有用化合物への変換を目指した天然物の化学修飾 : イオノフォア抗生物質Monensinの化学修飾
スポンサーリンク
概要
- 論文の詳細を見る
Monensin (1) is a representative compound of polyether ionophore antibiotics, which selectively transport Na^+ ions. In order to obtain potent Na^+ ionophores, the modification of the carboxyl group of monensin was carried out to yield monensylamino acids (2) and monensylamino acid-1,29-lactones (3). The Na^+ permeability of ion through the erythrocyte membrane of 2 and 3 was evaluated by the ^<23>Na-NMR method. Compound 2 showed less Na^+ ion transport activity than monensin, probably due to the lower lipophilicity caused by the conformational change of the chain moiety of the molecules. Although 3 showed higher lipophilisity than 1,3 had no Na^+ ion permeability, probably due to loss of the carboxyl group. As more lipophilic compounds possessing a carboxyl group was supposed to have more ion transport activity, 7-O-acylmonensins (8) and 7-O-alkylmonensins (11) were synthesized. Among these compounds, the value of Na^+ ion permeability of 7-O-benzylmonensin (11c) was 1.4 time that of 1. Further investigation was carried out by preparing various 7-O-(substituted benzyl) monensins (13), and 7-O-(p-ethylbenzyl) monensin (13b) exhibited the largest Na^+ ion permeability, about twice the value of 1. In order to convert monensin (1) to Ca^<2+> ionophore, 7-carboxylmethylmonensin (18) via protected 7-oxomonensin (15), and 25-carboxylmonensin (26) were prepared. In the course of the synthesis, 15 was clarified as a useful intermediate to give 7-amino and 7-alkyl derivatives. Ca^<2+> ion transport activities of 18 and 26 were determined by a CHCl_3 liquid membrane system. 25-carboxylmonensin (26) showed 70% of the activity of Ca^<2+> ionophore, lasalocid A, and compound 26 could be the lead compound for the preparation of a new Ca^<2+> ionophore.
- 公益社団法人日本薬学会の論文
- 1997-09-25
著者
関連論文
- ビス(P-クロルフェニル)カルピノール系殺ダニ剤のガスクロマトグラフィーによる定量
- 患者の自覚症状(訴え)及び患者背景の評価点を用いた医薬品副作用の推測に関する研究 : 第6報 薬剤性代謝障害
- P-25 メシマコブの低分子微量成分の研究(ポスター発表の部)
- Novel Annelations of Xanthines by the Reaction of 8-Aminoxanthines with Dimethyl Acetylene-dicarboxylate
- 新しい入試制度を体験して
- Synthesis of Isoselenazolo- or Isothiazolo[4,3-e][1,4]diazepines
- HPLC profiling of Phellinus linteus
- 105(P-62) Monensin二価誘導体のイオン輸送能とコンフォメーションに関する研究(ポスター発表の部)
- 73(P-63) メキシコ産ヒガンバナ科植物Zephyranthes carinataのアルカロイドとそのNMRスペクトルにおける特異な挙動(ポスター発表の部)
- 58(P-33) ポリエーテル抗生物質monensinおよび誘導体のNMRを用いた溶液中の立体配座推定へのアプローチ : Long range C-H結合定数を利用して(ポスター発表の部)
- 113(P48) イオノフォア抗生物質Monensinの化学修飾とイオン輸送活性(ポスター発表の部)
- これからの図書館
- 123(P70) イオノフォア抗生物質Monensinの化学修飾とイオン輸送活性(ポスター発表の部)
- NOVEL ANTIOXIDANTS FROM ROASTED PERILLA SEED
- Studies on Chemical Modification of Monensin. V. Synthesis, Sodium Ion Permeability, Antibacterial Activity, and Crystal Structure of 7-O-(4-Substituted benzyl)monensins
- Studies on Cardiac Ingredients of Plants. XI. Synthesis of New Bufotoxin Homologues Utilizing Scillarenin (the Genuine Aglycone of Proscillaridin), and Their Biological Activities
- Mechanism of an Early Lysis by Fatty Acids from Axenic Phormidium tenue (Musty Odor-Producing Cyanobacterium) and Its Growth Prolongation by Bacteria
- ENZYMATIC REGIOSELECTIVE ACYLATION OF 3-O-β-D-GALACTOPYRANOSYL-SN-GLYCEROL BY ACHROMOBACTER SP. LIPASE
- Auto-Growth Inhibitory Substance from the Fresh-Water Cyanobacterium Phormidium tenue
- Isolation and Identification of Anti-tumor-Promoting Principles from the Fresh-Water Cyanobacterium Phormidium tenue
- Studies on Glycolipids. VII. Isolation of Two New Sulfoquinovosyl Diacylglycerols from the Green Alga Chlorella vulgaris
- Studies on Glycolipids. VI. New Acyl-Distributed Glyceroglycolipids from the Nitrogen-Fixing Cyanobacterium Anabaena flos-aquae f. flos-aquae
- CARDIAC GLYCOSIDE-INDUCED ELEVATION OF INTRACELLULAR Na^+ ION CONCENTRATION IN HUMAN ERYTHROCYTES STUDIED BY ^Na NMR SPECTROSCOPY : RELATIONSHIP BETWEEN INOTROPY SPEED AND ELEVATION RATE OF INTRACELLULAR Na^+ ION CONCENTRATION
- Ring Transformation Medeated by Lewis Acids and Oxidizing Agents.Synthesis of 2-Methoxy-1H-imidazole from 5-Aminopyrimidin-4(3H)-one
- 強心性植物成分の研究(第10報)Tetrahydroproscillaridinの硝酸エステル体の合成とその薬理作用
- Studies on the Chemical Modification of Monensin. IV. Synthesis, Sodium Ion Permeability, and Biological Activity of 7-O-Acyl-and 7-O-Alkylmonensins
- Studies on Cardiac Ingredients of Plants. IX. Chemical Transformation of Proscillaridin by Utilizing Its 1,4-Cycloadducts as Key Compounds and Biological Activities of Their Derivatives
- A NOVEL GLYCEROGLYCOLIPID FROM THE NITROGEN-FIXING CYANOBACTERIUM ANABAENA FLOS-AQUAE F. FLOS-AQUAE
- The Oxidized Products of 8-Methoxypsoralen (8-MOP) with H_2O_2-NaOCl
- Studies on Glycolipids. III. Glyceroglycolipids from an Axenically Cultured Cyanobacterium, Phormidium tenue
- 強心性植物成分の研究(第8報)強心配糖体Proscillaridinの硝酸エステル体の合成とその薬理作用
- 12P-7-61 病棟 DI 活動の効率化を図る活動用紙作成の試み
- 薬物性白血球減少症の危険因子及び自覚症状に関する研究
- Utilization of Organoselenium Compounds. II. Reaction of Fused Isoselenazoles with Alkylamines(Organic,Chemical)
- Studies on the chemical Modification of Monensin. III. Synthesis and Sodium Ion transport Activity of macrocylic Monenslamino Acid-1,29-lactones
- Studies on the Chemical Modification of Monensin. II. : Measurement of Sodium Ion Permeability of Monensylamino Acids Using Sodium-23 Nuclear Magnetic Resonance Spectroscopy
- Studies on the Chemical Modification of Monensin. I. : Synthesis and Crystal Stuructures of NaBr Complexes of Monensylamino Acids
- Ring Transformation of a Diterpenoid Grayanol Derivative into 1-epi-Leucothol
- Reaction of Grayanotoxin-II with Lead Tetraacetate
- 入試制度と学生層の変化(入試制度と薬学教育)
- Studies on Cardiac Ingredients of Plants. V. : Chemical Transformation of Proscillaridin and Biological Activities of Derivaties
- Studies on Cardiac Ingredients of Plants. III. Structural Confirmation and Biological Activity of Reduced Proscillaridins(Organic,Chemical)
- ネジキLyonia ovalifolia DRUDE var.elliptica HAND.-MAZZ.の成分研究(第20報)Triterpenoid Glucoside, Lyofolic Acidの構造 その4 Protolyofoligenic Acidの構造
- ネジキLyonia ovalifolia DRUDE var.elliptica HAND.-MAZZ.の成分研究(第19報)Triterpenoid Glucoside, Lyofolic Acidの構造 その3 Lyofoligenic Acidの構造
- Correlation of Protolyofoligenic Acid with Cycloartenol
- ホツツジTripetaleia paniculata SIEB.et.ZUCC.の成分研究(第5報)花の成分と材の成分(その3)について
- ネジキLyonia ovalifolia DRUDE var. elliptica HAND.-MAZZ.の成分研究(第18報)Diterpenoid, Lyoniol-Dの構造およびLyoniol-A(Lyoniatoxin)とGrayanotoxin-Iの関連について
- 含窒素Triterpene誘導体の合成研究(第8報)ベツリン酸およびオレアノール酸誘導体
- ホツツジTripetaleia paniculata SIEB.et ZUCC.の成分研究(第4報)材の成分について その2 Lyonisideの構造
- ネパール産Lyonia ovalifolia DRUDE葉の成分研究
- 含窒素Triterpene誘導体の合成研究(第2報)A環に数種の含窒素環を縮合させたTriterpene誘導体
- Structure-Activity Relationship of Lyoniol-A and Related Compounds in Association with the Excitatory Effect on Muscle Spindle Afferents
- 有用化合物への変換を目指した天然物の化学修飾 : イオノフォア抗生物質Monensinの化学修飾
- 94(P31) 油糧種子に含有される抗酸化物質の研究 : ベニバナ油粕及び綿実油粕に含有される抗酸化物質の探索(ポスター発表の部)
- Studies on Cardiac Ingredients of Plants. VII : Chemical Transformation of Proscillaridin by Means of the Diels-Alder Reaction and Biological Activities of Its Derivatives
- PHOTOCHEMICAL TRANSFORMATION OF BUFADIENOLIDE
- Syntheses of Dihydrodioxepinopyridines, Dihydrodioxocinopyridines, and a Dihydrooxazepinopyridine
- Studies on the Chemical Transformations of Rotenoids. IV. : Synthesis of Novel Benzofuro[2,3-d]pyridazines Fused with Tetrazole, 1,2,4-Triazole and 1,2,4-Triazine
- Transformation of Pyrazolo [3,4-c] [1,5] benzothiazepines into Quinolines
- 新規複素環キノン"Benzo[g]pyrido[2,1-b]quinazoline-6,11-dioneおよびBenzo[g]pyrazolo[3,2-b]quinazoline-5,10-diones"の合成
- ナフトキノンを原料とするBenzo[α]phenazine誘導体の合成とその抗菌活性
- 薬科大学に附属薬局を
- 患者の自覚症状(訴え)及び患者背景の評価点を用いた医薬品副作用の推測に関する研究(第1報)薬物性肝障害
- Serotonin Derivative, N-(p-Coumaroyl) serotonin, Isolated from Safflower (cathamus tinctorius L.) Oil Cake Augments the Proliferation of Normal Human and Mouse Fibroblasts in Synergy with Basic Fibroblast Growth Factor (bFGF) or Epidermal Growth Factor (E
- New Steroid and Matairesinol Glycosides from Safflower (Carthamus tinctorius L.) Oil Cake
- Antioxidative Compounds Isolated from Safflower (Carthamus tinctorius L.) Oil Cake
- Synthesis of Coumarins by Nucleophilic Denitrocyclization Reaction(Organic,Chemical)
- 患者の自覚症状(訴え)及び患者背景の評価点を用いた医薬品副作用の推測に関する研究 : (第5報)消化器障害
- 患者の自覚症状(訴え)及び患者背景の評価点を用いた医薬品副作用の推測に関する研究(第4報) : 薬疹
- 医薬品の適正使用への医薬情報の応用研究 : 患者の訴え(自覚症状)及び患者背景の評価による副作用の推測
- 患者の自覚症状(訴え)及び患者背景の評価点を用いた医薬品副作用の推測に関する研究(第3報) : 白血球障害
- 患者の自覚症状(訴え)及び患者背景の評価点を用いた医薬品副作用の推測に関する研究(第2報) : 錐体外路障害
- Synthesis of Imidazo[4,5-c][1,2,6]thiadiazine 2-Oxides from Hydrolytes of Xanthines and Determination of Their Vasodilating Activity
- Synthesis of Imidazo[4,5-e][1,4]diazepine and Imidazo[4,5-e][1,4]-oxazepine Derivatives Using Caffeidine, a Hydrolysis Product of Caffeine
- Studies on Xanthine Derivatives. II. : Synthesis of 1,2,3,7-Tetrahydro-6H-purin-6-ones from Xanthine Hydrolyzates
- SEVEN NEW MONOGALACTOSYL DIACYLGLYCEROLS ISOLATED FROM THE AXENIC CYANOBACTERIUM PHORMIDIUM TENUE
- AN AUTOLYTIC SUBSTANCE IN A FRESHWATER CYANOBACTERIUM PHORMIDIUM TENUE
- Syntheses, Antitumor Activity and Vascular Relaxing Effect of Purino[7,8-g]-6-azapteridines and [1,2,4]Triazino-[3,2-f]purines(Organic,Chemical)
- 強心性植物成分の研究 : キサンチン誘導体の構造変換と生理活性について
- Synthesis of 5-Amino-4 (3H)-pyrimidinones. II. Synthesis of 5-Acyl- and 5-Alkylamino-3-phenyl-6-methyl-4 (3H)-pyrimidinones and Determination of Their Analgesic and Antiinflammatory Activities
- New Lignan Glycosides from Chinese Medicinal Plant, Sinopodophillum emodi
- OCCURRENCE OF PIEROSIDE C, A GRAYANOTOX-9-ENE DERIVATIVE, IN PIERIS JAPONICA
- ツツジ科植物に含まれるジテルペノイド
- アセビPieris japonica葉の成分研究.新ジテルペンAsebotoxin-Xおよび新ジテルペン配糖体Pieroside Aの単離と構造決定
- Carbon-13 Nuclear Magnetic Resonance Spectral Assignments of Grayanotoxin-I
- 公開講座を語る
- 醤油より4-Hydroxy-5-Methyl-3(2H)-Furanone(HMF)の簡易分離法
- NOVEL UTILIZATION OF ORGANOSELENIUM COMPOUNDS. I. A FACILE TRANSFORMATION OF FUSED ISOSELENAZOLES TO FUSED PYRIDINES
- NOVEL RING TRANSFORMATION OF 5-AMINO-4 (3H)-PYRIMIDINONES INTO IMIDAZOLES AND IMIDAZOLES INTO A 1,2,4-TRIAZINE
- AN UNUSUAL TRANSFORMATION OF 5-AMINO-6-METHYL-3-PHENYL-4 (3H)-PYRIMIDONE WITH SELENIUM DIOXIDE : X-RAY CRYSTAL STRUCTURE OF 3-PHENYLCARBAMOYL-4-METHYL-1,2,5-SELENADIAZOLE
- 第12回IUPAC天然物化学シンポジウム
- 2,6-ジブロムキノンクロルイミドによるカーバメート系殺虫剤の比色定量法
- 強心性植物成分の研究--ジヒドロウワバインの構造と生理活性について
- 大学図書館にはなるべく多くの一次資料を揃えたい(情報化時代を迎えた薬学図書館のあり方)
- 研究年報を生かすには……(大学紀要・研究所年報を考える)
- 秋, 各支部で盛大な支部大会を(支部活動への希望と意見)
- 有機化合物構造決定入門書
- 有機化学の教科書あれこれ
- 二本立ては止めて, 会場設営・会費徴収に工夫を(年会懇親会のあり方)
- 塩化パラジウムとp-ニトロソN,N-ジエチルアニリンを利用した含硫黄有機リン系殺虫剤の比色定量