Biological formation and reactions of the amido group

Reimann, Jessica E.; Byerrum, Richard U.

doi:10.1002/9780470771235.ch11

Cited by 2 publications

(2 citation statements)

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“…(2) Enediynes with an Amide Group: Systems 4 − 8. The amide group is a key unit in many biologically important macromolecules, which already indicates that amides are stable under physiological conditions. Although N,C-dialkynyl amides such as 12 or 20 (Scheme ) seem to be structurally different from an enediyne, we will show that they can undergo Bergman cyclization to a biradical in the same way as enediynes.…”

Section: Resultsmentioning

confidence: 99%

Computer Design of Anticancer Drugs. A New Enediyne Warhead

2000

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Seven criteria are developed and discussed that lead to the design of a new enediyne anticancer drug, which should have low toxicity but high biological selectivity and activity when attacking the DNA of tumor cells. These criteria concern (among others) the thermodynamic and kinetic stability of the species involved in the reaction of an enediyne, the biradical character and H-abstraction ability of the intermediate biradical generated in a Bergman reaction of the enediyne, and the basicity of the enediyne and its associated biradical. Thirteen different heteroenediynes were investigated with the help of B3LYP/6-31G(d,p) calculations to find a suitable candidate for a new enediyne anticancer drug, which fulfills the seven criteria. These calculations included the determination of reaction profiles for Bergman and retro-Bergman reactions, the calculation of singlet-triplet splittings of biradicals formed from enediynes, and the prediction of pK a values. Results were tested by using a larger basis set (6-311+G(3df,3pd)), another functional (BLYP), and coupled cluster methods such as CCSD(T) and the Brueckner orbitals-based BD(T) method. The best candidate for a new enediyne anticancer drug is an N,C-dialkynyl aldimine incorporated into a cyclodecaene ring.

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Section: Resultsmentioning

confidence: 99%

Computer Design of Anticancer Drugs. A New Enediyne Warhead

2000

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“…'A protein kinase from muscle was chosen for investigation because of its favorable binding constant for cAMP. 16 It was readily determined that cAMP-dependent protein kinase and cAMP-binding activities from muscle extracts could be quantitatively adsorbed on cellulose ester (Millipore) filters. The binding of cAMP to specific proteins from Escherichia coli and the adrenal cortex has recently been studied on Millipore filters.…”

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confidence: 99%

A Protein Binding Assay for Adenosine 3′:5′-Cyclic Monophosphate

Gilman

1970

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

2,878

608

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Abstract. A simple and sensitive assay for adenosine 3':5'-cyclic monophosphate (cAMP) has been developed that is based on competition for protein binding of the nucleotide, presumably to a cAMP-dependent protein kinase. The nucleotide-protein complex is adsorbed on a cellulose ester filter. Assay conditions are such that a binding constant approaching 10-9 M\1 is obtained, and the assay is thus sensitive to 0.05-0.10 pmol of cAMP.While assays for adenosine 3' :5'-cyclic monophosphate (cAMIP) are proliferating almost as rapidly as are newly discovered actions of the nucleotide, the tremendous current interest in the biological role of cAMP dictates the need for a sensitive, accurate, and readily performed procedure for estimation of its cellular levels. The methods currently availablel-8 do not have the extreme sensitivity required by the low tissue levels of the compound, or else they are laborious to perform, or both.The present study was initiated with the thought that the binding of

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Biological formation and reactions of the amido group

Cited by 2 publications

References 213 publications

Computer Design of Anticancer Drugs. A New Enediyne Warhead

Computer Design of Anticancer Drugs. A New Enediyne Warhead

A Protein Binding Assay for Adenosine 3′:5′-Cyclic Monophosphate

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