Ansamycins is a family of bacterial secondary metabolites that show

antimicrobial An antimicrobial is an agent that kills microorganisms (microbicide) or stops their growth (bacteriostatic agent). Antimicrobial medicines can be grouped according to the microorganisms they are used to treat. For example, antibiotics are used aga ...

activity against many

Gram-positive In bacteriology, gram-positive bacteria are bacteria that give a positive result in the Gram stain test, which is traditionally used to quickly classify bacteria into two broad categories according to their type of cell wall. The Gram stain is ...

and some

Gram-negative Gram-negative bacteria are bacteria that, unlike gram-positive bacteria, do not retain the crystal violet stain used in the Gram staining method of bacterial differentiation. Their defining characteristic is that their cell envelope consists ...

bacteria, and includes various compounds, including streptovaricins and rifamycins. In addition, these compounds demonstrate antiviral activity towards bacteriophages and

poxviruses ''Poxviridae'' is a family of double-stranded DNA viruses. Vertebrates and arthropods serve as natural hosts. The family contains 22 genera that are assigned to two subfamilies: ''Chordopoxvirinae'' and ''Entomopoxvirinae''. ''Entomopoxvirinae'' ...

. They are somewhat similar in structure to

macrolide 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. Macrolides belong to the polyketide class of natural products. ...

antibiotics, but because they have a lactam instead of a lactone, they do not belong in the class of macrolides. __TOC__

Structure

They are named ansamycins (from the Latin ansa, ''handle'') because of their unique structure, which consists of an aromatic moiety bridged by an aliphatic chain. The main difference between various derivatives of ansamycins is the aromatic moiety, which can be a

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white Crystal, crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 Parts-per notation ...

ring or a

naphthoquinone Naphthoquinones constitute a class of organic compounds structurally related to naphthalene. Two isomers are common for the parent naphthoquinones: * 1,2-Naphthoquinone * 1,4-Naphthoquinone Natural products * Alkannin * Hexahydroxy-1,4-nap ...

ring as in

rifamycin The rifamycins are a group of antibiotics that are synthesized either naturally by the bacterium '' Amycolatopsis rifamycinica'' or artificially. They are a subclass of the larger family of ansamycins. Rifamycins are particularly effective aga ...

and the naphthomycins. Another variation consists of benzene or a

benzoquinone Benzoquinone (C6H4O2) is a quinone with a single benzene ring. There are 2 (out of 3 hypothetical) benzoquinones: * 1,4-Benzoquinone, most commonly, right image (also ''para''-benzoquinone, ''p''-benzoquinone, ''para''-quinone, or just quinone) * ...

ring system as in

geldanamycin Geldanamycin is a 1,4-benzoquinone ansamycin Antitumor agent, antitumor antibiotic that inhibits the function of Hsp90 (Heat Shock Protein 90) by binding to the unusual ADP/ATP-binding pocket of the protein. HSP90 client proteins play important rol ...

or ansamitocin. Ansamycins were first discovered in 1959 by Sensi et al. from ''

Amycolatopsis ''Amycolatopsis'' is a genus of high GC-content bacteria within the family Pseudonocardiaceae. The genus is known for producing many types of antibiotics, including *Epoxyquinomicin, related to ''Amycolatopsis sulphurea'', are a class of weak ant ...

mediterranei'', an actinomycete bacterium.

Examples

Rifamycins are a subclass of ansamycins with high potency against mycobacteria. This resulted in their widespread use in the treatment of

tuberculosis Tuberculosis (TB), also known colloquially as the "white death", or historically as consumption, is a contagious disease usually caused by ''Mycobacterium tuberculosis'' (MTB) bacteria. Tuberculosis generally affects the lungs, but it can al ...

leprosy Leprosy, also known as Hansen's disease (HD), is a Chronic condition, long-term infection by the bacteria ''Mycobacterium leprae'' or ''Mycobacterium lepromatosis''. Infection can lead to damage of the Peripheral nervous system, nerves, respir ...

, and AIDS-related mycobacterial infections. Since then various analogues have been isolated from other

prokaryotes A prokaryote (; less commonly spelled procaryote) is a single-celled organism whose cell lacks a nucleus and other membrane-bound organelles. The word ''prokaryote'' comes from the Ancient Greek (), meaning 'before', and (), meaning 'nut' ...

References

{{reflist, 2 Polyketides Carbamates Lactams 1,4-Benzoquinones Ethers Ansamycins Polyketide antibiotics