Gallinamide A | CAS#1208232-55-6

MedKoo Cat#: 333112 | Name: Gallinamide A

Description:

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

Gallinamide A is potent and selective inhibitor of the human cysteine protease Cathepsin L1 that was first used as a moderate antimalarial agent. Gallinamide A is produced by marine cyanobacteria from Schizothrix species and Symploca sp. which have also shown to have possible anticancer agent, infectious diseases like leishmaniasis, trypanosomiasis and possible uses in Alzheimer's disease, among others.

Chemical Structure

Gallinamide A

CAS#1208232-55-6

Theoretical Analysis

MedKoo Cat#: 333112

Name: Gallinamide A

CAS#: 1208232-55-6

Chemical Formula: C31H52N4O7

Exact Mass: 592.3836

Molecular Weight: 592.78

Elemental Analysis: C, 62.81; H, 8.84; N, 9.45; O, 18.89

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

(25S,26S)-Gallinamide A; (25S,26S)-Symplostatin 4; Gallinamide A; Symplostatin 4;

IUPAC/Chemical Name

(S)-1-(((S)-1-(((S,E)-5-((S)-3-methoxy-2-methyl-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-5-oxopent-3-en-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl dimethyl-L-isoleucinate

InChi Key

ASRBKZHDORPEHO-KYJIWOQOSA-N

InChi Code

InChI=1S/C31H52N4O7/c1-12-20(6)28(34(9)10)31(40)42-25(16-19(4)5)30(39)33-23(15-18(2)3)29(38)32-21(7)13-14-26(36)35-22(8)24(41-11)17-27(35)37/h13-14,17-23,25,28H,12,15-16H2,1-11H3,(H,32,38)(H,33,39)/b14-13+/t20-,21-,22-,23-,25-,28-/m0/s1

SMILES Code

C(/C=C/[C@@H](NC([C@@H](NC([C@@H](OC([C@H]([C@H](CC)C)N(C)C)=O)CC(C)C)=O)CC(C)C)=O)C)(=O)N1[C@@H](C)C(OC)=CC1=O

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 592.78 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

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PMID: 34730959. 4: Taglialatela-Scafati O. New Hopes for Drugs against COVID-19 Come from the Sea. Mar Drugs. 2021 Feb 11;19(2):104. doi: 10.3390/md19020104. PMID: 33670191; PMCID: PMC7916939. 5: Ashhurst AS, Tang AH, Fajtová P, Yoon M, Aggarwal A, Stoye A, Larance M, Beretta L, Drelich A, Skinner D, Li L, Meek TD, McKerrow JH, Hook V, Tseng CK, Turville S, Gerwick WH, O'Donoghue AJ, Payne RJ. Potent in vitro anti- SARS-CoV-2 activity by gallinamide A and analogues via inhibition of cathepsin L. bioRxiv [Preprint]. 2020 Dec 24:2020.12.23.424111. doi: 10.1101/2020.12.23.424111. Update in: J Med Chem. 2022 Feb 24;65(4):2956-2970. PMID: 33398273; PMCID: PMC7781308. 6: Boudreau PD, Miller BW, McCall LI, Almaliti J, Reher R, Hirata K, Le T, Siqueira-Neto JL, Hook V, Gerwick WH. Design of Gallinamide A Analogs as Potent Inhibitors of the Cysteine Proteases Human Cathepsin L and Trypanosoma cruzi Cruzain. J Med Chem. 2019 Oct 24;62(20):9026-9044. doi: 10.1021/acs.jmedchem.9b00294. Epub 2019 Oct 4. PMID: 31539239; PMCID: PMC7240701. 7: Stoye A, Juillard A, Tang AH, Legac J, Gut J, White KL, Charman SA, Rosenthal PJ, Grau GER, Hunt NH, Payne RJ. Falcipain Inhibitors Based on the Natural Product Gallinamide A Are Potent in Vitro and in Vivo Antimalarials. J Med Chem. 2019 Jun 13;62(11):5562-5578. doi: 10.1021/acs.jmedchem.9b00504. Epub 2019 May 22. PMID: 31062592. 8: Liu S, Gao X, Zhang L, Qin S, Wei M, Liu N, Zhao R, Li B, Meng Y, Lin G, Lu C, Liu X, Xie M, Liu T, Zhou H, Qi M, Yang G, Yang C. A novel Anti-Cancer Stem Cells compound optimized from the natural symplostatin 4 scaffold inhibits Wnt/β-catenin signaling pathway. Eur J Med Chem. 2018 Aug 5;156:21-42. doi: 10.1016/j.ejmech.2018.06.046. Epub 2018 Jun 20. PMID: 30006166. 9: Conroy T, Guo JT, Elias N, Cergol KM, Gut J, Legac J, Khatoon L, Liu Y, McGowan S, Rosenthal PJ, Hunt NH, Payne RJ. Synthesis of gallinamide A analogues as potent falcipain inhibitors and antimalarials. J Med Chem. 2014 Dec 26;57(24):10557-63. doi: 10.1021/jm501439w. Epub 2014 Dec 8. PMID: 25412465. 10: Omotuyi OI. Methyl-methoxylpyrrolinone and flavinium nucleus binding signatures on falcipain-2 active site. J Mol Model. 2014 Aug;20(8):2386. doi: 10.1007/s00894-014-2386-2. Epub 2014 Aug 6. PMID: 25096811. 11: Miller B, Friedman AJ, Choi H, Hogan J, McCammon JA, Hook V, Gerwick WH. The marine cyanobacterial metabolite gallinamide A is a potent and selective inhibitor of human cathepsin L. J Nat Prod. 2014 Jan 24;77(1):92-9. doi: 10.1021/np400727r. Epub 2013 Dec 23. PMID: 24364476; PMCID: PMC3932306. 12: Stolze SC, Deu E, Kaschani F, Li N, Florea BI, Richau KH, Colby T, van der Hoorn RA, Overkleeft HS, Bogyo M, Kaiser M. The antimalarial natural product symplostatin 4 is a nanomolar inhibitor of the food vacuole falcipains. Chem Biol. 2012 Dec 21;19(12):1546-55. doi: 10.1016/j.chembiol.2012.09.020. PMID: 23261598; PMCID: PMC3601557. 13: Conroy T, Guo JT, Linington RG, Hunt NH, Payne RJ. Total synthesis, stereochemical assignment, and antimalarial activity of gallinamide A. Chemistry. 2011 Nov 25;17(48):13544-52. doi: 10.1002/chem.201102538. Epub 2011 Oct 18. PMID: 22006835. 14: Conroy T, Guo JT, Hunt NH, Payne RJ. Total synthesis and antimalarial activity of symplostatin 4. Org Lett. 2010 Dec 3;12(23):5576-9. doi: 10.1021/ol1024663. Epub 2010 Nov 4. PMID: 21049908. 15: Nunnery JK, Mevers E, Gerwick WH. Biologically active secondary metabolites from marine cyanobacteria. Curr Opin Biotechnol. 2010 Dec;21(6):787-93. doi: 10.1016/j.copbio.2010.09.019. Epub 2010 Oct 26. PMID: 21030245; PMCID: PMC3034308. 16: Taori K, Liu Y, Paul VJ, Luesch H. Combinatorial strategies by marine cyanobacteria: symplostatin 4, an antimitotic natural dolastatin 10/15 hybrid that synergizes with the coproduced HDAC inhibitor largazole. Chembiochem. 2009 Jul 6;10(10):1634-9. doi: 10.1002/cbic.200900192. 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