Organometallic Transformations from an .eta.3-Propargyl or .eta.2-Allenyl Ligand to .eta.3-Hydroxyallyl, .eta.3-Heterotrimethylenemethane, and .eta.6-Diallyl Ether Species

Huang, Tien-Shine; Hsu, Ray-Hsi; Yang, Ching-Shuenn; Chen, Jwu‐Ting; Lee, Gene‐Hsiang; Wang, Yu

doi:10.1021/om00021a045

Cited by 69 publications

(33 citation statements)

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“…[ 124 ] In addition to the use of [F 7 ,P 34 ]‐NPY, Zhang et al reported the short NPY analog [Lys(Pip‐ 68 Ga‐DOTA) 4 ,Bip 5 ]BVD15 (BVD15: [Pro 30 ,Tyr 32 ,Leu 34 ]‐NPY(28‐36)), which is able to bind the hY 1 R in vivo , as demonstrated by high contrast PET images of HEK293T::hY 1 R tumor xenografts in mice. [ 125 ] Besides the validation of hY 1 R binding in vivo with imaging agents, [F 7 ,P 34 ]‐NPY was also used in first studies for the generation of drug delivery compounds for targeted tumor therapy. Apart from that, only a few other publications describe a hY 1 R‐targeted anti‐cancer drug design.…”

Section: Targeting Of New G Protein‐coupled Receptorsmentioning

confidence: 99%

Targeting of peptide‐binding receptors on cancer cells with peptide‐drug conjugates

2020

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Specifically addressing cell surface molecules on cancer cells facilitates targeted cancer therapies that offer the potential to selectively destroy malignant cells, while sparing healthy tissue. Thus, undesired side-effects in tumor patients are highly reduced. Peptide-binding receptors are frequently overexpressed on cancer cells and therefore promising targets for selective tumor therapy. In this review, peptidebinding receptors for anti-cancer drug delivery are summarized with a focus on peptide ligands as delivery agents. In the first part, some of the most studied peptidebinding receptors are presented, and the ghrelin receptor and the Y 1 receptor are introduced as more recent targets for cancer therapy. Furthermore, nonpeptidic small molecules for receptor targeting on cancer cells are outlined. In the second part, peptide conjugates for the delivery of therapeutic cargos in cancer therapy are described.The essential properties of receptor-targeting peptides are specified, and recent developments in the fields of classical peptide-drug conjugates with toxic agents, radiolabeled peptides for radionuclide therapy, and boronated peptides for boron neutron capture therapy are presented. K E Y W O R D SBNCT, G protein-coupled receptor, internalization, peptide drug conjugate, tumor targeting

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Section: Targeting Of New G Protein‐coupled Receptorsmentioning

confidence: 99%

Targeting of peptide‐binding receptors on cancer cells with peptide‐drug conjugates

2020

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“…The stereochemical outcome of the transformation is predicted on the basis of the indicated model, which involves carbonyl addition through the closed six‐centered transition state A (Scheme ). Regarding the conformation of such square‐planar allenyliridium species A – D , it is shown in a related η 1 ‐allenylplatinum(II) complex, trans ‐[Pt(PPh 3 ) 2 (Br)(η 1 ‐CHCCH 2 )], that the allenyl moiety lies roughly perpendicular to the square coordination plane 22c…”

Section: Structure–selectivity Relationships Between Enynes 1 and Ligmentioning

confidence: 99%

Diastereo‐ and Enantioselective Iridium‐Catalyzed Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level: 1,3‐Enynes as Allenylmetal Equivalents

et al. 2012

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Chiralitätstransfer: Die Behandlung von konjugierten Eninen mit Alkoholen und einem Iridium‐Katalysator mit Segphos‐Ligand führt zur Bildung von Aldehyd‐Allenyl‐Iridium‐Komplexen und enantiomerenangereicherten Produkten einer Carbonyl‐anti‐(α‐methyl)propargylierung (siehe Schema). Die gleichen Produkte werden mit Aldehyden nach Transferhydrierung mit Ameisensäure als Reduktionsmittel erhalten.

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“…[6,7,14] Therefore, complex 5 is probably formed via the corresponding cationic η 3 -type complex [(PPh 3 ) 2 Pt{η 3 -CH 2 CC(CϵCPh)}] + (6), which could be produced as an equilibrium isomer of 2a by the spontaneous dissociation of a chloride ion (Scheme 6). Although cationic η 3 -type complex 6 was not observed directly by NMR spectroscopic analysis of cis-2a in any solvent tested, complex 5 resulted from the addition of PPh 3 in both CDCl 3 and [D 7 ]dmf (Scheme 5).…”

Section: Mechanistic Aspects Of the Transformation Of Monoplatinum Comentioning

confidence: 99%

Mono‐ or Diplatinum Complexes Containing a π‐Conjugated Pentadiynyl Ligand

et al. 2010

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The reaction of pentadiynyl halides XCH2C≡CC≡CPh (1) with equimolar amounts of Pt(C2H4)(PPh3)2 in C6D6 produced cis‐(PPh3)2PtX(η1‐CH2C≡CC≡CPh) (cis‐2) as a kinetic product. Complex cis‐2 isomerized to trans‐(PPh3)2PtX(η1‐CH2C≡CC≡CPh) (trans‐2) or trans‐(PPh3)2PtX[η1‐C(C≡CPh)=C=CH2] (trans‐3) under some reaction conditions. In contrast to the reaction of Pt(C2H4)(PPh3)2, treatment of 1 with Pt(PPh3)4 generated cationic platinacyclobutene [(PPh3)2Pt{η2‐CH2C(PPh3)=C(C≡CPh)}]+Cl– (5) together with cis‐2 and trans‐2. Moreover, 2 equiv. of Pt(C2H4)(PPh3)2 and 1 provided η1,η2‐coordinated diplatinum complex cis‐(PPh3)2PtCl[η1‐ CH2C≡C{(PPh3)2Pt(η2‐C≡CPh)}] (7) and/or metallacyclobutene diplatinum complex (PPh3)2Pt[η2‐CH2C{(PPh3)2PtCl}=C(C≡CPh)] (8). The coordination modes of these complexes depend on the ratio of pentadiynyl halide, Pt, and PPh3, as well as temperature and the nature of the solvents. Protonolysis of metallacyclobutene complexes 5 and 8 with HCl gave [cis‐(PPh3)2PtCl{η1‐C(C≡CPh)=C(PPh3)CH3}]+Cl– (9) and [(PPh3)2Pt{η3‐CH2{cis‐(PPh3)2PtCl}CCH(C≡CPh)}]+Cl– (10). Single‐crystal X‐ray diffraction analysis of 12 showed η3‐ and η1‐coordination structure.

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Organometallic Transformations from an .eta.3-Propargyl or .eta.2-Allenyl Ligand to .eta.3-Hydroxyallyl, .eta.3-Heterotrimethylenemethane, and .eta.6-Diallyl Ether Species

Cited by 69 publications

References 0 publications

Targeting of peptide‐binding receptors on cancer cells with peptide‐drug conjugates

Targeting of peptide‐binding receptors on cancer cells with peptide‐drug conjugates

Diastereo‐ and Enantioselective Iridium‐Catalyzed Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level: 1,3‐Enynes as Allenylmetal Equivalents

Mono‐ or Diplatinum Complexes Containing a π‐Conjugated Pentadiynyl Ligand

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