Overview on bismuth(III) and bismuth(V) complexes with activity against Helicobacter pylori

Dittes, Uwe; Vogel, E.; Keppler, Bernhard K.

doi:10.1016/s0010-8545(97)00042-8

Cited by 68 publications

(50 citation statements)

References 30 publications

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“…After 1 h, the mixture was quenched by the addition of brine (5 ml) and extracted with ethyl acetate (20 ml, three times). The organic extract was dried over MgSO 4 and concentrated under reduced pressure to leave an oil, which was chromatographed on alumina by using hexane as the eluent and which was recrystallized from hexane to afford compound 4 as colorless crystals (451 mg, 88% The cyclic organobismuth compounds obtained were dissolved in sterile dimethyl sulfoxide (DMSO) (analytical grade; Sigma, St. Louis, Mo.) and were stored frozen at Ϫ40°C until they were used.…”

Section: Bi-chlorodibenzo[c F][15]thiabismocine (Compound 3)mentioning

confidence: 99%

“…Since the 1990s, the physiological aspect of bismuth chemistry has received considerable attention, and much effort has been devoted to the synthesis of different types of bismuth compounds in order to improve their antibacterial activities (2,(4)(5)(6)10). Pharmacological investigation of new bismuth compounds has led to the development of medications with interesting activities for the treatment of infectious diseases.…”

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confidence: 99%

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Antibacterial Properties of Some Cyclic Organobismuth(III) Compounds

Kotani¹,

Nagai²,

Asahi³

et al. 2005

Antimicrob Agents Chemother

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Bismuth compounds are known for their low levels of toxicity in mammals, and various types of bismuth salts have been used to treat medical disorders. As part of our program to probe this aspect of bismuth chemistry, cyclic organobismuth compounds 1 to 8 bearing a nitrogen or sulfur atom as an additional ring member have been synthesized, and their antimicrobial activities against five standard strains of gramnegative and gram-positive bacteria were assessed. The eight-membered-ring compounds, compounds 1 to 3, exhibited MICs of less than 0.5 g/ml against Staphylococcus aureus and were more active than the sixmembered ones, compounds 5 to 8 (MICs, 4.0 to 16 g/ml). The gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis, and Enterococcus faecalis) were more susceptible to both types of ring compounds than the gram-negative ones (Escherichia coli and Pseudomonas aeruginosa). Treatment with polymyxin B nonapeptide increased the susceptibility of E. coli to cyclic organobismuth compounds, indicating the low permeability of the outer membrane of gram-negative bacteria to the compounds. Compound 1 also had activity against methicillin-resistant S. aureus, which had an MIC for 90% of the hospital stock strains of 1.25 g/ml. The killing curves for S. aureus treated with compound 1 or 3 revealed a static effect at a low dose (2؋ the MIC). However, when S. aureus was treated with 10؋ the MIC of compound 1 or 3, there was an approximately 3-log reduction in the viable cell number after 48 h of treatment. Electron microscopic inspection demonstrated a considerable increase in the size of S. aureus and the proportion of cells undergoing cell division after treatment with compound 1 at 0.5؋ the MIC.

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Section: Bi-chlorodibenzo[c F][15]thiabismocine (Compound 3)mentioning

confidence: 99%

mentioning

confidence: 99%

Antibacterial Properties of Some Cyclic Organobismuth(III) Compounds

Kotani¹,

Nagai²,

Asahi³

et al. 2005

Antimicrob Agents Chemother

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“…A complexação com sais de butilestanho, de algumas tiossemicarbazonas ativas contra Candida albicans, levou a uma diminuição ou perda da atividade, com uma piora na ação antifúngica à medida que se aumentava o número de grupos butila, possivelmente porque os complexos formados seriam demasiadamente volumosos, dificultando assim sua passagem através da membrana celular 79 . Consideramos de interesse mencionar aqui resultados recentes de atividade de complexos de bismuto(III) com tiossemicarbazonas que inibiram in vitro o crescimento de Helicobacter pylori, a bacté-ria causadora de úlcera 80 , e tiossemicarbazonas derivadas de tiofeno que apresentaram atividade amebicida, a qual aumenta pela complexação ao rutênio ou à platina 81 . A possibilidade de uso clíni-co desses complexos parece remota em razão de seu alto custo e do fato de se tratar de doenças negligenciadas, mas a investigação se mostra relevante já que o metronidazol, comumente usado, mostrou ter efeito carcinogênico e mutagênico.…”

Section: Tiossemicarbazonas Com Atividade Antibacteriana Antifúngicaunclassified

Semicarbazonas e tiossemicarbazonas: o amplo perfil farmacológico e usos clínicos

Beraldo¹

2004

Quím. Nova

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Recebido em 31/7/03; aceito em 24/9/03 SEMICARBAZONES AND THIOSEMICARBAZONES: THEIR WIDE PHARMACOLOGICAL PROFILE AND CLINICAL APPLICATIONS. This article shows that thiosemicarbazones, semicarbazones and their metal complexes can exhibit target selectivity along with a wide pharmacological profile. Complexes of thiosemicarbazones with cytotoxic or antitumoral activity are presented, some of which show activity against cisplatinum-resistant cells. The inhibition mechanism of the enzyme ribonucleoside diphosphate reductase (RDR), involved in DNA syntheses, by α(N)-heterocyclic thiosemicarbazones is discussed. The encouraging results of clinical trials with the RDR inhibitor 3-aminopyridine-2-carboxaldehyde thiosemicarbazone ("Triapine") against rapidly growing tumors are outlined. Examples are also given of thiosemicarbazones with antiviral and antimicrobial activity. The possible applications of semicarbazones as anticonvulsants with low toxicity and good therapeutic index are presented. . Ehrlich foi o fundador da quimioterapia e introduziu as primeiras idéias sobre relações estrutura-atividade e o conceito de índice terapêutico. Fez ainda uso de complexos metálicos, em especial os de arsênio, na preparação de drogas para o tratamento da sífilis 2 . Werner é considerado o pai da Química de Coordenação pelo desenvolvimento de sua teoria para explicar a estrutura e a ligação química nos complexos metálicos.Apesar da grande importância dos trabalhos desses e de outros pesquisadores, a Química Medicinal dedicou-se, durante muitos anos, principalmente ao estudo de compostos orgânicos e produtos naturais. A investigação a respeito do uso de complexos metálicos como fármacos teve início, de modo sistemático, apenas após a descoberta feita pelo físico Barnett Rosemberg, da atividade antitumoral do cis(diaminodicloro)platina(II), o "cisplatina" ou cis-ddp, em 1965 3 . Desde então, uma imensa variedade de complexos metálicos foi e tem sido investigada quanto às suas propriedades terapêuticas. É interessante observar que o primeiro número da revista Metal-Based Drugs apareceu em 1994.Tiossemicarbazonas e semicarbazonas (Figura 1) apresentam um amplo perfil farmacológico e constituem uma importante classe de compostos cujas propriedades têm sido extensivamente estudadas na Química Medicinal e, particularmente, na Química Medicinal Inorgânica, em razão de sua capacidade quelante e do papel da coordenação no seu mecanismo bioquímico de ação. Apesar da ampla versatilidade farmacológica desses compostos como uma classe, especificidades estruturais podem levar à manifestação de atividades específicas. Para os complexos metálicos, em alguns casos é possí-vel modular a atividade através do desenho do ligante ou através da escolha do metal, como veremos adiante.De modo geral pode-se dizer que tiossemicarbazonas e semicarbazonas agem, seja como inibidores de enzimas, através da complexação de metais endógenos ou através de reações de redox, seja através de interações com o ADN e da inibição da síntese do ADN. Além disso, alguns compl...

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“…Bismuth compounds have attracted considerable interest owing to their biological and medicinal utility [3][4][5].They have been utilized from more than two centuries in the treatment of gastrointestinal disorders such as dyspepsia, diarrhea and peptic ulcer [6][7][8][9]. Bismuth salts such as colloidal bismuth sub-citrate (CBS), bismuth sub-salicylate (BSS), and ranitidine bismuth citrate (RBC) are common agents used for Helicobacter pylori eradication therapy [10,11] and therefore promoted these compounds as antimicrobials [12][13][14][15][16][17][18][19][20]. It is known that metals are able to generate reactive oxygen species (ROS) which easily explain the treatment of cancer [21].…”

Section: Introductionmentioning

confidence: 99%

Bio-Medicinal Studies of Some New Triorganobismuth (V) Compounds

Kant¹,

Dm²,

Amresh³

2012

Int J of Chem Res

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Abstract-Some new triorganobismuth (V) amide were synthesized by earlier reported method and fully characterized by their elemental and I.R. spectral analysis along with their antimicrobial activity against different pathogenic bacterial and fungal strains and in-vitro antitumor activity against human breast and mammary cancer cell line. It was found that compounds have great potential as antitumor and antimicrobial agents.

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Overview on bismuth(III) and bismuth(V) complexes with activity against Helicobacter pylori

Cited by 68 publications

References 30 publications

Antibacterial Properties of Some Cyclic Organobismuth(III) Compounds

Antibacterial Properties of Some Cyclic Organobismuth(III) Compounds

Semicarbazonas e tiossemicarbazonas: o amplo perfil farmacológico e usos clínicos

Bio-Medicinal Studies of Some New Triorganobismuth (V) Compounds

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