Bleomycin A6
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| Category | Antibiotics |
| Catalog number | BBF-00161 |
| CAS | 37293-17-7 |
| Molecular Weight | 1497.65 |
| Molecular Formula | C60H96N20O21S2 |
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Description
Bleomycin is a glycopeptide anti-tumor antibiotic produced by Streptomyces verticillus B-80-Z2. It has anti-gram-positive bacteria, negative bacteria, and mycobacterial activity, and is particularly active against Mycobacterium phlei.
Specification
| Synonyms | zhengguangmycin A6 |
| IUPAC Name | [(2R,3S,4S,5R,6R)-2-[(2R,3S,4S,5S,6S)-2-[(1R,2S)-2-[[6-amino-2-[(1S)-3-amino-1-[[(2S)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[[(2R,3S,4S)-5-[[(2S,3R)-1-[2-[4-[4-[3-[4-(3-aminopropylamino)butylamino]propylcarbamoyl]-1,3-thiazol-2-yl]-1,3-thiazol-2-yl]ethylamino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-hydroxy-4-methyl-5-oxopentan-2-yl]amino]-1-(1H-imidazol-5-yl)-3-oxopropoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] carbamate |
| Canonical SMILES | CC1=C(N=C(N=C1N)C(CC(=O)N)NCC(C(=O)N)N)C(=O)NC(C(C2=CN=CN2)OC3C(C(C(C(O3)CO)O)O)OC4C(C(C(C(O4)CO)O)OC(=O)N)O)C(=O)NC(C)C(C(C)C(=O)NC(C(C)O)C(=O)NCCC5=NC(=CS5)C6=NC(=CS6)C(=O)NCCCNCCCCNCCCN)O |
| InChI | InChI=1S/C60H96N20O21S2/c1-25-38(77-51(80-49(25)64)30(17-36(63)84)72-18-29(62)50(65)90)55(94)79-40(46(31-19-69-24-73-31)99-59-48(44(88)42(86)34(20-81)98-59)100-58-45(89)47(101-60(66)96)43(87)35(21-82)97-58)56(95)74-27(3)41(85)26(2)52(91)78-39(28(4)83)54(93)71-16-9-37-75-33(23-102-37)57-76-32(22-103-57)53(92)70-15-8-14-68-12-6-5-11-67-13-7-10-61/h19,22-24,26-30,34-35,39-48,58-59,67-68,72,81-83,85-89H,5-18,20-21,61-62H2,1-4H3,(H2,63,84)(H2,65,90)(H2,66,96)(H,69,73)(H,70,92)(H,71,93)(H,74,95)(H,78,91)(H,79,94)(H2,64,77,80)/t26-,27+,28+,29-,30-,34-,35+,39-,40-,41-,42+,43+,44-,45-,46-,47-,48-,58+,59-/m0/s1 |
| InChI Key | FOUFFVYWFNBHHH-YNGSZULRSA-N |
Properties
| Appearance | White to off-white Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycobacteria |
| Melting Point | 169°C(dec.) |
| Density | 1.53 g/cm3 |
| Solubility | Soluble in Methanol, water |
Reference Reading
1. Bleomycin A6-loaded anionic liposomes with in situ gel as a new antitumoral drug delivery system
Weiming Ding, Yanfang Li, Xucheng Hou, Guiling Li Drug Deliv. 2016;23(1):88-94. doi: 10.3109/10717544.2014.905651. Epub 2015 Sep 4.
The goal is to develop an in situ gel system comprising anionic liposomes (AL) containing bleomycin A6 (BLM A6) dispersed within the thermosensitive in situ gel for sustained release. The results indicated that the gelation temperature decreased due to AL within gel. Similarly, viscosity and mechanical parameters, such as gel strength for gel, could be enhanced by inducing lipid material with negative charge (phosphatidylglycerol) at 37 °C, which provided against corrosion at physiological condition. The in vitro release experiments performed with a dialysis method revealed that in situ gel with AL exhibited the longer drug-release period compared to that with or without nonionic liposomes. An in vivo fluorescence imaging study suggested that the gel with AL loading FITC-BLM A6 stayed in administration site at least for five days. A thermosensitive in situ gel with anionic liposome was a promising carrier for hydrophilic BLM A6, to be used in parenteral delivery system for anti-tumor treatment.
2. [Effects of 764-3 on the organization and function of microtubules and microfilaments in bleomycin A6 activated rat alveolar macrophages]
H Zhang Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 1993 Aug;15(4):306-10.
Using bleomycin A6 (BLM A6) to stimulate normal and 764-3 pretreated alveolar macrophages (AM) in vitro, the distributions of microtubules (MTs) and microfilaments (MFs) were examined with an immunofluorescence microscope. Fluorescent strength was determined with a spectrophotometer and fluorospectrophotometer, and the adhering and spreading rates were determined. The results showed that BLM A6-stimulated AM spread fully and MTs increased markedly, forming a thick network in the cytoplasm. Much punctate and linear fluorescence was visible beneath the plasma membrane, these fluorescing structures were MFs. In the experimental cells MT and MF fluorescence was stronger than that in the control group. However, most of the above changes were reduced in the 764-3 pretreatment group. These results suggest that BLM A6 may promote the assembly and regulate reorganization of MTs and MFs, while 764-3 can stabilize these structures.
3. [Experimental studies on therapeutic effect of rat monoclonal antibody-bleomycin A6 conjugate against human colorectal cancer]
Y C Deng, Y S Zhen, S Zheng, M Jiang Yao Xue Xue Bao. 1993;28(6):410-5.
Bleomycin A6 (A6), a single component of bleomycin complex, is highly active against human colon and cecum cancer cells in vitro and xenografts in nude mice. R19, a rat monoclonal antibody against human cecum cancer Hce-8693 cells, was linked to A6. R19-A6 conjugate retained complete activity of McAb R19 and 10% activity of A6. As determined by clonogenic assay with human cecum cancer Hce-8693 cells for 1 hour exposure. The 50% inhibitory concentration (IC50) values for R19-A6, A6 and M3-A6 (conjugate of irrelevant Mc-A6) were 0.019, 1.05 and 1.00 mumol/L, respectively. The effect of the conjugate R19-A6 was 55-fold stronger than that of free A6 and 53-fold than irrelevant conjugate M3-A6. Clonogenic assay with human colon cancer HT-29 cells showed that the IC50 values were 0.078 mumol/L and 4.0 mumol/L for R19-A6 and free A6, respectively. The cytotoxicity to Hce-8693 and HT-29 cells was markedly blocked by unconjugated McAb R19 but not by irrelevant McAb MARK-3. The R19-A6 conjugate exerted 90% inhibition on the growth of cecum cancer Hce-8693 xenografts in nude mice, whereas equivalent doses of free A6, R19 plus A6 mixture and M3-A6 showed 52%, 34% and 48% inhibition, respectively. Histopathological examination showed no toxic changes in the heart, lung, liver, kidney and bone marrow in the R19-A6 conjugate treated animals.
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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 ╳
