104375-88-4Relevant academic research and scientific papers
Radiolabeled 5-iodo-3′-O-(17β-succinyl-5α-androstan-3-one) -2′-deoxyuridine and its 5′-monophosphate for imaging and therapy of androgen receptor-positive cancers: Synthesis and biological evaluation
Kortylewicz, Zbigniew P.,Nearman, Jessica,Baranowska-Kortylewicz, Janina
, p. 5124 - 5143 (2009)
High levels of androgen receptor (AR) are often indicative of recurrent, advanced, or metastatic cancers. These conditions are also characterized by a high proliferative fraction. 5-Radioiodo-3′-O-(17β-succinyl-5α- androstan-3-one)-2′-deoxyuridine 8 and 5
Nucleic Acid Conformation Influences Postsynthetic Suzuki-Miyaura Labeling of Oligonucleotides
Walunj, Manisha B.,Srivatsan, Seergazhi G.
, p. 2513 - 2521 (2020)
Chemoselective transformations that work under physiological conditions have emerged as powerful tools to label nucleic acids in cell-free and cellular environments. However, detailed studies investigating the influence of nucleic acid conformation on the
Primer extension reaction assays for incorporation of deoxynucleotide analogue into DNA
Wang, Xilong,Chen, Xun,Liu, Yonghui,Zhu, Jin
, p. 192 - 198 (2015)
Incorporation of deoxynucleotide analogues into DNA is important for the expansion of DNA functions. Primer extension reactions are commonly used for the assay of such reaction events. However, current assay protocols generally rely on radiolabeling, fluo
Synthesis of Phosphoramidite Monomers Equipped with Complementary Bases for Solid-Phase DNA Oligomerization
Romero-Pérez, Sonia,López-Martín, Isabel,Martos-Maldonado, Manuel C.,Somoza, álvaro,González-Rodríguez, David
, p. 41 - 45 (2020)
We describe the preparation of two monomers that bear complementary nucleobases at the edges (guanine-2′-deoxycytidine and 2-aminoadenine-2′-deoxyuridine) and that are conveniently protected and activated for solid-phase automated DNA synthesis. We report the optimized synthetic routes leading to the four nucleobase derivatives involved, their cross-coupling reactions into dinucleobase-containing monomers, and their oligomerization in the DNA synthesizer.
Tuning the Stereoselectivity of a DNA-Catalyzed Michael Addition through Covalent Modification
Dey, Surjendu,J?schke, Andres
, p. 11279 - 11282 (2015)
Complexes of G-quadruplex DNA and CuIIions have previously been applied as catalysts in asymmetric reactions, but the largely unspecific and noncovalent nature of the interaction has impeded understanding of the structural basis of catalysis. T
Design and Development of a Two-Color Emissive FRET Pair Based on a Photostable Fluorescent Deoxyuridine Donor Presenting a Mega-Stokes Shift
Barthes, Nicolas P. F.,Gavvala, Krishna,Bonhomme, Dominique,Dabert-Gay, Anne Sophie,Debayle, Delphine,Mély, Yves,Michel, Beno?t Y.,Burger, Alain
, p. 10733 - 10741 (2016)
We report the synthesis and site-specific incorporation in oligodeoxynucleotides (ODNs) of an emissive deoxyuridine analog electronically conjugated on its C5-position with a 3-methoxychromone moiety acting as a fluorophore. When incorporated in ODNs, thi
Introducing structural flexibility into porphyrin-DNA zipper arrays
Brewer, Ashley,Siligardi, Guiliano,Neylon, Cameron,Stulz, Eugen
, p. 777 - 782 (2011)
A more flexible nucleotide building block for the synthesis of new DNA based porphyrin-zipper arrays is described. Changing the rigid acetylene linker between the porphyrin substituent and the 2′-deoxyuridine to a more flexible propargyl amide containing
Metallocene - DNA: Synthesis, molecular and electronic structure and DNA incorporation of C5-ferrocenylthymidine derivatives
Pike, Andrew R.,Ryder, Lyndsey C.,Horrocks, Benjamin R.,Clegg, William,Elsegood, Mark R. J.,Connolly, Bernard A.,Houlton, Andrew
, p. 2891 - 2899 (2002)
Ferrocenylthymidine derivatives have been prepared by Pd-catalysed cross-coupling between ethynylferrocene or vinylferrocene and 5-iodo-2′-deoxyuridine. In the latter case a mixture of trans (2a) and gem (2b) isomers was obtained. The cis-vinylferrocenyl
Intelligent fluorescent nucleoside in sensing cytosine base: Importance of hydrophobic nature of perylene fluorophore
Bag, Subhendu Sekhar,Saito, Yoshio,Hanawa, Kazuo,Kodate, Satoshi,Suzuka, Isamu,Saito, Isao
, p. 6338 - 6341 (2006)
Fluorescence response upon hybridization of perylene labeled oligonucleotide probes depends on the microenvironment experienced by the perylene fluorophore. In mismatched duplex (PerU-C), enhanced fluorescence was observed while in matched dupl
Norepinephrine-Transporter-Targeted and DNA-Co-Targeted Theranostic Guanidines
Kortylewicz, Zbigniew P.,Coulter, Donald W.,Han, Guang,Baranowska-Kortylewicz, Janina
, p. 2051 - 2073 (2020)
High risk neuroblastoma often recurs, even with aggressive treatments. Clinical evidence suggests that proliferative activities are predictive of poor outcomes. This report describes syntheses, characterization, and biological properties of theranostic guanidines that target norepinephrine transporter and undergo intracellular processing, and subsequently their catabolites are efficiently incorporated into DNA of proliferating neuroblastoma cells. Radioactive guanidines are synthesized from 5-radioiodo-2′-deoxyuridine, a molecular radiotherapy platform with clinically proven minimal toxicities and DNA-targeting properties. The transport of radioactive guanidines into neuroblastoma cells is active as indicated by the competitive suppression of cellular uptake by meta-iodobenzylguanidine. The rate of intracellular processing and DNA uptake is influenced by the agent's catabolic stability and cell population doubling times. The radiotoxicity is directly proportional to DNA uptake and duration of exposure. Biodistribution of 5-[125I]iodo-3′-O-(?-guanidinohexanoyl)-2′-deoxyuridine in a mouse neuroblastoma model shows significant tumor retention of radioactivity. Neuroblastoma xenografts regress in response to the clinically achievable doses of this agent.
