bis((3-{[2-(2-{2-[(2R,3R)-2-[(2S,3S,4R)-4-[(2R,3R)-2-({6-amino-2-[(1S)-1-{[(2S)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-{[(2R,3S,4S,5S,6S)-3-{[(2S,3S,4R,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-4-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-5-yl]formamido}propyl)dimethylsulfanium) sulfate

• ChemBase ID: 134168
• Molecular Formular: C110H168N34O46S7
• Molecular Mass: 2927.16612
• Monoisotopic Mass: 2924.98969107
• SMILES: Cc1c(nc(nc1N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)C(=O)N[C@H]([C@H](c1c[nH]cn1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)O[C@H]1[C@H]([C@@H]([C@@H]([C@H](O1)CO)O)OC(=O)N)O)C(=O)N[C@H](C)[C@H]([C@H](C)C(=O)N[C@H]([C@@H](C)O)C(=O)NCCc1nc(cs1)c1ncc(s1)C(=O)NCCC[S+](C)C)O.Cc1c(nc(nc1N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)C(=O)N[C@H]([C@H](c1c[nH]cn1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)O[C@H]1[C@H]([C@@H]([C@@H]([C@H](O1)CO)O)OC(=O)N)O)C(=O)N[C@H](C)[C@H]([C@H](C)C(=O)N[C@H]([C@@H](C)O)C(=O)NCCc1nc(cs1)c1ncc(s1)C(=O)NCCC[S+](C)C)O.[O-]S(=O)(=O)[O-]
• Canonical SMILES: [O-]S(=O)(=O)[O-].OC[C@@H]1O[C@@H](O[C@H]([C@H](C(=O)N[C@@H]([C@H]([C@@H](C(=O)N[C@@H](C(=O)NCCc2scc(n2)c2ncc(s2)C(=O)NCCC[S+](C)C)[C@H](O)C)C)O)C)NC(=O)c2nc(nc(c2C)N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)c2nc[nH]c2)[C@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@H]([C@@H]1O)OC(=O)N)O.OC[C@@H]1O[C@@H](O[C@H]([C@H](C(=O)N[C@@H]([C@H]([C@@H](C(=O)N[C@@H](C(=O)NCCc2scc(n2)c2ncc(s2)C(=O)NCCC[S+](C)C)[C@H](O)C)C)O)C)NC(=O)c2nc(nc(c2C)N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)c2nc[nH]c2)[C@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@H]([C@@H]1O)OC(=O)N)O
• InChI: InChI=1S/2C55H83N17O21S3.H2O4S/c2*1-20-33(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)63-10-8-32-68-27(18-94-32)52-65-15-30(95-52)48(84)62-9-7-11-96(5)6;1-5(2,3)4/h2*14-15,18-19,21-25,28-29,34-43,53-54,64,73-75,77-81H,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)/t2*21-,22+,23+,24-,25-,28-,29+,34+,35+,36-,37+,38+,39-,40-,41-,42+,43-,53-,54-;/m00./s1
• InChIKey: OOXTWFJZZAJGKA-CNLAFNBISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis((3-{[2-(2-{2-[(2R,3R)-2-[(2S,3S,4R)-4-[(2R,3R)-2-({6-amino-2-[(1S)-1-{[(2S)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-{[(2R,3S,4S,5S,6S)-3-{[(2S,3S,4R,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-4-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-5-yl]formamido}propyl)dimethylsulfanium) sulfate
• IUPAC Traditional name: bis((3-{[2-(2-{2-[(2R,3R)-2-[(2S,3S,4R)-4-[(2R,3R)-2-({6-amino-2-[(1S)-1-{[(2S)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-{[(2R,3S,4S,5S,6S)-3-{[(2S,3S,4R,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-4-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-5-yl]formamido}propyl)dimethylsulfanium) sulfate
• Synonyms: Blenoxane; Bleo; Blexane; Bleomycin sulfate from Streptomyces verticillus

Database IDs

• CAS Number: 9041-93-4
• EC Number: 232-925-2
• MDL Number: MFCD00070310
• PubChem SID: 24891950; 24891650; 24891839; 24849358; 162228445
• PubChem CID: 16211317

CALCULATED PROPERTIES

• Acid pKa: 11.360471
• H Acceptors: 28
• H Donor: 20
• LogD (pH = 5.5): -9.024068
• LogD (pH = 7.4): -8.7239275
• Log P: -9.526255
• Molar Refractivity: 343.9909 cm^3
• Polarizability: 132.37552 Å^3
• Polar Surface Area: 627.07 Å^2
• Rotatable Bonds: 72
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble20 mg/mL; H2O: soluble20 mg/mL, clear, colorless
• Apperance: crystalline; white crystalline; white powder

Safety Information

• RTECS: EC5991990
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 46-40
• Safety Statements: 36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Product Information

• Grade: for fluorescence
• Potency: 1.5-2.0 units per mg
• Suitability: suitable for cell culture
• Cation Traces: Cu: <0.1%; Cu: ≤0.10%; Cu: ≤1000 mg/kg
• Quality: lyophilized
• Product Line: BioXtra

DETAILS

Sigma Aldrich - B2434

Application
Recommended for use as a selection agent at 10-100 μg/ml.
Bleomycin is used as a transformed cell selection agent, especially for plant transformants. Recommended for use at 10-100 g/ml. It is also used to induce pulmonary fibrosis and epithelial cell apoptosis. 1,2,3
Biochem/physiol Actions
An antineoplastic antibiotic isolated from Streptomyces verticillus. Binds to DNA, inhibits DNA synthesis and causes DNA scissions at specific base sequences. Needs to bind oxygen and a metal ion such as copper or iron to cleave DNA. Highly selective cleavage of RNA. Inducer and regulator of apoptosis in a variety of cells. Inhibits tumor angiogenesis.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 15361

Application
Recommended for use as a selection agent at 10-100 μg/ml.
Bleomycin sulfate is used to study tumor-specific cytotoxic activity in certain cell lines such as human normal oral cells(gingival fibrobast HGF, pulp cell HPC and periodontal ligament fibroblast HPLF), human oral squamous cell carcinoma (HSC-2, HSC-3, HSC-4, Ca9-22 and NA) and human promyelocytic leukemia HL-60 cells1. It is used to study free radical-mediated mechanisms of DNA strand scission/breaking and as a transformed cell selection agent, especially for plant transformants. Recommended for use as a selection agent at 10-100 μg/ml.
Other Notes
DNA degradation2,3; Action mechanism, minireview4
Biochem/physiol Actions
An antineoplastic antibiotic isolated from Streptomyces verticillus. Binds to DNA, inhibits DNA synthesis and causes DNA scissions at specific base sequences. Needs to bind oxygen and a metal ion such as copper or iron to cleave DNA. Highly selective cleavage of RNA. Inducer and regulator of apoptosis in a variety of cells. Inhibits tumor angiogenesis.

Sigma Aldrich - B8416

Application
Recommended for use as a selection agent at 10-100 μg/ml.
Other Notes
A mixture of bleomycin sulfate salts
Biochem/physiol Actions
An antineoplastic antibiotic isolated from Streptomyces verticillus. Binds to DNA, inhibits DNA synthesis and causes DNA scissions at specific base sequences. Needs to bind oxygen and a metal ion such as copper or iron to cleave DNA. Highly selective cleavage of RNA. Inducer and regulator of apoptosis in a variety of cells. Inhibits tumor angiogenesis.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - B5507

Application
Recommended for use as a selection agent at 10-100 μg/ml.
Other Notes
A mixture of bleomycin sulfate salts
Biochem/physiol Actions
An antineoplastic antibiotic isolated from Streptomyces verticillus. Binds to DNA, inhibits DNA synthesis and causes DNA scissions at specific base sequences. Needs to bind oxygen and a metal ion such as copper or iron to cleave DNA. Highly selective cleavage of RNA. Inducer and regulator of apoptosis in a variety of cells. Inhibits tumor angiogenesis.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information