A novel reagent (N_succinimidyl diphenylphosphate) for synthesis of active ester and peptide

Ogura, Haruo; Nagai, Sachiko; Takeda, Kazuyoshi

doi:10.1016/s0040-4039(00)92747-3

Cited by 36 publications

(12 citation statements)

References 4 publications

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“…Paclitaxel 2 was reacted with succinic anhydride to give paclitaxel hemisuccinate 3 in 74% yield (Figure 2, (18). Diphenyl chlorophosphate was treated with N-hydroxysuccinimide in the presence of triethyl amine at 0ºC to obtain N-hydroxysuccinimido diphenyl phosphate (SDPP) 4 ( Figure 2) (19). Paclitaxel hemisuccinate 3 was reacted with SDPP 4 in the presence of Et 3 N to give paclitaxel hemisuccinate-NHS ester 5 in 67% yield (Figure 2) (18).…”

Section: Resultsmentioning

confidence: 99%

Anticancer activity of drug conjugates in head and neck cancer cells

et al. 2016

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Sexually transmitted oral cancer/head and neck cancer is increasing rapidly. Human papilloma virus (HPV) is playing a role in the pathogenesis of a subset of squamous cell carcinoma of head and neck (SCCHN). Paclitaxel is a widely used anticancer drug for breast, ovarian, testicular, cervical, non-small cell lung, head and neck cancer. However, it is water insoluble and orally inactive. We report the synthesis of water soluble nanosize conjugates of paclitaxel, branched PEG, and EGFR-targeting peptide by employing native chemical ligation. We performed a native chemical ligation between the N-hydroxy succinimide (NHS) ester of paclitaxel succinate and cysteine at pH 6.5 to give the cysteine-conjugated paclitaxel derivative. The thiol functionality of cysteine was activated and subsequently conjugated to multiarm thiol-PEG to obtain the paclitaxel branched PEG conjugate. Finally, we conjugated an EGFR-targeting peptide to obtain conjugates of paclitaxel, branched PEG, and EGFR-targeting peptide. These conjugates show anticancer activity against squamous cell carcinoma of head and neck cells (SCCHN, Tu212).

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Section: Resultsmentioning

confidence: 99%

Anticancer activity of drug conjugates in head and neck cancer cells

et al. 2016

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“…However, side products formed during the course of the reaction make the NHS-esters difficult to purify, not to mention that the reaction is not effective in terms of atoms economy. Finally, in 1980, Ogura 46 developed an approach using a chlorophosphate to prepare the first the activated NHS reagent, namely N-succinimidyl diphenylphosphate (SDPP) (Scheme 8). It should be noted that SDPP can be stored for several months in a refrigerator.…”

Section: Carboxylic Acid Coupling Reaction With Activated N-hydroxysumentioning

confidence: 99%

An Overview of the Synthesis of Highly Versatile N-Hydroxysuccinimide Esters

et al. 2016

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N-Hydroxysuccinimide esters (NHS-esters) are important and widely used tools in various areas of chemistry including peptide synthesis, bioconjugate chemistry, functionalized materials and polymers. The usual strategy employed to prepare these active esters generally relies on the coupling reaction with a carboxylic acid and N-hydroxysuccinimide in the presence of a coupling agent. However, more recently, many other efficient strategies have emerged in the literature. This short review covers the literature devoted to the preparation of these valuable N-hydroxysuccinimide esters. 1 Introduction 2 N-Hydroxysuccinimide Coupling Reaction with Activated Carboxylic Acids 3 Carboxylic Acid Coupling Reaction with Activated N-Hydroxysuccinimide 4 Alcohol and Aldehyde Coupling Reaction with N-Hydroxysuccinimide under Oxidizing Conditions 5 Carbonylative Cross-Coupling Reaction 6 Conclusion

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“…Then the PTX-Suc Table 1 Structural formulas and thumbnail of HA and drugs. was activated by carbodiimide coupling reagent composed of diphenylphosphoryl chloride, NHS and triethylamine, and reacted with N-hydroxysuccinimide (NHS) to obtain PTX-NHS ester [30]. HA-ADH and PTX-NHS eater were mixed at pH 6.5 for 24 h to obtain HA-PTX conjugate.…”

Section: Ha-paclitaxel Bioconjugatementioning

confidence: 99%