Spinosad Factor A | CAS# 131929-60-7 | Pesticide

MedKoo Cat#: 571211 | Name: Spinosad Factor A

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Description:

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

Spinosad Factor A, also known as Spinosyn A, is a naturally derived fermentation product that is used as a pesticide against many different insects.

Chemical Structure

Spinosad Factor A

CAS#131929-60-7 (A)

Theoretical Analysis

MedKoo Cat#: 571211

Name: Spinosad Factor A

CAS#: 131929-60-7 (A)

Chemical Formula: C41H65NO10

Exact Mass: 731.4608

Molecular Weight: 731.97

Elemental Analysis: C, 67.28; H, 8.95; N, 1.91; O, 21.86

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 500.00	2 weeks
5mg	USD 1,150.00	2 Weeks

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Related CAS #

131929-60-7 (A) 131929-63-0 (D)

Synonym

Spinosad Factor A; Spinosad A; Spinosad-A; Spinosyn A; Spinosad factor A; Lepicidin A; Spinosyn-A

IUPAC/Chemical Name

(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-13-(((2R,5S,6R)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-9-ethyl-14-methyl-2-(((2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15-dione

InChi Key

SRJQTHAZUNRMPR-UYQKXTDMSA-N

InChi Code

InChI=1S/C41H65NO10/c1-10-26-12-11-13-34(52-36-17-16-33(42(5)6)23(3)48-36)22(2)37(44)32-20-30-28(31(32)21-35(43)50-26)15-14-25-18-27(19-29(25)30)51-41-40(47-9)39(46-8)38(45-7)24(4)49-41/h14-15,20,22-31,33-34,36,38-41H,10-13,16-19,21H2,1-9H3/t22-,23-,24+,25-,26+,27-,28-,29-,30-,31+,33+,34+,36+,38+,39-,40-,41+/m1/s1

SMILES Code

CC[C@H]1CCC[C@@H]([C@H](C(C2=C[C@H]3[C@@H]4C[C@H](O[C@@H]5O[C@H]([C@@H]([C@H]([C@H]5OC)OC)OC)C)C[C@H]4C=C[C@H]3[C@@H]2CC(O1)=O)=O)C)O[C@H]6CC[C@H](N(C)C)[C@H](O6)C

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

>2 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Spinosad Factor A is a a polyketide-derived macrolide.

In vitro activity:

Spinosad Factor A and its derivative LM-2I activate the tumor suppressor argininosuccinate synthase (ASS1) in breast cancer cells. This activation inhibits cancer cell growth by reducing pyrimidine synthesis. Spinosad Factor A and LM-2I offer a promising therapeutic strategy for tumors with low ASS1 expression and related diseases. Reference: Nat Commun. 2021 Apr 15;12(1):2263. https://pubmed.ncbi.nlm.nih.gov/33859183/

In vivo activity:

Spinosad Factor A and its derivative LM2I have potential therapeutic use in the treatment of colorectal cancer. Spinosad Factor A and LM21 had significant antiproliferative activity in colorectal xenograft tumors. Spinosad Factor A and LM2I also inhibited the EGFR pathway in vivo. Reference: J Nat Prod. 2023 Sep 22;86(9):2111-2121. https://pubmed.ncbi.nlm.nih.gov/37682035/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	10.0	13.66

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 731.97 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

Formulation protocol:

1. Kaniski AJ, Almahdi YA, Matti DI, McLaughlin AJ, Najem SM, Xhabija B. Spinosyn A exerts anti-tumorigenic effects on progesterone-sensitive ERα-positive breast cancer cells by modulating multiple signaling pathways. Biomed Pharmacother. 2024 Feb;171:116156. doi: 10.1016/j.biopha.2024.116156. Epub 2024 Jan 23. PMID: 38266623. 2. Zou Z, Hu X, Luo T, Ming Z, Chen X, Xia L, Luo W, Li J, Xu N, Chen L, Cao D, Wen M, Kong F, Peng K, Xie Y, Li X, Ma D, Yang C, Chen C, Yi W, Liu O, Liu S, Luo J, Luo Z. Naturally-occurring spinosyn A and its derivatives function as argininosuccinate synthase activator and tumor inhibitor. Nat Commun. 2021 Apr 15;12(1):2263. doi: 10.1038/s41467-021-22235-8. PMID: 33859183; PMCID: PMC8050083. 3. Peng K, Zou Z, Li J, Xie Y, Ming Z, Jiang T, Luo W, Hu X, Nie Y, Chen L, Luo T, Peng T, Ma D, Liu S, Luo ZY. Spinosyn A and Its Derivative Inhibit Colorectal Cancer Cell Growth via the EGFR Pathway. J Nat Prod. 2023 Sep 22;86(9):2111-2121. doi: 10.1021/acs.jnatprod.3c00276. Epub 2023 Sep 8. PMID: 37682035. 4. Nguyen J, Ghazali R, Batterham P, Perry T. Inhibiting the proteasome reduces molecular and biological impacts of the natural product insecticide, spinosad. Pest Manag Sci. 2021 Aug;77(8):3777-3786. doi: 10.1002/ps.6290. Epub 2021 Feb 5. PMID: 33481333.

In vitro protocol:

In vivo protocol:

1. Peng K, Zou Z, Li J, Xie Y, Ming Z, Jiang T, Luo W, Hu X, Nie Y, Chen L, Luo T, Peng T, Ma D, Liu S, Luo ZY. Spinosyn A and Its Derivative Inhibit Colorectal Cancer Cell Growth via the EGFR Pathway. J Nat Prod. 2023 Sep 22;86(9):2111-2121. doi: 10.1021/acs.jnatprod.3c00276. Epub 2023 Sep 8. PMID: 37682035. 2. Nguyen J, Ghazali R, Batterham P, Perry T. Inhibiting the proteasome reduces molecular and biological impacts of the natural product insecticide, spinosad. Pest Manag Sci. 2021 Aug;77(8):3777-3786. doi: 10.1002/ps.6290. Epub 2021 Feb 5. PMID: 33481333.

1: Afzal MB, Shad SA, Abbas N. Genetics, realized heritability and preliminary mechanism of spinosad resistance in Phenacoccus solenopsis Tinsley (Homoptera: Pseudococcidae): an invasive pest from Pakistan. Genetica. 2015 Dec;143(6):741-9. doi: 10.1007/s10709-015-9871-0. Epub 2015 Oct 22. PubMed PMID: 26494239. 2: Højland DH, Scott JG, Vagn Jensen KM, Kristensen M. Autosomal male determination in a spinosad-resistant housefly strain from Denmark. Pest Manag Sci. 2014 Jul;70(7):1114-7. doi: 10.1002/ps.3655. Epub 2013 Oct 10. PubMed PMID: 24105942. 3: Bai Y, Zhou PP, Fan P, Zhu YM, Tong Y, Wang HB, Yu LJ. Four-stage dissolved oxygen strategy based on multi-scale analysis for improving spinosad yield by Saccharopolyspora spinosa ATCC49460. Microb Biotechnol. 2015 May;8(3):561-8. doi: 10.1111/1751-7915.12264. Epub 2015 Mar 26. PubMed PMID: 25808914; PubMed Central PMCID: PMC4408188. 4: Snyder DE, Rumschlag AJ, Young LM, Ryan WG. Speed of flea knockdown of spinosad compared to afoxolaner, and of spinosad through 28 days post-treatment in controlled laboratory studies. Parasit Vectors. 2015 Nov 9;8:578. doi: 10.1186/s13071-015-1195-5. PubMed PMID: 26552479; PubMed Central PMCID: PMC4640350. 5: Yee WL. Temperature-Mediated Kill and Oviposition of Western Cherry Fruit Fly (Diptera: Tephritidae) in the Presence of Spinosad. J Econ Entomol. 2016 Feb;109(1):132-42. doi: 10.1093/jee/tov262. Epub 2015 Sep 9. PubMed PMID: 26352751. 6: Lebedev G, Abo-Moch F, Gafni G, Ben-Yakir D, Ghanim M. High-level of resistance to spinosad, emamectin benzoate and carbosulfan in populations of Thrips tabaci collected in Israel. Pest Manag Sci. 2013 Feb;69(2):274-7. doi: 10.1002/ps.3385. Epub 2012 Aug 24. PubMed PMID: 22926932. 7: Snyder DE, Meyer KA, Wiseman S, Trout CM, Young DR. Speed of kill efficacy and efficacy of flavored spinosad tablets administered orally to cats in a simulated home environment for the treatment and prevention of cat flea (Ctenocephalides felis) infestations. Vet Parasitol. 2013 Sep 23;196(3-4):492-6. doi: 10.1016/j.vetpar.2013.02.023. Epub 2013 Mar 5. PubMed PMID: 23522900. 8: Adak T, Mukherjee I. Investigating Role of Abiotic Factors on Spinosad Dissipation. Bull Environ Contam Toxicol. 2016 Jan;96(1):125-9. doi: 10.1007/s00128-015-1644-z. Epub 2015 Sep 8. PubMed PMID: 26350899. 9: Lan Z, Zhao C, Guo W, Guan X, Zhang X. Optimization of Culture Medium for Maximal Production of Spinosad Using an Artificial Neural Network - Genetic Algorithm Modeling. J Mol Microbiol Biotechnol. 2015;25(4):253-61. doi: 10.1159/000381312. Epub 2015 Jun 30. PubMed PMID: 26138116. 10: Shi J, Zhang L, Gao X. Characterisation of spinosad resistance in the housefly Musca domestica (Diptera: Muscidae). Pest Manag Sci. 2011 Mar;67(3):335-40. doi: 10.1002/ps.2073. Epub 2011 Jan 11. PubMed PMID: 21308959. 11: Flores S, Gomez LE, Montoya P. Residual control and lethal concentrations of GF-120 (spinosad) for Anastrepha spp. (Diptera: Tephritidae). J Econ Entomol. 2011 Dec;104(6):1885-91. PubMed PMID: 22299349. 12: Sántis EL, Hernández LA, Martínez AM, Campos J, Figueroa JI, Lobit P, Chavarrieta JM, Viñuela E, Smagghe G, Pineda S. Long-term foliar persistence and efficacy of spinosad against beet armyworm under greenhouse conditions. Pest Manag Sci. 2012 Jun;68(6):914-21. doi: 10.1002/ps.3250. Epub 2012 Jan 20. PubMed PMID: 22262560. 13: Hertlein MB, Mavrotas C, Jousseaume C, Lysandrou M, Thompson GD, Jany W, Ritchie SA. A review of spinosad as a natural product for larval mosquito control. J Am Mosq Control Assoc. 2010 Mar;26(1):67-87. Review. PubMed PMID: 20402353. 14: Akmoutsou P, Mademtzoglou D, Nakou I, Onoufriadis A, Papadopoulou X, Kounatidis I, Frantzios G, Papadakis G, Vasiliadis K, Papadopoulos NT, Mavragani-Tsipidou P. Evaluation of toxicity and genotoxic effects of spinosad and deltamethrin in Drosophila melanogaster and Bactrocera oleae. Pest Manag Sci. 2011 Dec;67(12):1534-40. doi: 10.1002/ps.2208. Epub 2011 May 27. PubMed PMID: 21626654. 15: Spinosad (Natroba) topical suspension for head lice. Med Lett Drugs Ther. 2011 Jun 27;53(1367):50-1. Review. PubMed PMID: 21701441. 16: Six RH, Everett WR, Myers MR, Mahabir SP. Comparative speed of kill of sarolaner (Simparica) and spinosad plus milbemycin oxime (Trifexis) against induced infestations of Ctenocephalides felis on dogs. Parasit Vectors. 2016 Feb 19;9:93. doi: 10.1186/s13071-016-1374-z. PubMed PMID: 26896448; PubMed Central PMCID: PMC4761127. 17: Miles M, Mayes M, Dutton R. The effects of spinosad, a naturally derived insect control agent, to the honeybee (Apis melifera). Meded Rijksuniv Gent Fak Landbouwkd Toegep Biol Wet. 2002;67(3):611-6. PubMed PMID: 12696428. 18: Bielza P, Quinto V, Grávalos C, Fernández E, Abellán J, Contreras J. Stability of spinosad resistance in Frankliniella occidentalis (Pergande) under laboratory conditions. Bull Entomol Res. 2008 Aug;98(4):355-9. doi: 10.1017/S0007485308005658. Epub 2008 Feb 18. PubMed PMID: 18279567. 19: McQuate GT, Peck SL, Barr PG, Sylva CD. Comparative evaluation of spinosad and phloxine B as toxicants in protein baits for suppression of three fruit fly (Diptera: Tephritidae) species. J Econ Entomol. 2005 Aug;98(4):1170-8. PubMed PMID: 16156568. 20: Snyder DE, Cruthers LR, Slone RL. Preliminary study on the acaricidal efficacy of spinosad administered orally to dogs infested with the brown dog tick, Rhipicephalus sanguineus (Latreille, 1806) (Acari: Ixodidae). Vet Parasitol. 2009 Dec 3;166(1-2):131-5. doi: 10.1016/j.vetpar.2009.07.046. Epub 2009 Aug 5. PubMed PMID: 19713042.