Derivatives of cyclic 3′,5′-adenosine monophosphate

Posternak, Th.; Sutherland, Earl W.; Henion, W.F.

doi:10.1016/0006-3002(62)90475-4

Cited by 348 publications

(76 citation statements)

References 6 publications

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“…N6-monobutyryl cyclic AMP was also able to stimulate the conversion of phosphorylase b to phosphorylase a in extracts from dog liver and heart, while N6,02'-dibutyryl cyclic AMP and 02'-monobutyryl cyclic AMP were practically without effect [6]. The data presented strongly support the interpretation that N6,02'-dibutyryl cyclic AMP exerts its sustained effects in HeLa cells (cf.…”

Section: Discussionsupporting

confidence: 81%

“…As the two monobutyryl derivatives cannot be separated chromatographically, contamination of 02'-monobutyryl cyclic AMP with N6-monobutyryl cyclic AMP was determined by chromatography after mild alkaline hydrolysis of the 02'-monobutyryl cyclic AMP leaving N6-monobutyryl cyclic AMP untouched [6]. It should be pointed out that N6-monobutyryl cyclic AMP exhibited less affinity (about 50°/,) to the protein kinase when added without prior acidification and ether extraction.…”

Section: Methodsmentioning

confidence: 99%

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N⁶‐Monobutyryladenosine 3′ : 5′‐Monophosphate as the Biologically Active Derivative of Dibutyryladenosine 3′ : 5′‐Monophosphate in HeLa S3 Cells

Kaukel

Mundhenk

Hilz

1972

European Journal of Biochemistry

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1. N6,02'-dibutyryl cyclic AMP and 02'-monobutyryl cyclic AMP had practically no affinity to Gilman's cyclic-AMP-binding kinase from muscle, while the N6-monobutyryl derivative was bound to the protein to nearly the same degree as cyclic AMP.2. N6-monobutyryl cyclic AMP was the only cyclic nucleotide accumulating inside HeLa cells when cultures were incubated with N6,02'-dibutyryl cyclic AMP. N6-monobutyryl cyclic AMP was also accumulated when cell homogenates acted on N6,02'-dibutyryl cyclic AMP, while cyclic AMP and 02'-monobutyryl cyclic AMP were rapidly degraded.3. The results indicate that N6-monobutyryl cyclic AMP is the true intracellular imitator of cyclic AMP when N6,02'-dibutyryl cylic AMP is added to tissues.

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Section: Discussionsupporting

confidence: 81%

Section: Methodsmentioning

confidence: 99%

N⁶‐Monobutyryladenosine 3′ : 5′‐Monophosphate as the Biologically Active Derivative of Dibutyryladenosine 3′ : 5′‐Monophosphate in HeLa S3 Cells

Kaukel

Mundhenk

Hilz

1972

European Journal of Biochemistry

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“…Attempts to determine whether raised concentrations of cyclic AMP have an effect in vivo equivalent to that anticipated from studies in vitro have included the administration of N6-2'-O-dibutyryl adenosine 3',5'-monophosphate (db cyclic AMP) to whole animals. Db cyclic AMP is more resistant than cyclic AMP to hydrolysis catalysed by cyclic nucleotide phosphodiesterases and may penetrate cell membranes more readily than the parent nucleotide (Posternak, Sutherland & Henion, 1962;Henion, Sutherland & Postemak, 1967).…”

Section: Introductionmentioning

confidence: 99%

THERMOREGULATORY EFFECTS OF N⁶‐2′‐O‐DIBUTYRYL ADENOSINE 3′,5′‐MONOPHOSPHATE IN THE RESTRAINED MOUSE

Dascombe

Milton

Nyemitei-Addo

et al. 1980

British J Pharmacology

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1The N6-2'-O-dibutyryl derivative of adenosine 3',5'-monophosphate (db cyclic AMP) has been micro-injected into the third cerebral ventricle of the unanaesthetized, restrained mouse and the effects on body temperature and thermoregulatory activities observed. 2 Db cyclic AMP (4, 16 and 32 jg) injected intracerebroventricularly produced hypothermia when compared with temperature responses to sodium n-butyrate (6.8 jg). 3 Hypothermia induced by db cyclic AMP in mice was associated with a fall in oxygen consumption together with behavioural and autonomic heat loss activities but not cutaneous vasodilatation. The effects on rectal temperature and oxygen consumption were dose-dependent. 4 The falls in rectal temperature and oxygen consumption induced by db cyclic AMP (4 ,ug) were decreased by elevation of the environmental temperature from 22 to 32°C and abolished at 36°C. 5 It is concluded db cyclic AMP may inhibit central events mediating the rise in metabolic heat production in mice upon exposure to cold environments.

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“…Dibutyryl-cAMP has been widely used in animal cell culture studies as a substitute for cAMP, since the latter seems to be not easily taken up by the cells and is rapidly hydrolyzed by PDE (PasTERNAK et al 1962;KAUKEL and HILZ 1972). According to the current view, when taken up by the cell, part of the dbcAMP is transformed mainly into N 6 -monobutyryl-cAMP, through deacylation at the 0 2 ' of the ribose (SWISLOCKI 1970;0' NEILL et al 1975), with liberation of a butyryl residue.…”

Section: Discussionmentioning

confidence: 99%

Arrest of the Cell Cycle Induced by Dibutyryl-Camp and Sodium Butyrate in Root Meristems of Lettuce

1986

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SUMMARY -Dibutyryl-cAMP was supplied to seedlings of Lactuca sativa L. cv.Great Lakes 118, and its effect on the cell cycle in root meristems was compared to that of dibutyryl-cGMP and sodium butyrate. Dibutyryl-cAMP and sodium butyrate induced a sharp decrease in the labelling index, attributable to an arrest of the cell cycle in G1 and possibly G2, whereas dibutyryl-cGMP was ineffective. The use of dibutyryl-cAMP and sodium butyrate in studies on the control of cell cycle and cell differentiation in growing roots is suggested. Various hypotheses on the mode of action of dibutyryl-cAMP are also discussed.

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Derivatives of cyclic 3′,5′-adenosine monophosphate

Cited by 348 publications

References 6 publications

N⁶‐Monobutyryladenosine 3′ : 5′‐Monophosphate as the Biologically Active Derivative of Dibutyryladenosine 3′ : 5′‐Monophosphate in HeLa S3 Cells

N⁶‐Monobutyryladenosine 3′ : 5′‐Monophosphate as the Biologically Active Derivative of Dibutyryladenosine 3′ : 5′‐Monophosphate in HeLa S3 Cells

THERMOREGULATORY EFFECTS OF N⁶‐2′‐O‐DIBUTYRYL ADENOSINE 3′,5′‐MONOPHOSPHATE IN THE RESTRAINED MOUSE

Arrest of the Cell Cycle Induced by Dibutyryl-Camp and Sodium Butyrate in Root Meristems of Lettuce

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Derivatives of cyclic 3′,5′-adenosine monophosphate

Cited by 348 publications

References 6 publications

N6‐Monobutyryladenosine 3′ : 5′‐Monophosphate as the Biologically Active Derivative of Dibutyryladenosine 3′ : 5′‐Monophosphate in HeLa S3 Cells

N6‐Monobutyryladenosine 3′ : 5′‐Monophosphate as the Biologically Active Derivative of Dibutyryladenosine 3′ : 5′‐Monophosphate in HeLa S3 Cells

THERMOREGULATORY EFFECTS OF N6‐2′‐O‐DIBUTYRYL ADENOSINE 3′,5′‐MONOPHOSPHATE IN THE RESTRAINED MOUSE

Arrest of the Cell Cycle Induced by Dibutyryl-Camp and Sodium Butyrate in Root Meristems of Lettuce

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N⁶‐Monobutyryladenosine 3′ : 5′‐Monophosphate as the Biologically Active Derivative of Dibutyryladenosine 3′ : 5′‐Monophosphate in HeLa S3 Cells

N⁶‐Monobutyryladenosine 3′ : 5′‐Monophosphate as the Biologically Active Derivative of Dibutyryladenosine 3′ : 5′‐Monophosphate in HeLa S3 Cells

THERMOREGULATORY EFFECTS OF N⁶‐2′‐O‐DIBUTYRYL ADENOSINE 3′,5′‐MONOPHOSPHATE IN THE RESTRAINED MOUSE