91229-97-9Relevant articles and documents
Synthesis of the Siderophore Coelichelin and Its Utility as a Probe in the Study of Bacterial Metal Sensing and Response
Williams, Jade C.,Sheldon, Jessica R.,Imlay, Hunter D.,Dutter, Brendan F.,Draelos, Matthew M.,Skaar, Eric P.,Sulikowski, Gary A.
, p. 679 - 682 (2019/02/07)
A convergent total synthesis of the siderophore coelichelin is described. The synthetic route also provided access to acetyl coelichelin and other congeners of the parent siderophore. The synthetic products were evaluated for their ability to bind ferric iron and promote growth of a siderophore-deficient strain of the Gram-negative bacterium Pseudomonas aeruginosa under iron restriction conditions. The results of these studies indicate coelichelin and several derivatives serve as ferric iron delivery vehicles for P. aeruginosa.
Structure-Activity Relationship of 18F-Labeled Phosphoramidate Peptidomimetic Prostate-Specific Membrane Antigen (PSMA)-Targeted Inhibitor Analogues for PET Imaging of Prostate Cancer
Dannoon, Shorouk,Ganguly, Tanushree,Cahaya, Hendry,Geruntho, Jonathan J.,Galliher, Matthew S.,Beyer, Sophia K.,Choy, Cindy J.,Hopkins, Mark R.,Regan, Melanie,Blecha, Joseph E.,Skultetyova, Lubica,Drake, Christopher R.,Jivan, Salma,Barinka, Cyril,Jones, Ella F.,Berkman, Clifford E.,Vanbrocklin, Henry F.
supporting information, p. 5684 - 5694 (2016/07/06)
A series of phosphoramidate-based prostate specific membrane antigen (PSMA) inhibitors of increasing lipophilicity were synthesized (4, 5, and 6), and their fluorine-18 analogs were evaluated for use as positron emission tomography (PET) imaging agents for prostate cancer. To gain insight into their modes of binding, they were also cocrystallized with the extracellular domain of PSMA. All analogs exhibited irreversible binding to PSMA with IC50 values ranging from 0.4 to 1.3 nM. In vitro assays showed binding and rapid internalization (80-95%, 2 h) of the radiolabeled ligands in PSMA(+) cells. In vivo distribution demonstrated significant uptake in CWR22Rv1 (PSMA(+)) tumor, with tumor to blood ratios of 25.6:1, 63.6:1, and 69.6:1 for [18F]4, [18F]5, and [18F]6, respectively, at 2 h postinjection. Installation of aminohexanoic acid (AH) linkers in the phosphoramidate scaffold improved their PSMA binding and inhibition and was critical for achieving suitable in vivo imaging properties, positioning [18F]5 and [18F]6 as favorable candidates for future prostate cancer imaging clinical trials.
Processes for the manufacture of macrocyclic depsipeptides and new intermediates
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Page/Page column 31-33, (2016/03/29)
The invention relates to a method or process for the chemical manufacture of depsipeptides of the formula I, wherein the symbols have the meaning defined in the description, to new intermediates and their manufacture, as well as related invention embodiments.
NOVEL BIOACTIVE SUBSTANCE
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Paragraph 0082-0083, (2018/02/08)
PROBLEM TO BE SOLVED: To provide a novel compound useful as an aminopeptidase A inhibitor. SOLUTION: This invention provides a compound represented by formula (I) or salt thereof, and a pharmaceutical composition comprising the same, wherein R1
THIOPHOSPHATE NUCLEOSIDES FOR THE TREATMENT OF HCV
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, (2014/09/16)
Provided herein are compounds, compositions and methods for the treatment of Flaviviridae infections, including HCV infections. In certain embodiments, the compounds are according to Formula 2001: where PD, Base, RA and RB are as provided herein. In certain embodiments, compounds and compositions of nucleoside derivatives are disclosed, which can be administered either alone or in combination with other anti-viral agents.
Novel thiol- and thioether-containing amino acids: Cystathionine and homocysteine families
Longobardo, Luigi,Cecere, Nunzia,DellaGreca, Marina,De Paola, Ivan
, p. 443 - 448 (2013/07/27)
Natural l-homocysteine and l,l-cystathionine, along with a series of unnatural analogues, have been prepared from l-aspartic and l-glutamic acid. Manipulation of the protected derivatives provided ω-iodoamino acids, which were used in thioalkylation react
Development of a solid-phase approach to the natural product class of Ahp-containing cyclodepsipeptides
Stolze, Sara C.,Meltzer, Michael,Ehrmann, Michael,Kaiser, Markus
experimental part, p. 1616 - 1625 (2012/05/04)
The 3-amino-6-hydroxy-2-piperidone (Ahp) containing cyclodepsipeptides are an interesting class of natural products that inhibit S1 (trypsin and chymotrypsin-like) serine protease in a reversible, noncovalent manner, turning them into potential chemical t
Efficient synthesis of benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-ω- iodoalkanoates
Koseki, Yohei,Yamada, Haruka,Usuki, Toyonobu
, p. 580 - 586 (2011/06/21)
The efficient synthesis of four benzyl 2-(S)-[(tert-butoxycarbonyl)amino]- ω-iodoalkanoates {benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-3- iodopropanoate, benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-4-iodobutanoate, benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-
A concise route to L-azidoamino acids: L-azidoalanine, L-azidohomo-alanine and L-azidonorvaline
Roth, Stefanie,Thomas, Neil R.
scheme or table, p. 607 - 609 (2010/09/18)
A simple and highly efficient synthetic route to three homologous azidoamino acids, starting from inexpensive, commercially available, protected natural amino acids is reported. The products can be used to introduce bioorthogonal handles into proteins. Ge
Potent and fully noncompetitive peptidomimetic inhibitor of multidrug resistance P-glycoprotein
Arnaud, Ophélie,Koubeissi, Ali,Ettouati, Laurent,Terreux, Rapha?l,Alamé, Ghina,Grenot, Catherine,Dumontet, Charles,Di Pietro, Attilio,Paris, Jo?lle,Falson, Pierre
supporting information; experimental part, p. 6720 - 6729 (2010/11/16)
Nα-Boc-l-Asp(OBn)-l-Lys(Z)-OtBu (reversin 121, 1), an inhibitor of the P-gp ABC transporter, was used to conceive compounds inhibiting the drug efflux occurring through the Hoechst 33342 and daunorubicin transport sites of P-gp, respectively H and R sites. Replacement of the aspartyl residue by trans-4-hydroxy-l-proline (4(R)Hyp) gave compounds 11 and 15 characterized by half-maximal inhibitory concentrations (IC50) of 0.6 and 0.2 μM, which are 2-and 7-fold lower than that of the parent molecule. The difference in IC50 between 11 and 15 rests on the carbonyl group of the peptidyl bond, reduced in 15. Those compounds are rather specific of P-gp, having no or limited activity on MRP1 and BCRP. 15 displayed no marked cytotoxicity up to 10-fold its IC50. Importantly, 15 equally inhibited the Hoechst 33342 and daunorubicin effluxes through a typical noncompetitive inhibition mechanism, suggesting its binding to a site different from the H and R drug-transport sites.
