Sinococuline | CAS#109351-36-2 | tumor cell growth inhibitor

MedKoo Cat#: 145459 | Name: Sinococuline

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Sinococuline is an effective tumor cell growth inhibitor whereas the toxicity of aknadinine and 1-nitroaknadinine towards all tested cells is low. Sinococuline protects against the antibody-mediated secondary-DENV infection in the AG129 mouse model. Sinococuline is an active constituent present in the phytopharmaceutical drug product containing Cocculus hirsutus plant extract, in vivo.

Chemical Structure

Sinococuline

CAS#109351-36-2

Theoretical Analysis

MedKoo Cat#: 145459

Name: Sinococuline

CAS#: 109351-36-2

Chemical Formula: C18H23NO5

Exact Mass: 333.1600

Molecular Weight: 333.38

Elemental Analysis: C, 64.85; H, 6.95; N, 4.20; O, 23.99

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

FK-1000; Sinococuline;

IUPAC/Chemical Name

(4bS,6S,7S,9S)-3,8-dimethoxy-6,7,9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthrene-4,6,7-triol

InChi Key

MFKPWBJXKCSPGK-KNORBDTNSA-N

InChi Code

1S/C18H23NO5/c1-23-12-4-3-9-7-10-14-17(24-2)15(21)11(20)8-18(14,5-6-19-10)13(9)16(12)22/h3-4,10-11,15,19-22H,5-8H2,1-2H3/t10-,11-,15-,18-/m0/s1

SMILES Code

COC1=CC=C2C[C@@H]3NCC[C@]4(C[C@H](O)[C@H](O)C(OC)=C34)C2=C1O

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 333.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Shukla R, Ahuja R, Beesetti H, Garg A, Aggarwal C, Chaturvedi S, Nayyar K, Arora U, Lal AA, Khanna N. Sinococuline, a bioactive compound of Cocculus hirsutus has potent anti-dengue activity. Sci Rep. 2023 Jan 19;13(1):1026. doi: 10.1038/s41598-023-27927-3. PMID: 36658277; PMCID: PMC9852271. 2: Bhadaliya C, Panigrahy BK, Goswami D, Maiti S, Gurule SJ, Khuroo AH. Development of a bioanalytical method for the quantification of sinococuline in human plasma and its application in phase I clinical pharmacokinetic study. Biomed Chromatogr. 2022 Apr;36(4):e5337. doi: 10.1002/bmc.5337. Epub 2022 Feb 3. PMID: 35028959. 3: Itokawa H, Tsuruoka S, Takeya K, Mori N, Sonobe T, Kosemura S, Hamanaka T. An antitumor morphinane alkaloid, sinococuline, from Cocculus trilobus. Chem Pharm Bull (Tokyo). 1987 Apr;35(4):1660-2. doi: 10.1248/cpb.35.1660. PMID: 3652302. 4: Liu WK, Wang XK, Che CT. Cytotoxic effects of sinococuline. Cancer Lett. 1996 Feb 6;99(2):217-24. doi: 10.1016/0304-3835(95)04065-x. PMID: 8616827. 5: Shukla R, Rajpoot RK, Poddar A, Ahuja R, Beesetti H, Shanmugam RK, Chaturvedi S, Nayyar K, Singh D, Singamaneni V, Gupta P, Gupta AP, Gairola S, Kumar P, Bedi YS, Jain T, Vashishta B, Patil R, Madan H, Madan S, Kalra R, Sood R, Vishwakarma RA, Reddy DS, Lal AA, Arora U, Khanna N. Cocculus hirsutus-Derived Phytopharmaceutical Drug Has Potent Anti-dengue Activity. Front Microbiol. 2021 Nov 29;12:746110. doi: 10.3389/fmicb.2021.746110. PMID: 34912307; PMCID: PMC8667597. 6: Tatapudi KK, Bandi S, Nagendla NK, Solipeta DR, Mudiam MKR, Katragadda SB. Chemical profiling and simultaneous quantification of major bioactive constituents from Cocculus hirsutus by UPLC-QqQ-MS. J Pharm Biomed Anal. 2023 Oct 25;235:115675. doi: 10.1016/j.jpba.2023.115675. Epub 2023 Aug 20. PMID: 37633166. 7: Dar SK, Kumar S, Maiti S, Dhawan S, Joglekar S, Arora U, Kalra R, Madan S, Lal AA, Singamaneni V, Gupta P, Nandi U, Singh D, Khuroo AH. Clinical safety and pharmacokinetic evaluation of aqueous extract of Cocculus hirsutus, an anti-viral phytopharmacetical drug as a potential for the treatment of dengue and COVID-19. Heliyon. 2022 May;8(5):e09416. doi: 10.1016/j.heliyon.2022.e09416. Epub 2022 May 13. PMID: 35582330; PMCID: PMC9098428. 8: Li YC, Kim BH, Cho SC, Bang MA, Kim S, Park DH. 6,7-di-O-acetylsinococuline (FK-3000) induces G2/M phase arrest in breast carcinomas through p38 MAPK phosphorylation and CDC25B dephosphorylation. Int J Oncol. 2015 Feb;46(2):578-86. doi: 10.3892/ijo.2014.2739. Epub 2014 Nov 7. PMID: 25384584; PMCID: PMC4277248. 9: Carraz M, Jossang A, Rasoanaivo P, Mazier D, Frappier F. Isolation and antimalarial activity of new morphinan alkaloids on Plasmodium yoelii liver stage. Bioorg Med Chem. 2008 Jun 1;16(11):6186-92. doi: 10.1016/j.bmc.2008.04.033. Epub 2008 Apr 18. PMID: 18456502. 10: Chang FR, Wu YC. New bisbenzylisoquinolines, fatty acid amidic aporphines, and a protoberberine from Formosan Cocculus orbiculatus. J Nat Prod. 2005 Jul;68(7):1056-60. doi: 10.1021/np050082a. PMID: 16038548. 11: Liao J, Lei Y, Wang JZ. [Chemical constituents of Cocculus orbiculatus var. mollis root]. Zhong Yao Cai. 2014 Feb;37(2):254-7. Chinese. PMID: 25095346.