Carbohydration of 1,4,8,11-tetraazacyclotetradecane (cyclam): synthesis and binding properties toward concanavalin A

Stephan, Holger; Röhrich, Anika; Noll, Steffi; Steinbach, Jörg; Kirchner, Ralf; Seidel, Jürgen

doi:10.1016/j.tetlet.2007.10.071

Cited by 12 publications

(7 citation statements)

References 25 publications

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“…As already found for PEGylated and carbohydrated cyclam derivatives, a red-shift of dd transition and an increase of molar absorptivity were observed for Cu(II) complexes with NT(8-13)-containing derivatives in comparison to cyclam [51,52]. The dd bands of the copper(II) complexes with 4, 5 and 7 have the maximum at about 710 nm which is indicative for apical interactions of pendant arms of the copper(II)-N4 chromophore [64][65][66][67].…”

Section: Complexation Properties and Radiochemistrysupporting

confidence: 78%

A novel tetrabranched neurotensin(8–13) cyclam derivative: Synthesis, 64Cu-labeling and biological evaluation

Röhrich

Bergmann

Kretzschmann

et al. 2011

Journal of Inorganic Biochemistry

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Section: Complexation Properties and Radiochemistrysupporting

confidence: 78%

A novel tetrabranched neurotensin(8–13) cyclam derivative: Synthesis, 64Cu-labeling and biological evaluation

Röhrich

Bergmann

Kretzschmann

et al. 2011

Journal of Inorganic Biochemistry

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“…Cyclam derivatives 2, 4 and 5 were synthesized and purified as described elsewhere. 41,42 Briefly, modification of cyclam via Michael addition reaction with methylacrylate and subsequent aminolysis of the tetraester-functionalized intermediate with excess of 1,2-diaminoethane led to the tetraamino-precursor 2. The glycocluster compounds 4 and 5 were prepared by glycosylation of 2 using the O-acetyl-protected glucosyl isothiocyanates.…”

Section: Methodsmentioning

confidence: 99%

Fragmentation reactions of singly and doubly protonated thiourea‐ and sugar‐substituted cyclams and their transition‐metal complexes

et al. 2008

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Cyclam macrocycles tetrasubstituted with amino-, thiourea-, and sugar-terminated side chains are ionized by electrospray ionization mass spectrometry (ESI-MS) as singly or doubly protonated species or as transition-metal complexes. Their fragmentation behavior is examined in a Fourier-transform ion-cyclotron-resonance (FT-ICR) mass spectrometer by collision-induced dissociation (CID) experiments. Typically, fragmentation occurs within the side chains through a number of different 1,2-elimination reactions irrespective of the absence or presence of a transition metal ion such as Co(2+), Ni(2+), or Zn(2+). A remarkable exception is Cu(2+), which induces ring cleavage reactions. This is traced back to an electron transfer from the cyclam nitrogen atoms to the Cu(2+) ion. The electron transfer creates a cation-radical within the macrocycle, which induces typical fragmentation reactions such as alpha-cleavages that lead to fragmentation within the macrocycle. This interpretation is in line with fragmentation experiments on unsubstituted cyclam and its complexes.

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“…Using this approach, anticancer drugs, such as camptothecin, doxorubicin, dimethoxycurcumin, etoposide, 5‐fluorouracil, and paclitaxel, have been transported by PEGylated dendrimers into cancerous tissue. Another promising strategy is the encapsulation of drug molecules into dendritic sugar‐containing biohybrids 180–182. Recently, we showed that sugar‐capped dendrimers can encapsulate and slowly release nanosized cluster molecules that selectively inhibit an enzyme involved in cancerogenisis 183…”

Section: Types Of Nanomaterials Currently Applied In Cancer Imaginmentioning

confidence: 99%

Nanomaterials: Applications in Cancer Imaging and Therapy

et al. 2011

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The application of nanomaterials (NMs) in biomedicine is increasing rapidly and offers excellent prospects for the development of new non-invasive strategies for the diagnosis and treatment of cancer. In this review, we provide a brief description of cancer pathology and the characteristics that are important for tumor-targeted NM design, followed by an overview of the different types of NMs explored to date, covering synthetic aspects and approaches explored for their application in unimodal and multimodal imaging, diagnosis and therapy. Significant synthetic advances now allow for the preparation of NMs with highly controlled geometry, surface charge, physicochemical properties, and the decoration of their surfaces with polymers and bioactive molecules in order to improve biocompatibility and to achieve active targeting. This is stimulating the development of a diverse range of nanometer-sized objects that can recognize cancer tissue, enabling visualization of tumors, delivery of anti-cancer drugs and/or the destruction of tumors by different therapeutic techniques.

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Carbohydration of 1,4,8,11-tetraazacyclotetradecane (cyclam): synthesis and binding properties toward concanavalin A

Cited by 12 publications

References 25 publications

A novel tetrabranched neurotensin(8–13) cyclam derivative: Synthesis, 64Cu-labeling and biological evaluation

A novel tetrabranched neurotensin(8–13) cyclam derivative: Synthesis, 64Cu-labeling and biological evaluation

Fragmentation reactions of singly and doubly protonated thiourea‐ and sugar‐substituted cyclams and their transition‐metal complexes

Nanomaterials: Applications in Cancer Imaging and Therapy

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