New chemistry of naturally occurring polyamines

Ganem, Bruce

doi:10.1021/ar00081a004

Cited by 118 publications

(49 citation statements)

References 61 publications

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“…Under physiological conditions the polyamines are largely protonated (Ganem, 1982) and the resulting cations carry a distributed positive charge which allows them to interact with anionic species. The polyamine cations interact with the negatively charged phosphate groups of DNA and it is thought that this interaction is the source of their antifungal activity (Waiters, 1995).…”

Section: Introductionmentioning

confidence: 99%

Experimental and Theoretical Studies of Charge Density Distribution in E-Tetraethyl-1,4-diammoniumbut-2-ene.2PF₆

McCormack¹,

Mallinson²,

Webster³

et al. 1997

Acta Crystallogr Sect B

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The [PF6]-salt of E-tetraethyl-l,4-diaminobut-2-ene has been synthesized and the crystal structure determined. The experimental electronic charge distribution has been obtained by fitting a multipole model to low-temperature, high-resolution, single-crystal X-ray diffraction data. A high-level ab initio molecular orbital calculation has also been performed for the cation, which is used as an antifungal agent. Both experimental and theoretical Laplacian distributions display maxima only at the bond critical points. This correlates with a calculated electrostatic potential which is positive at all points.represents one of the first of such a series and its purpose is to investigate the electronic charge distribution of a polyamine cation with known fungicidal properties, [Etetraethyl-l,4-diammoniumbut-2-ene] 2÷, TEDH22÷. Very recently Cohen, Ruble & Craven (1996) reported a similar study of spermine phosphate hexahydrate.It is also necessary to determine the electrostatic potential surface of the anion in order to confirm that an interaction with the anion is feasible. Ab initio molecular orbital calculations were therefore performed on the simplest model group which would approximate to the phosphate groups of the DNA helix, namely [PO2(OCH3)2]-.

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Section: Introductionmentioning

confidence: 99%

Experimental and Theoretical Studies of Charge Density Distribution in E-Tetraethyl-1,4-diammoniumbut-2-ene.2PF₆

McCormack¹,

Mallinson²,

Webster³

et al. 1997

Acta Crystallogr Sect B

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“…These alkyloxy propanolamines bearing a polyamine group can be expected to behave as gene therapy delivery systems [78]. Among polyamine-bearing natural products, polyamino-steroids form a novel, small group whose members and their analogues display interesting biological activities [79]. For example, Blagbrough et al reported polyamine amides from steroidal compounds such as cholic and lithocholic acid by acylation of tri-Boc protected spermine and thermine, and their binding affinities for calf thymus DNA were determined using an ethidium bromide fluorescence quenching assay.…”

Section: Future Potential Of Cholesterol As a Synthetic Building Blockmentioning

confidence: 99%

Cholesterol as synthetic building blocks for artificial lipids with characteristic physical, chemical and biological properties

Urata

Takaishi

2001

Eur. J. Lipid Sci. Technol.

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Cholesterol is one of the most widely distributed natural materials and has a unique chemical structure such as a steroid skeleton. Many types of chemical transformations of cholesterol functional groups have been developed. There is an interest in the derivatization of cholesterol and to introduce alkyl branched fatty acids into the molecule. These have found applications in the formulation of cosmetics and toiletries over the past few decades. An extraordinary interesting case is related to cholesteryl esters and their use in gene therapy delivery systems. These results can be attributed to their potential for forming cell-mimic membranes, because cholesterol is the most important building block of living cell membranes. In terms of organic synthesis, cholesterol is a strategically useful material. A typical case is remote functionalization by chemical reactions or by biocatalysis. In the future, cholesterol should be considered as a key compound, a building block for the construction of artificial lipid-like membranes by self-assembly. Also, as cholesterol is one of the members of the fat and oil family, fat and oil chemists should study and develop cholesterol chemistry even further.

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“…The interest in the isolation and synthesis of these alkaloids results from the structural complexity and therapeutical properties attributed to these macrocycles [2,3]. A broad biological activity has been revealed by members of the polyamine family, and the toxic or cytotoxic effects exhibited by several of these compounds [4][5][6][7][8][9]. The occurrence and biosynthesis of these macrocyclic structures has a restricted distribution in Nature [10], occurring in limited plant families, such as the Celastraceae [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

A new spermidine macrocyclic alkaloid isolated from Gymnosporia arenicola leaf

et al. 2015

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New chemistry of naturally occurring polyamines

Cited by 118 publications

References 61 publications

Experimental and Theoretical Studies of Charge Density Distribution in E-Tetraethyl-1,4-diammoniumbut-2-ene.2PF₆

Experimental and Theoretical Studies of Charge Density Distribution in E-Tetraethyl-1,4-diammoniumbut-2-ene.2PF₆

Cholesterol as synthetic building blocks for artificial lipids with characteristic physical, chemical and biological properties

A new spermidine macrocyclic alkaloid isolated from Gymnosporia arenicola leaf

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New chemistry of naturally occurring polyamines

Cited by 118 publications

References 61 publications

Experimental and Theoretical Studies of Charge Density Distribution in E-Tetraethyl-1,4-diammoniumbut-2-ene.2PF6

Experimental and Theoretical Studies of Charge Density Distribution in E-Tetraethyl-1,4-diammoniumbut-2-ene.2PF6

Cholesterol as synthetic building blocks for artificial lipids with characteristic physical, chemical and biological properties

A new spermidine macrocyclic alkaloid isolated from Gymnosporia arenicola leaf

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Product

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Experimental and Theoretical Studies of Charge Density Distribution in E-Tetraethyl-1,4-diammoniumbut-2-ene.2PF₆

Experimental and Theoretical Studies of Charge Density Distribution in E-Tetraethyl-1,4-diammoniumbut-2-ene.2PF₆