Paenibacterin

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Paenibacterin
Paenibacterin.svg
Identifiers
3D model (JSmol)
PubChem CID
  • InChI=1S/C79H145N17O17/c1-13-16-17-18-19-20-21-22-23-24-25-26-39-60(99)84-53(36-31-42-82)69(102)90-63(49(8)9)76(109)95-66-52(12)113-79(112)65(51(11)15-3)94-70(103)55(35-28-30-41-81)86-75(108)62(48(6)7)92-73(106)59-38-33-44-96(59)78(111)64(50(10)14-2)93-72(105)58(46-98)89-67(100)54(34-27-29-40-80)85-74(107)61(47(4)5)91-71(104)57(45-97)88-68(101)56(37-32-43-83)87-77(66)110/h47-59,61-66,97-98H,13-46,80-83H2,1-12H3,(H,84,99)(H,85,107)(H,86,108)(H,87,110)(H,88,101)(H,89,100)(H,90,102)(H,91,104)(H,92,106)(H,93,105)(H,94,103)(H,95,109)/t50-,51-,52+,53-,54-,55-,56-,57-,58-,59-,61-,62-,63-,64-,65-,66-/m0/s1
    Key: GZPVAWHDCVFCAB-APSGCZIASA-N
  • CCCCCCCCCCCCCCC(=O)N[C@@H](CCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@H]1[C@H](OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CCCN)CO)C(C)C)CCCCN)CO)[C@@H](C)CC)C(C)C)CCCCN)[C@@H](C)CC)C
Properties
C79H145N17O17
Molar mass 1605.131 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Paenibacterin is a mixture of antimicrobial lipopeptides isolated from Paenibacillus thiaminolyticus. [1] It contains three isomeric compounds which differ by the fatty acid side chain. [2]

Related Research Articles

Antibiotic Antimicrobial substance active against bacteria

An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of such infections. They may either kill or inhibit the growth of bacteria. A limited number of antibiotics also possess antiprotozoal activity. Antibiotics are not effective against viruses such as the common cold or influenza; drugs which inhibit viruses are termed antiviral drugs or antivirals rather than antibiotics.

Antimicrobial resistance Ability of a microbe to resist the effects of medication

Antimicrobial resistance (AMR) occurs when microbes evolve mechanisms that protect them from the effects of antimicrobials. Antibiotic resistance is a subset of AMR, that applies specifically to bacteria that become resistant to antibiotics.

Broad-spectrum antibiotic

A broad-spectrum antibiotic is an antibiotic that acts on the two major bacterial groups, Gram-positive and Gram-negative, or any antibiotic that acts against a wide range of disease-causing bacteria. These medications are used when a bacterial infection is suspected but the group of bacteria is unknown or when infection with multiple groups of bacteria is suspected. This is in contrast to a narrow-spectrum antibiotic, which is effective against only a specific group of bacteria. Although powerful, broad-spectrum antibiotics pose specific risks, particularly the disruption of native, normal bacteria and the development of antimicrobial resistance. An example of a commonly used broad-spectrum antibiotic is ampicillin.

Polymyxin

Polymyxins are antibiotics. Polymyxins B and E are used in the treatment of Gram-negative bacterial infections. They work mostly by breaking up the bacterial cell membrane. They are part of a broader class of molecules called nonribosomal peptides.

Cephalosporin Class of pharmaceutical drugs

The cephalosporins are a class of β-lactam antibiotics originally derived from the fungus Acremonium, which was previously known as "Cephalosporium".

A narrow-spectrum antibiotic is an antibiotic that is only able to kill or inhibit limited species of bacteria. Examples of narrow-spectrum antibiotics include fidaxomicin and sarecycline.

Daptomycin Antibiotic

Daptomycin, sold under the brand name Cubicin among others, is a lipopeptide antibiotic used in the treatment of systemic and life-threatening infections caused by Gram-positive organisms.

<i>Paenibacillus</i> Genus of bacteria

Paenibacillus is a genus of facultative anaerobic, endospore-forming bacteria, originally included within the genus Bacillus and then reclassified as a separate genus in 1993. Bacteria belonging to this genus have been detected in a variety of environments, such as: soil, water, rhizosphere, vegetable matter, forage and insect larvae, as well as clinical samples. The name reflects: Latin paene means almost, so the paenibacilli are literally "almost bacilli". The genus includes P. larvae, which causes American foulbrood in honeybees, P. polymyxa, which is capable of fixing nitrogen, so is used in agriculture and horticulture, the Paenibacillus sp. JDR-2 which is a rich source of chemical agents for biotechnology applications, and pattern-forming strains such as P. vortex and P. dendritiformis discovered in the early 90s, which develop complex colonies with intricate architectures as shown in the pictures:

Carbapenem 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 class of antibiotics, 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.

Imipenem

Imipenem is an intravenous β-lactam antibiotic discovered by Merck scientists Burton Christensen, William Leanza, and Kenneth Wildonger in the mid-1970s. Carbapenems are highly resistant to the β-lactamase enzymes produced by many multiple drug-resistant Gram-negative bacteria, thus play a key role in the treatment of infections not readily treated with other antibiotics.

Paenibacillus polymyxa, also known as Bacillus polymyxa, is a Gram-positive bacterium capable of fixing nitrogen. It is found in soil, plant tissues, marine sediments and hot springs. It may have a role in forest ecosystems and potential future applications as a biofertilizer and biocontrol agent in agriculture.

Cefoxitin

Cefoxitin is a second-generation cephamycin antibiotic developed by Merck & Co., Inc. from Cephamycin C in the year following its discovery, 1972. It was synthesized in order to create an antibiotic with a broader spectrum. It is often grouped with the second-generation cephalosporins. Cefoxitin requires a prescription and as of 2010 is sold under the brand name Mefoxin by Bioniche Pharma, LLC. The generic version of cefoxitin is known as cefoxitin sodium.

A lipopeptide is a molecule consisting of a lipid connected to a peptide. They are able to self-assemble into different structures. Many bacteria produced these molecules as a part of their metabolism, especially those of the genus Bacillus, Pseudomonas and Streptomyces. Certain lipopeptides are used as antibiotics. Other lipopeptides are toll-like receptor agonists. Certain lipopeptides can have strong antifungal and hemolytic activities. It has been demonstrated that their activity is generally linked to interactions with the plasma membrane, and sterol components of the plasma membrane could play a major role in this interaction. It is a general trend that adding a lipid group of a certain length to a lipopeptide will increase its bactericidal activity. Lipopeptides with a higher amount of carbon atoms, for example 14 or 16, in its lipid tail will typically have antibacterial activity as well as anti-fungal activity.

Antibiotic misuse

Antibiotic misuse, sometimes called antibiotic abuse or antibiotic overuse, refers to the misuse or overuse of antibiotics, with potentially serious effects on health. It is a contributing factor to the development of antibiotic resistance, including the creation of multidrug-resistant bacteria, informally called "super bugs": relatively harmless bacteria can develop resistance to multiple antibiotics and cause life-threatening infections.

Quinolone antibiotic Class of antibacterial drugs, subgroup of quinolones

A quinolone antibiotic is a member of a large group of broad-spectrum bacteriocidals that share a bicyclic core structure related to the substance 4-quinolone. They are used in human and veterinary medicine to treat bacterial infections, as well as in animal husbandry, specifically poultry production.

Friulimicin Chemical compound

Friulimicin B is a lipopeptide antibiotic produced by Actinoplanes friuliensis. It includes the unusual amino acid methylaspartate.

Streptomyces amritsarensis is a bacterium species from the genus Streptomyces which has been isolated from soil from Punjab in India. Streptomyces amritsarensis has antimicrobial activity.

Arylomycin

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.

A proteolipid is a protein covalently linked to lipid molecules, which can be fatty acids, isoprenoids or sterols. The process of such a linkage is known as protein lipidation, and falls into the wider category of acylation and post-translational modification. Proteolipids are abundant in brain tissue, and are also present in many other animal and plant tissues. They are proteins covalenently bound to fatty acid chains, often granting them an interface for interacting with biological membranes. They are not to be confused with lipoproteins, a kind of spherical assembly made up of many molecules of lipids and some apolipoproteins.

Antimicrobial spectrum

The antimicrobial spectrum of an antibiotic means the range of microorganisms it can kill or inhibit. Antibiotics can be divided into broad-spectrum antibiotics, extended-spectrum antibiotics and narrow-spectrum antibiotics based on their spectrum of activity. Detailedly, broad-spectrum antibiotics can kill or inhibit a wide range of microorganisms; extended-spectrum antibiotic can kill or inhibit Gram positive bacteria and some Gram negative bacteria; narrow-spectrum antibiotic can only kill or inhibit limited species of bacteria.

References

  1. Huang, En; Yousef, Ahmed E. (2014). "Paenibacterin, a novel broad-spectrum lipopeptide antibiotic, neutralises endotoxins and promotes survival in a murine model of Pseudomonas aeruginosa-induced sepsis". International Journal of Antimicrobial Agents. 44 (1): 74–77. doi:10.1016/j.ijantimicag.2014.02.018. PMID   24802906.
  2. Guo, Yaoqi; Huang, En; Yuan, Chunhua; Zhang, Liwen; Yousef, Ahmed E. (2012). "Isolation of a Paenibacillus sp. Strain and Structural Elucidation of its Broad-Spectrum Lipopeptide Antibiotic". Applied and Environmental Microbiology. 78 (9): 3156–3165. Bibcode:2012ApEnM..78.3156G. doi:10.1128/AEM.07782-11. PMC   3346447 . PMID   22367082.