Synthesis of a novel hexadentate chelating agent based on8-hydroxyquinoline

Shrader, William D.; Celebuski, Joseph E.; Kline, Steven J.; Johnson, David

doi:10.1016/s0040-4039(00)80294-4

Cited by 24 publications

(15 citation statements)

References 13 publications

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“…On the other hand, the addition of one equivalent of diethylenetriaminopentaacetic acid (DTPA) (pEu = 19.6 computed from known stability constants [17] ) results in a large dissociation of the Eu III tripodal chelate. Therefore, we estimate that the pEu value for the T2soxMe chelate is between 15 and 19, and the corresponding values for the other lanthanide ions studied here should be similar, referring to the range of values obtained for TsoxMe (15)(16).…”

Section: Solution Study: Thermodynamic Aspectssupporting

confidence: 62%

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A Novel Strategy for the Design of 8‐Hydroxyquinolinate‐Based Lanthanide Bioprobes That Emit in the Near Infrared Range

Comby

Imbert

Vandevyver

et al. 2007

Chemistry A European J

112

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A new polydentate tripodal ligand T2soxMe was synthesized to take advantage of the chelating effect of tridentate 8-hydroxyquinolinate subunits. Potentiometric and spectrophotometric titrations reveal seven pK(a) values of between 3.7 and 10.2. In water, the use of T2soxMe leads to thermodynamically stable and soluble Ln(III) complexes at physiological pH, with conditional stability constants in the range log beta(11)=7.8-8.6. The chelates are resistant toward hydrolysis and show interesting photophysical properties, particularly in the near infrared (NIR) range. The emission lifetimes of the Nd(III) and Yb(III) complexes recorded in D(2)O and H(2)O suggest the absence of water molecules in the first coordination sphere of the metal ions. Moreover, the low energy of the triplet state allows efficient energy transfer from the ligand to the metal ions: in water at pH 7.4, the sensitization efficacy of the NIR luminescence reaches 75 and approximately 100 % for Nd(III) and Yb(III), respectively, leading to overall quantum yields of 0.027 and 0.13 %; Er(III) luminescence is also detected. According to the WST-1 test, the Yb(III) podate at concentrations of up to 250 microM does not display sizeable cytotoxicity for Jurkat cells after 24 h of incubation. Finally, the same podate is shown to couple to human serum albumin, leading to an increase of 50 % in the NIR-luminescence intensity.

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Section: Solution Study: Thermodynamic Aspectssupporting

confidence: 62%

“…[14] In the next step, this product was condensed with activated 2-carboxy-8-hydroxyquinoline to give the tripodal ligand T2oxMe. Finally, the regiospecific sulfonation of the 8-hydroxyquinoline subunits was achieved by using oleum (H 2 SO 4 , SO 3 ), as already reported for 2-carboxy-8-hydroxyquinoline, [15] giving an overall yield of 27 %.…”

Section: Resultsmentioning

confidence: 97%

A Novel Strategy for the Design of 8‐Hydroxyquinolinate‐Based Lanthanide Bioprobes That Emit in the Near Infrared Range

Comby

Imbert

Vandevyver

et al. 2007

Chemistry A European J

112

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“…Various reagents like dimethyl sulphate, [17] N,N-dimethylcarbamoyl chloride, [18] ethyl chloroformate, [19] benzoyl halides, [20] acetic anhydrides, [21] and MsCl, [22] have been used as activators for this purpose [more recently, Sun and coworkers used hypervalent iodine (III) [23] as an activating agent]. Various reagents like dimethyl sulphate, [17] N,N-dimethylcarbamoyl chloride, [18] ethyl chloroformate, [19] benzoyl halides, [20] acetic anhydrides, [21] and MsCl, [22] have been used as activators for this purpose [more recently, Sun and coworkers used hypervalent iodine (III) [23] as an activating agent].…”

Section: Introductionmentioning

confidence: 99%

Regioselective Cyanation of Six‐Membered N‐Heteroaromatic Compounds Under Metal‐, Activator‐, Base‐ and Solvent‐Free Conditions

et al. 2019

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A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic CÀ H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent.

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“…Recent research in the area of oral iron-chelation therapy centers on the TRENSOX drugs. Both N-TRENSOX ( 1 ) [ 1 ] and O-TRENSOX ( 2 ) [ 2 ] have shown promising results in iron binding and water solubility studies [ 3 ]. These novel compounds contain three quinoline units which each contain two oxygen functional groups.…”

Section: Introductionmentioning

confidence: 99%

A General Synthesis of Tris-Indole Derivatives as Potential Iron Chelators

2005

Molecules

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Synthesis of a novel hexadentate chelating agent based on8-hydroxyquinoline

Cited by 24 publications

References 13 publications

A Novel Strategy for the Design of 8‐Hydroxyquinolinate‐Based Lanthanide Bioprobes That Emit in the Near Infrared Range

A Novel Strategy for the Design of 8‐Hydroxyquinolinate‐Based Lanthanide Bioprobes That Emit in the Near Infrared Range

Regioselective Cyanation of Six‐Membered N‐Heteroaromatic Compounds Under Metal‐, Activator‐, Base‐ and Solvent‐Free Conditions

A General Synthesis of Tris-Indole Derivatives as Potential Iron Chelators

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