Deacetylanisomycin
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| Category | Antibiotics |
| Catalog number | BBF-03481 |
| CAS | 27958-06-1 |
| Molecular Weight | 223.27 |
| Molecular Formula | C12H17NO3 |
| Purity | >99% by HPLC |
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Description
It is an antitumor antibiotic produced by the strain of Streptomyces SA 3097. It is an effective inhibitor of protein synthesis and plant growth regulator.
Specification
| Synonyms | (-)-Deacetylanisomycin; 3,4-Pyrrolidinediol, 2-(p-methoxybenzyl)-, (2R,3S,4S)-(-)-; Antibiotic SA 3097D1 |
| Storage | Store at 2-8°C |
| IUPAC Name | (2R,3S,4S)-2-[(4-methoxyphenyl)methyl]pyrrolidine-3,4-diol |
| Canonical SMILES | COC1=CC=C(C=C1)CC2C(C(CN2)O)O |
| InChI | InChI=1S/C12H17NO3/c1-16-9-4-2-8(3-5-9)6-10-12(15)11(14)7-13-10/h2-5,10-15H,6-7H2,1H3/t10-,11+,12+/m1/s1 |
| InChI Key | UMWAPBCLJQSOJX-WOPDTQHZSA-N |
| Source | Streptomyces griseolus |
Properties
| Appearance | White solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 390.7±37.0°C (Predicted) |
| Melting Point | 176-179°C |
| Density | 1.233±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol, Water |
Reference Reading
1. Inhibition of protein synthesis blocks long-term enhancement of generator potentials produced by one-trial in vivo conditioning in Hermissenda
J Forrester, T Crow Proc Natl Acad Sci U S A . 1990 Jun;87(12):4490-4. doi: 10.1073/pnas.87.12.4490.
A one-trial in vivo conditioning procedure produces short- and long-term cellular changes that can be detected in identified sensory neurons of the pathway mediating the conditioned stimulus. The memory of the associative experience in the conditioned stimulus pathway is expressed by short- and long-term enhancement of light-evoked generator potentials recorded from identified lateral and medial type B photoreceptors within the eyes of Hermissenda. To identify mechanisms of the induction and expression of short- and long-term enhancement in identified photoreceptors, we have investigated the effects of inhibiting protein synthesis during the application of the one-trial in vivo conditioning procedure. Anisomycin (1 microM) present during and after the conditioning trial blocked long-term enhancement without affecting the induction or expression of short-term enhancement. Application of a control compound, deacetylanisomycin (1 microM), or delaying the application of anisomycin until 1 hr after the conditioning trial did not block either long- or short-term enhancement. These results indicate that synthesis of proteins during or shortly after training may be a critical step in the formation of long-term memory of the associative experience.
2. Protein synthesis-dependent memory and neuronal enhancement in Hermissenda are contingent on parameters of training and retention
R R Ramirez, I A Muzzio, C C Gandhi, L D Matzel Learn Mem . 1998 Mar-Apr;4(6):462-77. doi: 10.1101/lm.4.6.462.
Following contiguous pairings of light and rotation, light alone elicits a conditioned contraction of Hermissenda's foot, indicative of an associative memory. After a 5-min retention interval, this conditioned response was evident following two or nine (but not one) conditioning trials but persisted for 90 min only after nine trials. In vivo incubation of animals in the protein synthesis inhibitor anisomycin (ANI; 1 microM) did not affect the conditioned response at the 5-min retention interval but significantly attenuated conditioned responding at the 90-min interval even following nine training trials. Deacetylanisomycin (DANI; 1 microM; an inactive form of anisomycin) had no effect on either 5- or 90-min retention. In a companion procedure, groups of isolated nervous systems were exposed to comparable light and rotation pairings, and the B photoreceptors (considered a site of storage for the associative memory) underwent electrophysiological analysis. An increase in neuronal excitability (indexed by depolarizing voltage responses to injected current) in the B photoreceptors paralleled the expression of conditioned responding in intact animals, that is, two training trials produced a short-term increase in excitability that dissipated within 45 min, whereas nine trials produced a persistent (at least 90-min) increase in excitability. In a fmal experiment, isolated nervous systems were exposed to nine training trials, and ANI or DANI was either present in the bathing medium before and during training or was introduced 5 min after training. Following training in ANI, a short-term (5- to 45-min) but not persistent (90-min) increase in excitability in the B photoreceptors was observed. ANI had no effect on either the short-term or persistent increase in excitability if the drug was applied 5 min after the last (ninth) training trial, and DANI had no effect on training-induced increases in excitability at any retention intervals. These results suggest that short-term retention in Hermissenda is protein synthesis independent but that new protein synthesis initiated during or shortly after the training event is necessary for even 90-min retention. Moreover, these results indicate that under some conditions, a critical threshold of training must be exceeded to initiate protein synthesis-dependent retention.
3. Requirement for protein synthesis in the regulation of a circadian rhythm by serotonin
A Eskin, M R Klass, S J Yeung Proc Natl Acad Sci U S A . 1984 Dec;81(23):7637-41. doi: 10.1073/pnas.81.23.7637.
Serotonin (5-HT, 5-hydroxytryptamine) regulates the phase of a circadian pacemaker located within the eye of Aplysia. We are attempting to define the cellular and biochemical events involved in the regulatory pathway through which serotonin acts. Previously, we have shown that an activation of adenylate cyclase and an increase in cAMP are events in the 5-HT phase-shifting pathway. In this paper, we examine the role of protein synthesis in mediating the effect of 5-HT and cAMP on the phase of the circadian rhythm. Exposure of eyes to anisomycin, an inhibitor of protein synthesis, completely blocked the advance shift in phase produced by 5-HT. Although anisomycin by itself can produce phase shifts, it did not affect the rhythm at the phases where the blocking experiments were performed. The specificity of action of anisomycin was investigated in two ways. First, deacetylanisomycin, an analogue of anisomycin that is inactive in inhibiting protein synthesis, did not affect the shift in phase produced by 5-HT. Second, anisomycin did not inhibit two other effects of 5-HT on the eye that also appear to be mediated by cAMP: an inhibition of spontaneous optic nerve activity and an increase in the photosensitivity of the eye. The step in the 5-HT phase-shifting pathway that is sensitive to anisomycin appears to occur after the cAMP step because anisomycin also inhibits the ability of 8-benzylthio-cAMP to shift the phase of the rhythm. We have also examined whether 5-HT directly regulates the synthesis of any proteins in the eye. Using two-dimensional gel electrophoresis, we have found that 5-HT appears to increase the synthesis of a protein with an apparent molecular weight of 67,000. Our results indicate that protein synthesis is necessary for 5-HT to shift the phase of the rhythm and that 5-HT appears to regulate the expression of at least one protein in the eye.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
