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Molecules (Basel, Switzerland) Dec 2017In the present paper, we report the synthesis and evaluation of in vitro antimicrobial activities of aziridine-thiourea derivatives. A series of aziridines in reaction...
In the present paper, we report the synthesis and evaluation of in vitro antimicrobial activities of aziridine-thiourea derivatives. A series of aziridines in reaction with isocyanates and isothiocyanates to obtain urea and thiourea derivatives were used. The structures of all new products were confirmed based on spectroscopic data (¹H-NMR, C-NMR, HR-MS). These compounds were screened for their in vitro antimicrobial activity against a panel of Gram-positive and Gram-negative strains of bacteria. Six of the tested compounds appeared to be promising agents against reference strains of , and . Subsequently, compounds exhibiting promising antibacterial activity were tested against twelve clinical isolates of from three different sources of infection. The most bactericidal compounds (MIC = 16-32 µg/mL) showed better antibacterial activity against MRSA than ampicillin and streptomycin. The in vitro cytotoxicity analysis on L929 murine fibroblast and HeLa human tumor cell line using the MTT assay allowed us to select the least toxic compounds for future investigation.
Topics: Anti-Bacterial Agents; Aziridines; Cell Death; Escherichia coli; HeLa Cells; Humans; Indicators and Reagents; Microbial Sensitivity Tests; Staphylococcus aureus; Thiourea; Urea
PubMed: 29295572
DOI: 10.3390/molecules23010045 -
Molecules (Basel, Switzerland) Oct 2022Multi-substituted pyrroles are synthesized from regiospecific aziridine ring-opening and subsequent intramolecular cyclization with a carbonyl group at the -position in...
Multi-substituted pyrroles are synthesized from regiospecific aziridine ring-opening and subsequent intramolecular cyclization with a carbonyl group at the -position in the presence of Lewis acid or protic acid. This method is highly atom economical where all the atoms of the reactants are incorporated into the final product with the removal of water. This new protocol is applied to the synthesis of various pyrroles, including natural products.
Topics: Pyrroles; Lewis Acids; Aziridines; Biological Products; Water
PubMed: 36296466
DOI: 10.3390/molecules27206869 -
IARC Monographs on the Evaluation of... 1999
Topics: Animals; Aziridines; Carcinogenicity Tests; Carcinogens; Humans; Kidney; Mutagenicity Tests; Mutagens; Salmonella typhimurium
PubMed: 10476433
DOI: No ID Found -
Chemical Reviews Mar 2012
Review
Topics: Animals; Aziridines; Cyclopropanes; Enzymes; Epoxy Compounds; Humans
PubMed: 22017381
DOI: 10.1021/cr200073d -
CA: a Cancer Journal For Clinicians 1964
Topics: Adrenal Cortex Hormones; Antineoplastic Agents; Cyclophosphamide; Dactinomycin; Gonadal Steroid Hormones; Humans; Methotrexate; Neoplasms; Progestins; Quinacrine; Thiotepa; Vinblastine
PubMed: 14129472
DOI: 10.3322/canjclin.14.2.67 -
Vaccine Aug 1990Viral antigens for human and veterinary vaccines are still inactivated with formaldehyde. This is not an ideal inactivant and the problems of formaldehyde inactivation... (Review)
Review
Viral antigens for human and veterinary vaccines are still inactivated with formaldehyde. This is not an ideal inactivant and the problems of formaldehyde inactivation of vaccines are discussed. Vaccines inactivated with aziridines are superior in safety and antigenicity. Aziridines inactivate viruses in a first-order reaction and the inactivation rate and endpoint can be determined. The preparation and application of the aziridine compound binary ethylenimine (BEI) and the necessary conditions for and controls of the inactivation process are described and discussed. A computer program has been written for assistance in the use of BEI for controlled inactivation of viral antigens.
Topics: Animals; Antigens, Viral; Aziridines; Humans; Vaccines, Inactivated
PubMed: 2204242
DOI: 10.1016/0264-410x(90)90083-x -
Report on Carcinogens : Carcinogen... 2011
Topics: Animals; Aziridines; Carcinogenicity Tests; Carcinogens, Environmental; Environmental Exposure; Government Regulation; Guidelines as Topic; Humans; Molecular Structure; Occupational Exposure; Rats
PubMed: 21860477
DOI: No ID Found -
British Journal of Pharmacology Jan 2013EO9 (Apaziquone) is a bioreductive drug that has a chequered history. It underwent clinical trial but failed to show activity in phase II clinical trials when... (Review)
Review
EO9 (Apaziquone) is a bioreductive drug that has a chequered history. It underwent clinical trial but failed to show activity in phase II clinical trials when administered i.v. Poor drug delivery to tumours caused by a combination of rapid pharmacokinetic elimination and poor penetration through avascular tissue were the major factors responsible for EO9's poor efficacy. Based upon an understanding of why EO9 failed, a further clinical trial against patients with superficial transitional cell carcinoma of the bladder was conducted. The rationale for this was that intravesical administration directly into the bladder would circumvent the drug delivery problem, and any drug reaching the blood supply would be rapidly cleared thereby reducing the risk of systemic exposure. EO9 was well tolerated, and clinical activity against marker lesions was recorded in both phase I and II clinical trials. This article charts the pharmacological history of EO9 and discusses the potential implications that 'the EO9 story' has for the development of other loco-regional therapies.
Topics: Administration, Intravesical; Animals; Antineoplastic Agents; Area Under Curve; Aziridines; Carcinoma, Non-Small-Cell Lung; Carcinoma, Transitional Cell; Disease Models, Animal; Drug Delivery Systems; Humans; Immunohistochemistry; Indolequinones; Lung Neoplasms; Treatment Failure; Urinary Bladder; Urinary Bladder Neoplasms
PubMed: 22509926
DOI: 10.1111/j.1476-5381.2012.01996.x -
Science (New York, N.Y.) Feb 2017Cysteine can be specifically functionalized by a myriad of acid-base conjugation strategies for applications ranging from probing protein function to antibody-drug...
Cysteine can be specifically functionalized by a myriad of acid-base conjugation strategies for applications ranging from probing protein function to antibody-drug conjugates and proteomics. In contrast, selective ligation to the other sulfur-containing amino acid, methionine, has been precluded by its intrinsically weaker nucleophilicity. Here, we report a strategy for chemoselective methionine bioconjugation through redox reactivity, using oxaziridine-based reagents to achieve highly selective, rapid, and robust methionine labeling under a range of biocompatible reaction conditions. We highlight the broad utility of this conjugation method to enable precise addition of payloads to proteins, synthesis of antibody-drug conjugates, and identification of hyperreactive methionine residues in whole proteomes.
Topics: Actins; Aziridines; Cysteine; Gene Editing; Gene Knockout Techniques; Immunoconjugates; Methionine; Mutation; Oxidation-Reduction; Phosphopyruvate Hydratase; Protein Domains; Proteins; Proteomics; Saccharomyces cerevisiae; Saccharomyces cerevisiae Proteins; Sodium Hypochlorite
PubMed: 28183972
DOI: 10.1126/science.aal3316 -
The British Journal of Cancer.... Jul 1996
Review
Topics: Animals; Antineoplastic Agents; Aziridines; Biotransformation; Indolequinones; Indoles; Mitomycin; NAD(P)H Dehydrogenase (Quinone); Oxidation-Reduction
PubMed: 8763836
DOI: No ID Found