Anthramycin
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| Category | Antibiotics |
| Catalog number | BBF-00696 |
| CAS | 4803-27-4 |
| Molecular Weight | 315.32 |
| Molecular Formula | C16H17N3O4 |
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Description
It is produced by the strain of Streptomyces refuineus var. thermotolerans. It has a weak activity against gram-negative bacteria, and has the effect of inhibiting metamorphoses, vaginal trichomonas and rat tube nematode. It has inhibitory effect on sarcoma 180, L-1210, CA-755, Ascitic ascites type and solid type cancer.
Specification
| Synonyms | Antramycin; ANTHRAMYCIN; Antibiotic PBA; (E)-5,10,11,11a-Tetrahydro-9,11-dihydroxy-8-methyl-5-oxo-1H-pyrrolo(2,1-c)(1,4)-benzodiazepine-2-acrylamide; 3-(9,11-dihydroxy-8-methyl-5-oxo-5,10,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-2-yl)-acrylamide |
| IUPAC Name | (E)-3-(4,6-dihydroxy-3-methyl-11-oxo-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-8-yl)prop-2-enamide |
| Canonical SMILES | CC1=C(C2=C(C=C1)C(=O)N3C=C(CC3C(N2)O)C=CC(=O)N)O |
| InChI | InChI=1S/C16H17N3O4/c1-8-2-4-10-13(14(8)21)18-15(22)11-6-9(3-5-12(17)20)7-19(11)16(10)23/h2-5,7,11,15,18,21-22H,6H2,1H3,(H2,17,20)/b5-3+ |
| InChI Key | VGQOVCHZGQWAOI-HWKANZROSA-N |
Properties
| Appearance | Yellow Small Rhombic Crystal |
| Antibiotic Activity Spectrum | Gram-negative bacteria; neoplastics (Tumor); parasites |
| Boiling Point | 679.9 °C at 760 mmHg |
| Melting Point | 188-194 °C (dec.) |
| Density | 1.505 g/cm3 |
| Solubility | Soluble in Acetonitrile, DMF |
Reference Reading
1. Sensitivity and permeability of the anthramycin producing organism Streptomyces refuineus to anthramycin and structurally related antibiotics
L H Hurley, J S Rokem J Antibiot (Tokyo) . 1981 Sep;34(9):1171-4. doi: 10.7164/antibiotics.34.1171.
Streptomyces refuineus, the microorganism which produces the DNA reactive antibiotic anthramycin, has shown to possess a quite specific mechanism to survive and grow in the presence of this antibiotic. Stationary phase cells are insensitive to anthramycin since the antibiotic is prevented form entering these cells. However, cells in early log phase are inhibited by concentrations of anthramycin that are later produced by these same cells. Significantly, sibiromycin, a closely related antibiotic, is taken up by cells of S. refuineus independent of the age of the culture. Anthramycin reacts in vitro equally as well as DNA isolated from S. refuineus and other procaryotic and eucaryotic cells. When S. refuineus has reached the production phase the anthramycin is probably biosynthesized outside the cell membrane which also becomes specifically impermeable to anthramycin.
2. Topical delivery of anthramycin I. Influence of neat solvents
Jonathan Hadgraft, Tasnuva Haque, David E Thurston, Majella E Lane, Khondaker M Rahman Eur J Pharm Sci . 2017 Jun 15;104:188-195. doi: 10.1016/j.ejps.2017.03.043.
Anthramycin (ANT) was the first pyrrolobenzodiazepine (PBD) molecule to be isolated, and is a potent cytotoxic agent. Although the PBD family has been investigated for use in systemic chemotherapy, their application in the management of actinic keratoses (AK) or skin cancer has not been investigated to date. In the present work, anthramycin (ANT) was selected as a model PBD compound, and the skin penetration of the molecule was investigated using conventional Franz diffusion cells. Finite dose permeation studies of ANT were performed using propylene glycol (PG), 1,3-butanediol (BD), dipropylene glycol (DiPG), Transcutol P® (TC), propylene glycol monocaprylate (PGMC), propylene glycol monolaurate (PGML) and isopropyl myristate (IPM). The skin penetration of BD, DiPG, PG and TC was also measured. Penetration of ANT through human skin was evident for TC, PG and PGML with the active appearing to "track" the permeation of the vehicle in the case of TC and PG. Deposition of ANT in skin could be correlated with skin retention of the vehicle in the case of IPM, PGMC and PGML. These preliminary findings confirm the ability of ANT to penetrate human skin and, given the potency of the molecule, suggest that further investigation is justified. Additionally, the findings emphasise the critical importance of understanding the fate of the excipient for the rational design of topical formulations.
3. Topical delivery of anthramycin II. Influence of binary and ternary solvent systems
Jonathan Hadgraft, Tasnuva Haque, David E Thurston, Majella E Lane, Khondaker Miraz Rahman Eur J Pharm Sci . 2018 Aug 30;121:59-64. doi: 10.1016/j.ejps.2018.05.002.
Anthramycin (ANT) is a member of the pyrolobenzodiazepine family and is a potent cytotoxic agent. Previously, we reported the topical delivery of ANT from a range of solvents that may also act as skin penetration enhancers (SPEs). The skin penetration and uptake was monitored for simple solutions of ANT in propylene glycol (PG), dipropylene glycol (DiPG), Transcutol P (TC), isopropyl myristate (IPM), propylene glycol monocaprylate (PGMC) and propylene glycol monolaurate (PGML). The amounts of PG, DiPG and TC that were taken up by, and that penetrated the skin were also measured, with a clear dependence of ANT penetration on the rate and extent of PG and TC permeation. The present work investigates ANT skin delivery from a range of binary and ternary systems to determine any potential improvement in skin uptake compared with earlier results for the neat solvents. Following miscibility and stability studies a total of eight formulations were taken forward for evaluation in human skin in vitro. Binary systems of PG and water did not result in any skin permeation of ANT. Combining PG with either PGMC or PGML did promote skin penetration of ANT but no significant improvement was evident compared with PG alone. More complex ternary systems based on PG, DiPG, PGMC, PGML and water also did not show significant improvements on ANT permeation, compared with single solvents. Total skin penetration and retention of ANT ranged from 1 to 6% across all formulations studied. Where ANT was delivered to the receptor phase there were also high amounts of PG permeation with >50% and ~35% PG present for the binary systems and ternary vehicles, respectively. These findings along with our previous paper confirm PG as a suitable solvent / SPE for ANT either alone or in combination with PGML or PGMC. The results also underline the necessity for empirical testing to determine whether or not a vehicle is acting as a SPE for a specific active in a topical formulation.
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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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
