CAS Number143-67-9
Synonymsvinbalastine; Velsar; EINECS 205-606-0; Vincaleukoblastine, (2'β)-, sulfate (1:1); VLB; velbe; velban; Vinblastine-d3; (2'β)-Vincaleukoblastine sulfate (1:1); Periblastine; vincaleukoblastine, (3β,4'β)-, sulfate (1:1); VLB Vincaleukoblastine sulfate salt; (+)-vinblastine; Vinblastine (sulfate); Vinblastine sulfate; Vincaleukoblastine sulfate salt; MFCD00082457; exal; rozevinsulfate
Molecular FormulaC46H60N4O13S
Molecular Weight909.05
Purity96-102 (HPLC)%
Density1.37 g/cm3
Melting Point267 °C (dec.) (lit.)
Appearancepowder
EINECS205-606-0
Symbol
Signal WordWarning
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| Chemical & Physical Properties | |
|---|---|
| CAS Number | 143-67-9 |
| Catalog No. | 2A-9012929 |
| Chinese Name | 硫酸长春碱 |
| Synonyms | vinbalastine; Velsar; EINECS 205-606-0; Vincaleukoblastine, (2'β)-, sulfate (1:1); VLB; velbe; velban; Vinblastine-d3; (2'β)-Vincaleukoblastine sulfate (1:1); Periblastine; vincaleukoblastine, (3β,4'β)-, sulfate (1:1); VLB Vincaleukoblastine sulfate salt; (+)-vinblastine; Vinblastine (sulfate); Vinblastine sulfate; Vincaleukoblastine sulfate salt; MFCD00082457; exal; rozevinsulfate |
| Molecular Formula | C46H60N4O13S |
| Molecular Weight | 909.05 |
| Purity | 96-102 (HPLC) |
| Density | 1.37 g/cm3 |
| Melting Point | 267 °C (dec.) (lit.) |
| Appearance | powder |
| Water Solubility | ≥1 g/100 mL at 24.5 ºC |
| Storage Condition | Store at 2-8ºC. |
| Packaging | II |
| Application | Vinblastine sulfate is a cytotoxic alkaloid that targets various cancer types. Vinblastine can inhibit the formation of microtubules, and the IC50 value for inhibiting nAChR is 8.9 μM. |
| EINECS | 205-606-0 |
| HTC | 2942000000 |
| PubChem ID | 24278771 |
| MDL Number | MFCD00082457 |
| SMILES | OS(O)(=O)=O.[H][C@@]12CN(CCc3c([nH]c4ccccc34)[C@@](C1)(C(=O)OC)c5cc6c(cc5OC)N(C)[C@@]7([H])[C@](O)([C@H](OC(C)=O)[C@]8(CC)C=CCN9CC[C@]67[C@]89[H])C(=O)OC)C[C@](O)(CC)C2 |
| InChI | 1S/C46H58N4O9.H2O4S/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7;1-5(2,3)4/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3;(H2,1,2,3,4)/t28-,37-,38+,39+,42-,43+,44+,45-,46-;/m0./s1 |
| InChI Key | KDQAABAKXDWYSZ-PNYVAJAMSA-N |
| Beilstein/REAXYS | 3659812 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | 6.1(a) |
| MSDS | msds/12929_1_143_67_9.pdf |
| Bioactivity | Vinblastine sulfate is a cytotoxic alkaloid used against various cancer types. Vinblastine sulfate inhibits the formation of microtubule and suppresses nAChR with an IC50 of 8.9 μM. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin Natural Products >> Alkaloid Research Areas >> Cancer Target IC50: 8.9 μM(nAChR)[1] In Vitro Vinblastine does not depolymerize spindle microtubules, yet it powerfully blocks mitosis (for example, IC50 0.8 nM in HeLa cells) and cells die by apoptosis[2]. In NB4 cells, vinblastine produces alteration of p53 and DNA fragmentation. Vinblastine treatment has an antiproliferative effect via the induction of apoptosis producing Bax/Bcl-2 imbalance. Vinblastine treatment suppresses NFκB expression and depresses NFκB-DNA binding activity while maintaining JNK activation that subsequently results in apoptotic response through caspase-dependent pathway[3]. Vinblastine is found to trigger apoptosis as evidenced by the loss of mitochondrial membrane potential, the release of both cytochrome c and apoptosis inducing factor, activation of caspase-9 and 3, and cleavage of Poly (ADP-ribose)-Polymerase[4]. In Vivo Vinblastine is a widely used anticancer drug with undesired side effects. Its conjugation with carrier molecules could be an efficient strategy to reduce these side effects[5]. References [1]. McKay DB, et al. Nicotinic and nonnicotinic receptor-mediated actions of vinblastine. Proc Soc Exp Biol Med. 1993 Jul;203(3):372-6. [2]. Pandya P, et al. Molecular recognition pattern of cytotoxic alkaloid vinblastine with multiple targets. J Mol Graph Model. 2014 Nov;54:1-9. [3]. Calviño E, et al. JNK and NFκB dependence of apoptosis induced by vinblastine in human acute promyelocytic leukaemia cells. Cell Biochem Funct. 2015 Jun;33(4):211-9. [4]. Selimovic D, et al. Vinblastine-induced apoptosis of melanoma cells is mediated by Ras homologous A protein (Rho A) via mitochondrial and non-mitochondrial-dependent mechanisms. Apoptosis. 2013 Aug;18(8):980-97. [5]. Bánóczi Z, et al. Synthesis and in vitro antitumor effect of vinblastine derivative-oligoarginine conjugates. Bioconjug Chem. 2010 Nov 17;21(11):1948-55. Chemical & Physical Properties Density 1.37 g/cm3 Melting Point 267 °C (dec.)(lit.) Molecular Formula C46H60N4O13S Molecular Weight 909.053 Exact Mass 908.387756 PSA 237.08000 LogP 4.35970 InChIKey KDQAABAKXDWYSZ-KKVPHILVSA-N SMILES CCC1(O)CC2CN(CCc3c([nH]c4ccccc34)C(C(=O)OC)(c3cc4c(cc3OC)N(C)C3C(O)(C(=O)OC)C(OC(C)=O)C5(CC)C=CCN6CCC43C65)C2)C1.O=S(=O)(O)O Storage condition 2~8°C Water Solubility ≥1 g/100 mL at 24.5 ºC |
| Use of | Vinblastine sulfate is a cytotoxic alkaloid used against various cancer types. Vinblastine sulfate inhibits the formation of microtubule and suppresses nAChR with an IC50 of 8.9 μM. Properties Articles36 Name vincaleukoblastine sulfate Synonym More Synonyms Vinblastine Sulfate Biological Activity Description Vinblastine sulfate is a cytotoxic alkaloid used against various cancer types. Vinblastine sulfate inhibits the formation of microtubule and suppresses nAChR with an IC50 of 8.9 μM. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin Natural Products >> Alkaloid Research Areas >> Cancer IC50: 8.9 μM(nAChR)[1] In Vivo Vinblastine is a widely used anticancer drug with undesired side effects. Its conjugation with carrier molecules could be an efficient strategy to reduce these side effects[5]. References [1]. McKay DB, et al. Nicotinic and nonnicotinic receptor-mediated actions of vinblastine. Proc Soc Exp Biol Med. 1993 Jul;203(3):372-6. [2]. Pandya P, et al. Molecular recognition pattern of cytotoxic alkaloid vinblastine with multiple targets. J Mol Graph Model. 2014 Nov;54:1-9. [3]. Calviño E, et al. JNK and NFκB dependence of apoptosis induced by vinblastine in human acute promyelocytic leukaemia cells. Cell Biochem Funct. 2015 Jun;33(4):211-9. [4]. Selimovic D, et al. Vinblastine-induced apoptosis of melanoma cells is mediated by Ras homologous A protein (Rho A) via mitochondrial and non-mitochondrial-dependent mechanisms. Apoptosis. 2013 Aug;18(8):980-97. [5]. Bánóczi Z, et al. Synthesis and in vitro antitumor effect of vinblastine derivative-oligoarginine conjugates. Bioconjug Chem. 2010 Nov 17;21(11):1948-55. Chemical & Physical Properties Molecular Formula C46H60N4O13S Exact Mass 908.387756 PSA 237.08000 LogP 4.35970 InChIKey KDQAABAKXDWYSZ-KKVPHILVSA-N |
| Transport Info | Product name: Vinblastine sulfate |
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