PRODIGIOSIN. STRUCTURE AND PARTIAL SYNTHESIS<sup>1</sup>

Wasserman, Harry H.; McKeon, James E.; Smith, Lewis; Forgione, Peter

doi:10.1021/ja01487a075

Cited by 68 publications

(27 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The structure of prodigiosin, the archetypal prodiginine, was elucidated in the early 1960s by partial and total chemical synthesis revealing a pyrrolyl dipyrromethene core skeleton (Wasserman et al 1960;Rapoport and Holden 1962). The three pyrrolic rings of prodigiosin are conventionally labelled as pyrrolic ring A, ring B, and ring C (Fig.…”

Section: Chemistry Of Prodigiosinmentioning

confidence: 99%

Prodigiosin and its potential applications

2015

View full text Add to dashboard Cite

Since a decade, there has been a strong consumer demand for more natural products. This has augmented inclination towards substitution of synthetic colorants with natural pigments. Natural pigments not only have the capacity to increase the marketability of products, they also demonstrate valuable biological activities as antioxidants and anticancer agents. There is a long history of exploitation of natural products produced by bacteria as sources of pharmaceutically important, bioactive compounds. Among natural pigments, pigments from microbial sources are potentially suitable alternatives to synthetic pigments. The red pigment prodigiosin (PG) has unusual properties, which have long been documented. The red-pigmented prodiginines are bioactive secondary metabolites produced by both Gram-negative and Gram-positive bacteria. Prodigiosins are characterized by a common pyrrolyl pyrromethene skeleton, and the biological role of these pigments in the producer organisms remains unclear. Bacterial prodigiosins and their synthetic derivatives are effective proapoptotic agents against various cancer cell lines, with multiple cellular targets including multi-drug resistant cells with little or no toxicity towards normal cell lines. However, research into the biology of pigment production will stimulate interest in the bioengineering of strains to synthesize useful prodiginine derivatives. This review article highlights the characteristics and potential applications of prodigiosin pigment from Serratia as prodigiosins are real potential therapeutic drugs.

show abstract

Section: Chemistry Of Prodigiosinmentioning

confidence: 99%

Prodigiosin and its potential applications

2015

View full text Add to dashboard Cite

show abstract

“…Members of this family are produced by microorganisms such as Serratia marescensa and Streptomyces. They were fi rst isolated in the 1920s, their structural features were identifi ed in the 1930s, and structure elucidation was completed in the 1960s (Wasserman et al, 1960;Rapoport and Holden, 1962).…”

Section: Prodigiosinmentioning

confidence: 99%

Natural product chemistry and anticancer drug discovery

Huryn¹,

Wipf²

2008

Cancer Drug Design and Discovery

View full text Add to dashboard Cite

“…A, Pyrryldipyrrylmethene structure of prodigiosin confirmed by synthesis (RApOPORT and HOLDEN, 1960, 1962); B, original tripyrrylmethene structure proposed by Paramount to final elucidation of the structure was identification of a compound excreted by mutant 9-3-3 of S. marcescens and shown to be a precursor of prodigiosin (SANTER and VOGEL, 1956). WASSERMAN et al (1960b) concluded that the compound was a 2,2'-bipyrrole aldehyde with the probable structure of 4-methoxy-2,2' -bipyrrole-5-carboxaldehyde (MBC) ; this compound could condense with 2-methyl-3-amylpyrrole (MAP) to form prodigiosin, making the pigment a pyrryldipyrrylmethene (see Fig. 2).…”

Section: O-ocmentioning

confidence: 97%

“…This mutant does not form the volatile precursor MAP, but accumulates MBC, the stable precursor (SANTER and VOGEL, 1956), that provided the key to the structure of prodigiosin (WASSERMAN et al, 1960b;HOLDEN, 1960, 1962). If provided with MAP produced by mutants blocked at points 1, 2, 3 or 4, mutant 9-3-3 forms prodigiosin.…”

Section: Biosynthesismentioning

confidence: 99%

Biosynthesis

1967

View full text Add to dashboard Cite

All rights, especially that of translation into f oreign 1anguages, reserved. It is also forbidden to reproduce this book, either who1e or in part, by photomechanical means (photostat, microfilm and/or microcard) or by other procedure without written pennission from Springcr-Vcrlag Berlin Heide1bCig GmbH. DedicationFor most areas of scientific pursuit, there is usually that rare investigator who has the imagination to conceive ideas, who has faith in his visions, and who has the ability to critically test his concepts in the laboratory. Almost invariably, this scientist also inspires younger men to enthusiastically enter into his research program. To him should go the accolades and the recognitions of the esteem in which he is held. As only a small part of this esteem, we wish to dedicate these books to Professor SELMAN A. W AKSMAN in appreciation of his leadership and contributions in all facets of antibiotic research. PrefaceThe idea for publishing these books on the mechanism of action and on the biosynthesis of antibiotics was born of frustration in our attempts to keep abreast of the literature. Gone were the years when we were able to keep a bibliography on antibiotics and feel confident that we could find everything that was being published on this sUbject. These fields of investigation were moving forward so rapidly and were encompassing so wide a range of specialized areas in microbiology and chemistry that it was almost impossible to keep abreast of developments. In our naivete and enthusiasm, however, we were unaware that we were toying with an idea that might enmesh us, that we were creating an entity with a life of its own, that we were letting loose a Golom who instead of being our servant would be our master.That we set up ideals for these books is obvious; they would be current guides to developments and information in the areas of mechanism of action and biosynthesis of antibiotics. For almost every subject, we wished to enlist the aid of an investigator who himself had played a part in determining the nature of the phenomena that were being discussed. One concept for the books was that they include only antibiotics for which a definitive, well-documented mechanism of action or biosynthetic pathway was known. Yet, such an approach would not entirely serve the purpose we projected, for it would not encompass all of the information available in these fields of antibiotic investigations and blind searches for the original literature would still have to be made. We therefore chose to include any and all antibiotics about which some pertinent information had been published. It was obvious even at the start that such a compilation, integration, and analysis of information could never be complete unless scientific investigations ceased at the moment the last manuscript was submitted-an end that was neither desirable nor possible. An addendum was therefore included at the end of the volume and left open for the addition of new information until the last pages of the regular articles had been printed.The...

show abstract

PRODIGIOSIN. STRUCTURE AND PARTIAL SYNTHESIS¹

Cited by 68 publications

References 0 publications

Prodigiosin and its potential applications

Prodigiosin and its potential applications

Natural product chemistry and anticancer drug discovery

Biosynthesis

Contact Info

Product

Resources

About

PRODIGIOSIN. STRUCTURE AND PARTIAL SYNTHESIS1

Cited by 68 publications

References 0 publications

Prodigiosin and its potential applications

Prodigiosin and its potential applications

Natural product chemistry and anticancer drug discovery

Biosynthesis

Contact Info

Product

Resources

About

PRODIGIOSIN. STRUCTURE AND PARTIAL SYNTHESIS¹