.
- Murata,Beppu,Takikawa,Otsuka,Kasama,Seyama
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Read Online
- Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
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The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.
- Tan, Wen-Yun,Lu, Yi,Zhao, Jing-Feng,Chen, Wen,Zhang, Hongbin
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supporting information
p. 6648 - 6653
(2021/09/08)
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- METHOD FOR HOMOGENIZING BILE ACID DERIVATIVES
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The present invention relates to a process for producing bile acid derivatives having a protected hydroxyl group in the 3 position comprising contacting a bile acid derivative having an unprotected 3-alpha-hydroxyl group with a specific lipase. The present invention further relates to a bile acid derivative obtained or obtainable by the process, to the use of the bile acid derivative obtained or obtainable by the process for producing lithocholic acid and also to a process for producing lithocholic acid and to lithocholic obtained by the process. The invention further relates to the use of lithocholic acid obtained or obtainable by the process for producing ursodeoxycholic acid or ursodeoxycholic acid derivatives.
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Paragraph 0101-0104
(2021/05/28)
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- Preparation method of lithocholic acid and intermediates thereof
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The invention discloses a synthesis method of lithocholic acid and an intermediates thereof. According to the preparation method of the lithocholic acid intermediate, a compound I reacts with hydrogento generate a compound II in a mixed solvent by taking palladium on carbon as a catalyst and adding specific alkali; a low-price botanical bulk fermentation product BA is used as a raw material, andlithocholic acid is synthesized through side chain construction, hydrogenation, reduction, hydrolysis and other reactions; and the selectivity of 5beta hydrogen in the hydrogenation reaction is improved, high-toxicity reagents such as hydrazine hydrate are prevented from being used for hydroxyl due to removal of other animal-derived cholic acids, and the method is environmentally friendly, high insafety, simple in route, mild in reaction condition and suitable for industrial mass production.
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Paragraph 0084-0085; 0092
(2021/02/20)
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- Method for synthesizing lithocholic acid by taking BA as raw material
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The invention discloses a method for synthesizing lithocholic acid. According to the method, 21-hydroxy-20-methylpregn-4-en-3-one (BA) is used as a raw material and successively subjected to an oxidation reaction, a Wittig reaction and a reduction reaction to synthesize lithocholic acid. The method for synthesizing lithocholic acid has the advantages of environmental protection, simple steps, fewside reactions, high yield, usage cheap and easily available raw materials, and suitableness for industrial production, and overcomes the problems of high synthesis cost, low yield and unsuitability for large-scale industrial production in the prior art.
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Paragraph 0055-0057
(2020/09/01)
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- Optimization of EphA2 antagonists based on a lithocholic acid core led to the identification of UniPR505, a new 3α-carbamoyloxy derivative with antiangiogenetic properties
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The EphA2 receptor has been validated in animal models as new target for treating tumors depending on angiogenesis and vasculogenic mimicry. In the present work, we extended our current knowledge on structure-activity relationship (SAR) data of two related classes of antagonists of the EphA2 receptor, namely 5β-cholan-24-oic acids and 5β-cholan-24-oyl L-β-homotryptophan conjugates, with the aim to develop new antiangiogenic compounds able to efficiently prevent the formation of blood vessels. As a result of our exploration, we identified UniPR505, N-[3α-(Ethylcarbamoyl)oxy-5β-cholan-24-oyl]-L-β-homo-tryptophan (compound 14), as a submicromolar antagonist of the EphA2 receptor capable to block EphA2 phosphorylation and to inhibit neovascularization in a chorioallantoic membrane (CAM) assay.
- Incerti, Matteo,Russo, Simonetta,Corrado, Miriam,Giorgio, Carmine,Ballabeni, Vigilio,Chiodelli, Paola,Rusnati, Marco,Scalvini, Laura,Callegari, Donatella,Castelli, Riccardo,Vacondio, Federica,Ferlenghi, Francesca,Tognolini, Massimiliano,Lodola, Alessio
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supporting information
(2020/01/29)
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- ISOLITHOCHOLIC ACID OR ISOALLOLITHOCHOLIC ACID AND DEUTERATED DERIVATIVES THEREOF FOR PREVENTING AND TREATING CLOSTRIDIUM DIFFICILE-ASSOCIATED DISEASES
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The present invention relates to isolithocholic acid (3?-hydroxy-5?-cholan-24-oic acid, iso-LCA) and isoallolithocholic acid (3?-hydroxy-5α-cholan-24-oic acid) and their deuterated analogs for preventing or treating Clostridium difficile-associated disease in a mammalian subject.
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- 3-MODIFIED ISO-/ISOALLO-LITHOCHOLIC ACID DERIVATIVES OR THEIR HOMO-ANALOGS FOR PREVENTING AND TREATING CLOSTRIDIOIDES DIFFICILE-ASSOCIATED DISEASES
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The present invention relates to isolithocholic acid (3β-hydroxy-5β-cholan-24-oic acid) and isoallolithocholic acid (3β-hydroxy-5α-cholan-24-oic acid) together with the respective 22-homo-analogs or the deuterated analogs, which are modified in 3-position
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- Method for synthesizing lithocholic acid from hyodeoxycholic acid as raw material
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The invention discloses a method for synthesizing a lithocholic acid from a hyodeoxycholic acid as the raw material. The hyodeoxycholic acid is used as the starting material, the lithocholic acid is produced through the seven reaction steps of 24-carboxylesterification, carboxylation of 3alpha-hydroxyl and 6alpha-hydroxyl through oxidation, selective reduction, acylation, hydrazone formation, hydrazoneremoval, and hydrolysis. The starting material is cheap and easy to get, no hydrazine hydrate is used in the synthesis process, the technological conditions for synthesis are safe, environmentally friendly and mild, the total yield is relatively high, and the method is suitable for industrial production.
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- Method for synthesizing lithocholic acid from deoxycholic acid as raw material
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The invention belongs to the field of organic chemicals, relates to a method for synthesizing lithocholic acid, and in particular relates to a method for synthesizing lithocholic acid from deoxycholicacid as a raw material. The method comprises the following steps: by taking deoxycholic acid as an initial raw material; carrying out oxidation and a hydrazone generation reaction, and further carrying out a reduction reaction, thereby obtaining the lithocholic acid. The method provided by the invention is low in initial raw material price, easy in raw material obtaining, short in synthesis stepand is a completely novel synthesis route; reagents used in the method are easy to preserve and safe and nontoxic, and the method is gentle in reaction condition, simple in aftertreatment, high in efficiency and total yield and applicable to industrial production.
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Paragraph 0056; 0057
(2018/12/13)
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- The invention relates to a raw material synthetic stone androstenedione cholic acid (by machine translation)
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The invention discloses a high-purity stone of cholic acid synthesis method, comprises the following steps: to androstenedione as the starting material, through the 3 bit enol ether protection, wittig reaction, 3 bit vinyl alcohol the ether escapes protection, 17 site side chain addition, 3 bit carbonyl reduction, saponification reaction, seven-step reaction of catalytic hydrogenation to obtain high-purity of target substance. The method of the invention uses cheap and easily obtained androstenedione as raw materials, innovative synthetic lithocholic, simple process route, each step the reaction yield is high, and the cost is low, the large-scale production of stone cholic acid difficult problem, is suitable for industrial production. (by machine translation)
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Paragraph 0017; 0024
(2019/01/08)
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- Method for synthesizing lithocholic acid by taking hyodeoxycholic acid as raw material
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The invention belongs to the field of organic chemistry, and relates to a lithocholic acid synthetic method, and particularly to a method for synthesizing lithocholic acid by taking hyodeoxycholic acid as a raw material. The synthetic method provided by the invention takes hyodeoxycholic acid as the raw material, the hyodeoxycholic acid is oxidized to generate hydrazone reaction, and then the lithocholic acid is obtained through reduction. The synthetic method provided by the invention has the advantages that starting raw materials are cheap and easily obtained, the synthetic steps are short,a brand new synthetic route is provided, the required reagent is easily stored, safe and non-toxic, the reaction condition is gentle, the aftertreatment is simple, the energy efficiency and the wholeyield are high, and the method is suitable for industrial production.
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Paragraph 0044; 0048; 0049; 0050; 0055
(2018/12/02)
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- Method for synthesizing lithocholic acid from chenodeoxycholic acid as raw material
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The invention belongs to the field of organic chemistry, and relates to a synthesis method of lithocholic acid, in particular to a method for synthesizing the lithocholic acid from chenodeoxycholic acid as a raw material. According to the synthesis method, with the chenodeoxycholic acid as the raw material, after oxidation, a hydrazone formation reaction is performed, and then a reduction reactionis performed to obtain the lithocholic acid. In the synthesis method, the starting material is cheap and easy to obtain and synthesis steps are short, so that the synthesis method is a brand-new synthesis route; by the synthesis method, a required reagent is easy to store, safe and non-toxic, a reaction condition is mild, posttreatment is simple, the energy efficiency and the total yield are high; the synthesis method is suitable for industrial production.
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Paragraph 0044; 0048; 0049; 0050; 0051; 0054; 0055; 0057
(2018/11/03)
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- Steroid compound 3-site hydroxyl configuration inversion method
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The invention discloses a steroid compound 3-site hydroxyl configuration inversion method. The method specifically comprises the following steps that (1) a steroid compound containing a 3-site hydroxyl reacts with an acyl chloride compound; (2) the product obtained in the step (1) and a substituting agent are subjected to SN2 nucleophilic substitution reaction under existing of a phase transfer catalyst; and (3) the product obtained in the step (2) is subjected to a hydrolysis reaction. Compared with a Mitsunobu method, the method does not need to use triphenylphosphine and azodiformate pricedhigher, and accordingly the production cost is greatly lowered; meanwhile, a p-nitrobenzoic acid derivative which seriously affects the water environment does not need to be used, and therefore the method is more environmentally friendly. The method adopts cesium acetate/18-crown ether-6 system to conduct 3-site hydroxyl configuration inversion, can remarkably reduce occurrence of side reactions,accordingly a higher reaction yield is obtained, and the method is finally applicable to industrialized production.
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Paragraph 0093; 0099; 0100
(2018/12/14)
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- METHODS FOR PREPARATION OF BILE ACIDS AND DERIVATIVES THEREOF
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The present application relates to a method of preparing compounds of Formula (I) or a pharmaceutically acceptable salt, solvate, or amino acid conjugate thereof, R1 is H, α-OH, β-ΟΗ, or an oxo group.
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- The synthesis and antitumor activity of lithocholic acid and its derivatives
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In this paper, a new and concise synthetic route of lithocholic acid (LCA) using commercially available steroid source deoxycholic acid is reported. A series of amide derivatives of LCA were also synthesized and investigated for their activity against the growth of MCF-7 and MCF-7/ADR cells using the sulforhodamine B assay. For MCF-7, the most potent compound 20 showed a 20-fold higher antitumor activity than LCA. For MCF-7/ADR, the most potent compound 24 showed a 22-fold higher antitumor activity than LCA. The transwell migration assay of 20 was evaluated on MDA-MB-231 cells. The colony formation and apoptosis assays of 20 were performed on MCF-7 and MCF-7/ADR cell lines.
- He, Xiao-Long,Xing, Yajing,Gu, Xiang-Zhong,Xiao, Jie-Xin,Wang, Ying-Ying,Yi, Zhengfang,Qiu, Wen-Wei
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- Method for synthesizing lithocholic acid from cholic acid
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The invention discloses a method for synthesizing lithocholic acid from cholic acid. According to the method, cholic acid is used as a starting raw material, and lithocholic acid is synthesized through the following four steps of reaction: selective protection of 3alpha-OH; oxidation of 7alpha-OH and 12alpha-OH into carbonyl groups; hydrolysis; and Huang Min-lon reduction. The raw material used in the method is easily available and cheap, and the method is few in synthesis steps and side reactions, simple in after-treatment, high in overall yield and suitable for industrial production.
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- Method for synthesizing lithocholic acid from chenodeoxycholic acid as raw material
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The invention discloses a method for synthesizing lithocholic acid from chenodeoxycholic acid as a raw material. According to the method, chenodeoxycholic acid is adopted as an initial raw material, and the lithocholic acid is prepared through two steps of synthesis of selective oxidation with 7alpha-OH and Huang Min-lon reduction. The method is low in price and easy in initial raw material obtaining, short in synthesis step, simple in aftertreatment, high in total yield and applicable to industrial production.
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Paragraph 0040; 0041; 0042
(2017/10/13)
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- PROCESS AND INTERMEDIATES FOR THE 6,7-ALPHA-EPOXIDATION OF STEROID 4,6-DIENES
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The invention relates to a process for preparing a compound of general formula (la): wherein R2, Y, R4and R5are as defined herein, wherein the epoxidation is conducted using an oxidant and methyltrioxorhenium as a catalyst (MeReO3). The invention also relates to certain compounds per se.The compounds are intermediates in the synthesis of synthetic bile acids.
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- Method for synthesizing lithocholic acid from hyodesoxycholic acid
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The invention discloses a method for synthesizing lithocholic acid, comprising: using hyodesoxycholic acid as a start material, and performing two-step reaction of 6Alpha-OH selective oxidation and Huang Minglon reduction to synthesize the lithocholic acid. The start material herein is low in price and easy to obtain, the synthetic steps are short, posttreatment is simple, few side reactions are employed, and the method is applicable to industrial production.
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Paragraph 0040; 0041; 0042
(2017/08/29)
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- 6-ALKYL-7-HYDROXY-4-EN-3-ONE STEROIDS AS INTERMEDIATES FOR THE PRODUCTION OF STEROIDAL FXR MODULATORS
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The invention relates to compounds of formula (I), wherein R1, R2, Y, R4 and R5 are as defined herein. The compounds are intermediates in the synthesis of synthetic bile acids.
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- Synthesizing method of lithocholic acid
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The invention discloses a synthesizing method of lithocholic acid. The synthesizing method is characterized in that deoxycholic acid is used as the raw material, and the deoxycholic acid is subjected to reactions such as methyl esterification protection, acetic anhydride protection of 3 hydroxyl groups, dewatering, hydrogenation and hydrolysis to synthesize the lithocholic acid. The synthesizing method is simple in step, few in side reaction, high in yield, easy in raw material obtaining, suitable for industrial production, and capable of solving the problems that the prior art is excessively high in synthesizing cost, low in yield and not suitable for large-scale industrial production.
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- Triplet energy management between two signaling units through cooperative rigid scaffolds
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Through-bond triplet exciplex formation in donor-acceptor systems linked through a rigid bile acid scaffold has been demonstrated on the basis of kinetic evidence upon population of the triplet acceptors (naphthalene, or biphenyl) by through-bond triplet-
- Miro, Paula,Vayá, Ignacio,Sastre, Germán,Jiménez, M. Consuelo,Marin, M. Luisa,Miranda, Miguel A.
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supporting information
p. 713 - 716
(2016/01/12)
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- Structure-Activity Relationships and Mechanism of Action of Eph-ephrin Antagonists: Interaction of Cholanic Acid with the EphA2 Receptor
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The Eph-ephrin system, including the EphA2 receptor and the ephrinA1 ligand, plays a critical role in tumor and vascular functions during carcinogenesis. We previously identified (3α,5β)-3-hydroxycholan-24-oic acid (lithocholic acid) as an Eph-ephrin antagonist that is able to inhibit EphA2 receptor activation; it is therefore potentially useful as a novel EphA2 receptor-targeting agent. Herein we explore the structure-activity relationships of a focused set of lithocholic acid derivatives based on molecular modeling investigations and displacement binding assays. Our exploration shows that while the 3-α-hydroxy group of lithocholic acid has a negligible role in recognition of the EphA2 receptor, its carboxylate group is critical for disrupting the binding of ephrinA1 to EphA2. As a result of our investigation, we identified (5β)-cholan-24-oic acid (cholanic acid) as a novel compound that competitively inhibits the EphA2-ephrinA1 interaction with higher potency than lithocholic acid. Surface plasmon resonance analysis indicates that cholanic acid binds specifically and reversibly to the ligand binding domain of EphA2, with a steady-state dissociation constant (KD) in the low micromolar range. Furthermore, cholanic acid blocks the phosphorylation of EphA2 as well as cell retraction and rounding in PC3 prostate cancer cells, two effects that depend on EphA2 activation by the ephrinA1 ligand. These findings suggest that cholanic acid can be used as a template structure for the design of effective EphA2 antagonists, and may have potential impact in the elucidation of the role played by this receptor in pathological conditions.
- Tognolini, Massimiliano,Incerti, Matteo,Hassan-Mohamed, Iftiin,Giorgio, Carmine,Russo, Simonetta,Bruni, Renato,Lelli, Barbara,Bracci, Luisa,Noberini, Roberta,Pasquale, Elena B.,Barocelli, Elisabetta,Vicini, Paola,Mor, Marco,Lodola, Alessio
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experimental part
p. 1071 - 1083
(2012/08/08)
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- Characterization of rabbit aldose reductase-like protein with 3β-hydroxysteroid dehydrogenase activity
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In this study, we isolated the cDNA for a rabbit aldose reductase-like protein that shared an 86% sequence identity to human aldo-keto reductase (AKR)1 1B10 and has been assigned as AKR1B19 in the AKR superfamily. The purified recombinant AKR1B19 was similar to AKR1B10 and rabbit aldose reductase (AKR1B2) in the substrate specificity for various aldehydes and α-dicarbonyl compounds. In contrast to AKR1B10 and AKR1B2, AKR1B19 efficiently reduced 3-keto-5α/β-dihydro-C19/C21/C24-steroids into the corresponding 3β-hydroxysteroids, showing Km of 1.3-9.1 μM and kcat of 1.1-7.6 min-1. The stereospecific reduction was also observed in the metabolism of 5α- and 5β- dihydrotestosterones in AKR1B19-overexpressing cells. The mRNA for AKR1B19 was ubiquitously expressed in rabbit tissues, and the enzyme was co-purified with 3β-hydroxysteroid dehydrogenase activity from the lung. Thus, AKR1B19 may function as a 3-ketoreductase, as well as a defense system against cytotoxic carbonyl compounds in rabbit tissues. The molecular determinants for the unique 3-ketoreductase activity were investigated by replacement of Phe303 and Met304 in AKR1B19 with Gln and Ser, respectively, in AKR1B10. Single and double mutations (F303Q, M304S and F303Q/M304S) significantly impaired this activity, suggesting the two residues play critical roles in recognition of the steroidal substrate.
- Endo, Satoshi,Matsunaga, Toshiyuki,Kumada, Sho,Fujimoto, Airi,Hara, Akira,Ohno, Satoshi,El-Kabbani, Ossama,Hu, Dawei,Toyooka, Naoki,Mano, Jun'Ichi,Tajima, Kazuo
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p. 23 - 30,8
(2020/08/20)
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- TGR5 MODULATORS AND METHODS OF USE THEROF
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The invention relates to compounds of Formula A: or a salt, solvate, hydrate, or prodrug thereof. The compounds of Formula A are TGR5 modulators useful for the treatment of various diseases, including metabolic disease, inflammatory disease, liver disease, autoimmune disease, cardiac disease, kidney disease, cancer, and gastrointestinal disease.
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Page/Page column 38-39
(2010/06/22)
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- Anchoring cationic amphiphiles for nucleotide delivery significance of DNA release from cationic liposomes for transfection
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We have designed and synthesized lithocholic acid-based cationic amphiphile molecules as components of cationic liposomes for gene transfection (lipofection). To study the relationship between the molecular structures of those amphiphilic molecules, particularly the extended hydrophobic appendant (anchor) at the 3-hydroxyl group, and transfection efficiency, we synthesized several lithocholic and isolithocholic acid derivatives, and examined their transfection efficiency. We also compared the physico-chemical properties of cationic liposomes prepared from these derivatives. We found that isolithocholic acid derivatives exhibit higher transfection efficiency than the corresponding lithocholic acid derivatives. This result indicates that the orientation and extension of hydrophobic regions influence the gene transfection process. Isolithocholic acid derivatives showed a high ability to encapsulate DNA in a compact liposome-DNA complex and to protect it from enzymatic degradation. Isolithocholic acid derivatives also facilitated the release of DNA from the liposome-DNA complex, which is a crucial step for DNA entry into the nucleus. Our results show that the transfection efficiency is directly influenced by the ability of the liposome complex to release DNA, rather than by the DNA-encapsulating ability. Molecular modeling revealed that isolithocholic acid derivatives take relatively extended conformations, while the lithocholic acid derivatives take folded structures. Thus, the efficiency of release of DNA from cationic liposomes in the cytoplasm, which contributes to high transfection efficiency, appears to be dependent upon the molecular shape of the cationic amphiphiles.
- Hirashima, Naohide,Minatani, Kazuhiro,Hattori, Yoshifumi,Ohwada, Tomohiko,Nakanishi, Mamoru
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p. 1117 - 1122
(2008/02/07)
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- Synthesis of ester-linked lithocholic acid dimers
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Four lithocholic acid dimers were synthesised via esterification. The ester-linked dimer, 3-oxo-5β-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3α,5β), was obtained by condensation of methyl lithocholate with 3-oxo-5β-cholan-24-oic acid. Borohydride reduction of this ester-linked dimer gave 3α-hydroxy-5β-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3α,5β), which was acetylated to 3α-acetoxy-5β-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3α,5β). Reaction of methyl lithocholate with oxalyl chloride yielded the oxalate dimer, bis(5β-cholan-24-oic acid methyl ester)-3α-yl oxalate.
- Nahar, Lutfun,Turner, Alan B.
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p. 1157 - 1161
(2007/10/03)
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- Preparation of bile acids
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Certain bile acids find use in the pharmaceutical industry. In view of the wide distribution of serious diseases such as HIV, AIDS and Bovine Spongiform Encephalopathy (BSE) it is desirable to avoid—as far as practicable—to have any components of animal origin in medicaments in order to eliminate any danger of infection. The present invention relates to a method of providing bile acids from non-animal starting materials.
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- Biodegradable polanhydrides derived from dimers of bile acids, and use thereof as controlled drug release systems
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New biodegradable polyanhydrides are disclosed, which are prepared by homopolymerization of dimer of bile acid, especially lithocholic acid, or bycopolymerization with linear dicarboxylic acid, especially sebacic acid. These biodegradable polyanhydrides have degradation kinetics and a release rate that make them particularly useful for controlled drug release. More specifically, the degradation kinetics of such anhydrides and the release rate of molecules embedded therein make them useful as matrices for controlled drug release systems. The rates of degradation and release can be adjusted by the copolymer composition. The near zero-order kinetrics of release of the drug embedded in the matrices made of such anhydrides, make the same particularly useful since they can deliver an active ingredient at a constant rate for long period of time, avoiding the inauspicious saw-tooth pattern of conventional systemic administration.
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- A NOVEL CARBOXYL PROTECTING GROUP - THE CARBOXAMIDE DERIVED FROM 5,6-DIHYDROPHENANTHRIDINE -
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Carboxyl groups protected as the amides derived from 5,6-dihydrophenanthridine are stable under a wide range of conditions and can be selectively deprotected by oxidation on treatment with cerium(IV)
- Uchimaru, Tadafumi,Narasaka, Koichi,Mukaiyama, Teruaki
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p. 1551 - 1554
(2007/10/02)
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