WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H100090
CAS#: 9041-93-4 (sulfate)
Description: Bleomycin sulfate is a mixture of the sulfate salts of basic glycopeptide antineoplastic antibiotics isolated from Streptomyces verticillus. Bleomycin sulfate forms complexes with iron that reduce molecular oxygen to superoxide and hydroxyl radicals which cause single- and double-stranded breaks in DNA; these reactive oxygen species also induce lipid peroxidation, carbohydrate oxidation, and alterations in prostaglandin synthesis and degradation.
Hodoodo Cat#: H100090
Name: Bleomycin sulfate
CAS#: 9041-93-4 (sulfate)
Chemical Formula: C55H85N17O25S4
Exact Mass: 0.00
Molecular Weight: 1,512.620
Elemental Analysis: C, 43.67; H, 5.66; N, 15.74; O, 26.44; S, 8.48
Related CAS #: 9041-93-4 (sulfate) 11056-06-7 (free base)
Synonym: BLEO; BLM; BLEO cell; BLEO-cell; BLEOcell; Bleolem; Bleomycin sulfate; US brand name: Blenoxane. Blanoxan.
IUPAC/Chemical Name: (3-(2'-((3S,6R,7S,8S,11S)-1-(6-amino-2-((S)-3-amino-1-(((S)-2,3-diamino-3-oxopropyl)amino)-3-oxopropyl)-5-methylpyrimidin-4-yl)-3-((R)-(((2R,3S,4S,5S,6S)-3-(((2R,3S,4S,5R,6R)-4-(carbamoyloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)(1H-imidazol-4-yl)methyl)-7-hydroxy-11-((R)-1-hydroxyethyl)-6,8-dimethyl-1,4,9,12-tetraoxo-2,5,10,13-tetraazapentadecan-15-yl)-[2,5'-bithiazole]-4-carboxamido)propyl)dimethylsulfonium hydrogensulfate
InChi Key: BRDAHBLYMDUECM-QIMPUPMHSA-N
InChi Code: 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
SMILES Code: C[S+](CCCNC(C1=CSC(C2=CN=C(CCNC([C@H]([C@H](O)C)NC([C@@H](C)[C@H](O)[C@@H](C)NC([C@H]([C@@H](O[C@H]3[C@@H](O[C@@H]4[C@@H](O)[C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O4)[C@@H](O)[C@H](O)[C@H](CO)O3)C5=CNC=N5)NC(C6=NC([C@@H](NC[C@H](N)C(N)=O)CC(N)=O)=NC(N)=C6C)=O)=O)=O)=O)S2)=N1)=O)C.O=S(O)([O-])=O
Appearance: Solid powder
Purity: >90% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info: Bleomycin is a glycopeptide antibiotic produced by the bacterium Streptomyces verticillus. Bleomycin refers to a family of structurally related compounds. When used as an anticancer agent, the chemotherapeutical forms are primarily bleomycin A2 and B2. The drug is used in the treatment of Hodgkin's lymphoma (as a component of the ABVD and BEACOPP regimen), squamous cell carcinomas, and testicular cancer, as well as in the treatment of plantar warts and as a means of effecting pleurodesis. The mechanism of action involves breaking DNA. Bleomycin is on the World Health Organization's List of Essential Medicines that are needed for a basic health system. Mechanism of Action Although the exact mechanism of action of BLENOXANE is unknown, available evidence indicates that the main mode of action is the inhibition of DNA synthesis with some evidence of lesser inhibition of RNA and protein synthesis. Bleomycin is known to cause single, and to a lesser extent, double-stranded breaks in DNA. In in vitro and in vivo experiments, bleomycin has been shown to cause cell cycle arrest in G2 and in mitosis. When administered into the pleural cavity in the treatment of malignant pleural effusion, BLENOXANE acts as a sclerosing agent. Bleomycin sulfate Chemical Formula: C55H85N17O25S4 Molecular Weight: 1512.62 Elemental Analysis: C, 43.67; H, 5.66; N, 15.74; O, 26.44; S, 8.48 Bleomycin Chemical Formula: C55H84N17O21S3+ Exact Mass: 1414.5184 Molecular Weight: 1415.55 Elemental Analysis: C, 46.67; H, 5.98; N, 16.82; O, 23.73; S, 6.79
Biological target: | Bleomycin sulfate is a DNA synthesis inhibitor.It was revealed that the number of EdU-positive cells in BLM (Bleomycin) groups was notably smaller than that in the NC group, displaying less cell proliferation, suggesting that BLM inhibits the growth of glioma cells. In addition, the levels of inflammatory factors TNF-α and INF-γ were determined, so as to detect the incidence of glioma in the early stage. It was found that the NC group had remarkably higher levels than the other two groups, while the 10 mU/ mL BLM group had obviously declined levels, suggesting that 10 mU/mL BLM can inhibit the production of inflammatory factors, further repressing the occurrence of brain glioma. These findings imply that the increased TNF-α level can further stimulate the development of brain glioma, thus aggravating the inflammatory responses. However, the level declined after the treatment with BLM, indicating that the symptoms are improved after treatment with BLM, and that BLM has favorable therapeutic effects on brain glioma. Reference: J BUON. 2020 Mar-Apr;25(2):1076-1083. https://www.jbuon.com/archive/25-2-1076.pdf |
In vitro activity: | It was revealed that the number of EdU-positive cells in BLM (Bleomycin) groups was notably smaller than that in the NC group, displaying less cell proliferation, suggesting that BLM inhibits the growth of glioma cells. In addition, the levels of inflammatory factors TNF-α and INF-γ were determined, so as to detect the incidence of glioma in the early stage. It was found that the NC group had remarkably higher levels than the other two groups, while the 10 mU/ mL BLM group had obviously declined levels, suggesting that 10 mU/mL BLM can inhibit the production of inflammatory factors, further repressing the occurrence of brain glioma. These findings imply that the increased TNF-α level can further stimulate the development of brain glioma, thus aggravating the inflammatory responses. However, the level declined after the treatment with BLM, indicating that the symptoms are improved after treatment with BLM, and that BLM has favorable therapeutic effects on brain glioma. Reference: J BUON. 2020 Mar-Apr;25(2):1076-1083. https://www.jbuon.com/archive/25-2-1076.pdf |
In vivo activity: | The early changes in C (day 7) and P–V loop data (CST and area, day 7) were accompanied by histological evidence of fibrotic deposition and gene expression that were apparent as early as days 7 and 14, respectively. These results are significant because they demonstrate that low-dose systemic exposure to i.p. BLM (Bleomycin) is able to induce physiological and morphological changes as early as day 7 in C57BL/6 mice and indicate that lung function is a robust and physiologically relevant tool to guide future efforts in drug discovery for IPF. Reference: Exp Physiol. 2018 Dec;103(12):1692-1703. https://physoc.onlinelibrary.wiley.com/doi/full/10.1113/EP087322 |
Solvent | Max Conc. mg/mL | Max Conc. mM | |
---|---|---|---|
Solubility | |||
Soluble in DMSO, not in water | 0.0 | 100.00 |
The following data is based on the product molecular weight 1,512.62 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
---|---|---|---|
1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
Formulation protocol: | 1. Jin H, Luo C. Bleomycin inhibits proliferation and promotes apoptosis of brain glioma cells via TGF-β/Smad signaling pathway. J BUON. 2020 Mar-Apr;25(2):1076-1083. PMID: 32521909. 2. Headley L, Bi W, Wilson C, Collum SD, Chavez M, Darwiche T, Mertens TCJ, Hernandez AM, Siddiqui SR, Rosenbaum S, Johnston RA, Karmouty-Quintana H. Low-dose administration of bleomycin leads to early alterations in lung mechanics. Exp Physiol. 2018 Dec;103(12):1692-1703. doi: 10.1113/EP087322. Epub 2018 Oct 17. PMID: 30260066. |
In vitro protocol: | 1. Jin H, Luo C. Bleomycin inhibits proliferation and promotes apoptosis of brain glioma cells via TGF-β/Smad signaling pathway. J BUON. 2020 Mar-Apr;25(2):1076-1083. PMID: 32521909. |
In vivo protocol: | 1. Headley L, Bi W, Wilson C, Collum SD, Chavez M, Darwiche T, Mertens TCJ, Hernandez AM, Siddiqui SR, Rosenbaum S, Johnston RA, Karmouty-Quintana H. Low-dose administration of bleomycin leads to early alterations in lung mechanics. Exp Physiol. 2018 Dec;103(12):1692-1703. doi: 10.1113/EP087322. Epub 2018 Oct 17. PMID: 30260066. |
1: Li X, Lan Y, He Y, Liu Y, Luo H, Yu H, Song N, Ren S, Liu T, Hao C, Guo Y, Zhang L. Heparan Sulfate and Chondroitin Sulfate Glycosaminoglycans Are Targeted by Bleomycin in Cancer Cells. Cell Physiol Biochem. 2017;43(3):1220-1234. doi: 10.1159/000481763. Epub 2017 Oct 5. PMID: 28982096.
2: Lazo JS, Sebti SM. Bleomycin. Cancer Chemother Biol Response Modif. 1997;17:40-5. PMID: 9551207.
3: Lazo JS. Bleomycin. Cancer Chemother Biol Response Modif. 1999;18:39-45. PMID: 10800476.
4: Lester EP, Matz GJ. Bleomycin. Otolaryngol Head Neck Surg (1979). 1979 Jul- Aug;87(4):399-400. doi: 10.1177/019459987908700401. PMID: 92001.
5: Broughton A, Strong JE. Radioimmunoassay of bleomycin. Cancer Res. 1976 Apr;36(4):1418-21. PMID: 56999.
6: Povirk LF, Austin MJ. Genotoxicity of bleomycin. Mutat Res. 1991 Mar;257(2):127-43. doi: 10.1016/0165-1110(91)90022-n. PMID: 1706477.
7: McAloon C. Bleomycin sulfate in the treatment of mosaic plantar verrucae. J Foot Ankle Surg. 1997 Jan-Feb;36(1):70-1. doi: 10.1016/s1067-2516(97)80017-8. PMID: 9031033.
8: Eser M, Gökçeimam M, Eyvaz K, Tutal F, Geçer MÖ, Göktaş S, Uzun H, Kaptanoglu L, Kurt N. Effect of local bleomycin sulfate application on seroma formation in a rat mastectomy and axillary lymph node dissection model. Eur J Pharmacol. 2014 Jan 15;723:375-80. doi: 10.1016/j.ejphar.2013.10.067. Epub 2013 Nov 11. PMID: 24231620.
9: Umezawa H. Recent studies on bleomycin. Lloydia. 1977 Jan-Feb;40(1):67-81. PMID: 69246.
10: Lazo JS, Sebti SM. Bleomycin. Cancer Chemother Biol Response Modif. 1994;15:44-50. PMID: 7540032.
11: Buecker JW, Heaton CL. Bleomycin sulfate--postoperative intralesional usage for giant condylomata. J Dermatol Surg Oncol. 1985 Oct;11(10):972-3. doi: 10.1111/j.1524-4725.1985.tb01378.x. PMID: 2413094.
12: Saitta P, Krishnamurthy K, Brown LH. Bleomycin in dermatology: a review of intralesional applications. Dermatol Surg. 2008 Oct;34(10):1299-313. doi: 10.1111/j.1524-4725.2008.34281.x. Epub 2008 Jun 27. PMID: 18616538.
13: Rudders RA. Bleomycin: pulmonary toxicity. Ann Intern Med. 1973 Apr;78(4):618. doi: 10.7326/0003-4819-78-4-618_1. PMID: 4121001.
14: Adler S, Shimaoka K, Tsukada Y. Letter: Bleomycin toxicity. JAMA. 1976 Jun 28;235(26):2814. doi: 10.1001/jama.235.26.2814c. PMID: 58999.
15: Perez-Guerra F, Harkleroad LE, Walsh RE, Costanzi JJ. Acute bleomycin lung. Am Rev Respir Dis. 1972 Dec;106(6):909-13. doi: 10.1164/arrd.1972.106.6.909. PMID: 4118373.
16: Evans WE, Yee GC, Crom WR, Pratt CB, Green AA. Clinical pharmacology of bleomycin and cisplatin. Head Neck Surg. 1981 Nov-Dec;4(2):98-110. doi: 10.1002/hed.2890040204. PMID: 6171547.
17: Evans WE, Yee GC, Crom WR, Pratt CB, Green AA. Clinical pharmacology of bleomycin and cisplatin. Drug Intell Clin Pharm. 1982 Jun;16(6):448-58. doi: 10.1177/106002808201600602. PMID: 6178575.
18: Habs M, Schmähl D. Carcinogenicity of bleomycin sulfate and peplomycin sulfate after repeated subcutaneous application to rats. Oncology. 1984;41(2):114-9. doi: 10.1159/000225804. PMID: 6200809.
19: Sollitto RJ, Pizzano DM. Bleomycin sulfate in the treatment of mosaic plantar verrucae: a follow-up study. J Foot Ankle Surg. 1996 Mar- Apr;35(2):169-72. doi: 10.1016/s1067-2516(96)80036-6. PMID: 8722887.
20: Niitani H. [Bleomycin]. Gan To Kagaku Ryoho. 1987 Nov;14(11):3173-9. Japanese. PMID: 2445296.