Structure and Synthesis of Distamycin A

Arcamone, Federico; Penco, Susanna; Orezzi, P.; Nicolella, V.; Pirelli, Annamaria

doi:10.1038/2031064a0

Cited by 230 publications

(164 citation statements)

References 7 publications

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“…Proximicins show a structural similarity with netropsin and distamycin, pyrrolamidone antibiotics produced by Streptomyces netropsis [13] and "S. distallicus" [14], respectively. These g-peptide antibiotics have as characteristic structural element an N-methyl-pyrrol ring instead of the furan ring as in the case of proximicins.…”

Section: Discussionmentioning

confidence: 99%

Proximicin A, B and C, Novel Aminofuran Antibiotic and Anticancer Compounds Isolated from Marine Strains of the Actinomycete Verrucosispora†

et al. 2008

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A family of three novel aminofuran antibiotics named as proximicins was isolated from the marine Verrucosispora strain MG-37. Proximicin A was detected in parallel in the marine abyssomicin producer "Verrucosispora maris" AB-18-032. The characteristic structural element of proximicins is 4-amino-furan-2-carboxylic acid, a hitherto unknown g -amino acid. Proximicins show a weak antibacterial activity but a strong cytostatic effect to various human tumor cell lines.

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Section: Discussionmentioning

confidence: 99%

Proximicin A, B and C, Novel Aminofuran Antibiotic and Anticancer Compounds Isolated from Marine Strains of the Actinomycete Verrucosispora†

et al. 2008

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“…The structure of this antibiotic also obtained by total synthesis [8] , is characterized by three residues of 1 -methyl-4-aminopyrrole-2-carboxylic acid and two side chains, the first constituted by a formyl group, and the second by a propionamidine chain ( fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Some structural requirements for the antibiotic action of distamycins

et al. 1971

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“…Very recently a series of compounds structurally related to distamycin A have been synthesized by Arcamone et al [9,10]. Analogues of distamycin A with increasing numbers of methylpyrrole residues oligopeptides to DNA their complex formation with DNA was of great interest.…”

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confidence: 99%

Binding of Analogues of the Antibiotics Distamycin A and Netropsin to Native DNA

Zimmeer¹,

Luck²,

Thrum³

et al. 1972

European Journal of Biochemistry

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Binding effects of DNA with two distamycin A analogues containing four and five l-methylpyrrole residues (distamycin A contains three of these residues) and with a degradation product of netropsin have been investigated by ultraviolet absorbance, melting and circular dichroism measurements.Increasing numbers of the methylpyrrole groups (3 to 5) enhance the thermal stability of the oligopeptide complex. On the other hand elimination of the basic groups of the netropsin molecule decreases the melting temperature of the oligopeptide * DNA complex enormously. The circular dichroism spectrum of DNA is also less affected by the degradation product compared to netropsin. Circular dichroism spectra of the complexes exhibit a pronounced band a t the longer wavelength region and indicate an increasing chirality in the complex with increasing number of chromophores of the oligopeptides.From the results it is concluded that electrostatic attraction of the oligopeptides by interaction of the propionamidino and guanidino groups with the negative phosphate sites of DNA is important for the formation of the complex. However, non-ionic forces, which have been discussed earlier, seem to be involved and may be attributed to the chromophore residues oriented in the helical grooves.The different binding tendency of the oligopeptides with DNA is discussed together with the biological activity of the oligopeptides. I n the present work the behaviour of the oligopeptide -DNA complexes with distamycin A and its analogues together with netropsin and its derivative has been investigated by ultraviolet absorbance, melting and circular dichroism measurements. The previously reported data on the melting be-

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Structure and Synthesis of Distamycin A

Cited by 230 publications

References 7 publications

Proximicin A, B and C, Novel Aminofuran Antibiotic and Anticancer Compounds Isolated from Marine Strains of the Actinomycete Verrucosispora†

Proximicin A, B and C, Novel Aminofuran Antibiotic and Anticancer Compounds Isolated from Marine Strains of the Actinomycete Verrucosispora†

Some structural requirements for the antibiotic action of distamycins

Binding of Analogues of the Antibiotics Distamycin A and Netropsin to Native DNA

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