Synthesis and Coordination Chemistry of the First Water-Soluble Dithio−Bis(phosphine) Ligands [(HOH2C)2P(CH2)2S−X−S(CH2)2P(CH2OH)2] (X = (CH2)3 or C6H4). X-ray Crystal Structure of [Pd(HOH2C)2P(CH2)2S(CH2)3S(CH2)2P(CH2OH)2](Cl)21

Smith, Charles J.; Reddy, V. Sreenivasa; Karra, Srinivasa; Katti, Kattesh V.; Barbour, Leonard J.

doi:10.1021/ic961319g

Cited by 22 publications

(44 citation statements)

References 24 publications

(26 reference statements)

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“…The corresponding 99m Tc complex, 99m Tc-P 2 S 2 -COOH, can be formed in >95% yield. To demonstrate the potential of this chelate to efficiently label peptides, 99m Tc-P 2 S 2 -COOH was coupled to the N-terminal region of the truncated nine-amino acid bombesin analogue, 5-Ava-Gln-Trp-Ala-Val-Gly-His-Leu-Met-NH 2 [BBN (7)(8)(9)(10)(11)(12)(13)(14) ], to form 99m Tc-P 2 S 2 -BBN (7)(8)(9)(10)(11)(12)(13)(14) . Conjugation to the peptide was performed in borate buffer (pH 8.5) by applying the prelabeling approach in yields of >60%.…”

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confidence: 99%

^99mTc-Labeling and in Vivo Studies of a Bombesin Analogue with a Novel Water-Soluble Dithiadiphosphine-Based Bifunctional Chelating Agent

et al. 1999

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Recent progress in the synthesis of water-soluble phosphine ligand systems and their corresponding 99mTc complexes prompted the development of a new bifunctional chelating agent (BFCA) based on a tetradentate dithiadiphosphine framework (P2S2-COOH). The detailed synthesis of this new BFCA is described here. The corresponding 99mTc complex, 99mTc-P2S2-COOH, can be formed in >95% yield. To demonstrate the potential of this chelate to efficiently label peptides, 99mTc-P2S2-COOH was coupled to the N-terminal region of the truncated nine-amino acid bombesin analogue, 5-Ava-Gln-Trp-Ala-Val-Gly-His-Leu-Met-NH2 [BBN(7-14)], to form 99mTc-P2S2-BBN(7-14). Conjugation to the peptide was performed in borate buffer (pH 8.5) by applying the prelabeling approach in yields of >60%. In competitive binding assays, using Swiss 3T3 mouse fibroblast cells against [125I-Tyr4]bombesin, Re-P2S2-BBN(7-14) exhibited an IC50 value of 0.8 +/- 0.4 nM. The pharmacokinetic studies of 99mTc-P2S2-BBN(7-14) and its ability to target tissue expressing gastrin-releasing peptide (GRP) receptors were performed in normal mice. The 99mTc-P2S2-BBN(7-14) exhibited fast and efficient clearance from the blood pool (0.6 +/- 0.1% ID, 4 h postinjection) and excretion through the renal and hepatobiliary pathways (56.4 +/- 8.2 and 28.1 +/- 7.9% ID, 4 h postinjection, respectively). Significant uptake in the pancreas was observed (pancreatic acini cells express bombesin/GRP receptors), producing pancreas:blood and pancreas:muscle ratios of ca. 22 and 80, respectively, at 4 h postinjection.

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confidence: 99%

^99mTc-Labeling and in Vivo Studies of a Bombesin Analogue with a Novel Water-Soluble Dithiadiphosphine-Based Bifunctional Chelating Agent

et al. 1999

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“…For example, amide and thioether functionalized primary phosphines, 5 and 9 respectively, upon treatment with 37% formaldehyde produced the corresponding amide/thioether functionalized water soluble phosphines 21 and 22 respectively in near quantitative yield (Scheme 10) [47]. Indeed, these reactions proceed at 25°C in ethanol-aqueous media in the absence of transition metal catalysts.…”

Section: Formylation Reactions Of Primary Phosphinesmentioning

confidence: 99%

“…The thioether functionalized bisphosphonates, 7 and 8, upon reduction with LiAlH 4 produced the corresponding S 2 P 2 and S 3 P 2 primary bisphosphine frameworks 9 and 10 respectively in good yields (Scheme 4) [47,48].…”

Section: Thioether Functionalized Primary Bisphosphinesmentioning

confidence: 99%

“…These thioether functionalized primary bisphosphines 9 and 10 showed modest oxidative stabilities and have found applications as novel precursors in the development of functionalized water-soluble phosphines via formylation reactions across P-H bonds (see below) [47].…”

Section: Thioether Functionalized Primary Bisphosphinesmentioning

confidence: 99%

“…Recent studies in our laboratory have demonstrated that formylation of P-H bonds can be achieved without the aid of transition metal catalysts under mild reaction conditions [47]. For example, amide and thioether functionalized primary phosphines, 5 and 9 respectively, upon treatment with 37% formaldehyde produced the corresponding amide/thioether functionalized water soluble phosphines 21 and 22 respectively in near quantitative yield (Scheme 10) [47].…”

Section: Formylation Reactions Of Primary Phosphinesmentioning

confidence: 99%

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New Vistas in Chemistry and Applications of Primary Phosphines

Katti¹,

Pillarsetty²,

Kannan³

2003

New Aspects in Phosphorus Chemistry III

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Primary phosphines (R-PH 2 ) are an important class of compounds in organophosphorus chemistry. Although discovered over a century ago, their chemistry and applications have gained prominence in recent years. This review discusses recent developments on synthesis, molecular structure, properties, and applications of primary phosphines. In particular, discussions on synthesis and properties emphasize recent results from our laboratory on the chemical architecture of amide, thioether, and carboxylate functionalized primary bisphosphines. The utility of bromo-and aminopropyl phosphines (X(CH 2 ) 3 PH 2 ; X=Br or NH 2 ) as building blocks to produce 'designer' primary phosphines that display exceptional oxidative stability is described. The review also discusses the utility of carboxylate functionalized primary phosphines for incorporation on to peptides and their potential applications in catalysis and biomedicine.

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Synthese des ersten Biokonjugats aus einem chelatisierenden Bisphosphan und einem Peptid ausgehend von einem neuartigen funktionalisierten Phosphor(III)-hydrid-Synthon

et al. 1999

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Eine bemerkenswerte Oxidationsbeständigkeit zeichnet das Carboxy‐funktionalisierte primäre Bisphosphan 1 aus. Es kann über die COOH‐Gruppe mit Biomolekülen zu Konjugaten verknüpft werden, ohne daß die PH2‐Gruppen vorher geschützt werden müssen. Ein neuartiges, wasserlösliches Bisphosphan wurde durch die Reaktion der PH2‐Gruppen von 1 mit Formaldehyd unter milden Bedingungen erhalten.

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Synthesis and Coordination Chemistry of the First Water-Soluble Dithio−Bis(phosphine) Ligands [(HOH₂C)₂P(CH₂)₂S−X−S(CH₂)₂P(CH₂OH)₂] (X = (CH₂)₃ or C₆H₄). X-ray Crystal Structure of [Pd(HOH₂C)₂P(CH₂)₂S(CH₂)₃S(CH₂)₂P(CH₂OH)₂](Cl)₂¹

Cited by 22 publications

References 24 publications

^99mTc-Labeling and in Vivo Studies of a Bombesin Analogue with a Novel Water-Soluble Dithiadiphosphine-Based Bifunctional Chelating Agent

^99mTc-Labeling and in Vivo Studies of a Bombesin Analogue with a Novel Water-Soluble Dithiadiphosphine-Based Bifunctional Chelating Agent

New Vistas in Chemistry and Applications of Primary Phosphines

Synthese des ersten Biokonjugats aus einem chelatisierenden Bisphosphan und einem Peptid ausgehend von einem neuartigen funktionalisierten Phosphor(III)-hydrid-Synthon

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