Chemistry of Cyclic Nucleotides and Cyclic Nucleotide Analogs

Revankar, Ganapathi R.; Robins, Roland K.

doi:10.1007/978-3-642-68111-0_2

Cited by 18 publications

(3 citation statements)

References 466 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…8-Bromocyclic GMP is 2-5 times more active than cyclic GMP itself as an activator of cyclic GMPdependent protein kinase (Kuo et al, 1974;1976), Table 1 The effect of haemoglobin on the cyclic nucleotide content of the bovine retractor penis muscle and its response to nerve stimulation and inhibitory factor and it is resistant to degradation by phosphodiesterase (Revanker & Robins, 1982). This makes the compound a useful probe for investigating the cellular effects of cyclic GMP.…”

Section: -Bromocyclic Gmpmentioning

confidence: 99%

Cyclic GMP mediates neurogenic relaxation in the bovine retractor penis muscle

Bowman

Drummond

1984

British J Pharmacology

View full text Add to dashboard Cite

1 Field stimulation of the non-adrenergic, non-cholinergic inhibitory nerves to the bovine isolated retractor penis muscle evoked a relaxation that was preceded by a rise in the tissue content of cyclic GMP. There was no change in the content of cyclic AMP. 2 The selective cyclic GMP phosphodiesterase inhibitor, 2-o-propoxyphenyl-8-azapurin-6-one (M&B 22948), elevated the tissue's cyclic GMP content, and potentiated both the relaxation and the rise in cyclic GMP produced by inhibitory nerve stimulation. 3 Sodium nitroprusside and an inhibitory factor extracted from the bovine retractor penis muscle mimicked the effects of inhibitory nerve stimulation in that they each produced relaxation associated with a selective rise in cyclic GMP concentration. 4 Haemoglobin (in the form of erythrocyte haemolysate) and N-methylhydroxylamine, which are known to block guanylate cyclase, blocked the relaxation and the rise in cyclic GMP content produced by inhibitory nerve stimulation, inhibitory factor and sodium nitroprusside. Haemoglobin itself caused a rise in muscle tone and at the same time reduced the cyclic GMP content of the tissue. 5 8-Bromocyclic GMP, a permeant derivative of cyclic GMP, produced a relaxation of the muscle that, as expected, was not blocked by haemoglobin. 6 Vasoactive intestinal polypeptide, prostaglandin E1 and forskolin each produced relaxation associated with a selective rise in cyclic AMP content. Their effects were not blocked by haemoglobin or N-methylhydroxylamine. 7 It is concluded that inhibitory nerve stimulation in the bovine retractor penis muscle produces a relaxation that is mediated by cyclic GMP, although some substances relax the muscle without affecting cyclic GMP levels. The results are also compatible with the view that the extracts of muscle contain the inhibitory neurotransmitter.

show abstract

Section: -Bromocyclic Gmpmentioning

confidence: 99%

Cyclic GMP mediates neurogenic relaxation in the bovine retractor penis muscle

Bowman

Drummond

1984

British J Pharmacology

View full text Add to dashboard Cite

show abstract

“…Cyclic AMP and c-di-AMP are good candidates for this kind of signaling, since they also are stable under low pH (and high temperature). The half-life of cAMP is close to 30 min at 100°C in 1N HCl ( Revankar and Robins, 1982 ), while c-di-AMP shows slow degradation into different intermediaries at 90°C and pH below 3 ( Ora et al, 2012 ).…”

Section: Resultsmentioning

confidence: 99%

Nucleotide Second Messenger-Based Signaling in Extreme Acidophiles of the Acidithiobacillus Species Complex: Partition Between the Core and Variable Gene Complements

et al. 2019

View full text Add to dashboard Cite

Cyclic and linear nucleotides are key elements of the signal transduction networks linking perception of the environment to specific cellular behavior of prokaryotes. These molecular mechanisms are particularly important in bacteria exposed to different, and frequently simultaneous, types of extreme conditions. This is the case in acidithiobacilli, a group of extremophilic bacteria thriving in highly acidic biotopes, that must also cope with significant variations in temperature, osmotic potentials and concentrations of various transition metals and metalloids. Environmental cues sensed by bacteria are transduced into differential levels of nucleotides acting as intracellular second messengers, promoting the activation or inhibition of target components and eliciting different output phenotypes. Cyclic (c) di-GMP, one of the most common bacterial second messengers, plays a key role in lifestyle changes in many bacteria, including acidithiobacilli. The presence of functional c-di-GMP-dependent signal transduction pathways in representative strains of the best-known linages of this species complex has been reported. However, a comprehensive panorama of the c-di-GMP modulated networks, the cognate input signals and output responses, are still missing for this group of extremophiles. Moreover, little fundamental understanding has been gathered for other nucleotides acting as second messengers. Taking advantage of the increasing number of sequenced genomes of the taxon, here we address the challenge of disentangling the nucleotide-driven signal transduction pathways in this group of polyextremophiles using comparative genomic tools and strategies. Results indicate that the acidithiobacilli possess all the genetic elements required to establish functional transduction pathways based in three different nucleotide-second messengers: (p)ppGpp, cyclic AMP (cAMP), and c-di-GMP. The elements related with the metabolism and transduction of (p)ppGpp and cAMP appear highly conserved, integrating signals related with nutrient starvation and polyphosphate metabolism, respectively. In contrast, c-di-GMP networks appear diverse and complex, differing both at the species and strain levels. Molecular elements of c-di-GMP metabolism and transduction were mostly found scattered along the flexible genome of the acidithiobacilli, allowing the identification of probable control modules that could be critical for substrate colonization, biofilm development and intercellular interactions. These may ultimately convey increased endurance to environmental stress and increased potential for gene sharing and adaptation to changing conditions.

show abstract

“…N6-monobutyryl CAMP, N6-benzoyl CAMP, and 17P-esrradiol were obtained from Sigma (St. Louis, MO). All other cAMP analogues were provided by Dr. R.K. Robins (Revankar and Robins, 1982). Tamoxifen (ICI-46474) was obtained from Stuart (Wilmington, DE).…”

Section: Methodsmentioning

confidence: 99%

Site selective cyclic amp analogues are antagonistic to estrogen stimulation of growth and proto‐oncogene expression in human breast‐cancer cells

Katsaros

Ally

Cho‐Chung

1988

Intl Journal of Cancer

View full text Add to dashboard Cite

Studies from our laboratory suggested that regulation of the growth of hormone-dependent mammary tumors may depend on the antagonistic action between estrogen and cyclic AMP (CAMP). Estrogen stimulates whereas cAMP arrests the growth of mammary carcinomas induced by 7,12-dimethylbenz(a)anthracine (DMBA) in the rat (Cho-Chung and Gullino, 1974). During growth arrest of the tumors after either hormone removal (ovariectomy) or treatment of the hosts with N6, d'-dibutyryl-CAMP (DBcAMP), estrogen binding decreases whereas cAMP binding and CAMP-dependent protein kinase activity increase in the cytosol and nuclei of the tumor cells (Bodwin et al., 1978). It was further demonstrated that the growth of DMBA-induced mammary tumors is associated with an enhanced expression of a cellular oncogene, c-rasH, The p21-transforming protein of the ras gene product (Shih et al., 1979) was a predominant in vitro translation product of mRNAs of the growing tumors, and a sharp reduction of the translated p2 1 protein preceded regression of these tumors after either ovariectomy or DBcAMP treatment (Huang and Cho-Chung, 1984).Recent studies on cAMP binding kinetics, using purified preparations of CAMP-dependent protein kinases, identified cAMP analogues that are potent activators of protein kinase and selectively bind to either one of the 2 different cAMP binding sites (Rannels and Corbin, 1980) of protein kinase. Generally, analogues modified at the C-8 position of adenine ring are Site 1-selective and those modified at the C-6 position are Site 2-selective (Rannels and Corbin, 1980). Furthermore, the Site 1-and Site 2-selective analogues in combination demonstrate synergism of binding to and activation of protein kinase (Robinson-Steiner and Corbin, 1983; Qgreid et al., 1985). the effect of site-selective cAMP analogues on the growth and cellular proto-oncogene expression that can be stimulated by estrogen in human MCF-7 breast-cancer cells. MATERIAL AND METHODS MaterialCAMP, DBcAMP, and 8-bromo-CAMP were from Boehringer Mannheim (Indianapolis, IN). N6-monobutyryl CAMP, N6-benzoyl CAMP, and 17P-esrradiol were obtained from Sigma (St. Louis, MO). All other cAMP analogues were provided by Dr. R.K. Robins (Revankar and Robins, 1982). Tamoxifen (ICI-46474) was obtained from Stuart (Wilmington, DE). Improved minimal essential medium (IMEM) was obtained from NIH Media and Glassware Section. Dulbecco's phosphate-buffered saline (PBS), fetal bovine serum (FBS), trypsin-EDTA solution, penicillin-streptomycin solution, Lglutamine, and N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid (HEPES) buffer 1 M stock solution, PH 7.3, were obtained from GIBCO (Grand Island, NY). The MCF-7 breastcancer cell line was provided by Dr. M. Lippman. Cell cultureMCF-7 cells were grown in IMEM with no phenol red (Berthois et al., 1986), containing 6.5 % of charcoal-stripped serum, HEPES 20 mM, penicillin-streptomycin, and extra glutamine. Cells were grown at 37°C in humidified incubators in an atmosphere of 5 % C02.For cell growth experiments, 1-2 X lo5 cells/...

show abstract

Chemistry of Cyclic Nucleotides and Cyclic Nucleotide Analogs

Cited by 18 publications

References 466 publications

Cyclic GMP mediates neurogenic relaxation in the bovine retractor penis muscle

Cyclic GMP mediates neurogenic relaxation in the bovine retractor penis muscle

Nucleotide Second Messenger-Based Signaling in Extreme Acidophiles of the Acidithiobacillus Species Complex: Partition Between the Core and Variable Gene Complements

Site selective cyclic amp analogues are antagonistic to estrogen stimulation of growth and proto‐oncogene expression in human breast‐cancer cells

Contact Info

Product

Resources

About