Albomycin

Last updated
Albomycin d2 bound to iron Albomycin d2-iron bound.svg
Albomycin δ2 bound to iron

Albomycins are a group of naturally occurring antibiotics belonging to the class of sideromycins, which are "compounds composed of iron carriers called siderophores linked to antibiotic moieties". They are particularly effective against Gram-negative bacteria of the family Enterobacteriaceae and few Gram-positive bacteria such s Streptococcus pneumoniae , Bacillus subtilis and Staphylococcus aureus . [1] [2] In 2000 a group of scientists from SmithKline Beecham Pharmaceuticals, UK reported that the antibiotic part of albomycin in vitro can inhibit seryl-tRNA synthetase from both eukaryotic and prokaryotic representatives. [3]

Structure

Albomycins are naturally occurring sideromycins produced by some streptomycetes. The siderophore part of albomycin δ2 is similar to ferrichrome. It contains three molecules of δ-N-hydroxy-δ-N-acetyl ornithine linked to a serine, all by peptide linkage. The C-terminus of the serine is linked to another serine attached to the antibiotically active 4’-thio (N4-carbamoyl-3-methyl) cytidine moiety. The trihydroxamate part serves the siderophore function as it can trap Fe+3 and is essential for active transport of the antibiotic. Iron-free albomycin δ2 has a molecular weight of 992 Da, and when loaded with iron it is 1045 Da. [4]

Albomycin d1.svg
Albomycin δ1
Albomycin d2.svg
Albomycin δ2
Albomycin e.svg
Albomycin ε

Related Research Articles

<span class="mw-page-title-main">Macrolide</span> Class of natural products

Macrolides are a class of mostly natural products with a large macrocyclic lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, may be attached. The lactone rings are usually 14-, 15-, or 16-membered. Macrolides belong to the polyketide class of natural products. Some macrolides have antibiotic or antifungal activity and are used as pharmaceutical drugs. Rapamycin is also a macrolide and was originally developed as an antifungal, but is now used as an immunosuppressant drug and is being investigated as a potential longevity therapeutic.

<span class="mw-page-title-main">Methicillin</span> Antibiotic medication

Methicillin (USAN), also known as meticillin (INN), is a narrow-spectrum β-lactam antibiotic of the penicillin class.

<i>Streptococcus pneumoniae</i> Species of bacterium

Streptococcus pneumoniae, or pneumococcus, is a Gram-positive, spherical bacteria, alpha-hemolytic member of the genus Streptococcus. They are usually found in pairs (diplococci) and do not form spores and are non motile. As a significant human pathogenic bacterium S. pneumoniae was recognized as a major cause of pneumonia in the late 19th century, and is the subject of many humoral immunity studies.

<span class="mw-page-title-main">Transformation (genetics)</span> Genetic alteration of a cell by uptake of genetic material from the environment

In molecular biology and genetics, transformation is the genetic alteration of a cell resulting from the direct uptake and incorporation of exogenous genetic material from its surroundings through the cell membrane(s). For transformation to take place, the recipient bacterium must be in a state of competence, which might occur in nature as a time-limited response to environmental conditions such as starvation and cell density, and may also be induced in a laboratory.

<span class="mw-page-title-main">Siderophore</span> Iron compounds secreted by microorganisms

Siderophores (Greek: "iron carrier") are small, high-affinity iron-chelating compounds that are secreted by microorganisms such as bacteria and fungi. They help the organism accumulate iron. Although a widening range of siderophore functions is now being appreciated, siderophores are among the strongest (highest affinity) Fe3+ binding agents known. Phytosiderophores are siderophores produced by plants.

<span class="mw-page-title-main">DD-transpeptidase</span>

DD-transpeptidase is a bacterial enzyme that catalyzes the transfer of the R-L-αα-D-alanyl moiety of R-L-αα-D-alanyl-D-alanine carbonyl donors to the γ-OH of their active-site serine and from this to a final acceptor. It is involved in bacterial cell wall biosynthesis, namely, the transpeptidation that crosslinks the peptide side chains of peptidoglycan strands.

<span class="mw-page-title-main">Tigecycline</span> Chemical compound

Tigecycline, sold under the brand name Tygacil, is a tetracycline antibiotic medication for a number of bacterial infections. It is a glycylcycline administered intravenously. It was developed in response to the growing rate of antibiotic resistant bacteria such as Staphylococcus aureus, Acinetobacter baumannii, and E. coli. As a tetracycline derivative antibiotic, its structural modifications has expanded its therapeutic activity to include Gram-positive and Gram-negative organisms, including those of multi-drug resistance.

<span class="mw-page-title-main">Carbapenem</span> Class of highly effective antibiotic agents

Carbapenems are a class of very effective antibiotic agents most commonly used for the treatment of severe bacterial infections. This class of antibiotics is usually reserved for known or suspected multidrug-resistant (MDR) bacterial infections. Similar to penicillins and cephalosporins, carbapenems are members of the beta-lactam antibiotics drug class, which kill bacteria by binding to penicillin-binding proteins, thus inhibiting bacterial cell wall synthesis. However, these agents individually exhibit a broader spectrum of activity compared to most cephalosporins and penicillins. Furthermore, carbapenems are typically unaffected by emerging antibiotic resistance, even to other beta-lactams.

<span class="mw-page-title-main">Cefepime</span> Fourth-generation Cephalosporin Antibiotic

Cefepime is a fourth-generation cephalosporin antibiotic. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both types of organism than third-generation agents. A 2007 meta-analysis suggested when data of trials were combined, mortality was increased in people treated with cefepime compared with other β-lactam antibiotics. In response, the U.S. Food and Drug Administration (FDA) performed their own meta-analysis which found no mortality difference.

<span class="mw-page-title-main">Cefotaxime</span> Chemical compound

Cefotaxime is an antibiotic used to treat a number of bacterial infections in human, other animals and plant tissue culture. Specifically in humans it is used to treat joint infections, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, sepsis, gonorrhea, and cellulitis. It is given either by injection into a vein or muscle.

<span class="mw-page-title-main">Lincosamides</span> Group of antibiotics

Lincosamides are a class of antibiotics, which include lincomycin, clindamycin, and pirlimycin.

<span class="mw-page-title-main">Natural competence</span> Ability of cells to alter their own genetics by taking up extracellular DNA

In microbiology, genetics, cell biology, and molecular biology, competence is the ability of a cell to alter its genetics by taking up extracellular ("naked") DNA from its environment in the process called transformation. Competence may be differentiated between natural competence, a genetically specified ability of bacteria which is thought to occur under natural conditions as well as in the laboratory, and induced or artificial competence, which arises when cells in laboratory cultures are treated to make them transiently permeable to DNA. Competence allows for rapid adaptation and DNA repair of the cell. This article primarily deals with natural competence in bacteria, although information about artificial competence is also provided.

<span class="mw-page-title-main">Lincomycin</span> Chemical compound

Lincomycin is a lincosamide antibiotic that comes from the actinomycete Streptomyces lincolnensis. A related compound, clindamycin, is derived from lincomycin by using thionyl chloride to replace the 7-hydroxy group with a chlorine atom with inversion of chirality. It was released for medical use in September 1964.

In enzymology, a serine—tRNA ligase is an enzyme that catalyzes the chemical reaction

<i>SARS</i> (gene) Protein-coding gene in the species Homo sapiens

SARS and cytoplasmic seryl-tRNA synthetase are a human gene and its encoded enzyme product, respectively. SARS belongs to the class II amino-acyl tRNA family and is found in all humans; its encoded enzyme, seryl-tRNA synthetase, is involved in protein translation and is related to several bacterial and yeast counterparts.

<span class="mw-page-title-main">Pathogenic bacteria</span> Disease-causing bacteria

Pathogenic bacteria are bacteria that can cause disease. This article focuses on the bacteria that are pathogenic to humans. Most species of bacteria are harmless and are often beneficial but others can cause infectious diseases. The number of these pathogenic species in humans is estimated to be fewer than a hundred. By contrast, several thousand species are part of the gut flora present in the digestive tract.

<span class="mw-page-title-main">Sideromycin</span> Class of chemical compounds

Sideromycins are a group of antibiotics linked to siderophores by covalent bonds. Examples of naturally occurring sideromycins are albomycin and salmycin. Sideromycins have some unique merits as antibiotic. They can actively bypass permeability barriers (membranes) to deliver the drug inside the target bacterial cell, irrespective of the size and polarity of the antibiotic moiety contained into it. Most importantly as they are substrates of high affinity siderophore transport systems they can be effective to kill bacteria at very low concentration. Also the delivery of the antibiotic will be highly target specific, so wouldn't affect the host system. Sideromycins is being considered as a new microbe-selective antibacterial agent, which can limit the emergence of resistance.

Ornibactin is a siderophore, or small iron-binding compound secreted by bacteria to transport iron into the cell. Ornibactin is produced by Burkholderia cenocepacia under iron-deficient conditions. B. cenocepacia is known to opportunistically infect humans, specifically ones suffering from cystic fibrosis.

<span class="mw-page-title-main">Arylomycin</span> Group of chemical compounds

The arylomycins are a class of antibiotics initially isolated from a soil sample obtained in Cape Coast, Ghana. In this initial isolation, two families of closely related arylomycins, A and B, were identified. The family of glycosylated arylomycin C lipopeptides were subsequently isolated from a Streptomyces culture in a screen for inhibitors of bacterial signal peptidase. The initially isolated arylomycins have a limited spectrum of activity against Gram-positive bacteria, including Staphylococcus aureus and Streptococcus pneumoniae. The only activity against Gram-negative bacteria was seen in strains with a compromised outer membrane.

<span class="mw-page-title-main">Cefiderocol</span> Antibiotic

Cefiderocol, sold under the brand name Fetroja among others, is an antibiotic used to treat complicated urinary tract infections when no other options are available. It is indicated for the treatment of multi-drug-resistant Gram-negative bacteria including Pseudomonas aeruginosa. It is given by injection into a vein.

References

  1. Pramanik, A.; Stroeher, U.; Krejci, J.; Standish, A.; Bohn, E.; Paton, J.; Autenrieth, I.; Braun, V. (October 2007). "Albomycin is an effective antibiotic, as exemplified with Yersinia enterocolitica and Streptococcus pneumoniae". International Journal of Medical Microbiology . 297 (6): 459–469. doi:10.1016/j.ijmm.2007.03.002. PMID   17459767.
  2. Pramanik, A.; Braun, V. (June 2006). "Albomycin Uptake via a Ferric Hydroxamate Transport System of Streptococcus pneumoniae R6". Journal of Bacteriology . 188 (11): 3878–3886. doi:10.1128/jb.00205-06. PMC   1482914 . PMID   16707680.
  3. Stefanska, Anna L.; Fulston, Mark; Houge-Frydrych, Catherine S.V; Jones, Jo J.; Warr, Stephen R. (June 2000). "A Potent Seryl tRNA Synthetase Inhibitor SB-217452 Isolated from a Streptomyces species". The Journal of Antibiotics . 53 (12): 1346–1353. doi: 10.7164/antibiotics.53.1346 . PMID   11217799.
  4. Hartmann, Anton; Fiedler, Hans-Peter; Braun, Volkmar (September 1979). "Uptake and Conversion of the Antibiotic Albomycin by Escherichia coli K-12". European Journal of Biochemistry . 99 (3): 517–524. doi: 10.1111/j.1432-1033.1979.tb13283.x . PMID   387415.