Synthesis and antidiuretic activities of novel glycoconjugates of arginine-vasopressin.

Abstract:

:Arginine-vasopressin (AVP) was acylated with various acyl azides (2a-j) in pH 9.1 buffer to give AVP derivatives (11a-j) modified at the tyrosine side chain with a carbohydrate via a spacer arm. Glycoconjugates of AVP modified at the N-terminal amide (12a-e) were also synthesized from AVP and carboxylic acids (3a-e) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole as coupling agent. Analogues (11a-j) exhibited greater in vivo antidiuretic activity than AVP. AVP and glycoconjugates (12a-e) were stable in rat plasma. On the other hand, glycoconjugates (11a-i) were found to readily convert to AVP according to first order kinetics. Hence, 11a-j are considered to be prodrugs of AVP.

authors

Susaki H,Suzuki K,Ikeda M,Yamada H,Watanabe HK

doi

10.1248/cpb.46.1530

subject

Has Abstract

pub_date

1998-10-01 00:00:00

pages

1530-7

issue

10

eissn

0009-2363

issn

1347-5223

journal_volume

46

pub_type

杂志文章
  • Antidiabetogenic constituents from the Thai traditional medicine Cotylelobium melanoxylon.

    abstract::The methanolic extracts from the wood and bark of Cotylelobium melanoxylon were found to inhibit plasma glucose elevation after sucrose loading in rats and triglyceride elevation after olive oil loading in mice. A new stilbene dimer, melanoxylin A, together with the known stilbene dimers [(+)-ampelopsin F, (+)-isoampe...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.487

    authors: Matsuda H,Asao Y,Nakamura S,Hamao M,Sugimoto S,Hongo M,Pongpiriyadacha Y,Yoshikawa M

    更新日期:2009-05-01 00:00:00

  • Cycloartane glycosides from Cimicifuga dahurica.

    abstract::A new cycloartane bisdesmoside and two new trinorcycloartane glycosides, along with four known cycloartane compounds, were isolated from the rhizomes of Cimicifuga dahurica (Ranunculaceae). The structures of the new compounds were elucidated as 3-O-alpha-L-arabinopyranosyl cimigenol 15-O-beta-D-glucopyranoside, 24-hyd...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1468

    authors: Zhang QW,Ye WC,Hsiao WW,Zhao SX,Che CT

    更新日期:2001-11-01 00:00:00

  • Antiulcer activities of glycyrrhetinic acid derivatives in experimental gastric lesion models.

    abstract::Glycyrrhetinic acid (Ia) and eighteen related derivatives were examined for antiulcer activity using stress-induced gastric lesions (restraint plus water immersion at 25 degrees C) in mice and rats as screening tests. Among the compounds tested, dihemiphthalate derivatives of 18 alpha- or 18 beta-olean-12-ene-3 beta,3...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.2500

    authors: Yano S,Harada M,Watanabe K,Nakamaru K,Hatakeyama Y,Shibata S,Takahashi K,Mori T,Hirabayashi K,Takeda M

    更新日期:1989-09-01 00:00:00

  • Benzylidene 2-aminoimidazolones derivatives: synthesis and in vitro evaluation of anti-tumor carcinoma activity.

    abstract::A series of benzylidene 2-aminoimidazolones derivatives were synthesized. Most compounds displayed strong inhibitory activity on the proliferation of human HepG2 cells in vitro. The active compounds were further evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against five human ca...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00340

    authors: Ling Y,Wang ZQ,Xiao YA,Zhu C,Shen L,Wang XM,Hui Y,Wang XY

    更新日期:2013-01-01 00:00:00

  • Progress in Development of Interventions to Prevent Birth Defects in Diabetic Pregnancies.

    abstract::Diabetic embryopathy is a diabetic complication, in which maternal hyperglycemia in early pregnancy causes birth defects in newborn infants. Under maternal diabetic conditions, hyperglycemia disturbs intracellular molecular activities and organelles functions. These include protein misfolding in the endoplasmic reticu...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.c18-01013

    authors: Han L,Jiang Z,Zheng X,Qiu J,Hu Y,Li X

    更新日期:2019-01-01 00:00:00

  • Cytotoxic activity and DNA-binding properties of isoeuxanthone derivatives.

    abstract::In this study, the interactions of different groups substituted isoeuxanthone derivatives with calf thymus DNA (ct DNA) were investigated by spectrophotometric methods and viscosity measurements. Results indicated that the xanthone derivatives could intercalate into the DNA base pairs by the plane of xanthone ring and...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00789

    authors: Wang HF,Yan H,Gao X,Niu B,Guo R,Wei L,Xu B,Tang N

    更新日期:2014-01-01 00:00:00

  • Bitterness-Suppressing Effect of Umami Dipeptides and Their Constituent Amino Acids on Diphenhydramine: Evaluation by Gustatory Sensation and Taste Sensor Testing.

    abstract::Diphenhydramine, a sedating antihistamine, is an agonist of human bitter taste receptor 14 (hTAS2R14). Diphenhydramine hydrochloride (DPH) was used as a model bitter medicine to evaluate whether the umami dipeptides (Glu-Glu and Asp-Asp) and their constituent amino acids (Glu, Asp) could suppress its bitterness intens...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c19-00736

    authors: Okuno T,Morimoto S,Nishikawa H,Haraguchi T,Kojima H,Tsujino H,Arisawa M,Yamashita T,Nishikawa J,Yoshida M,Habara M,Ikezaki H,Uchida T

    更新日期:2020-01-01 00:00:00

  • Spectrophotometric and atomic absorption determination of ramipril, enalapril maleate and fosinopril through ternary complex formation with molybdenum (V)-thiocyanate (Mo(V)-SCN).

    abstract::Three different sensitive and accurate spectroscopic procedures were developed for the determination of three angiotensin-converting enzyme inhibitors, namely, ramipril, enalapril maleate and fosinopril. The first two spectrophotometric (extractive and non-extractive) procedures were based on ternary complex formation...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1521

    authors: Baraka MM,El-Sadek M,Moussa EM,Abd-Alaty NM

    更新日期:2008-11-01 00:00:00

  • Control of Drug Diffusion Behavior of Xanthan and Locust Bean Gum Gel by Agar Gel.

    abstract::Oral gel formulations are known as easy to administer drug products for patients who have problems taking drugs including those with conditions such as dysphagia. In addition, there are numerous commercially available oral gel products, most of which are immediate-release formulation that release their pharmaceutical ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00135

    authors: Hishikawa Y,Kakino Y,Tsukamoto H,Tahara K,Onodera R,Takeuchi H

    更新日期:2016-01-01 00:00:00

  • Synthesis and biological evaluation of 1,2,3,4-tetrahydroisoquinoline derivatives as potent and selective M2 muscarinic receptor antagonists.

    abstract::A series of 1,2,3,4-tetrahydroisoquinoline derivatives containing the 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one skeleton were prepared and evaluated for their in vitro binding affinities to muscarinic receptors and for antagonism of bradycardia in vivo. Among them, compound 3f had the highest affinity for ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.672

    authors: Watanabe T,Kinoyama I,Takizawa K,Hirano S,Shibanuma T

    更新日期:1999-05-01 00:00:00

  • Constituents of the Vietnamese medicinal plant Orthosiphon stamineus.

    abstract::From the MeOH extract of the aerial part of Vietnamese Orthosiphon stamineus, five new isopimarane-type diterpenes [orthosiphols F-J (1-5)] and two new diterpenes [staminols A (6) and B (7)] with a novel carbon-framework, to which we proposed the name "staminane", and three new highly-oxygenated staminane-type diterpe...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1711

    authors: Tezuka Y,Stampoulis P,Banskota AH,Awale S,Tran KQ,Saiki I,Kadota S

    更新日期:2000-11-01 00:00:00

  • Biomimetic oxidation of curcumin with hydrogen peroxide catalyzed by 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides in dichloromethane.

    abstract::The biomimetic oxidation of curcumin, a main turmeric pigment with hydrogen peroxide catalyzed by different 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides [TAPFe(III)Cl] in dichloromethane has been studied to give a C-C coupled curcumin dimer in 40-70% yield. The structure of the dimer has been elucidated by (1)H...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.1345

    authors: Chauhan SM,Kandadai AS,Jain N,Kumar A

    更新日期:2003-11-01 00:00:00

  • Preparations of cyclic sulfoxide derivatives and their evaluation as transdermal penetration enhancers.

    abstract::Novel cyclic sulfoxides, such as 2-octyl, 2-dodecyl and 2-hexadecyltetrahydrothiophene-1-oxide were prepared by the alkylation of tetrahydrothiophene-1-oxide. Additionally, 2-methyl, 2-ethyl and 2-propyl-5-dodecyltetrahydro-thiophene-1-oxide were conducted by further alkylation. Their enhancing activity on the penetra...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.1961

    authors: Aoyagi T,Yamamura M,Matsui K,Nagase Y

    更新日期:1992-07-01 00:00:00

  • Formation and conformation of baicalin-berberine and wogonoside-berberine complexes.

    abstract::It is well-known that baicalin-berberine complex (1) precipitates in the water decoction of numerous Chinese Medicinal formulae containing Radix Scutellariae and Rhizoma Coptidis or Cortex Phellodendri. In the current study, ionic interaction between the carboxylate ion of baicalin and the quaternary ammonium ion of b...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.60.706

    authors: Wang JR,Tanaka T,Zhang H,Kouno I,Jiang ZH

    更新日期:2012-01-01 00:00:00

  • Tannins of cornaceous plants. I. Cornusiins A, B and C, dimeric monomeric and trimeric hydrolyzable tannins from Cornus officinalis, and orientation of valoneoyl group in related tannins.

    abstract::Cornusiin A (1), cornusiin B (2) and cornusiin C (3), new dimeric, monomeric and trimeric hydrolyzable tannins, were isolated from the fruits of Cornus officinalis (Cornaceae). Their structures, including the orientation of the valoneoyl group in 1 and 3, were established on the basis of chemical and spectroscopic dat...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.2083

    authors: Hatano T,Ogawa N,Kira R,Yasuhara T,Okuda T

    更新日期:1989-08-01 00:00:00

  • Design, Synthesis, and Biological Evaluation of Beauveriolide Analogues Bearing Photoreactive Amino Acids.

    abstract::Beauveriolides I and III, which are naturally occurring cyclodepsipeptides, have been reported to bind to sterol O-acyltransferase (SOAT), inhibiting its ability to synthesize cholesteryl esters. To facilitate an analysis of the binding site(s) of these compounds, we designed beauveriolide analogues 1a-d wherein the L...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00095

    authors: Masuda Y,Aoyama K,Yoshida M,Kobayashi K,Ohshiro T,Tomoda H,Doi T

    更新日期:2016-07-01 00:00:00

  • Method for optical resolution of racemic homochlorcyclizine and comparison of optical isomers in antihistamine activity and pharmacokinetics.

    abstract::A method was developed for semi-preparative scale enantioseparation of racemic homochlorcyclizine (HCZ) by high performance liquid chromatography (HPLC) on Chiralcel OD column. The best resolution was achieved using an eluent composed of n-hexane plus 0.2 M isopropylamine. By this method, about 5.0 mg of racemic HCZ c...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.1341

    authors: Nishikata M,Nakai A,Fushida H,Miyake K,Arita T,Kitagawa S,Kunitomo M,Iseki K,Miyazaki K

    更新日期:1992-05-01 00:00:00

  • Biotransformation of a taxadiene by ginkgo cell cultures and the tumor multi-drug resistant reversal activities of the metabolites.

    abstract::The biotransformation of 2α,5α,10β-triacetoxy-14-oxo-taxa-4(20),11-diene (1) by cultured Gingko cells afforded four products. Their structures were identified on the basis of analyses of the chemical and spectroscopic (IR, MS, ¹H- and ¹³C-NMR) data. Among them, 2, 3 and 5 were three new compounds, and 4 displayed pote...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.1038

    authors: Xie D,Zhang Y,Zou J,Yin D,Chen X,Dai J

    更新日期:2011-01-01 00:00:00

  • Immobilized triazine-type dehydrocondensing reagents for carboxamide formation: ROMP-Trz-Cl and ROMP(OH)-Trz-Cl.

    abstract::New triazine-type dehydrocondensing reagents, such as ROMP-Trz-Cl and ROMP(OH)-Trz-Cl, were synthesized by a ring opening metathesis polymerization (ROMP) method, and these showed higher loading than conventional polymer-supported condensing reagents. These polymers effect the formation of amides in good yields by add...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.825

    authors: Hioki K,Kameyama S,Tani S,Kunishima M

    更新日期:2007-05-01 00:00:00

  • Synthesis of new N-analogous corollosporine derivatives with antibacterial activity by laccase-catalyzed amination.

    abstract::Corollosporine isolated from the marine fungus Corollospora maritima and N-analogous corollosporines are antimicrobial substances. Owing to the basic structure of the N-analogous corollosporines, they have become an attractive target for laccase-catalyzed derivatisation. In this regard we report on the straightforward...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.781

    authors: Mikolasch A,Hessel S,Salazar MG,Neumann H,Manda K,Gōrdes D,Schmidt E,Thurow K,Hammer E,Lindequist U,Beller M,Schauer F

    更新日期:2008-06-01 00:00:00

  • Synthesis and evaluation of pyrrolin-2-one compounds, a series of plasminogen activator inhibitor-1 inhibitors.

    abstract::A novel series of furan-2-one and pyrrolin-2-one derivatives having PAI-1 (plasminogen activator inhibitor-1) inhibitory activity were synthesized and evaluated for their antithrombotic activity in a rat arterial thrombosis model. Among the synthesized compounds, 5f (T-1776Na) was found to have good selectivity for PA...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.979

    authors: Miyazaki H,Ogiku T,Sai H,Moritani Y,Ohtani A,Ohmizu H

    更新日期:2009-09-01 00:00:00

  • Synthesis, characterization, cytotoxic activities, and DNA-binding studies of ternary copper(II) complexes with new coumarin derivatives.

    abstract::In this study, two novel complexes [Cu(MCVH)phen(H(2)O)].ClO(4) (1) and [Cu(MCLH)phen(H(2)O)].ClO(4) (2) (here, MCVH(2)=(7-hydroxy-4-methyl-8-coumarinyl) valine, MCLH(2)=(7-hydroxy-4-methyl-8-coumarinyl) leucine) have been synthesized and characterized by elemental analyses, molar conductance, infrared spectra (IR), (...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.1003

    authors: Jia L,Xu XM,Xu J,Chen LH,Jiang P,Cheng FX,Lu GN,Wang Q,Wu JC,Tang N

    更新日期:2010-08-01 00:00:00

  • Synthesis and antioxidant activity of styrylsulfonylmethyl 1,3,4-oxadiazoles, pyrazolyl/isoxazolyl-1,3,4-oxadiazoles.

    abstract::A new class of mono and bis heterocycles-styrylsulfonylmethyl 1,3,4-oxadiazoles, pyrazolyl/isoxazolyl-1,3,4-oxadiazoles were prepared and studied their antioxidant activity. The compound methyl substituted 2-(p-methylphenylamino-sulfonylmethyl)-5-[Z-(p-methylstyrylsulfonylmethyl)]-1,3,4-oxadiazole displayed slightly h...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00652

    authors: Mallikarjuna Reddy G,Muralikrishna A,Padmavathi V,Padmaja A,Krishna Tilak T,Appa Rao C

    更新日期:2013-01-01 00:00:00

  • Flavonol glycosides in leaves of two Diospyros species.

    abstract::Fourteen flavonol glycosides including two new compounds were isolated from the leaves of two Diospyros plants (D. cathayensis and D. rhombifolia). The structures of isolated compounds were determined by spectroscopic analysis. The scavenging activity of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical of the isolated com...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.591

    authors: Furusawa M,Tanaka T,Ito T,Nakaya K,Iliya I,Ohyama M,Iinuma M,Murata H,Inatomi Y,Inada A,Nakanishi T,Matsushita S,Kubota Y,Sawa R,Takahashi Y

    更新日期:2005-05-01 00:00:00

  • Synthesis and evaluation of novel 2-oxo-1,2-dihydro-3-quinolinecarboxamide derivatives as serotonin 5-HT4 receptor agonists.

    abstract::A series of N-azabicycloalkyl-1-alkyl-2-oxo-1,2-dihydro-3-quinolinecarboxamides were synthesized and tested for serotonin 5-HT4 receptor-stimulating effects in the regulation of electrically-evoked contraction in guinea pig muscle. Among them, N-azabicycloalkyl-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide (8c,...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.2003

    authors: Suzuki M,Ohuchi Y,Asanuma H,Kaneko T,Yokomori S,Ito C,Isobe Y,Muramatsu M

    更新日期:2000-12-01 00:00:00

  • Hydrophobicity parameters determined by reversed-phase liquid chromatography. XVI: A new hydrogen-accepting parameter for monosubstituted thiophenes and furans for correlating retention factors and octanol-water partition coefficients.

    abstract::We recently proposed a new hydrogen-accepting parameter, S(HA), for monosubstituted (di)azines on the basis of the heat of formation calculated by the conductor-like screening model (COSMO) method. In this work, S(HA) values for monosubstituted thiophenes and furans were calculated and the results were applied to the ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.1196

    authors: Yamagami C,Tachikawa H

    更新日期:2003-10-01 00:00:00

  • Oxygenated hexylitaconates from a marine sponge-derived fungus Penicillium sp.

    abstract::In the course of our search for bioactive metabolites from marine organisms, new hexylitaconic acid derivatives (1-4), along with (3S)-hexylitaconic acid (5), were isolated from a sponge-derived fungus Penicillium sp. Based on the NMR and MS data, the structures of compounds 1-4 were defined as α,β-dicarboxylic acid d...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.120

    authors: Li JL,Zhang P,Lee YM,Hong J,Yoo ES,Bae KS,Jung JH

    更新日期:2011-01-01 00:00:00

  • Constituents of the leaves of Woodfordia fruticosa Kurz. I. Isolation, structure, and proton and carbon-13 nuclear magnetic resonance signal assignments of woodfruticosin (woodfordin C), an inhibitor of deoxyribonucleic acid topoisomerase II.

    abstract::Woodfruticosin (woodfordin C), a new cyclic dimeric hydrolyzable tannin having an inhibitory activity toward deoxyribonucleic acid (DNA) topoisomerase II, has been isolated from the leaves of Woodfordia fruticosa Kurz (Lythraceae) along with three known flavonol glycosides and three known flavonol glycoside gallates. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.2687

    authors: Kadota S,Takamori Y,Nyein KN,Kikuchi T,Tanaka K,Ekimoto H

    更新日期:1990-10-01 00:00:00

  • Pharmacokinetics of [6]-gingerol after intravenous administration in rats with acute renal or hepatic failure.

    abstract::The pharmacokinetics of [6]-gingerol were investigated in rats with acute renal failure induced by bilateral nephrectomy, or those with acute hepatic failure induced by a single oral administration of carbon tetrachloride (CCl4), to clarify the contribution of the kidney and liver to the elimination process of [6]-gin...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.1295

    authors: Naora K,Ding G,Hayashibara M,Katagiri Y,Kano Y,Iwamoto K

    更新日期:1992-05-01 00:00:00

  • Abietane diterpenoids from the barks of Cryptomeria japonica.

    abstract::From the bark of Cryptomeria japonica were isolated sugikurojins I (1) and J (2), and an abietane derivative (3) was obtained for the first time as a natural product. These structures were elucidated primarily through extensive NMR experiments. Sugikurojin I (1) has a unique skeleton incorporating an abietane diterpen...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.574

    authors: Yoshikawa K,Suzuki K,Umeyama A,Arihara S

    更新日期:2006-04-01 00:00:00