Formylbenzene Diazonium Hexafluorophosphate Reagent for Tyrosine-Selective Modification of Proteins and the Introduction of a Bioorthogonal Aldehyde

Gavrilyuk, Julia; Ban, Hyun Seung; Nagano, Masanobu; Hakamata, Wataru; Barbas, Carlos F.

doi:10.1021/bc300410p

Cited by 97 publications

(108 citation statements)

References 39 publications

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“…In order to independently assess the activity of aplaviroc conjugated to a carrier IgG without anti-HIV-1 activity, trastuzumab, an anti-Her2 monoclonal antibody (MAb), was used as a model human IgG for chemical modification and testing. Bioconjugation conditions were selected on the basis of our previous study (30) and were further optimized here (for full optimization details, see the tables in section S3 in the supplemental material). The two-step conjugation methodology involved modification of the IgG with FBDP (4-formylbenzene diazonium hexafluorophosphate) followed by ligation of the antibody to aplaviroc-oxyamine (Fig.…”

Section: Resultsmentioning

confidence: 99%

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Antibody Conjugation Approach Enhances Breadth and Potency of Neutralization of Anti-HIV-1 Antibodies and CD4-IgG

Gavrilyuk

Ban

Uehara

et al. 2013

J Virol

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Section: Resultsmentioning

confidence: 99%

“…In a 1.5-ml tube, an antibody solution (99 l; 1.5 mg/ml in 0.1 M Na 2 HPO 4 [pH 8.0]) and 10 equivalents of 4-formylbenzene diazonium hexafluorophosphate (FBDP; 1 l; 10 mM solution in CH 3 CN) were combined (30). The solution was mixed gently and was allowed to react for 30 min at room temperature with intermittent mixing.…”

Section: Methodsmentioning

confidence: 99%

Antibody Conjugation Approach Enhances Breadth and Potency of Neutralization of Anti-HIV-1 Antibodies and CD4-IgG

Gavrilyuk

Ban

Uehara

et al. 2013

J Virol

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“…However, experiments with N-acyl methylamides of histidine, serine, cysteine, tryptophan and lysine revealed reactivity the latter two towards cyclic diazodicarboxamid. In addition histidine, tryptophan and unoxidized cysteine exhibited reactivity towards a diazonium hexafluorophosphate derivative [69,70]. Even if both reagents exhibit a high chemoselectivity for tyrosine, side reactions with other amino acids are inevitable.…”

Section: Conjugation Via Tyrosinementioning

confidence: 99%

Antibody Conjugates: From Heterogeneous Populations to Defined Reagents

2015

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Monoclonal antibodies (mAbs) and their derivatives are currently the fastest growing class of therapeutics. Even if naked antibodies have proven their value as successful biopharmaceuticals, they suffer from some limitations. To overcome suboptimal therapeutic efficacy, immunoglobulins are conjugated with toxic payloads to form antibody drug conjugates (ADCs) and with chelating systems bearing therapeutic radioisotopes to form radioimmunoconjugates (RICs). Besides their therapeutic applications, antibody conjugates are also extensively used for many in vitro assays. A broad variety of methods to functionalize antibodies with various payloads are currently available. The decision as to which conjugation method to use strongly depends on the final purpose of the antibody conjugate. Classical conjugation via amino acid residues is still the most common method to produce antibody conjugates and is suitable for most in vitro applications. In recent years, however, it has become evident that antibody conjugates, which are generated via site-specific conjugation techniques, possess distinct advantages with regard to in vivo properties. Here, we give a comprehensive overview on existing and emerging strategies for the production of covalent and non-covalent antibody conjugates.

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“…Examples of existing crystalline aryl diazonium are p-nitro benzenediazonium tetrafluoroborate [25] and formyl benzenediazonium hexafluorophsophate [26]. CDNBD applications in both analytical and syntheses utilize reagent solution in situ.…”

Section: Introductionmentioning

confidence: 99%

Modeling of 4-Carboxyl-2,6-dinitrobenzenediazonium Ion (CDNBD) Hydrolysis Through Addition of Water and Alkaline Buffer in a Strongly Acidic Medium

Thomas

Bioku

2015

J Solution Chem

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The transition from aryl diazonium reagent solution to a crystalline form has substantial merits, namely augmented stability and versatility. Absorbance decay data was from photometric titration with hydroxyl ion, supplied incrementally by water and alkaline buffer (pH 12.0), to 4-carboxyl-2,6-dinitrobenzenediazonium ion (CDNBD) and simpler analogs in a strongly acidic medium. The data were fitted to nested models (mono-and bi-exponential decay). Akaike's Information Criterion was used for statistical model comparison. Preferred model identification shows simpler diazonium analogs are less reactive towards hydroxyl ion when alkaline buffer solution is the diluting medium. In contrast, CDNBD hydrolysis is faster when an alkaline diluting medium is added, owing to profound positive effect of strong electron withdrawing groups on its electrophilic reactivity. Acidic diluting medium was shown, unambiguously, as a critical requirement for maintaining CDNBD, in an acidic solution as the cation species. Key input process variables were reliably predicted, using model parameters like V 1=2 and V T 1=2 , thus giving direction for optimal synthesis of crystalline CDNBD.

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Formylbenzene Diazonium Hexafluorophosphate Reagent for Tyrosine-Selective Modification of Proteins and the Introduction of a Bioorthogonal Aldehyde

Cited by 97 publications

References 39 publications

Antibody Conjugation Approach Enhances Breadth and Potency of Neutralization of Anti-HIV-1 Antibodies and CD4-IgG

Antibody Conjugation Approach Enhances Breadth and Potency of Neutralization of Anti-HIV-1 Antibodies and CD4-IgG

Antibody Conjugates: From Heterogeneous Populations to Defined Reagents

Modeling of 4-Carboxyl-2,6-dinitrobenzenediazonium Ion (CDNBD) Hydrolysis Through Addition of Water and Alkaline Buffer in a Strongly Acidic Medium

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