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MedKoo Cat#: 412454 | Name: Caulerpin

Description:

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

Caulerpin is a bisindolic alkaloid that has been obtained from many species of the genus Caulerpa. Caulerpin Showed In-Vitro Anticancer Activity against Colorectal Cancer. Caulerpin is a promising therapeutic or adjuvant agent for the attenuation of inflammation triggered by Hp infection, as well as its related adverse clinical outcomes. Caulerpin exhibited antiviral activities against chikungunya virus and herpes simplex virus type 1. Caulerpin and some of its derivatives showed inhibitory activity against Alzheimer's disease.

Chemical Structure

Caulerpin
Caulerpin
CAS#26612-48-6

Theoretical Analysis

MedKoo Cat#: 412454

Name: Caulerpin

CAS#: 26612-48-6

Chemical Formula: C24H18N2O4

Exact Mass: 398.1267

Molecular Weight: 398.42

Elemental Analysis: C, 72.35; H, 4.55; N, 7.03; O, 16.06

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.
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Related CAS #
No Data
Synonym
Caulerpin; Caulerpine;
IUPAC/Chemical Name
Cycloocta(1,2-b:5,6-b')diindole-6,13-dicarboxylic acid, 5,12-dihydro-, dimethyl ester
InChi Key
PVWALMHWUOWPPA-HCOJNGAVSA-N
InChi Code
InChI=1S/C24H18N2O4/c1-29-23(27)17-11-15-13-7-3-6-10-20(13)26-22(15)18(24(28)30-2)12-16-14-8-4-5-9-19(14)25-21(16)17/h3-12,25-26H,1-2H3/b15-11-,16-12-,17-11+,18-12+,21-17-,22-18-
SMILES Code
O=C(C1=C2NC3=C(C=CC=C3)C/2=C/C(C(OC)=O)=C4NC5=C(C=CC=C5)C/4=C/1)OC
Appearance
Solid powder
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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

Preparing Stock Solutions

The following data is based on the product molecular weight 398.42 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.

Recalculate based on batch purity %
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: Russo T, Coppola F, Leite C, Carbone M, Paris D, Motta A, Di Cosmo A, Soares AMVM, Mollo E, Freitas R, Polese G. An alien metabolite vs. a synthetic chemical hazard: An ecotoxicological comparison in the Mediterranean blue mussel. Sci Total Environ. 2023 May 29:164476. doi: 10.1016/j.scitotenv.2023.164476. Epub ahead of print. PMID: 37257616. 2: Mert-Ozupek N, Calibasi-Kocal G, Olgun N, Basbinar Y, Cavas L, Ellidokuz H. In-silico molecular interactions among the secondary metabolites of Caulerpa spp. and colorectal cancer targets. Front Chem. 2022 Dec 6;10:1046313. doi: 10.3389/fchem.2022.1046313. PMID: 36561138; PMCID: PMC9763605. 3: Rocha DHA, Pinto DCGA, Silva AMS. Macroalgae Specialized Metabolites: Evidence for Their Anti-Inflammatory Health Benefits. Mar Drugs. 2022 Dec 19;20(12):789. doi: 10.3390/md20120789. PMID: 36547936; PMCID: PMC9783307. 4: Mert-Ozupek N, Calibasi-Kocal G, Olgun N, Basbinar Y, Cavas L, Ellidokuz H. An Efficient and Quick Analytical Method for the Quantification of an Algal Alkaloid Caulerpin Showed In-Vitro Anticancer Activity against Colorectal Cancer. Mar Drugs. 2022 Nov 30;20(12):757. doi: 10.3390/md20120757. PMID: 36547904; PMCID: PMC9781365. 5: Dissanayake IH, Bandaranayake U, Keerthirathna LR, Manawadu C, Silva RM, Mohamed B, Ali R, Peiris DC. Integration of in vitro and in-silico analysis of Caulerpa racemosa against antioxidant, antidiabetic, and anticancer activities. Sci Rep. 2022 Dec 2;12(1):20848. doi: 10.1038/s41598-022-24021-y. Erratum in: Sci Rep. 2023 Mar 9;13(1):3962. PMID: 36460661; PMCID: PMC9718753. 6: Erol E, Orhan MD, Avsar T, Akdemir A, Okudan ES, Alim Toraman GO, Topcu G. Anti-SARS-CoV-2 and cytotoxic activity of two marine alkaloids from green alga Caulerpa cylindracea Sonder in the Dardanelles. RSC Adv. 2022 Oct 19;12(46):29983-29990. doi: 10.1039/d2ra03358e. PMID: 36321101; PMCID: PMC9580487. 7: Young CS, Lee CS, Sylvers LH, Venkatesan AK, Gobler CJ. The invasive red seaweed, Dasysiphonia japonica, forms harmful algal blooms: Mortality in early life stage fish and bivalves and identification of putative toxins. Harmful Algae. 2022 Oct;118:102294. doi: 10.1016/j.hal.2022.102294. Epub 2022 Aug 10. PMID: 36195420. 8: Schiano V, Cutignano A, Maiello D, Carbone M, Ciavatta ML, Polese G, Fioretto F, Attanasio C, Palladino A, Felline S, Terlizzi A, D'Angelo L, de Girolamo P, Turano M, Lucini C, Mollo E. An Alkaloid from a Highly Invasive Seaweed Increases the Voracity and Reproductive Output of a Model Fish Species. Mar Drugs. 2022 Aug 12;20(8):513. doi: 10.3390/md20080513. PMID: 36005516; PMCID: PMC9410225. 9: Cuomo P, Medaglia C, Allocca I, Montone AMI, Guerra F, Cabaro S, Mollo E, Eletto D, Papaianni M, Capparelli R. Caulerpin Mitigates Helicobacter pylori-Induced Inflammation via Formyl Peptide Receptors. Int J Mol Sci. 2021 Dec 5;22(23):13154. doi: 10.3390/ijms222313154. PMID: 34884957; PMCID: PMC8658387. 10: El-Mageed HRA, Abdelrheem DA, Ahmed SA, Rahman AA, Elsayed KNM, Ahmed SA, El-Bassuony AA, Mohamed HS. Combination and tricombination therapy to destabilize the structural integrity of COVID-19 by some bioactive compounds with antiviral drugs: insights from molecular docking study. Struct Chem. 2021;32(4):1415-1430. doi: 10.1007/s11224-020-01723-5. Epub 2021 Jan 8. PMID: 33437137; PMCID: PMC7791912. 11: Cantarino SJ, Coutinho R, Soares AR, Duarte HM, Martinez ST. Microwave irradiation is a suitable method for caulerpin extraction from the green algae Caulerpa racemosa (Chlorophyta, Caulerpaceae). Nat Prod Res. 2022 Apr;36(8):2149-2153. doi: 10.1080/14786419.2020.1844684. Epub 2020 Nov 23. PMID: 33222553. 12: Abdelrheem DA, Ahmed SA, Abd El-Mageed HR, Mohamed HS, Rahman AA, Elsayed KNM, Ahmed SA. The inhibitory effect of some natural bioactive compounds against SARS-CoV-2 main protease: insights from molecular docking analysis and molecular dynamic simulation. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2020;55(11):1373-1386. doi: 10.1080/10934529.2020.1826192. Epub 2020 Oct 1. PMID: 32998618; PMCID: PMC7544954. 13: Ahmed SA, Abdelrheem DA, El-Mageed HRA, Mohamed HS, Rahman AA, Elsayed KNM, Ahmed SA. Destabilizing the structural integrity of COVID-19 by caulerpin and its derivatives along with some antiviral drugs: An in silico approaches for a combination therapy. Struct Chem. 2020;31(6):2391-2412. doi: 10.1007/s11224-020-01586-w. Epub 2020 Jul 23. PMID: 32837118; PMCID: PMC7376526. 14: Abdelrheem DA, Abd El-Mageed HR, Mohamed HS, Rahman AA, Elsayed KNM, Ahmed SA. Bis-indole alkaloid caulerpin from a new source Sargassum platycarpum: isolation, characterization, in vitro anticancer activity, binding with nucleobases by DFT calculations and MD simulation. J Biomol Struct Dyn. 2021 Sep;39(14):5137-5147. doi: 10.1080/07391102.2020.1784285. Epub 2020 Jun 24. PMID: 32579063. 15: Mehra R, Bhushan S, Bast F, Singh S. Marine macroalga Caulerpa: role of its metabolites in modulating cancer signaling. Mol Biol Rep. 2019 Jun;46(3):3545-3555. doi: 10.1007/s11033-019-04743-5. Epub 2019 Apr 12. PMID: 30980271. 16: Magliozzi L, Maselli V, Almada F, Di Cosmo A, Mollo E, Polese G. Effect of the algal alkaloid caulerpin on neuropeptide Y (NPY) expression in the central nervous system (CNS) of Diplodus sargus. J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2019 Apr;205(2):203-210. doi: 10.1007/s00359-019-01322-8. Epub 2019 Mar 9. PMID: 30852662. 17: Vitale RM, D'Aniello E, Gorbi S, Martella A, Silvestri C, Giuliani ME, Fellous T, Gentile A, Carbone M, Cutignano A, Grauso L, Magliozzi L, Polese G, D'Aniello B, Defranoux F, Felline S, Terlizzi A, Calignano A, Regoli F, Di Marzo V, Amodeo P, Mollo E. Fishing for Targets of Alien Metabolites: A Novel Peroxisome Proliferator-Activated Receptor (PPAR) Agonist from a Marine Pest. Mar Drugs. 2018 Nov 3;16(11):431. doi: 10.3390/md16110431. PMID: 30400299; PMCID: PMC6267082. 18: Del Coco L, Felline S, Girelli CR, Angilè F, Magliozzi L, Almada F, D'Aniello B, Mollo E, Terlizzi A, Fanizzi FP. ¹H NMR Spectroscopy and MVA to Evaluate the Effects of Caulerpin-Based Diet on Diplodus sargus Lipid Profiles. Mar Drugs. 2018 Oct 18;16(10):390. doi: 10.3390/md16100390. PMID: 30340347; PMCID: PMC6213232. 19: Lucena AMM, Souza CRM, Jales JT, Guedes PMM, de Miranda GEC, de Moura AMA, Araújo-Júnior JX, Nascimento GJ, Scortecci KC, Santos BVO, Souto JT. The Bisindole Alkaloid Caulerpin, from Seaweeds of the Genus Caulerpa, Attenuated Colon Damage in Murine Colitis Model. Mar Drugs. 2018 Sep 7;16(9):318. doi: 10.3390/md16090318. PMID: 30205459; PMCID: PMC6163434. 20: Lunagariya J, Bhadja P, Zhong S, Vekariya R, Xu S. Marine Natural Product Bis-indole Alkaloid Caulerpin: Chemistry and Biology. Mini Rev Med Chem. 2019;19(9):751-761. doi: 10.2174/1389557517666170927154231. PMID: 28971770.