Bleomycin sulfate
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| Category | Antibiotics |
| Catalog number | BBF-04214 |
| CAS | 9041-93-4 |
| Molecular Weight | 1415.60 (free base) |
| Molecular Formula | C55H84N17O21S3.xH2SO4 |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04214 | 100 mg | $1099 | In stock |
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Add to cartDescription
Bleomycin sulfate is a glycopeptide antibiotic isolated from streptomyces verticillus. It intercalates and cleaves DNA and RNA, resulting in their synthesis suppression, which can be used as an antineoplastic agent.
Specification
| Synonyms | Blexane; Blenoxane; Bleomycin sulfate salt |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | 3-[[2-[2-[2-[[(2S,3R)-2-[[(2S,3S,4R)-4-[[(2S,3R)-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,5S,6S)-3-[(2R,3S,4S,5R,6R)-4-carbamoyloxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxy-2-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]ethyl]-1,3-thiazol-5-yl]-1,3-thiazole-4-carbonyl]amino]propyl-dimethylsulfanium;hydrogen sulfate |
| 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=C(S5)C6=NC(=CS6)C(=O)NCCC[S+](C)C)O.OS(=O)(=O)[O-] |
| InChI | InChI=1S/C55H83N17O21S3.H2O4S/c1-20-33(69-46(72-44(20)58)25(12-31(57)76)64-13-24(56)45(59)82)50(86)71-35(41(26-14-61-19-66-26)91-54-43(39(80)37(78)28(16-73)90-54)92-53-40(81)42(93-55(60)88)38(79)29(17-74)89-53)51(87)67-22(3)36(77)21(2)47(83)70-34(23(4)75)49(85)63-10-8-32-65-15-30(95-32)52-68-27(18-94-52)48(84)62-9-7-11-96(5)6;1-5(2,3)4/h14-15,18-19,21-25,28-29,34-43,53-54,64,73-75,77-81H,7-13,16-17,56H2,1-6H3,(H13-,57,58,59,60,61,62,63,66,67,69,70,71,72,76,82,83,84,85,86,87,88);(H2,1,2,3,4)/t21-,22+,23+,24-,25-,28-,29+,34-,35-,36-,37+,38+,39-,40-,41-,42-,43-,53+,54-;/m0./s1 |
| InChI Key | BRDAHBLYMDUECM-QIMPUPMHSA-N |
Properties
| Appearance | Off-white Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Melting Point | >170°C (dec.) |
| Solubility | Soluble in Water, Methanol |
| LogP | -4.20880 |
Reference Reading
1. Nano-designed CO donor ameliorates bleomycin-induced pulmonary fibrosis via macrophage manipulation
Cheng Zhang, Shichen Zhang, Mizhen Xia, Bingdong Song, Dexiang Xu, Chunyu Guo, Yanni Xue, Yingying Cui, Zhengmei Xia, Weirong Hu, Jun Fang J Control Release . 2022 Jan;341:566-577. doi: 10.1016/j.jconrel.2021.11.047.
Idiopathic pulmonary fibrosis (IPF) is a progressive and irreversible interstitial pulmonary disease due to chronic inflammatory responses. The prognosis of IPF is very poor, however, the therapeutic options are very limited. Previously we developed a polymeric micellar drug delivery system of carbon monoxide (CO) that is a pivotal anti-inflammatory gaseous molecule, i.e., SMA/CORM2, which exhibited therapeutic potentials against dextran sulfate sodium (DSS)-induced mouse colitis and acetaminophen (APAP) induced liver injury. Along this line, here we investigate the applicability of SMA/CORM2 on IPF using a bleomycin (BLM)-induced pulmonary fibrosis model. Severe inflammation and the consequent pulmonary fibrosis were triggered by BLM, whereas SMA/CORM2 treatment remarkably suppressed the inflammation progression and ameliorated the formation of fibrosis. CO is the effector molecule of SMA/CORM2, which exerted the therapeutic/protective effect mostly through suppressing the reprogramming of anti-inflammatory macrophages as revealed by the decreased expressions of CD206 and arginase-1 that were remarkably upregulated by BLM exposure. The suppression of macrophage polarization accompanied the downregulated hypoxia-inducible factor-1α (HIF-1α) and its target molecule heme oxygenase-1 (HO-1), suggesting a HIF-1α/HO-1 pathway for modulating macrophage reprogramming. As the downstream event of anti-inflammatory macrophage polarization, the alveolar epithelial to mesenchymal transition that is the major source of myofibroblast, the hallmark of IPF, was significantly suppressed by SMA/CORM2 via a TGF-β/Smad2/3 pathway. Compared to native CORM2 of equivalent dose, SMA/CROM2 exhibited a much better protective effect indicating its superior bioavailability as an enhanced permeability and retention (EPR) effect-based nanomedicine. We thus anticipate the application of SMA/CORM2 as a therapeutic candidate for IPF as well as other inflammatory diseases and disorders.
2. Heparan Sulfate and Chondroitin Sulfate Glycosaminoglycans Are Targeted by Bleomycin in Cancer Cells
Heng Luo, Lijuan Zhang, Sumei Ren, Yanli He, Xiulian Li, Ying Lan, Ni Song, Cui Hao, Yong Liu, Haibo Yu, Tianwei Liu, Yunliang Guo Cell Physiol Biochem . 2017;43(3):1220-1234. doi: 10.1159/000481763.
Background/aims:Bleomycin is a clinically used anti-cancer drug that produces DNA breaks once inside of cells. However, bleomycin is a positively charged molecule and cannot get inside of cells by free diffusion. We previously reported that the cell surface negatively charged glycosaminoglycans (GAGs) may be involved in the cellular uptake of bleomycin. We also observed that a class of positively charged small molecules has Golgi localization once inside of the cells. We therefore hypothesized that bleomycin might perturb Golgi-operated GAG biosynthesis.Methods:We used stable isotope labeling coupled with LC/MS analysis of GAG disaccharides simultaneously from bleomycin-treated and non-treated cancer cells. To further understand the cytotoxicity of bleomycin and its relationship to GAGs, we used sodium chlorate to inhibit GAG sulfation and commercially available GAGs to compete for cell surface GAG/bleomycin interactions in seven cell lines including CHO745 defective in both heparan sulfate and chondroitin sulfate biosynthesis.Results:we discovered that heparan sulfate GAG was significantly undersulfated and the quantity and disaccharide compositions of GAGs were changed in bleomycin-treated cells in a concentration- and time-dependent manner. We revealed that bleomycin-induced cytotoxicity was directly related to cell surface GAGs.Conclusion:GAGs were targeted by bleomycin both at cell surface and at Golgi. Thus, GAGs might be the biological relevant molecules that might be related to the bleomycin-induced fibrosis in certain cancer patients, a severe side effect with largely unknown molecular mechanism.
3. Intralesional bleomycin sulfate injection for the treatment of verruca plantaris
Robert Salk, Troy S Douglas J Am Podiatr Med Assoc . 2006 May-Jun;96(3):220-5. doi: 10.7547/0960220.
Sixty-two patients were treated for single or multiple warts by intralesional injection of bleomycin sulfate (1.5 U/mL) and then were observed for 6 months. The dose varied according to the size of the lesion and ranged from 0.25 to 1.0 mL per injection per lesion, up to a maximum dose of 3 mL. The total cure rate was 87% after one or two injections. Twelve of the 62 patients required a second injection.
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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 ╳
