Calvatic acid
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00599 |
| CAS | 54723-08-9 |
| Molecular Weight | 191.14 |
| Molecular Formula | C8H5N3O3 |
Online Inquiry
Description
Calvatic acid is an antibiotic produced by Calvatia craniformis (Shw.) Fr. It has anti-gram-positive and negative bacteria (weak) activity, and inhibits Yoshida sarcoma and L-1210 cell activity.
Specification
| Synonyms | p-Carboxyphenylazoxycyanide; Benzoic acid, 4-(cyano-NNO-azoxy)- |
| IUPAC Name | (4-carboxyphenyl)-cyanoimino-oxidoazanium |
| Canonical SMILES | C1=CC(=CC=C1C(=O)O)[N+](=NC#N)[O-] |
| InChI | InChI=1S/C8H5N3O3/c9-5-10-11(14)7-3-1-6(2-4-7)8(12)13/h1-4H,(H,12,13) |
| InChI Key | LDRFVNKBORCKQS-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor) |
| Boiling Point | 399.1°C at 760 mmHg |
| Melting Point | 182-183°C(dec.) |
| Density | 1.39 g/cm3 |
| Solubility | Soluble in methanol, ethanol, acetone, DMSO, ethyl acetate, chloroform, ether |
Reference Reading
1. Inhibition of human placenta glutathione transferase P1-1 by the antibiotic calvatic acid and its diazocyanide analogue--evidence for multiple catalytic intermediates
G Antonini, G Pitari, A M Caccuri, G Ricci, D Boschi, R Fruttero, A Gasco, P Ascenzi Eur J Biochem. 1997 May 1;245(3):663-7. doi: 10.1111/j.1432-1033.1997.00663.x.
The inhibition mechanism of the dimeric human placenta glutathione transferase (GST) P1-1 by calvatic acid and the reaction intermediates, i.e. the diazocyanide analogue of calvatic acid, has been investigated at pH 7.0 and 30.0 degrees C. Experiments performed at different molar ratios of inhibitor/GST P1-1 indicate that 1 mol calvatic acid inactivates 1 mol GST P1-1, containing two catalytically equivalent active sites. However, 2 mol of the diazocyanide analogue of calvatic acid inactivate 1 mol GST P1-1. Two disulfide bridges/dimer, probably between Cys47 and Cys101, have been formed during the reaction of GST P1-1 with calvatic acid and its diazocyanide analogue. The apparent second-order rate constants for GST P1-1 inactivation by calvatic acid and its diazocyanide analogue are 2.4+/-0.3 M(-1) s(-1) and (8.5+/-0.7) x 10(3) M(-1) s(-1), respectively. The reaction of calvatic acid with free L-cysteine can be described by a simple process with an apparent second-order rate constant of (5.0+/-0.4) x 10(1) M(-1) s(-1). In contrast, a transient species occurs during the reaction of the diazocyanide analogue of calvatic acid with free L-cysteine. Kinetics may be described by a second-order process [the rate constant being (8.0+/-0.5) x 10(3) M(-1) s(-1)] followed by a first-order decay [the rate constant corresponding to (1.2+/-0.1) x 10(1) s(-1)]. Calvatic acid represents an enzyme inhibitor acting much slower than its reaction intermediates (i.e. its diazocyanide analogue).
2. Interactions between calvatic acid and related compounds with rat liver microsomes
A Miglietta, E Gadoni, M Buffa, A Olivero, L Gabriel Eur J Drug Metab Pharmacokinet. 1995 Oct-Dec;20(4):249-54. doi: 10.1007/BF03190240.
In this study we examined the interactions of liver microsomes with the antibiotic calvatic acid and with structural analogues, some of which had shown antimicrotubular properties. These drugs decreased cytochrome P-450 content differently according to the substitutions on the azoxy function and the ethoxycarbonyl derivatives were found to be the most effective ones. The decrease in cytochrome P-450 could be prevented by addition of cysteine or GSH, suggesting an involvement of sulphydryl groups. Furthermore, chromatographic analyses showed that ethoxycarbonyl derivatives were completely metabolized, and this would explain the different behaviour of these compounds towards microtubular protein when they were incubated with purified bovine brain protein or with liver or hepatoma extracts.
3. Antimicrotubular effect of calvatic acid and of some related compounds
E Gadoni, L Gabriel, A Olivero, C Bocca, A Miglietta Cell Biochem Funct. 1995 Dec;13(4):231-8. doi: 10.1002/cbf.290130403.
A structure-activity relationship has been established between calvatic acid and some related synthetic compounds, and their ability to inhibit GTP-induced microtubular protein polymerization in vitro. These compounds were effective in a dose- and a time-dependent manner. The most active drug was the p-chloro substituted compound, which showed its inhibitory activity without any preincubation period, which the others needed. Since if cysteine was present, polymerization was no longer affected, an involvement of titratable -SH groups of tubulin could be suggested. In contrast, taxol-induced polymerization was only slightly inhibited by these compounds, and colchicine-binding activity was not generally impaired.
Recommended Products
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
