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  • Cell & Developmental Biology  (12)
  • Organic Chemistry  (8)
  • Wiley-Blackwell  (20)
  • American Geophysical Union (AGU)
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  • Wiley-Blackwell  (20)
  • American Geophysical Union (AGU)
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  • 1
    Electronic Resource
    Electronic Resource
    X-Ray Crystallographic and MO Studies on the Conformation of Corynoline and the Related Compounds (1986)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 69 (1986), S. 1418-1423 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The crystal structure of (±)-corynoline (1) has been determined by X-ray diffraction methods. The rings B and C form the half-chair and the twist-half-chair conformations, respectively. The B/C ring conjunction exists in an anti-cis conformation, with a N … H—O intramolecular H-bond. Conformational energy calculation by the CNDO/2 method show that the conformations of 1, (+)-chelidonine (2), and their acetates, observed in crystal structures, are all in the one of total energy minimum.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19860690614
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  • 2
    Electronic Resource
    Electronic Resource
    Reactions of Chiral 2-(tert-Butyl)-2H,4H-1,3-dioxin-4-ones Bearing Functional Groups in the 6-Position and Diastereoselective Catalytic Hydrogenation to cis-2,6-Disubstituted 1,3-Dioxan-4-ones (1987)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 70 (1987), S. 2137-2145 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (R)-5-Bromo-6-(bromomethyl)-2-(tert-butyl)-2H,4H-1,3-dioxin-4-one (2) derived from (R)-3-hydroxybutanoic acid is used for substitutions and chain elongations at the side-chain C-atom in the 6-position of the heterocycle (→3-6, 10-13). Subsequent simultaneous reductive debromination and double-bond hydrogenation (Pd/C,H2)occurs with essentially complete diastereoselectivity (〉98% ds), with H transfer from the face opposite to the t-Bu group (→15-20, Table 1). Hydrolytic cleavages of the dioxanones then lead to enantiomerically pure β-hydroxy-acid derivatives (overall self-reproduction of the stereogenic center of 3-hydroxybutanoic acid or alkylation in the 4-position of this acid with preservation of configuration).
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19870700819
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  • 3
    Electronic Resource
    Electronic Resource
    Crystal Structure of (-)-Corycavinium (+)-10-Camphorsulfonate, a biosynthetic intermediate to hexahydrobenzo[c]phenanthridine alkaloids (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 243-251 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The crystal structure of (-)-corycavinium (+)-10-camphorsulfonate has been investigated by X-ray analysis. The structure of (-)-corycavinium ion ( = (-)-(7S,13S,14R)-5,6,13,13a-tetrahydro-13a-hydroxy-7-methyl-2,3;9,10-bis(methylenedioxy)-8H-dibenzo[a,g]quinolizinium), has been determined. The conformation with B/C-cis-conjunction, a twisted half-chair of ring B, and a half-chair of ring C, as well as α-oriented substituted groups N…Me, C…Me, and C…OH is revealed. Feeding experiments with cell suspension cultures of Corydalis incisa (Papaveraceae) defined the intermediacy of (-)-corycavinium in the route from protoberberine-type to hexahydrobenzo[c]phenanthridine-type of alkaloids. On the basis of the present crystal conformation, the stereospecificity of the relating enzyme is biogenetically considered.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770126
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  • 4
    Electronic Resource
    Electronic Resource
    Conformational Features of 7,8,13β,14α-Tetrahydro-N7-methylcorysaminium, a biosynthetic intermediate to the protopine-type alkaloid corycavine (1995)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 78 (1995), S. 80-86 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The crystal structure of (±)-7,8,13β,14α-tetrahydro-N7-(13C)methylcorysaminium iodide (13C-3a·I) was investigated by X-ray analysis and thus the relative configuration (7S*,13S*,14S*) established (Fig. 1). The conformation of 3a was shown to have a cis-junction of the B/C rings and the rings A and D in an antiperiplanar position relative to the C(13)—C(14) bond (‘anti-cis’), a twisted half-chair for ring B, and a half-chair for ring C (Figs. 2 and 3). Conformation analysis by 1H-NMR data indicated that the crystal conformation of 3a is also the preferred one in MeOH solution.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19950780108
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  • 5
    Electronic Resource
    Electronic Resource
    Medium-sized cyclophanes, 37.Part 36: Ref.[1]. [n.2]metacyclophanediquinones: Synthesis, conformational studies and reduction to tetrahydroxy[n.2]metacyclophanes (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 995-1001 
    Details
    ISSN: 0947-3440
    Keywords: [n.2]Metacyclophanes, hydroxy- ; Thallium oxidation ; [n.2]Metacyclophanediquinones ; anti and syn Conformers ; Ring inversion ; Hydrogen bonding, intramolecular ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The title compounds, [n.2]metacyclophanediquinones 6a-f, were prepared by oxidation of the corresponding di-tert-butyldihydroxy[n.2]metacyclophanes 5a-f with Tl(OCOCF3)3 in CF3COOH. When [n.2]quinonophanes 6a-e were reduced with Zn powder in acetic acid, the corresponding tetrahydroxy derivatives 8a-e were obtained, which were converted to the tetraacetates 9a-e. The solution conformations of diquinones 6a-f and tetrahydroxy[n.2]MCPs 8a-e are sensitive to the chain length of the bridges. The ring inversion barriers determined by variable-temperature 1H-NMR spectroscopy decrease with increasing length of the bridges. In addition, a solvent effect on the ratio of anti to syn conformers was found to occur in tetrahydroxy[6.2]metacyclophane 8d and dihydroxy[6.2]metacyclophanes 5d, 10d, and 12d. The conformationally rigid tetraacetoxy[n.2]metacyclophanes 9 exhibit fixed „anti“ and „syn“ conformations. The anti and syn ratio is strongly governed by the number of methylene bridges. Thus, a anti-to-syn ratio of the tetraacetoxy[5.2]- (9c) and -[6.2]metacyclophane (9d) differing from that of the tetraols 8c and 8d was obtained. This difference is due to the ring inversion of 8c and 8d. The assignment of anti and syn conformations was confirmed by 1H-NMR analyses. The dynamics of the ring inversion is also discussed.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199506141
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  • 6
    Electronic Resource
    Electronic Resource
    Growth-inhibiting effect of tumor necrosis factor on human umbilical vein endothelial cells is enhanced with advancing age in vitro (1990)
    New York, NY [u.a.] : Wiley-Blackwell
    Journal of Cellular Physiology 142 (1990), S. 31-38 
    Details
    ISSN: 0021-9541
    Keywords: Life and Medical Sciences ; Cell & Developmental Biology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Medicine
    Notes: We have examined the effects of in vitro aging on the growth capacity of human umbilical vein endothelial cells (HUVECs) under the influence of tumor necrosis factor (TNF) with or without interferon-γ (IFN-γ). The growth and colony-forming abilities of control cells were impaired with advancing age in vitro, especially at later stages (more than 70-80% of life span completed). It was found that treatment with TNF inhibited growth and colony-forming efficiency at any in vitro age. The effects of TNF were shown to increase with increasing in vitro age, as reflected by a more pronounced increase in doubling times, a decrease in saturation density, and a reduction in colony-forming efficiency. However, the characteristics of TNF receptors, including the dissociation constant, and the number of TNF-binding sites per cell-surface area remained rather constant. The effect of TNF was augmented by IFN-γ at a dose that alone affected growth and colony formation only slightly. The augmentation by IFN-γ was also found to depend on in vitro age; the synergy with TNF in the deterioration of colony-forming ability was observed only in “aged” cells. These results suggest that the intrinsic responsiveness of HUVECs to growth-inhibiting factors, as well as to growth-stimulating factors, changes during aging in vitro.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jcp.1041420105
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  • 7
    Electronic Resource
    Electronic Resource
    Endothelin modulates osteopontin and osteocalcin messenger ribonucleic acid expression in rat osteoblastic osteosarcoma cells (1993)
    New York, N.Y. : Wiley-Blackwell
    Journal of Cellular Biochemistry 53 (1993), S. 176-180 
    Details
    ISSN: 0730-2312
    Keywords: osteoblasts ; endothelin ; osteopontin ; osteocalcin ; Life and Medical Sciences ; Cell & Developmental Biology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Chemistry and Pharmacology , Medicine
    Notes: Endothelins (ETs) are vasoconstrictive peptides produced mainly by endothelial cells. The ET receptors are expressed in many types of cells including osteoblast-like cells. The purpose of this study was to examine the effects of endothelin on the expression of osteoblastic phenotype-related genes. We found that endothelin-1 (ET-1) enhanced approximately two-fold the mRNA expression of both osteopontin and osteocalcin genes in rat osteoblastic osteosarcoma ROS17/2.8 cells. These effects were dose-dependent, peaking at 10-7 M. The ET-1 enhancement of the abundance of osteopontin and osteocalcin mRNAs was time-dependent, with a maximal effect at 24 h. ET-1 modulation of the expression of the two phenotype-related gene products of osteoblasts suggests that endothelin is one of the cytokines which modulate osteoblastic functions and that this molecule may play a role in the regulation of bone metabolism.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jcb.240530211
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  • 8
    Electronic Resource
    Electronic Resource
    Scleraxis messenger ribonucleic acid is expressed in C2C12 myoblasts and its level is down-regulated by bone morphogenetic protein-2 (BMP2) (1997)
    New York, N.Y. : Wiley-Blackwell
    Journal of Cellular Biochemistry 67 (1997), S. 66-74 
    Details
    ISSN: 0730-2312
    Keywords: scleraxis ; C2C12 myoblasts ; mRNA ; BMP2 ; HLH-type transcription factor ; Life and Medical Sciences ; Cell & Developmental Biology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Chemistry and Pharmacology , Medicine
    Notes: We examined the mRNA expression of scleraxis, a non-myogenic helix-loop-helix type transcription factor in C2C12 myogenic cells. Scleraxis mRNA has been shown to be expressed in sclerotome and perichondrium of the embryos. We found that C2C12 cells express 1.2 kb scleraxis mRNA constitutively. Since BMP was reported to induce ectopic bone formation when implanted in muscle, we examined the effects of BMP on scleraxis expression. Scleraxis mRNA expression in C2C12 cells was suppressed by the treatment with BMP2. This suppression was observed at 200 ng/ml but not at the lower concentrations. BMP2 treatment suppressed scleraxis mRNA level within 24 h and lasted at least up to 48 h. Electrophoresis mobility shift assay showed that the proteins in the crude nuclear extracts prepared from C2C12 cells bound to an Scx-E-box sequence, CATGTG, which is preferentially recognized by scleraxis. This binding was competed out by 100-fold molar excess of cold Scx-E-box sequence but not by the one with mutations in the E-box. This band was supershifted by the addition of antiserum raised against scleraxis. BMP2 treatment suppressed the Scx-E binding activity in C2C12 cells. This suppression of the Scx-E-box binding activity was in parallel to the BMP2 suppression of the transcriptional activity of the Scx-E-CAT reporter gene transfected into C2C12 cells. These data indicated that although the default pathway for C2C12 cells is to differentiate into muscle cells, these cells do express non-myogenic transcription factor, scleraxis, whose expression is suppressed by BMP2. J. Cell. Biochem. 67:66-74, 1997. © 1997 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
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  • 9
    Electronic Resource
    Electronic Resource
    Fibroblast growth factor downregulates expression of a basic helix-loop-helix-type transcription factor, scleraxis, in a chondrocyte-like cell line, TC6 (1998)
    New York, N.Y. : Wiley-Blackwell
    Journal of Cellular Biochemistry 70 (1998), S. 468-477 
    Details
    ISSN: 0730-2312
    Keywords: scleraxis ; transcription factor ; FGF ; chondrocyte ; bHLH ; Life and Medical Sciences ; Cell & Developmental Biology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Chemistry and Pharmacology , Medicine
    Notes: Scleraxis is a basic helix-loop-helix-type transcription factor that is expressed in sclerotome. Fibroblast growth factor (FGF) is one of the cytokines produced by the cells in skeletal tissues and is a potent modulator of skeletogenesis. The aim of this study was to examine the effects of FGF on the expression of scleraxis in chondrocyte-like cells, TC6. In these cells, scleraxis mRNA was constitutively expressed as a 1.2kb message at a high level in contrast to its low levels of expression in fibroblast-like cells or osteoblast-like cells. Upon treatment with FGF, scleraxis mRNA level was decreased within 12 h. This effect was at its nadir at 24 h and the scleraxis mRNA level returned to its base line level by 48 h. The FGF effect was maximal at 1 ng/ml. FGF effects on scleraxis were blocked by actinomycin D but not by cycloheximide, suggesting the involvement of transcriptional events that do not require new protein synthesis. The FGF effects on scleraxis were blocked by genistein, suggesting the involvement of tyrosine kinase in the post-receptor signaling. TGFβ treatment of TC6 cells enhanced scleraxis mRNA expression; however, combination of the saturation doses of FGF and TGFβ resulted in suppression of scleraxis mRNA level. BMP2 also suppressed scleraxis mRNA expression in TC6 cells and no further suppression was observed in combination with FGF. These results indicate that scleraxis is expressed in chondrocyte-like TC6 cells and it is one of the targets of FGF action in these cells. J. Cell. Biochem. 70:468-477. © 1998 Wiley-Liss, Inc.
    Additional Material: 8 Ill.
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  • 10
    Electronic Resource
    Electronic Resource
    Osteopontin expression and function: Role in bone remodeling (1998)
    New York, N.Y. : Wiley-Blackwell
    Journal of Cellular Biochemistry 72 (1998), S. 92-102 
    Details
    ISSN: 0730-2312
    Keywords: osteopontin ; enhanced cell survival ; inhibition of apoptosis ; bone remodeling ; Life and Medical Sciences ; Cell & Developmental Biology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Chemistry and Pharmacology , Medicine
    Notes: The cytokine and cell attachment protein osteopontin (OPN) is not necessary for the development and survival of mice in a clean animal facility. The primary role of OPN appears to be that of facilitating recovery of the organism after injury or infection, which generally causes an increase in its expression. It also is essential for some forms of bone remodeling. OPN stimulates cellular signaling pathways via various receptors found on most cell types and can encourage cell migration. OPN modulates immune and inflammatory responses and possibly negatively regulates Ras signaling pathways. Its apparent ability to enhance cell survival by inhibiting apoptosis may explain why the metastatic proficiency of tumor cells increases with increased OPN expression. J. Cell. Biochem. Suppls. 30/31:92-102, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
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