95922-26-2Relevant academic research and scientific papers
Synthesis and structural characterization of hexacoordinate silicon, germanium, and titanium complexes of the E. coli siderophore enterobactin
Baramov, Todor,Keijzer, Karlijn,Irran, Elisabeth,Moesker, Eva,Baik, Mu-Hyun,Suessmuth, Roderich
, p. 10536 - 10542 (2013)
The E. coli siderophore enterobactin, one of the strongest FeIII chelators known to date, is also capable of binding SiIV under physiological conditions. We report on the synthesis and structural characterization of the tris(catecholate) SiIV-enterobactin complex and its GeIV and TiIV analogues. Comparative structural analysis, supported by quantum-chemical calculations, reveals the correlation between the ionic radius and the structural changes in enterobactin upon complexation. Copyright
Formation of a tris(catecholato) iron(iii) complex with a nature-inspired cyclic peptoid ligand
Oh, Jinyoung,Kang, Dahyun,Hong, Sugyeong,Kim, Sun H.,Choi, Jun-Ho,Seo, Jiwon
supporting information, p. 3459 - 3463 (2021/03/22)
Siderophore-mimicking macrocyclic peptoids were synthesized. Peptoid3with intramolecular hydrogen bonds showed an optimally arranged primary coordination sphere leading to a stable catecholate-iron complex. The tris(catecholato) structure of 3-Fe(iii) was determined with UV-vis, fluorescence, and EPR spectroscopies and DFT calculations. The iron binding affinity was comparable to that of deferoxamine, with enhanced stability upon air exposure.
PEPTOID-BASED CHELATING LIGANDS FOR SELECTIVE METAL CHELATION
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Paragraph 0116-0117, (2020/04/29)
The present disclosure provides peptoid-based chelating ligands, corresponding cyclic peptoids, and methods of making thereof. Functional groups may be tailored for high metal binding affinity and selectivity. The side chains of a cyclic peptoid according to the present disclosure may be selected based on, for example, high affinity for actinide or other metal ions, selectivity for actinide or other metal ions, the ability to recover a metal once it is bound to the peptoid, and whether the overall peptoid should be hydrophobic or hydrophilic. Unlike siderophores, peptoid-based chelating ligands of the present disclosure are not readily hydrolyzed under physiological conditions. Therefore, peptoid-based chelating ligands may be, for example, used to treat actinide (e.g., iron and lead) poisoning in vivo. Moreover, peptoid-based chelating ligands of the present disclosure may be used for medical imaging, chelation therapy, drug delivery, and separation technologies, for example.
ANTIBACTERIAL SIDEROMYCINS
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Page/Page column 61; 62, (2016/03/13)
A compound, comprising: an Fe(III)-binding and/or Fe(III)-bound siderophore; one or more optional linker covalently bound to the siderophore; and daptomycin covalently bound to the linker, or, if no linker is present, then to the siderophore; or pharmaceu
DENDRITIC COMPOUNDS INCLUDING A CHELATING, FLUOROCHROME OR RECOGNITION AGENT, COMPOSITIONS INCLUDING SAME AND USES THEREOF
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Paragraph 0294; 0295; 0296, (2016/08/29)
The invention relates to dendritic compounds comprising a chelating, fluorochrome or recognition agent of formula (I), to compositions comprising same, and to uses thereof, wherein in said formula (I): T, L1, D, R, L2, V and n are as defined in the description.
Facile and Versatile Chemoenzymatic Synthesis of Enterobactin Analogues and Applications in Bacterial Detection
Lee, Albert A.,Chen, Yi -Chen S.,Ekalestari, Elisa,Ho, Sheng -Yang,Hsu, Nai -Shu,Kuo, Tang -Feng,Wang, Tsung -Shing Andrew
supporting information, p. 12338 - 12342 (2016/10/13)
Siderophores, such as enterobactin (Ent), are small molecules that can be selectively imported into bacteria along with iron by cognate transporters. Siderophore conjugates are thus a promising strategy for delivering functional reagents into bacteria. In this work, we present an easy-to-perform, one-pot chemoenzymatic synthesis of functionalized monoglucosylated enterobactin (MGE). When functionalized MGE is conjugated to a rhodamine fluorophore, which affords RhB-Glc-Ent, it can selectively label Gram-negative bacteria that utilize Ent, including some E. coli strains and P. aeruginosa. V. cholerae, a bacterium that utilizes linearized Ent, can also be weakly targeted. Moreover, the targeting is effective under iron-limiting but not iron-rich conditions. Our results suggest that the RhB-Glc-Ent probe is sensitive not only to the bacterial strain but also to the iron condition in the environment.
Symmetrical 1,3-dicarbonyl biscatecholamide ligands as sequestering agents for uranyl decorporation
Zhang, Qingchun,Jin, Bo,Peng, Rufang,Lei, Shan,Chu, Shijin
, p. 417 - 423 (2015/02/05)
The synthesis of a series of new symmetrical 1,3-dicarbonyl biscatecholamide ligands CH2[COX(CH2)nCAM; X = O, NH; n = 2, 3, 4]2 [CAM = 2,3-Ph(OH)2CONH] is presented. 1H NMR, 13C
Total synthesis and structure revision of mirubactin, and its iron binding activity
Kishimoto, Shinji,Nishimura, Shinichi,Kakeya, Hideaki
supporting information, p. 1303 - 1305 (2015/11/23)
Dechloro-chlorocatechelin A (3), a deschloro-derivative of a microbial siderophore chlorocatechelin A (2), was synthesized from 2,3-dihydroxybenzoic acid, D-arginine, and 1-benzyl Dglutamate. The spectral data were unambiguously identical with those of mi
HIV INTEGRASE INHIBITORS
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Page/Page column 62, (2012/08/27)
Provided herein, inter alia, are novel compounds for the inhibition of HIV integrase. The compounds disclosed herein are useful for methods of treating HIV infection in a subject in need thereof.
Conjugates of methyl 6-aminopenicillanate with biscatechol-hydroxamate chelators: synthesis and siderophoric activity
Schobert, Rainer,Stangl, Andreas,Hannemann, Kerstin
, p. 7799 - 7808 (2007/10/03)
A synthesis of biscatechol-hydroxamate and triscatechol chelators and of conjugates of the former with methyl 6-aminopenicillanate is described. It is based on the multiple use of the ylide Ph3PCCO as a C2 building block in one-pot c
