Vincristine sulfate

SKU: V0014

Category: Antibiotics

Synonyms: VCR , 22-Oxovincaleukoblastine , NSC 67574 , Oncovin , Lilly 37231 , Leucristine , Leurocristine , LS-228; 2068-78-2
CAS-Number: C₄₆H₅₆N₄O₁₀ . H₂SO₄
Molecular Formula: 923.04
Molecular Weight

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥95% (HPLC)
Identity: 1H-NMR
Appearance: White to off-white powder

Properties

Solvents: water (50 mg/ml), DMSO (5 mg/ml)

Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.
Handling Advice: Protect from light and moisture.
Long Term Storage: -20°C
Short Term Storage: +4°C
Shipping: AMBIENT

Transportation: Packing Group II
RIDADR: UN2811
Signal word: Danger
GHS Symbol: GHS06+GHS08
Precautionary statements: P264-P281-P301 + P310
Hazard statements: H300-H341-H361fd

Description: Vincristine is an antimitotic vinca alkaloid isolated from Vinca Rosea. It irreversibly blocks mitosis by binding to tubulin (Ki = 85 nM) and inhibiting tubulin polymerization. It is a anticancer agent and arrests cell cycle in G2/M-phase by blocking mitotic spindle formation. Vincristine triggers Raf-1 activation, phosphorylation of bcl-2-family proteins, induction of p53 expression and induces apoptosis and autophagy in several tumor cell lines. It inhibits VEGF production in leukemia cell lines. Vincristine has some immunosuppressant effect. Vincristine may also interfere with amino acid, cyclic AMP, and glutathione metabolism, calmodulin-dependent Ca2+-transport, cellular respiration and nucleic acid and lipid biosynthesis. Vincristine inhibits monoamine oxidase (MAO), induces of IL-1β production and activates the NLRP3-inflammasome mediated processing of IL-1β.
InChi: InChI=1S/C46H56N4O10.H2O4S/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6,1-5(2,3)4/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3,(H2,1,2,3,4)/t28-,37+,38-,39-,42+,43-,44-,45+,46+,/m1./s1
References: (1) A.C. Aisenberg, Nature 200, 484 (1963) , (2) M.A. Jordan, et al., Cancer Res. 45, 2741 (1985) , (3) J.K. Son, et al., J. Med. Chem. 33, 1845 (1990) , (4) B.V. Harmon, et al., Cell Prolif. 25, 523 (1992) , (5) S. Lobert, et al., Biochemistry 35, 6806 (1996) , (6) E. Hamel, Med. Res. Rev. 16, 207 (1996) , (7) M.V. Blagosklonny, et al., Cancer Res. 57, 130 (1997) , (8) A. Jordan, et al., Med. Res. Rev. 18, 259 (1998) (Review) , (9) L.G. Wang, Cancer Chemother. Pharmacol. 44, 355 (1999) (Review) , (10) E. Groninger, et al., Br. J. Haematol. 111, 875 (2000) , (11) Z. Zhan, et al., Autophagy 8, 109 (2012) , (12) R. Mackeh, et al., J. Cell Sci. 126, 1071 (2013) (Review) , (13) J. Wong, et al., Cancer Biol. Ther. 15, 1395 (2014)
InChi Key: AQTQHPDCURKLKT-JKDPCDLQSA-N
Smiles: O=S(O)(O)=O.O[C@@]1(C(OC)=O)[C@]2([H])N(C([H])=O)C3=C(C=C([C@@](C(OC)=O)(C[C@@H](C[C@]4(CC)O)C[N@@](C4)CC5)C6=C5C(C=CC=C7)=C7N6)C(OC)=C3)[C@]28[C@@]([C@](C=CC9)(CC)[C@H]1OC(C)=O)([H])N9CC8

Vincristine is an antimitotic vinca alkaloid isolated from Vinca Rosea. It irreversibly blocks mitosis by binding to tubulin (Ki = 85 nM) and inhibiting tubulin polymerization. It is a anticancer agent and arrests cell cycle in G2/M-phase by blocking mitotic spindle formation. Vincristine triggers Raf-1 activation, phosphorylation of bcl-2-family proteins, induction of p53 expression and induces apoptosis and autophagy in several tumor cell lines. It inhibits VEGF production in leukemia cell lines. Vincristine has some immunosuppressant effect. Vincristine may also interfere with amino acid, cyclic AMP, and glutathione metabolism, calmodulin-dependent Ca2+-transport, cellular respiration and nucleic acid and lipid biosynthesis. Vincristine inhibits monoamine oxidase (MAO), induces of IL-1β production and activates the NLRP3-inflammasome mediated processing of IL-1β.

SKU: V0014 Category: Antibiotics

Additional information

Additional information

Synonyms	VCR, 22-Oxovincaleukoblastine, NSC 67574, Oncovin, Lilly 37231, Leucristine, Leurocristine, LS-228
Purity	≥95% (HPLC)
Appearance	White to off-white powder
CAS-Number	2068-78-2
Molecular Formula	C46H56N4O10 . H2SO4
Molecular Weight	923.04
Identity	1H-NMR
Solvents	water (50 mg/ml), DMSO (5 mg/ml)
Smiles	O=S(O)(O)=O.O[C@@]1(C(OC)=O)[C@]2([H])N(C([H])=O)C3=C(C=C([C@@](C(OC)=O)(C[C@@H](C[C@]4(CC)O)C[N@@](C4)CC5)C6=C5C(C=CC=C7)=C7N6)C(OC)=C3)[C@]28[C@@]([C@](C=CC9)(CC)[C@H]1OC(C)=O)([H])N9CC8
InChi Key	AQTQHPDCURKLKT-JKDPCDLQSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Hazard statements	H300-H341-H361fd
Precautionary statements	P264-P281-P301 + P310
GHS Symbol	GHS06+GHS08
Signal word	Danger
RIDADR	UN2811
Transportation	Packing Group II
References	(1) A.C. Aisenberg, Nature 200, 484 (1963), (2) M.A. Jordan, et al., Cancer Res. 45, 2741 (1985), (3) J.K. Son, et al., J. Med. Chem. 33, 1845 (1990), (4) B.V. Harmon, et al., Cell Prolif. 25, 523 (1992), (5) S. Lobert, et al., Biochemistry 35, 6806 (1996), (6) E. Hamel, Med. Res. Rev. 16, 207 (1996), (7) M.V. Blagosklonny, et al., Cancer Res. 57, 130 (1997), (8) A. Jordan, et al., Med. Res. Rev. 18, 259 (1998) (Review), (9) L.G. Wang, Cancer Chemother. Pharmacol. 44, 355 (1999) (Review), (10) E. Groninger, et al., Br. J. Haematol. 111, 875 (2000), (11) Z. Zhan, et al., Autophagy 8, 109 (2012), (12) R. Mackeh, et al., J. Cell Sci. 126, 1071 (2013) (Review), (13) J. Wong, et al., Cancer Biol. Ther. 15, 1395 (2014)
InChi	InChI=1S/C46H56N4O10.H2O4S/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6,1-5(2,3)4/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3,(H2,1,2,3,4)/t28-,37+,38-,39-,42+,43-,44-,45+,46+,/m1./s1
Quantity	25 mg, 50 mg, Bulk