Cross-reactivity associated with delayed type hypersensitivity (DTH) arising from cephem antibiotics with a tetrazolyl group in the C-3 side chain was investigated by clinical testing and animal experiments. Clinical cross-reaction testing was performed with the leucocyte migration inhibition test (LMIT) with respect to sixteen patients with hypersensitivity induced by cephems with a tetrazolyl group in the C-3 side chain. The proportion of positive LMIT cross-reactions to cephems with a tetrazolyl group in the C-3 side chain was 78% (25/32), to cephems without a tetrazolyl group, 5% (1/22), and to penams, 0% (0/12). The proportion of positives in tests performed with methyl-tetrazolethiol (MTT) and hydroxyethyl-tetrazolethiol (HTT), which essentially represent the structures of the C-3 side-chains in the allergenic drugs, was 29% (4/14), while the corresponding proportion for 7-aminocephalosporanic acid (7ACA), which represents the skeleton structure of the cephem antibiotics, was 33% (1/3). The animal experiments were performed with guinea pigs, with latamoxef, cefoperazone and MTT as the sensitizing agents and testing for cross-reactivity by means of delayed type intradermal reactions as well as the LMIT. The results of intradermal testing and the LMIT agreed almost completely, thus providing strong support for the clinical results. Latamoxef and cefoperazone displayed the same cross-reactivity, manifesting cross-reactions with MTT, HTT and 7ACA as well as with cephems having a tetrazolyl group in the C-3 side chain. Moreover, DTH induced by MTT displayed cross-reactivity with cephems possessing tetrazolyl groups in the C-3 side chain. The above results indicate that free MTT radicals, as well as the skeleton ring structure represented by 7ACA, are strongly involved in DTH arising from cephem antibiotics with a tetrazolyl group in the C-3 side chain.

Download full-text PDF

Source
http://dx.doi.org/10.1093/jac/24.2.251DOI Listing

Publication Analysis

Top Keywords

tetrazolyl group
28
c-3 side
28
side chain
28
group c-3
24
cephems tetrazolyl
20
delayed type
12
cephem antibiotics
12
type hypersensitivity
8
tetrazolyl
8
c-3
8

Similar Publications

3-Tetrazolyl-β-carboline derivatives as potential neuroprotective agents.

Bioorg Med Chem

September 2024

University of Coimbra, Coimbra Chemistry Centre-Institute of Molecular Sciences, and Department of Chemistry, 3004-535 Coimbra, Portugal. Electronic address:

3-Tetrazolyl-β-carbolines were prepared by the Pictet-Spengler approach using a tryptophan analogue as building block, in which the carboxylic acid was replaced by the bioisosteric tetrazole group. Knowing that β-carbolines are often associated with psychopharmacological effects, the study of the 3-tetrazolyl-β-carbolines as potential neuroprotective agents against Parkinson's disease was investigated. The evaluation of neuroprotective effects against 1-methyl-4-phenylpyridin-1-ium (MPP)-induced cytotoxicity allowed to identify compounds with relevant neuroprotective activity.

View Article and Find Full Text PDF

Development of energetic catalysts with high energy density and strong catalytic activity has become the focus and frontier of research, which is expected to improve the combustion performance and ballistic properties of solid propellants. In this work, three energetic catalysts, M(HO)(AFCA)·HO (AFCA = 3-aminofurazan-4-carboxylic acid, M = Cu, Co, Fe), are designed and synthesized based on the coordination reaction of transition metal ions and the energetic ligand. The target products are characterized by single crystal X-ray diffraction, Fourier transform infrared spectroscopy, differential thermal analysis, optical microscopy, and scanning electron microscopy.

View Article and Find Full Text PDF

The electrochemically enabled α-C(sp)-H azolation of ketones.

Chem Commun (Camb)

September 2023

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, P. R. China.

C-H/N-H cross-coupling has become a key technology for the selective conjugation of azole drug molecules. However, the development of new synthetic models and green chemical methods is imperative to enhance the construction of multi-functional compounds and compounds with unique functional groups. We herein reported an electrochemical synthesis of α-tetrazolyl ketones with excellent yields and broad substrate scope, encompassing electron-donating and electron-withdrawing groups of aryl ketones, heterocycles, and alkyl and various ketone drugs.

View Article and Find Full Text PDF

Synthesis of New Polyheterocyclic Pyrrolo[3,4-]pyridin-5-ones via an Ugi-Zhu/Cascade/Click Strategy.

Molecules

May 2023

Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. Ferrocarril San Rafael Atlixco 186, Col. Leyes de Reforma 1A Sección, Iztapalapa, Mexico City 09310, Mexico.

A diversity-oriented synthesis (DOS) of two new polyheterocyclic compounds was performed via an Ugi-Zhu/cascade (-acylation/ Diels-Alder cycloaddition/decarboxylation/dehydration)/click strategy, both step-by-step to optimize all involved experimental stages, and in one pot manner to evaluate the scope and sustainability of this polyheterocyclic-focused synthetic strategy. In both ways, the yields were excellent, considering the high number of bonds formed with release of only one carbon dioxide and two molecules of water. The Ugi-Zhu reaction was carried out using the 4-formylbenzonitrile as orthogonal reagent, where the formyl group was first transformed into the pyrrolo[3,4-]pyridin-5-one core, and then the remaining nitrile group was further converted into two different nitrogen-containing polyheterocycles, both via click-type cycloadditions.

View Article and Find Full Text PDF

In this work, we describe the design, synthesis, and structure-activity relationship of 6-(tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as inhibitors of Casein kinase 2 (CK2). At first, we optimized the reaction conditions for the azide-nitrile cycloaddition in the series of 6-cyano-7-aminoazolopyridimines and sodium azide. The regioselectivity of this process has been shown, as the cyano group of the pyrimidine cycle was converted to tetrazole while the nitrile of the azole fragment did not react.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!