Synthesis and Spectral Characterization of a Rotaxane of β-Cyclodextrin Threaded by a 4,4′-Diaminostilbene

Kunitake, Masashi; Kotoo, Kengo; Manabe, Osamu; Muramatsu, Tsuyoshi; Nakashima, Naotoshi

doi:10.1246/cl.1993.1033

Cited by 26 publications

(11 citation statements)

References 7 publications

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“…It is often desirable to covalently attach dyes to solid substrates, and this is commonly achieved by reacting an amine‐substituted dye with 2,4,6‐trichloro‐1,3,5‐triazine to give a chlorotriazine‐functionalized “reactive dye” which couples with nucleophilic surface groups 6. This chlorotriazine chemistry works well in water, so it is compatible with the use of hydrophobic binding to direct rotaxane formation 7. The reactive dye rotaxane 1 was synthesized from amine 2 as shown in Scheme ; the free reactive dye 3 was prepared by the same procedure in the absence of cyclodextrin.…”

Section: Methodsmentioning

confidence: 99%

CD44 stimulation by fragmented hyaluronic acid induces upregulation of urokinase‐type plasminogen activator and its receptor and subsequently facilitates invasion of human chondrosarcoma cells

Kobayashi

Suzuki

Kanayama

et al. 2002

Intl Journal of Cancer

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It has been established that fragmented hyaluronic acid (HA), but not native high molecular weight HA, can induce angiogenesis, cell proliferation and migration. We have studied the outside-in signal transduction pathways responsible for fragmented HA-mediated cancer cell invasion. In our study, we have studied the effects of CD44 stimulation by ligation with HA upon the expression of matrix metalloproteinases (MMPs)-2 and -9 as well as urokinase-type plasminogen activator (uPA), its receptor (uPAR) and its inhibitor (PAI-1) and the subsequent induction of invasion of human chondrosarcoma cell line HCS-2/8. Our study indicates that CD44; hyaluronic acid; invasion; MAP kinase; uPA receptor (uPAR) Tumor cell invasion is a complex, multistep process that involves cell adhesion and the controlled degradation of the extracellular matrix (ECM) by tumor cell-associated proteases. 1 Among these proteases, MMPs-2 and -9, also known as gelatinases, 2 and urokinase-type plasminogen activator (uPA), a serine protease that activates plasminogen to plasmin enabling the degradation of the ECM, have a main role in the metastatic proteolytic cascade. 3 Tissue inhibitors of gelatinase activity (e.g., TIMP-2) are involved in the MMP-2 activation process; in concert with membrane type 1-MMP (MT1-MMP) and in the inhibition of gelatinolytic activity. uPA bound to its cell-surface receptor, uPAR, is the principal participant in ECM degradation. 4 Plasminogen activator inhibitors (PAI) also regulate the catalytic activity of PA. Therefore proteolysis, the central step for cancer metastasis, should occur as a result of an imbalance between proteinases and their specific inhibitors. 2 The cellular functions are dependent upon a number of cell surface adhesion proteins and CD44 has been implicated as one such molecule. 5 CD44 has been shown to promote tumor cell adhesion, migration, invasion and angiogenesis, crucial steps in the process of metastasis. CD44 is a transmembrane glycoprotein known to bind hyaluronic acid (HA) in its extracellular domain. 6 CD44 is known to exist in many different isoforms arising by alternative splicing events. 7 HA is a nonsulfated, linear glycosaminoglycan consisting of repeating unit of (␤,1-4)-D-glucuronic acid-(␤,1-3)-N-acethyl-D-glucosamine. 8 Several studies have suggested that high and low molecular weight species of HA exhibit different biologic effects on cells: low molecular weight but not native HA has been shown to stimulate the expression of cytokines, proinflammatory chemokines and cell adhesion molecules (IL-1␤, TNF-␣ and insulin-like growth factor, inducible NO synthase, metalloelastase, VCAM-1 and ICAM-1) possibly through a mechanism involving the cellular HA receptor, CD44. 9 -17 Fragmented HA can also induce cell proliferation, migration and angiogenesis. 9,18 The mechanisms through which fragmented HA exerts its biologic functions have been only partially elucidated. There is a growing body of evidence that the CD44-induced signals are dependent on protein kinase C (PKC) activation 1...

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Section: Methodsmentioning

confidence: 99%

CD44 stimulation by fragmented hyaluronic acid induces upregulation of urokinase‐type plasminogen activator and its receptor and subsequently facilitates invasion of human chondrosarcoma cells

Kobayashi

Suzuki

Kanayama

et al. 2002

Intl Journal of Cancer

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“…terathiafulvalene (TTF) moieties [74], were transferred as L-B films from the water surface with a transfer ratio of 1 to the solid substrate. Charge-transfer interactions in the L-B films were then studied and new sensing devices were proposed [75][76][77][78][79].…”

Section: Langmuir-blodgett (L-b) Techniquementioning

confidence: 99%

Electrochemistry of Cyclodextrin Inclusion Complexes of Pharmaceutical Compounds

Radi¹

2010

TOCBMJ

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Electrochemistry of cyclodextrins (CDs) and cyclodextrin inclusion complexes with different pharmaceutical compounds is reviewed. The article highlights some electrochemical investigations of the CD-drugs interactions in solution. Cyclodextrin modified electrodes and their applications as electrochemical sensors in pharmaceutical analysis based on the self-assembly of CD derivatives on metal electrodes and nanoparticles, and cyclodextrin-modified multiwalled carbon nanotubes are also discussed.

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“…Einige Biphenylen-und Stilben-CyclodextrinRotaxane wurden aber auch auf anderem Wege erhalten. [75] Beispielsweise gelang die Synthese eines b-Cyclodextrin-Polyfluoren-Polyrotaxans mit Anthracen-Endgruppen mithilfe einer Yamamoto-Kupplung. [76] 2.2.5.…”

Section: Angewandte Chemieunclassified

Isolierte molekulare Drähte

2007

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In den erstaunlich unterschiedlichen Strukturen, die bisher als “isolierte molekulare Drähte” (insulated molecular wires, IMWs) beschrieben wurden, zeigt sich, wie vielfältig die Ansätze zur elektrisch‐chemischen Isolierung auf molekularer Ebene sind. Gemeinsam verdeutlichen diese Systeme die Bedeutung von Einkapselungsstrategien bei der Entwicklung optoelektronischer Materialien und organischer Halbleiter. Dieser Aufsatz beleuchtet die Synthese und die strukturelle Charakterisierung von IMWs. Struktur‐Eigenschafts‐Beziehungen sollen zudem erklären, wie eine Isolierung die Leistungsmerkmale eines molekularen Drahtes verbessern kann. Wir konzentrieren uns auf drei IMW‐Arten: Polyrotaxane, polymerumhüllte π‐Systeme und dendronisierte Polymere. Die Eigenschaften dieser Systeme werden mit denjenigen von konjugierten Polymeren verglichen, die in mesoporöse Netzwerke und Zeolithe eingefädelt sind. Der Einschluss molekularer Drähte verstärkt so unterschiedliche Eigenschaften wie Lumineszenz, elektrische Transportgrößen und die chemische Beständigkeit, sodass Anwendungen in Elektrolumineszenzdisplays, Sensoren und der photochemischen Wasserstofferzeugung denkbar werden.

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Synthesis and Spectral Characterization of a Rotaxane of β-Cyclodextrin Threaded by a 4,4′-Diaminostilbene

Abstract: A rotaxane, in which a stilbene moiety threads the cavity of β-cyclodextrin (β-CyD), has been synthesized. The rotaxane structure has been proved by uv-visible and induced circular dichlorism (CD) spectra.

Cited by 26 publications

References 7 publications

CD44 stimulation by fragmented hyaluronic acid induces upregulation of urokinase‐type plasminogen activator and its receptor and subsequently facilitates invasion of human chondrosarcoma cells

CD44 stimulation by fragmented hyaluronic acid induces upregulation of urokinase‐type plasminogen activator and its receptor and subsequently facilitates invasion of human chondrosarcoma cells

Electrochemistry of Cyclodextrin Inclusion Complexes of Pharmaceutical Compounds

Isolierte molekulare Drähte

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