Influence of alterations in the purine ring on biological activity of cytokinins

Rogozińska, Janina; Kroon, C.; Salemink, C. A.

doi:10.1016/0031-9422(73)85105-2

Cited by 24 publications

(9 citation statements)

References 13 publications

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“…The results obtained here indicate that the replacement of nitrogen atom by carbon atom in the 1-position of the purine ring of BOA and POA develops a cytokinin activity, while similar replacement in the 3-position causes a decrease in the activity. This was consistent with earlier findings that nitrogen atom in the 3-position of the purine ring is important for high cytokinin activity (Rogozinska et al 1973, Sugiyama (?/a/. 1975.…”

Section: Resultssupporting

confidence: 93%

“…Skoog et al (1967) indicated that 8-azakinetin and 6benzylamino-8-azapurine were only about 5% as active as the corresponding purine derivatives, 7-(3-Methyl-2butenylamino)pyrazolo|4,3-rflpyrimidine (Hecht et al 1971), 4 -(3 -methyl -2 -butenylamino)pyrazolol3,4 -c/lpyrimidine (Hecht et al 1975) and 4-(3-methyl-2-butenylamino)pyrrolo-|2,3-^/|pyrimidine (Hecht et a/,1975, Skoog et al 1975) were more than 100 times less active than 6-(3-methyl-2-butenylamino)purine. Torigoe et al (1972) reported that 8-benzyl amino 2 methyl-s-triazolol l,5-o|pyrazine, 8-benzylarnino-2mcthyl-5-triazoIol 1,5-alpyridine and 4(7)-benzylaminobenzimidazole were 100-300 times less active than kinetin, Rogozinska et al (1973) reported that 7-furfurylamino-imidazo|4,5-/;|pyridine and 4-furfurylaminoimidazo|4,5-clpyridine were 15 and 2000 times less active than kinetin respectively, and that 7 (3 methyl-2-butenylaniino)imidazo-14,5-6 Ipyridine and 4-(3-methyl-2-butenylamino)imidazo-|4,5-clpyridine were 2 and 1000 times less active than 6 (3-methyl-2-butenylamino)purine respectively. Thus, in all instances, modification in the purine moiety lowered the cytokinin activity.…”

Section: Resultsmentioning

confidence: 99%

“…Investigations on relationships between chemical structure and cytokinin activity indicated that the compounds with high activity were A'^-substituted adenines (Skoog et al 1967, Skoog andArmstrong 1970), Modification of the purine ring always lowered cytokinin activity (Skoog et al 1967, Hecht et al 1971, Torigoe et al 1972, Rogozinska et al 1973. Thus, Skoog and Armstrong (1970) considered that an intact purine ring is necessary for high cytokinin activity.…”

Section: Introductionmentioning

confidence: 99%

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Cytokinin Activity of Benzoylaminodeazapurines, Pentanoylaminodeazapurines and their Corresponding Purine Analogs in Five Bioassays

Matsubara

Sugiyama

Hashizume

1978

Physiologia Plantarum

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Cytokinin activities of 6‐benzoylamino‐1, 6‐benzoylamino‐3‐, 6‐pentanoylamino‐1‐ and 6‐pentanoylamino‐3‐deazapurines and their corresponding purine analogs, 6‐benzoylaminopurine and 6‐pentanoylaminopurine, were examined using five bioassay systems, tobacco callus growth, bud formation on tobacco callus, lettuce seed germination, fresh weight increase of radish cotyledons and retardation of chlorophyll degradation in radish cotyledons. 6‐Benzoylamino‐ and 6‐pentanoylamino‐1‐deazapurines showed stronger cytokinin activity than their corresponding purine analogs in all bioassays used. In tobacco callus growth, 6‐benzoylamino‐1‐deazapurine was nearly as active as zeatin, one of the most active adenylate cytokinins. On the other hand, 6‐benzoylamino‐ and 6‐pentanoylamino‐3‐deazapurines were as active as or less active than corresponding purine analogs.

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Section: Resultssupporting

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cytokinin Activity of Benzoylaminodeazapurines, Pentanoylaminodeazapurines and their Corresponding Purine Analogs in Five Bioassays

Matsubara

Sugiyama

Hashizume

1978

Physiologia Plantarum

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“…The same conclusion was reached from the fact that gibberellic acid was found not to reverse the growth inhibitory (12,13), most growth inhibitory analogs (15)(16)(17) were found to have a more general function when evaluated at a given concentration for reversal of inhibition by added cytokinin and for correlation of inhibitory activity with structural features usually associated with cytokinin-active species (14).…”

Section: Methodsmentioning

confidence: 58%

“…The successful preparation of a class of antagonists suggested that additional heterocyclic series of anticytokinins should exist. Several potentially inhibitory analogs have been prepared (15)(16)(17), but none of these fulfilled the criteria for anticytokinin activity to nearly the same extent as the original class of anticytokinins (14). The present report describes a new class of potential cytokinin antagonists, the activity of which is consistent with the criteria specified for anticytokinins.…”

mentioning

confidence: 99%

Anticytokinin activity of substituted pyrrolo[2,3- d ]pyrimidines

Skoog

Schmitz²,

Hecht³

et al. 1975

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

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Ten substituted pyrrolo[2,3-dpyrimidines were tested as cytokinins and anticytokinins in the tobacco bioassay. Eight new anticytokinins were identified and two were found to be highly active. The most potent species were 4-cyclohexylamino-and 4-cyclopentylamino-2-methylthiopyrrolo[2,3-djpyrimidine, of which 0.05 and 0.009 AM concentrations, respectively, were required to produce detectable inhibition of the growth of tobacco callus cultured on a medium containing 0.003 uM 6(3-methyl-2-butenylamino)purine. The inhibition of growth by moderate (<6.6 uM) concentrations of these compounds was reversible by equal or higher concentrations of 6-(3-methyl-2-butenylamino)purine, but not by indole-3-acetic acid or gibberellic acid. These substituted pyrrolo[2,3-djpyrimidines were also found to enhance bud formation at high cytokinin concentrations, suggesting that a cytokinin may act at more than one cellular site in exerting its growth-promoting and morphogenetic effects.Cytokinins are a class of hormones which promote cell division and participate in the regulation of growth and morphogenesis in plants (1). Although all plants are thought to require cytokinins for growth, intact plants generally grow without exogenous cytokinins, presumably because they make their own. In fact, several highly active cytokinins have been found to occur naturally as N6-substituted adenine derivatives at the purine, ribonucleoside, and ribonucleotide levels (1). Cytokinins are also present in the transfer RNA's of most forms of life, although their presence in tRNA has not been shown to be related to their regulation of growth (1, 2).Cytokinins have been found to influence the behavior of mammalian cells. They have been reported, for example, to inhibit platelet aggregation (3) and the growth of several mammalian cell lines, including cancerous lines (4-6 and references in 5). N6-(3-Methyl-2-butenyl)adenosine (i6Ado) has been reported to be an immunosuppressive agent (7) and to induce hematological remissions in leukemia patients (8,9). Several cytokinins, including i6Ado, have also been shown to be capable of regulating the growth of phytohemagglutinin-transformed human lymphocytes (10 and references therein), presumably by involvement in cyclic AMP metabolism, and i6Ado was shown to act as a competitive inhibitor of beef heart cyclic AMP phosphodiesterase (11).To facilitate the study of the mechanism of cytokinin action and provide potential chemotherapeutic agents, we designed and synthesized a class of structural analogs of cytokinins which behave as anticytokinins in plant bioassays (12,13). Proof that these "anticytokinins" act at the same cellular sites as the cytokinins is not presently accessible, since cytokinin-anticytokinin interaction is not monitored at the molecular level, but this interpretation has been proposed on the basis of the observed biological activities of the analogs in several assays and on the close structural relationship between cytokinins and anticytokinins (14). The successful preparation of a class...

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