Teichomycins, new antibiotics from Actinoplanes teichomyceticus nov. sp. I. Description of the producer strain, fermentation studies and biological properties.

Parenti, Francesco; Beretta, G.; Berti, Marisa; Arioli, V.

doi:10.7164/antibiotics.31.276

Cited by 201 publications

(98 citation statements)

References 4 publications

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“…The results of the examination of the analogs that incorporate the two peripheral modifications (14)(15)(16)(17) and their combination with the pocket-modified vancomycin analog in 18 were even more revealing. In addition to showing that this may be successfully achieved, they highlight that it is not necessarily the most effective individual variants of the two peripheral modifications that combine to produce the desired effects but rather, that it is a combination that allows expression of the two independent mechanisms.…”

Section: Resultsmentioning

confidence: 99%

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Peripheral modifications of [Ψ[CH ₂ NH]Tpg ⁴ ]vancomycin with added synergistic mechanisms of action provide durable and potent antibiotics

Okano

Isley

Boger

2017

Proc. Natl. Acad. Sci. U.S.A.

171

215

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Significance In a quest for antibiotics that may display durable clinical lifetimes, analogs of the glycopeptide antibiotics, including vancomycin, have been designed that not only directly overcome the molecular basis of existing vancomycin resistance but also contain two added peripheral modifications that endow them with two additional independent mechanisms of actions not found in the parent antibiotics. It is shown that such peripherally and binding pocket-modified vancomycin analogs display little propensity for acquired resistance by vancomycin-resistant Enterococci and that both their antimicrobial potency and durability against such challenges follow trends (three > two > one mechanisms of action) that are now predictable.

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Section: Resultsmentioning

confidence: 99%

“…Vancomycin (15), teicoplanin (16), and three recently approved semisynthetic derivatives, oritavancin (17), dalbavancin (18), and telavancin (19), are widely used to treat refractory bacterial infections, including methicillin-resistant Staphylococcus aureus (MRSA) (20). Vancomycin (1) (Fig.…”

mentioning

confidence: 99%

Peripheral modifications of [Ψ[CH ₂ NH]Tpg ⁴ ]vancomycin with added synergistic mechanisms of action provide durable and potent antibiotics

Okano

Isley

Boger

2017

Proc. Natl. Acad. Sci. U.S.A.

171

215

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“…Actinoplanes teichomyceticus (ATCC 31121) [9], Streptomyces lividans 66 (John Innes Collection 1326) [10] and the plasmid plJ702 (carrying the thiostrepton resistance gene) [10] were used.…”

Section: Strains Plasmids and Antibioticsmentioning

confidence: 99%

Cloning of a DNA region of Actinoplanes teichomyceticus conferring teicoplanin resistance

Moroni¹,

Granozzi²,

Lorenzetti³

et al. 1989

FEBS Letters

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Teicoplanin is a glycopeptide antibiotic, produced by Actinoplanes teichomyceticus, active against Gram positive bacteria and recently introduced into clinical practice. It blocks cell wall biosynthesis by inhibiting peptidoglycan polymerization. The mechanism(s) of resistance of the producer strains of this class of antibiotics have not yet been characterized. We have constructed a genomic bank of A. teichomyceticus in Streptomyces lividans. A clone from this bank, pTR168, was able to confer resistance to teicoplanin on its sensitive host. The restriction map of plasmid pTR 168 and the hybridization pattern to A. teichomyceticus DNA were determined; we have also studied the mechanism of this resistance which seems correlated with a reduced binding of the antibiotic to the cell wall.

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“…Currently the antibiotics of last resort are glycopeptides of the vancomycin family. The vancomycin-related antibiotics bind to the bacterial cell wall D-Ala-D-Ala terminal group, blocking the process of wall-building of Gram-positive bacteria under aerobic and anaerobic conditions [27,28]. Several members of the macrocyclic antibiotics, e. g. avoparcin, teicoplanin, ristocetin A and vancomycin, are used more wisely today.…”

Section: Introductionmentioning

confidence: 99%

HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic‐based chiral stationary phases: A review

Ilisz

Berkecz

Péter

2006

J of Separation Science

156

105

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The search for new and effective chiral selectors capable of separating a wide variety of enantiomeric compounds is an ongoing process. In the past decade, macrocyclic antibiotics have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance by means of HPLC, TLC and electrophoresis. More chiral analytes have been resolved through the use of glycopeptides than with all the other macrocyclic antibiotics combined (ansamycins, thiostrepton, aminoglycosides, etc.). The glycopeptides avoparcin, teicoplanin, ristocetin A and vancomycin have been extensively used as chiral selectors in the form of chiral bonded phases in HPLC, and HPLC stationary phases based on these glycopeptides have been commercialized. Teicoplanin, vancomycin, their analogs and ristocetin A seem to be the most useful glycopeptide HPLC bonded phases for the enantioseparation of proteins and unusal native and derivatized amino acids. In fact, the macrocyclic glycopeptides are to some extent complementary to one another: where partial enantioresolution is obtained with one glycopeptide, there is a high probability that baseline or better separation can be obtained with another. This review sets out to characterize the physicochemical properties of these antibiotics and their application in the enantioseparations of amino acids. The mechanism of separation, the sequence of elution of the stereoisomers and the relation to the absolute configuration are also discussed.

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Teichomycins, new antibiotics from Actinoplanes teichomyceticus nov. sp. I. Description of the producer strain, fermentation studies and biological properties.

Cited by 201 publications

References 4 publications

Peripheral modifications of [Ψ[CH ₂ NH]Tpg ⁴ ]vancomycin with added synergistic mechanisms of action provide durable and potent antibiotics

Peripheral modifications of [Ψ[CH ₂ NH]Tpg ⁴ ]vancomycin with added synergistic mechanisms of action provide durable and potent antibiotics

Cloning of a DNA region of Actinoplanes teichomyceticus conferring teicoplanin resistance

HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic‐based chiral stationary phases: A review

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Teichomycins, new antibiotics from Actinoplanes teichomyceticus nov. sp. I. Description of the producer strain, fermentation studies and biological properties.

Cited by 201 publications

References 4 publications

Peripheral modifications of [Ψ[CH 2 NH]Tpg 4 ]vancomycin with added synergistic mechanisms of action provide durable and potent antibiotics

Peripheral modifications of [Ψ[CH 2 NH]Tpg 4 ]vancomycin with added synergistic mechanisms of action provide durable and potent antibiotics

Cloning of a DNA region of Actinoplanes teichomyceticus conferring teicoplanin resistance

HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic‐based chiral stationary phases: A review

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Peripheral modifications of [Ψ[CH ₂ NH]Tpg ⁴ ]vancomycin with added synergistic mechanisms of action provide durable and potent antibiotics

Peripheral modifications of [Ψ[CH ₂ NH]Tpg ⁴ ]vancomycin with added synergistic mechanisms of action provide durable and potent antibiotics