ISMSC 2007 - Università degli Studi di Pavia

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Amplification of a Molecular Solomon Knot PSB 39 Cari D.Pentecost, Nicholas Tangchaivang, Kelly S. Chichak, Andrea J. Peters, Stuart J. Cantrill and J. Fraser Stoddart California NanoSystems Institute and Department of Chemistry and Biochemistry, University of California Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095, USA (cari@chem.ucla.edu) The four-noded, two-component link known as the Solomon Knot (SK) has been said to contain all of the wisdom of King Solomon. For several centuries, many cultures have adopted this emblem to represent knowledge. SKs can be found in many different settings from adorning the crowns of African kings to being incorporated into the architecture of university libraries. With the advent of new synthetic methodologies that are advancing under the umbrella of templatedirected synthesis, chemists are beginning more and more to appreciate the subtleties of topologically interesting structures, and have consequently pursued the synthesis of their molecular analogues. For example, the complete molecular construction of the Borromean ring (BR) topology and its derivatives has been achieved successfully from 18 individual components under strict dynamic covalent, coordinative and supramolecular control. In a similar fashion, we have recently obtained the SK molecular topology from 12 individual components, resulting from mixing Cu(II) and Zn(II) metal templates in a 1:1 ratio, leading to the formation of the SKs in preference to the BRs. This finding suggests that, in these dynamic mechanically interlocked systems, there is present, under the appropriate conditions, a dynamic combinatorial library, from which it is possible, during a crystallization process that is kinetically controlled, to amplify (Box) one of the members of the library. [1] (a) Chichak, K. S.; Cantrill, S. J.; Pease, A. R.; Chiu, S.-H.; Cave, G. W. V.; Atwood, J. L.; Stoddart, J. F. Science 2004, 304, 1308–1312. (b) Cantrill, S. J.; Chichak, K. S.; Peters, A. J.; Stoddart, J. F. Acc. Chem. Res. 2005, 38, 1–9.. [2] Pentecost, C.D.; Peters, A. J.; Chichak, K. S.; Cave, G. W. V.; Cantrill, S.J.; Stoddart, J. F. Angew. Chem. 2006, 45, 4099–4104. [3] Pentecost, C.D.; Chichak, K. S.; Peters, A. J.; Cave, G. W. V.; Cantrill, S.J.; Stoddart, J. F. Angew. Chem. 2007, 46, 218–222 Self-Assembled Resorcinarene Monolayers on Gold Jade Pettersen a , Mauro Mocerino a , Mark Ogden a , Andrew Ross b , Peter Eadington b a Nanochemistry Research Institute, Curtin University of Technology, Perth, Australia. b CSIRO Petroleum, Australian Resources Research Centre, Perth, Australia. PSB 40 Self Assembled Monolayers (SAM's) are highly ordered structures formed by the spontaneous adsorption of a compound onto a suitable substrate. A variety of sulfur species are known to adsorb onto gold, for example physisorbed monolayers are formed in the presence of dialkyl sulfides, while chemisorbed monolayers are formed from disulfides, thiols and thioacetates. 1 Monolayers of simple sulfur functionalised resorcinarenes have been reported by a variety of groups and have been used for applications as diverse as coating gold nanoparticles 2 to selective sensing devices 3 . Resorcinarenes are typically used as receptors, and are capable of complexing with a wide range of guest molecules. 4 Their bowl-like shape and eight hydroxyl groups on the upper rim make them an ideal scaffold on which to build more complex structures. Our goal is to prepare surfaces composed of various fuctionalised resorcinarenes for applications in sensing. The work presented will include the synthesis of a variety of resorcinarenes as well as recent work involving their use in the formation of self-assembled monolayers. [1] J. Love, L. Estroff, J. Kriebel, R. Nuzzo, G. Whitesides, Chem. Rev., 2005, 105,1103-1169. [2] B. Kim, R. Balasubramanian, W. Perez-Segarra, A. Wei, B. Decker and J. Mattay, Supramol. Chem., 2005, 17,173-180. [3] J. Faull, and V. Gupta, Thin Solid Films, 2003, 440, 129-137. [4] P. Timmerman, W. Verboom, and D. Reinhoudt, Tetrahedron,1996, 52, 2663-2704.
PSB 41 1,3,5-Tris(2-aminophenyl)benzene: a novel platform for anion receptors. Piotr Pitek Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Fax: +48-22-8225996; E-mail: ppiatek@chem.uw.edu.pl The design, synthesis and application of 1,3,5-Tris(2’-aminophenyl)benzene (1) as a novel, rigid, aromatic platform for molecular receptors is presented. This molecular scaffold was efficiently prepared via Suzuki-Miyaura cross-coupling reaction of 2-aminophenylboronic acid with 1,3,5-triiodobenzene in the presence of Ba(OH)2, Pd(OAc)2 and (2biphenyl)dicyclohexylphosphine. 1 Alternatively, triamine 1 can be prepared via one-pot borylation of 2-bromoaniline and cross-coupling of the resulting boronate ester with 1,3,5triiodobenzene. NH 2 B(OH) 2 + I I I Pd[P(Ph 3)] 4 Ba(OH) 2 Dioxane Cy 2P 1,3,5-Tris(2’-aminophenyl)benzene 1 was used as a molecular platform for the preparation of a simple, acyclic, amide-functionalized tripodal receptor 2. The solid-state structure of receptor 2 reveals that it adopts two arms “up” one “down” (partial cone) conformation. The interaction of receptor 2 with various anions was investigated in acetonitril-d6 solution. Those studies have shown that 2 display significant affinity for acetate and chloride anions (Ka=2410 and 1540 respectively). Weak binding interactions were seen for other anions including H2PO4 - and Br - . Computation studies suggest that the lowest energy conformation for 2-Cl complex is cone conformation which is stabilized by three hydrogen bonding interactions. O n Pr NH 2 n Pr HN HN n Pr O O Cl - [1] P. Pitek, N. Somiany, Synlett, 2005, 2027-2030. O n Pr NH NH 2 1 Cl - H 2N H 2N nPr nPr O HN O HN PSB 42 Ds-oligonucleotide-peptide conjugates featuring peptides from the leucine zipper region of Fos as switchable receptors for the oncoprotein Jun. Cecilia Portela a , Fernando Albericio b , Ramón Eritja c , Luis Castedo a and José Luis Mascareñas a . a Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidade de Santiago de Compostela, Campus Sur, 15782 Santiago de Compostela, Spain. b Institut de Recerca Biomèdica de Barcelona, Parc Científic de Barcelona, Josep Samitier 1-5, E-08028 Barcelona, Spain. c Institut de Biologia Molecular de Barcelona, CID-CSIC, Jordi Girona 18-26, E-08034 Barcelona, Spain. The nuclear oncoproteins Fos and Jun are members of the well known familiy of transcription factors that bind specific DNA sequences by means of a bZIP motif [1]. These proteins are overexpressed in a variety of cancers and proliferative diseases and therefore there is a great interest in antagonizing their activity [2]. Our studies are focused on the construction of ds-oligonucleotide-peptide conjugates that can selectively target the oncoprotein Jun, owing to the presence of a bivalent binding surface provided by the peptide and the oligonucleotide (see Figure). We herein decribe the synthesis of covalent conjugates between ds-DNA and a 35-aminoacid peptidic region of the hydrophobic leucine region of c-Fos and demonstrate that these synthetic ds-DNA peptide hybrids exhibit better c-Jun sequestrating properties than either the oligonucleotide or the peptide as isolated entities. The recognition strategy allows for switching the Jun-trapping capability of the constructs by using appropriately designed ssDNAs. [1] Glover, J. N. M.; Harrison, S. C. Nature 1995, 373, 257. [2] Angel, P-; Karin, M. Biochimica et Biophysica Acta 1991, 1072, 129.
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nd International Symposium on Macro
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Eric Anslyn University of Texas at
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1 Map of Salice Terme 7 5 6 3 9 2 8
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Symposium Program All sessions will
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11:40 - 12:00 Oral Presentation: V.
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PSA 22 Anion Receptors Based On The
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PSA 72 Molecular Tectonics: STM Stu
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PSB 11 Dual binding properties of p
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PSB 57 Removal Of Heavy Metal Ions
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40 years of polyazamacrocycles. A p
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PL 5 Anion-Templated Assembly of In
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Exercising Demons: Synthetic Molecu
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Synthetic Strategies and Structural
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Anion binding as a conformational a
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Supramolecular control of a metal c
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OP 3 Control of molecular architect
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Catalyst discovery using dynamic co
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Cucurbit[n]uril Molecular Container
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OP 15 From non-mesomorphic nature t
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OP 19 Pyrrolic Tripodal Receptors f
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PSA 1 Efficient synthesis of pseudo
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Tetra-Cationic phthalocyanines Yasi
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PSA 9 Cell penetrating borosilica n
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PSA 13 Halide anion interactions wi
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Sensing with cavitands: Moving from
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Lead(II) complexation by calix[4]-h
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Functional [2×2] Grids Xiao-Yu Cao
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Neutral supramolecular systems inco
Page 57 and 58: PSA 33 Ratiometric Ion Sensors by R
Page 59 and 60: A photocontrollable receptor for Cu
Page 61 and 62: New emitters for mass spectrometric
Page 63 and 64: PSA 45 A fast-moving electrochemica
Page 65 and 66: Macrocyclic Porphyrin-Bidentate Che
Page 67 and 68: PSA 53 Electronic spectroscopy of e
Page 69 and 70: PSA 57 Self-assembly of calixarene/
Page 71 and 72: PSA 61 Piperazine Containing Polyam
Page 73 and 74: PSA 65 Synthesis of Self-Assembly S
Page 75 and 76: PSA 69 Assembly of Metallomacrocycl
Page 77 and 78: Supra-Biomolecular Tandem Assays -
Page 79 and 80: PSA 77 Synthesis and molecular reco
Page 81 and 82: PSA 81 Reaction of phthalic aldehyd
Page 83 and 84: Binding of perrhenate and pertechne
Page 85 and 86: PSA 89 Supramolecular assemblies of
Page 87 and 88: Polytopic Ligands for the Recovery
Page 89 and 90: PSB 1 Rosette Nanotubes as Scaffold
Page 91 and 92: PSB 5 Towards the development of ne
Page 93 and 94: PSB 9 A Quantitative [2]Rotaxane Sy
Page 95 and 96: Metal Complexes of the Polyether Io
Page 97 and 98: PSB 17 Metal controlled anion inter
Page 99 and 100: Crown Ether-tert-Ammonium Salt Comp
Page 101 and 102: PSB 25 A Minimalist Design for Self
Page 103 and 104: PSB 29 Control of Translation of th
Page 105 and 106: PSB 33 Multinuclear NMR, ESI MS and
Page 107: PSB 37 New Anthracene-based cycloph
Page 111 and 112: Simple Isophthalamide Derivatives A
Page 113 and 114: PSB 49 On Sokolov’s approach to a
Page 115 and 116: PSB 53 New chromogenic sensors usin
Page 117 and 118: PSB 57 Removal of heavy metal ions
Page 119 and 120: PSB 61 Molecular Recognition of Ele
Page 121 and 122: PSB 65 Switching of Self to non-Sel
Page 123 and 124: Investigation of -cyclodextrin bind
Page 125 and 126: Novel ditopic probes for different
Page 127 and 128: PSB 77 Synthesis, supramolecular ar
Page 129 and 130: PSB 81 Tripodal polyamines as anion
Page 131 and 132: PSB 85 Templated Synthesis of Large
Page 133 and 134: PSB 89 Direct C-C coupling of 1,2,4
Page 135 and 136: PSB 93 The study of cytotoxicity ef
Page 137 and 138: PSB 97 Development of innovative so
Page 139 and 140: Campbell B. PSA 39 Campbell F. PSB
Page 141 and 142: Jensen L.G. PSA 82 Jeppesen J.O. IL
Page 143 and 144: Peters A.J. PSB 39 Peters A.J. PSB
Page 145 and 146: Sponsors of ISMSC 2007 The contribu
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ISMSC 2007 - Università degli Studi di Pavia

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