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9041-93-4 molecular structure
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(3-{[2-(2-{2-[(2R,3R)-2-[(2R,3R,4S)-4-[(2S)-2-({6-amino-2-[(1S)-1-{[(2R)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-{[(2S,3R,4R,5R,6R)-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-4-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium hydrogen sulfate

ChemBase ID: 72576
Molecular Formular: C55H85N17O25S4
Molecular Mass: 1512.6223
Monoisotopic Mass: 1511.47853531
SMILES and InChIs

SMILES:
S(=O)(=O)(O)[O-].[C@H](C(c1nc[nH]c1)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@@H]([C@H](C(=O)N[C@H]([C@@H](C)O)C(=O)NCCc1nc(cs1)c1nc(cs1)C(=O)NCCC[S+](C)C)C)O)C)NC(=O)c1nc(nc(c1C)N)[C@@H](NC[C@H](C(=O)N)N)CC(=O)N
Canonical SMILES:
[O-]S(=O)(=O)O.OC[C@H]1O[C@H](OC([C@@H](C(=O)N[C@H]([C@@H]([C@H](C(=O)N[C@@H](C(=O)NCCc2scc(n2)c2scc(n2)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/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(26-14-61-19-65-26)91-54-43(39(80)37(78)29(15-73)90-54)92-53-40(81)42(93-55(60)88)38(79)30(16-74)89-53)51(87)66-22(3)36(77)21(2)47(83)70-34(23(4)75)49(85)63-10-8-32-67-28(18-94-32)52-68-27(17-95-52)48(84)62-9-7-11-96(5)6;1-5(2,3)4/h14,17-19,21-25,29-30,34-43,53-54,64,73-75,77-81H,7-13,15-16,56H2,1-6H3,(H13-,57,58,59,60,61,62,63,65,66,69,70,71,72,76,82,83,84,85,86,87,88);(H2,1,2,3,4)/t21-,22+,23-,24-,25+,29-,30-,34-,35+,36-,37+,38-,39-,40+,41?,42+,43-,53-,54-;/m1./s1
InChIKey:
WUIABRMSWOKTOF-PATWWPTKSA-N

Cite this record

CBID:72576 http://www.chembase.cn/molecule-72576.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3-{[2-(2-{2-[(2R,3R)-2-[(2R,3R,4S)-4-[(2S)-2-({6-amino-2-[(1S)-1-{[(2R)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-{[(2S,3R,4R,5R,6R)-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-4-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium hydrogen sulfate
IUPAC Traditional name
(3-{[2-(2-{2-[(2R,3R)-2-[(2R,3R,4S)-4-[(2S)-2-({6-amino-2-[(1S)-1-{[(2R)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-{[(2S,3R,4R,5R,6R)-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-4-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium hydrogensulfate
Synonyms
Blenoxane
Bleomycin sulfate
CAS Number
9041-93-4
PubChem SID
162037501
PubChem CID
46930981

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S1214 external link Add to cart Please log in.
Data Source Data ID
PubChem 46930981 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 11.390325  H Acceptors 28 
H Donor 20  LogD (pH = 5.5) -8.810552 
LogD (pH = 7.4) -8.510408  Log P -9.312738 
Molar Refractivity 343.8348 cm3 Polarizability 132.3703 Å3
Polar Surface Area 627.07 Å2 Rotatable Bonds 36 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Storage Condition
-20°C expand Show data source
Target
DNA/RNA synthesis expand Show data source
Salt Data
Sulfate expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S1214 external link
Research Area
Description Cancer
Biological Activity
Description Bleomycin sulfate (Blenoxane) is a glycopeptide antibiotic and an anticancer agent for squamous cell carcinomas (SCC) with IC50 of 4 nM in UT-SCC-19A cells.
Targets UT-SCC-129 cells
IC50 4 nM [1]
In Vitro UT-SCC-12A and UT-SCC-12B are both more resistant to Bleomycin sulfate with IC50 of 14.2 nM and 13 nM, respectively. [1] Alveolar macrophages incubated with 0.01 μg/mL to 1μg /mL Bleomycin sulfate for 18 hours secretes significantly more fibroblast growth factor than macrophages incubated without Bleomycin sulfate. Macrophages stimulated with Bleomycin sulfate continues to produce significant amounts of fibroblast growth factor even after Bleomycin sulfate is removed and replaced with fresh (Bleomycin sulfate-free) media. Fibroblast growth factor secretion by Bleomycin sulfate-stimulated alveolar macrophages is inhibited by cycloheximide, and the 5-lipoxygenase inhibitors NDGA (nordihydroguairetic acid) and BW755c, indicating not only a requirement for protein synthesis but also for metabolites of the 5-lipoxygenase pathway of arachidonic acid metabolism for full expression of activity. [2] Bleomycin sulfate (400 μg/mL) incubation for 24 hours decreases the viability of NTera-2 cells, and increases caspase-3, -8 and -9 activities, Bax and cytoplasmic cytochrome c levels and decreases Bcl-2 levels. [3] In terms of unstable aberrations, the clastogenic effect of Bleomycin sulfate on ADIPO-P2 cells persists for at least 10 days after exposure. Bleomycin sulfate-induced telomere instability in mammalian cells persists for several generations after exposure. Moreover, the appearance of telomere fusions in Bleomycin sulfate-exposed cells 10 days after treatment suggests that Bleomycin sulfate can induce delayed telomere instability. [4]
In Vivo Day 7 post-Bleomycin sulfate, CD45+ cells in BALf in NOX-/- is 1.7-fold > WT, 57% of which are Mf that decreases by 67% in WT and 83% in NOX-/- by Day 21. [5]
Clinical Trials Bleomycin sulfate plus Rituximab, Doxorubicin, Vinblastine or Dacarbazine has entered phase II clinical trial hodgkin lymphoma.
Features
Combination Therapy
Description The combination of Cisplatin and Bleomycin sulfate with 5-fluorouracil produces synergistic and antagonistic genotoxic effects, depending on the concentrations used, which could impose a higher risk of secondary effects associated with their genotoxic effects. [6]
Protocol
Cell Assay [4]
Cell Lines ADIPO-P2 cells
Concentrations 2.5 μg/mL
Incubation Time 30 minutes
Methods ADIPO-P2 cells are grown in D-MEM high glucose medium supplemented with 20% fetal calf serum, penicillin (100 U/mL) and streptomycin (100 μg/mL) at 37 °C and 5% CO2 atmosphere. Cells are cultured as monolayer in TC25 Corning flasks containing 1.5 × 105 cells/mL. For each experiment, two flasks are set up, one for the control and one for the treated culture. During the log phase of growth ADIPO-P2 cells are treated with a 30 minutes pulse of 2.5 μg/mL of Bleomycin sulfate. Control cultures are set up in parallel but not exposed to Bleomycin sulfate. Time of exposure and concentration of Bleomycin sulfate are chosen according to previous studies carried out in our laboratory with mammalian cells exposed to Bleomycin sulfate. At the end of the pulse treatment with Bleomycin sulfate, the cells are washed twice with Hank's balanced salt solution and kept in culture with fresh culture medium until harvesting. Cells are continuously maintained in culture during 5 passages or subcultures after treatment. Subcultivation is carried out whenever the cultures became confluent (approximately 4 × 105 cells/mL of culture medium). To estimate cell growth, at the time of subcultivation cells are collected by trypsinization, an aliquot of about 200 μL stained with 0.4% trypan blue, and the number of viable cells is determined. Cells are then suspended in fresh culture medium and dispensed into new culture flasks containing 1 × 105 cells/mL to continue growing. The rest of the cells is discarded or dispensed in another flask for cytogenetic analysis, which is performed at 18 hours and 10 days after the end of treatments. To analyze chromosomal aberrations, colchicine (0.1 μg/mL) is added to cell cultures during the last 3 hours of culture. Chromosome preparations are made following standard procedures. After harvesting, cells are hypotonically shocked, fixed in methanol:acetic acid (3:1), spread onto glass slides and processed for PNA-FISH. Two independent experiments are carried out.
Animal Study [5]
Animal Models gp91phox-/- mice, mmp12-/- mice and C57BL6 mice
Formulation Saline
Doses 0.075 U/mL
Administration Administered via i.t.
References
[1] Jääskelä-Saari HA, et al. Acta Otolaryngol Suppl. 1997, 529, 241-244.
[2] Denholm EM, et al. Am J Pathol. 1989, 134(2), 355-363.
[3] Cort A, et al. Mol Med Report. 2012, 5(6), 1481-1486.
[4] Paviolo NS, et al. Mutat Res. 2012, 734(1-2), 5-11.
[5] Banerjee ER, et al. Stem Cell Res Ther. 2012, 3(3), 21.
[6] Danesi CC, et al. Mutat Res. 2012.

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PATENTS

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