Reticulol | CAS#26246-41-3 | cAMP inhibitor

MedKoo Cat#: 407825 | Name: Reticulol

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Description:

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

Reticulol is an isocoumarin derivative produced by certain species of Streptomyces that inhibits cAMP phosphodiesterase (IC50 = 41 µM). Reticulol was isolated from the culture broth of the strain Streptoverticillium sp. NA-4803. Recticulol (M.W. 222.2) exhibited a potent in vitro cytotoxicity against A427, a human lung tumor cell line, and B16F10, a mouse melanoma cell line.

Chemical Structure

Reticulol

CAS#26246-41-3

Theoretical Analysis

MedKoo Cat#: 407825

Name: Reticulol

CAS#: 26246-41-3

Chemical Formula: C11H10O5

Exact Mass: 222.0528

Molecular Weight: 222.20

Elemental Analysis: C, 59.46; H, 4.54; O, 36.00

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 450.00	2 Weeks
5mg	USD 1,300.00	2 Weeks

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Related CAS #

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Synonym

Reticulol; 6,8-dihydroxy-7-methoxy-3-methyl Isocoumarin, NSC 294978;

IUPAC/Chemical Name

6,8-dihydroxy-7-methoxy-3-methyl-1H-2-benzopyran-1-one

InChi Key

LREZRXWUEZCZRU-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H10O5/c1-5-3-6-4-7(12)10(15-2)9(13)8(6)11(14)16-5/h3-4,12-13H,1-2H3

SMILES Code

O=C1C2=C(O)C(OC)=C(O)C=C2C=C(C)O1

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

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Reticulol is an isocoumarin derivative produced by certain species of Streptomyces that inhibits cAMP phosphodiesterase (IC50 = 41 µM). It also inhibits DNA topoisomerase I when used at a concentration of 45 µM in B16F10 melanoma cells. Reticulol has antifungal activity against T. mentagrophyes with a MIC of 1.8 µM. It is cytotoxic against A427 human lung and B16F10 mouse melanoma cells at concentrations of 25 and 200 µM, respectively, and inhibits lung metastasis in mice.

In vitro activity:

In this study, isolates were tested for antifood allergic bioactivities in immunoglobulin E-mediated rat basophilic leukemia-2H3 cells. Reticulol significantly decreased the rates of degranulation and histamine release with IC50 values of 13.5 and 13.7 μM, respectively. These results suggest that reticulol could be a potential anti-food allergic medicine. Reference: J Agric Food Chem. 2018 Feb 14;66(6):1369-1376. https://pubmed.ncbi.nlm.nih.gov/29355320/

In vivo activity:

Reticulol combined with Adriamycin inhibited B16F10 melanoma tumor growth compared to mice treated with Adriamycin alone (1 mg/kg). These results suggested that reticulol inactivates Topo I, which is involved in tumor metastasis, and exhibits excellent cytotoxic efficacy against B16F10 melanoma, when combined with Adriamycin, in a mouse model. Reference: Chemotherapy. 2003 Sep;49(5):257-63. https://pubmed.ncbi.nlm.nih.gov/14504438/

Preparing Stock Solutions

The following data is based on the product molecular weight 222.20 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. Niu S, Liu Q, Xia JM, Xie CL, Luo ZH, Shao Z, Liu G, Yang XW. Polyketides from the Deep-Sea-Derived Fungus Graphostroma sp. MCCC 3A00421 Showed Potent Antifood Allergic Activities. J Agric Food Chem. 2018 Feb 14;66(6):1369-1376. doi: 10.1021/acs.jafc.7b04383. Epub 2018 Feb 2. PMID: 29355320. 2. Boonlarppradab C, Suriyachadkun C, Suphothina S, Tobwor P. Bireticulol, a bioactive isocoumarin dimer from Streptomyces sp. BCC24731. J Antibiot (Tokyo). 2011 Mar;64(3):267-70. doi: 10.1038/ja.2010.171. Epub 2011 Jan 12. PMID: 21224860. 3. Lim DS, Kwak YS, Lee KH, Ko SH, Yoon WH, Lee WY, Kim CH. Topoisomerase I inactivation by reticulol and its in vivo cytotoxicity against B16F10 melanoma. Chemotherapy. 2003 Sep;49(5):257-63. doi: 10.1159/000072451. PMID: 14504438. 4. Lim DS, Kwak YS, Kim JH, Ko SH, Yoon WH, Kim CH. Antitumor efficacy of reticulol from Streptoverticillium against the lung metastasis model B16F10 melanoma. Lung metastasis inhibition by growth inhibition of melanoma. Chemotherapy. 2003 Jun;49(3):146-53. doi: 10.1159/000070621. PMID: 12815208.

In vitro protocol:

In vivo protocol:

1. Lim DS, Kwak YS, Lee KH, Ko SH, Yoon WH, Lee WY, Kim CH. Topoisomerase I inactivation by reticulol and its in vivo cytotoxicity against B16F10 melanoma. Chemotherapy. 2003 Sep;49(5):257-63. doi: 10.1159/000072451. PMID: 14504438. 2. Lim DS, Kwak YS, Kim JH, Ko SH, Yoon WH, Kim CH. Antitumor efficacy of reticulol from Streptoverticillium against the lung metastasis model B16F10 melanoma. Lung metastasis inhibition by growth inhibition of melanoma. Chemotherapy. 2003 Jun;49(3):146-53. doi: 10.1159/000070621. PMID: 12815208.

1: Purbaya S, Harneti D, Safriansyah W, Rahmawati, Wulandari AP, Mulyani Y, Supratman U. Secondary Metabolites of Biscogniauxia: Distribution, Chemical Diversity, Bioactivity, and Implications of the Occurrence. Toxins (Basel). 2023 Dec 6;15(12):686. doi: 10.3390/toxins15120686. PMID: 38133190; PMCID: PMC10747060. 2: Niu S, Liu Q, Xia JM, Xie CL, Luo ZH, Shao Z, Liu G, Yang XW. Polyketides from the Deep-Sea-Derived Fungus Graphostroma sp. MCCC 3A00421 Showed Potent Antifood Allergic Activities. J Agric Food Chem. 2018 Feb 14;66(6):1369-1376. doi: 10.1021/acs.jafc.7b04383. Epub 2018 Feb 2. PMID: 29355320. 3: Prompanya C, Dethoup T, Bessa LJ, Pinto MM, Gales L, Costa PM, Silva AM, Kijjoa A. New isocoumarin derivatives and meroterpenoids from the marine sponge- associated fungus Aspergillus similanensis sp. nov. KUFA 0013. Mar Drugs. 2014 Oct 14;12(10):5160-73. doi: 10.3390/md12105160. PMID: 25317534; PMCID: PMC4210891. 4: Boonlarppradab C, Suriyachadkun C, Suphothina S, Tobwor P. Bireticulol, a bioactive isocoumarin dimer from Streptomyces sp. BCC24731. J Antibiot (Tokyo). 2011 Mar;64(3):267-70. doi: 10.1038/ja.2010.171. Epub 2011 Jan 12. PMID: 21224860. 5: Ryoo IJ, Xu GH, Kim YH, Choo SJ, Ahn JS, Bae K, Yoo ID. Reticulone, a novel free radical scavenger produced by Aspergillus sp. J Microbiol Biotechnol. 2009 Dec;19(12):1573-5. doi: 10.4014/jmb.0906.06033. PMID: 20075621. 6: Lim DS, Kwak YS, Lee KH, Ko SH, Yoon WH, Lee WY, Kim CH. Topoisomerase I inactivation by reticulol and its in vivo cytotoxicity against B16F10 melanoma. Chemotherapy. 2003 Sep;49(5):257-63. doi: 10.1159/000072451. PMID: 14504438. 7: Lim DS, Kwak YS, Kim JH, Ko SH, Yoon WH, Kim CH. Antitumor efficacy of reticulol from Streptoverticillium against the lung metastasis model B16F10 melanoma. Lung metastasis inhibition by growth inhibition of melanoma. Chemotherapy. 2003 Jun;49(3):146-53. doi: 10.1159/000070621. PMID: 12815208. 8: Furutani Y, Shimada M, Hamada M, Takeuchi T, Umezawa H. Reticulol, an inhibitor of cyclic adenosine 3', 5'-monophosphate phosphodiesterase. J Antibiot (Tokyo). 1975 Jul;28(7):558-60. doi: 10.7164/antibiotics.28.558. PMID: 168174. 9: Mitscher LA, Andres WW, McCrae W. Reticulol, a new metabolic isocoumarin. Experientia. 1964 May 15;20(5):258-9. doi: 10.1007/BF02151790. PMID: 5856305.

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PROTAC P3

MedKoo CAT#: 463068

CAS#: unknown