145075-81-6 Usage
Description
OSW-1 is a saponin that has been found in O. saundersiae and has antiviral and anticancer activities. It is an inhibitor of oxysterol-binding protein (OSBP) and its paralog OSBP-related protein 4 (ORP4) with Ki values of 16 and 71 nM, respectively, in radioligand binding assays using HEK293T cell lysates. It induces OSBP translocalization from the cytoplasm to the trans-Golgi network and decreases intracellular levels of OSBP in HEK293 cells. OSW-1 inhibits replication of a variety of enteroviruses (IC50s = 2.4-9.4 nM), including replication of coxsackievirus B3 (CVB3) in infected HeLa R19 cells in an OSBP-dependent manner when used at a concentration of 3 nM. It also inhibits replication of hepatitis C virus (HCV) but not mouse hepatitis virus (MHV), a coronavirus. It protects against CVA9 and echovirus 2 infection in HeLa cells when used at a concentration of 10 nM. OSW-1 inhibits growth of HeLa and HEK293 cells (GI50s = 0.33 and 0.22 nM, respectively).
Uses
OSW-1 is a unique steroidal saponin displaying selective cytotoxicity against cancer cell lines. From Ornithogalum Saundersiae bulbs.
Check Digit Verification of cas no
The CAS Registry Mumber 145075-81-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,5,0,7 and 5 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 145075-81:
(8*1)+(7*4)+(6*5)+(5*0)+(4*7)+(3*5)+(2*8)+(1*1)=126
126 % 10 = 6
So 145075-81-6 is a valid CAS Registry Number.
InChI:InChI=1/C47H68O15/c1-24(2)8-15-34(50)25(3)47(55)37(21-33-31-14-11-28-20-29(49)16-18-45(28,5)32(31)17-19-46(33,47)6)60-44-41(59-26(4)48)39(36(52)23-58-44)62-43-40(38(53)35(51)22-57-43)61-42(54)27-9-12-30(56-7)13-10-27/h9-13,24-25,29,31-33,35-41,43-44,49,51-53,55H,8,14-23H2,1-7H3/t25-,29-,31+,32-,33-,35-,36+,37-,38+,39+,40-,41-,43+,44+,45+,46+,47-/m1/s1
145075-81-6Relevant articles and documents
A new synthesis of potent antitumor saponin OSW-1 via Wittig rearrangement
Tsubuki, Masayoshi,Matsuo, Sohichiro,Honda, Toshio
, p. 229 - 232 (2008)
OSW-1 and its analogues in which thiophene ring was introduced at the side chain were synthesized employing Wittig rearrangement of 17E(20)-ethylidene-16α-(4′-methyl-2′-thienyl)methyloxy steroid. The synthesis required nine steps from the known 17E(20)-ethylidene-16α-hydroxy steroid in 15.6% overall yield.
Synthesis of analogues of a potent antitumor saponin OSW-1
Morzycki, Jacek W.,Wojtkielewicz, Agnieszka,Wolczynski, Slawomir
, p. 3323 - 3326 (2007/10/03)
A series of side chain analogues (5a-e), a 22-glycosylated isomer (10), and 16β-O-L-arabinosyl (13a) or 16β-O-D-xylosyl (13b) analogues of OSW-1 were synthesized. All analogues were found to be less cytotoxic against breast and endometrial cancer cell lines than the natural product.
Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity.
Morzycki, Jacek W,Wojtkielewicz, Agnieszka
, p. 1269 - 1274 (2007/10/03)
The potent antitumor agent OSW-1 was synthesized from the protected aglycone in different ways. It was proven that direct glycosylation of the aglycone in its hemiketal form could be achieved, affording the protected OSW-1 in a moderate yield. Alternatively, regioselective protection of the triol obtained by reduction of the aglycone, followed by glycosylation, deprotection and oxidation yielded the same OSW-1 derivative. The third approach to this compound consisted of glycosylation of the previously described lactol [Morzycki, J. W.; Gryszkiewicz, A. Polish J. Chem. 2001, 75, 983-989], reaction of the resulting aldehyde with a Grignard reagent, and oxidation. OSW-1 obtained on removal of the protective groups was identical with the natural product.