Rottlerin | CAS#82-08-6

MedKoo Cat#: 407481 | Name: Rottlerin

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Description:

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

Rottlerin is an angiogenesis inhibitor and an inhibitor of protein kinase Cdelta (PKCdelta) and calmodulin kinase III. Rottlerin as a novel chemotherapy agent for adrenocortical carcinoma. Rottlerin induces cyclooxygenase-2 upregulation through an ATF4 and reactive oxygen species-independent pathway in HEI-OC1 cells. Rottlerin exerts its anti-tumor activity through inhibition of Skp2 in breast cancer cells. Rottlerin suppresses growth of human pancreatic tumors in nude mice, and pancreatic cancer cells isolated from Kras(G12D) mice.

Chemical Structure

Rottlerin

CAS#82-08-6

Theoretical Analysis

MedKoo Cat#: 407481

Name: Rottlerin

CAS#: 82-08-6

Chemical Formula: C30H28O8

Exact Mass: 516.1784

Molecular Weight: 516.55

Elemental Analysis: C, 69.76; H, 5.46; O, 24.78

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 250.00	2 Weeks
50mg	USD 750.00	2 Weeks

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Related CAS #

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Synonym

Rottlerin; Kamalin; Mallotoxin; NSC 56346; NSC 94525.

IUPAC/Chemical Name

(E)-1-(6-((3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl)-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl)-3-phenyl-2-propen-1-one

InChi Key

DEZFNHCVIZBHBI-ZHACJKMWSA-N

InChi Code

InChI=1S/C30H28O8/c1-15-24(33)19(27(36)22(16(2)31)25(15)34)14-20-26(35)18-12-13-30(3,4)38-29(18)23(28(20)37)21(32)11-10-17-8-6-5-7-9-17/h5-13,33-37H,14H2,1-4H3/b11-10+

SMILES Code

CC1(C)C=CC2=C(O)C(CC3=C(C(C)=C(C(C(C)=O)=C3O)O)O)=C(O)C(C(/C=C/C4=CC=CC=C4)=O)=C2O1

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Rottlerin has IC50 values for PKCδ of 3-6 μM, PKCα,β,γ of 30-42 μM, PKCε,η,ζ of 80-100 μM. Rottlerin acts as a direct mitochondrial uncoupler, and stimulates autophagy by targeting a signaling cascade upstream of mTORC1. Rottlerin induces apoptosis via caspase 3 activation.

In vitro activity:

The effects of rottlerin on CYP2C8 inhibition and EET formation insinuate further exploration for cancer therapy. Rottlerin showed highly potent and selective CYP2C8 inhibition (IC50 < 0.1 μM) in human liver microsomes. Reference: Chem Biol Interact. 2023 Aug 1;380:110524. https://pubmed.ncbi.nlm.nih.gov/37146929/

In vivo activity:

In a highly aggressive mouse mammary carcinoma model, rottlerin has significant potential to augment the anti-metastatic efficacy of paclitaxel via impeding EMT activation along with attenuating its treatment-associated toxicological alterations. Reference: Chem Biol Interact. 2022 Oct 1;366:110109. https://pubmed.ncbi.nlm.nih.gov/35995259/

	Solvent	mg/mL	mM
Solubility
	DMSO	12.5	24.20

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 516.55 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. Manhas D, Bhatt S, Rai G, Kumar V, Bharti S, Dhiman S, Jain SK, Sharma DK, Ojha PK, Gandhi SG, Goswami A, Nandi U. Rottlerin renders a selective and highly potent CYP2C8 inhibition to impede EET formation for implication in cancer therapy. Chem Biol Interact. 2023 Aug 1;380:110524. doi: 10.1016/j.cbi.2023.110524. Epub 2023 May 3. PMID: 37146929. 2. Lama Z, Gaudin Y, Blondel D, Lagaudrière-Gesbert C. Kinase inhibitors tyrphostin 9 and rottlerin block early steps of rabies virus cycle. Antiviral Res. 2019 Aug;168:51-60. doi: 10.1016/j.antiviral.2019.04.014. Epub 2019 May 7. PMID: 31071352. 3. Manhas D, Mir KB, Tripathi N, Bharti S, Dhiman S, Wazir P, Sharma DK, Goswami A, Nandi U. Rottlerin promotes anti-metastatic events by ameliorating pharmacological parameters of paclitaxel: An in-vivo investigation in the orthotopic mouse model of breast cancer. Chem Biol Interact. 2022 Oct 1;366:110109. doi: 10.1016/j.cbi.2022.110109. Epub 2022 Aug 19. PMID: 35995259. 4. Zhu Y, Wang M, Zhao X, Zhang L, Wu Y, Wang B, Hu W. Rottlerin as a novel chemotherapy agent for adrenocortical carcinoma. Oncotarget. 2017 Apr 4;8(14):22825-22834. doi: 10.18632/oncotarget.15221. PMID: 28423559; PMCID: PMC5410265.

In vitro protocol:

In vivo protocol:

1. Manhas D, Mir KB, Tripathi N, Bharti S, Dhiman S, Wazir P, Sharma DK, Goswami A, Nandi U. Rottlerin promotes anti-metastatic events by ameliorating pharmacological parameters of paclitaxel: An in-vivo investigation in the orthotopic mouse model of breast cancer. Chem Biol Interact. 2022 Oct 1;366:110109. doi: 10.1016/j.cbi.2022.110109. Epub 2022 Aug 19. PMID: 35995259. 2. Zhu Y, Wang M, Zhao X, Zhang L, Wu Y, Wang B, Hu W. Rottlerin as a novel chemotherapy agent for adrenocortical carcinoma. Oncotarget. 2017 Apr 4;8(14):22825-22834. doi: 10.18632/oncotarget.15221. PMID: 28423559; PMCID: PMC5410265.

1: Alav I, Pordelkhaki P, Rodriguez-Navarro J, Neo O, Kessler C, Awodipe RJ, Cliffe P, Pulavan N, Marton HL, Gibbons S, Buckner MMC. Natural products from food sources can alter the spread of antimicrobial resistance plasmids in Enterobacterales. Microbiology (Reading). 2024 Aug;170(8). doi: 10.1099/mic.0.001496. PMID: 39190025. 2: Kraus A, Kratzer B, Sehgal ANA, Trapin D, Khan M, Boucheron N, Pickl WF. Macropinocytosis Is the Principal Uptake Mechanism of Antigen-Presenting Cells for Allergen-Specific Virus-like Nanoparticles. Vaccines (Basel). 2024 Jul 18;12(7):797. doi: 10.3390/vaccines12070797. PMID: 39066435; PMCID: PMC11281386. 3: Wang D, Li Y, Li G, Liu M, Zhou Z, Wu M, Song S, Bian Y, Dong J, Li X, Du Y, Zhang T, Shi Y. Inhibition of PKC-δ retards kidney fibrosis via inhibiting cGAS- STING signaling pathway in mice. Cell Death Discov. 2024 Jul 7;10(1):314. doi: 10.1038/s41420-024-02087-z. PMID: 38972937; PMCID: PMC11228024. 4: Qin P, Zhou P, Huang Y, Long B, Gao R, Zhang S, Zhu B, Li YQ, Li Q. Upregulation of rate-limiting enzymes in cholesterol metabolism by PKCδ mediates endothelial apoptosis in diabetic wound healing. Cell Death Discov. 2024 May 29;10(1):263. doi: 10.1038/s41420-024-02030-2. PMID: 38811564; PMCID: PMC11137154. 5: Silva NBS, Menezes RP, Gonçalves DS, Santiago MB, Conejo NC, Souza SL, Santos ALO, da Silva RS, Ramos SB, Ferro EAV, Martins CHG. Exploring the antifungal, antibiofilm and antienzymatic potential of Rottlerin in an in vitro and in vivo approach. Sci Rep. 2024 May 15;14(1):11132. doi: 10.1038/s41598-024-61179-z. PMID: 38750088; PMCID: PMC11096346. 6: Xue W, Zhu B, Zhao K, Huang Q, Luo H, Shou Y, Huang Z, Guo H. Targeting LRP6: A new strategy for cancer therapy. Pharmacol Res. 2024 Jun;204:107200. doi: 10.1016/j.phrs.2024.107200. Epub 2024 May 6. PMID: 38710241. 7: Kam MK, Park JY, Yun GH, Sohn HY, Park JH, Choi J, Koh YH, Jo C. Rottlerin Enhances the Autophagic Degradation of Phosphorylated Tau in Neuronal Cells. Mol Neurobiol. 2024 Apr 27. doi: 10.1007/s12035-024-04182-9. Epub ahead of print. PMID: 38671330. 8: Xavier AET, Veronez LC, Nagano LFP, Correa CAP, Baroni M, Ramos MS, Queiroz RGP, Fernandes Molina CA, Yunes JA, Brandalise SR, Antonini SAR, Tone LG, Valera ET, Scrideli CA. Low PRKAB2 Expression Is Associated with Poor Outcomes in Pediatric Adrenocortical Tumors, and Treatment with Rottlerin Increases the PRKAB2 Level and Inhibits Tumorigenic Aspects in the NCI-H295R Adrenocortical Cancer Cell Line. Cancers (Basel). 2024 Mar 8;16(6):1094. doi: 10.3390/cancers16061094. PMID: 38539429; PMCID: PMC10968902. 9: Voronin D, Tricoche N, Peguero R, Kaminska AM, Ghedin E, Sakanari JA, Lustigman S. Repurposed Drugs That Activate Autophagy in Filarial Worms Act as Effective Macrofilaricides. Pharmaceutics. 2024 Feb 9;16(2):256. doi: 10.3390/pharmaceutics16020256. PMID: 38399310; PMCID: PMC10891619. 10: Dobhal K, Garg R, Singh A, Semwal A. Insight into the Natural Biomolecules (BMs): Promising Candidates as Zika Virus Inhibitors. Infect Disord Drug Targets. 2024;24(7):e020224226681. doi: 10.2174/0118715265272414231226092146. PMID: 38318833. 11: Voss S, Adair LD, Achazi K, Kim H, Bergemann S, Bartenschlager R, New EJ, Rademann J, Nitsche C. Cell-Penetrating Peptide-Bismuth Bicycles. Angew Chem Int Ed Engl. 2024 Mar 4;63(10):e202318615. doi: 10.1002/anie.202318615. Epub 2024 Jan 19. PMID: 38126926. 12: Zhang Y, Song J, Zhou Y, Jia H, Zhou T, Sun Y, Gao Q, Zhao Y, Pan Y, Sun Z, Chu P. Discovery of selective and potent USP22 inhibitors via structure-based virtual screening and bioassays exerting anti-tumor activity. Bioorg Chem. 2023 Dec;141:106842. doi: 10.1016/j.bioorg.2023.106842. Epub 2023 Sep 21. PMID: 37769523. 13: Teixeira SC, Paschoalino M, de Souza G, Rosini AM, de Lima Junior JP, Luz LC, Fajardo Martínez AF, Alves RN, Almeida MPO, Damasceno JL, Silva MJB, Ietta F, Barbosa BF, Ferro EAV, Gomes Martins CH. Rottlerin impairs early and late steps of Toxoplasma gondii infection in human trophoblast cells and villous explants. Chem Biol Interact. 2023 Oct 1;384:110716. doi: 10.1016/j.cbi.2023.110716. Epub 2023 Sep 16. PMID: 37722575. 14: Lu J, Yu M, Li J. PKC-δ Promotes IL-1β-Induced Apoptosis of Rat Chondrocytes and Via Activating JNK and P38 MAPK Pathways. Cartilage. 2024 Sep;15(3):315-327. doi: 10.1177/19476035231181446. Epub 2023 Jul 25. PMID: 37491820; PMCID: PMC11418514. 15: Kim Y, Kim HK, Kang S, Kim H, Go GW. Rottlerin suppresses lipid accumulation by inhibiting de novo lipogenesis and adipogenesis via LRP6/mTOR/SREBP1C in 3T3-L1 adipocytes. Food Sci Biotechnol. 2023 Jun 30;32(10):1445-1452. doi: 10.1007/s10068-023-01339-5. PMID: 37457404; PMCID: PMC10349001. 16: Choi JC, Jung SW, Choi IY, Kang YL, Lee DH, Lee SW, Park SY, Song CS, Choi IS, Lee JB, Oh C. Rottlerin-Liposome Inhibits the Endocytosis of Feline Coronavirus Infection. Vet Sci. 2023 May 30;10(6):380. doi: 10.3390/vetsci10060380. PMID: 37368766; PMCID: PMC10302841. 17: Ojha D, Jessop F, Bosio CM, Peterson KE. Effective inhibition of HCoV-OC43 and SARS-CoV-2 by phytochemicals in vitro and in vivo. Int J Antimicrob Agents. 2023 Sep;62(3):106893. doi: 10.1016/j.ijantimicag.2023.106893. Epub 2023 Jun 18. PMID: 37339711; PMCID: PMC10277159. 18: Tran NKC, Jeong JH, Sharma N, Nguyen YND, Tran HP, Dang DK, Park JH, Byun JK, Jin D, Xiaoyan Z, Ko SK, Nah SY, Kim HC, Shin EJ. Ginsenoside Re blocks Bay k-8644-induced neurotoxicity via attenuating mitochondrial dysfunction and PKCδ activation in the hippocampus of mice: Involvement of antioxidant potential. Food Chem Toxicol. 2023 Aug;178:113869. doi: 10.1016/j.fct.2023.113869. Epub 2023 Jun 10. PMID: 37308051. 19: Shindo S, Pierrelus R, Ikeda A, Nakamura S, Heidari A, Pastore MR, Leon E, Ruiz S, Chheda H, Khatiwala R, Kumagai T, Tolson G, Elderbashy I, Ouhara K, Han X, Hernandez M, Vardar-Sengul S, Shiba H, Kawai T. Extracellular Release of Citrullinated Vimentin Directly Acts on Osteoclasts to Promote Bone Resorption in a Mouse Model of Periodontitis. Cells. 2023 Apr 8;12(8):1109. doi: 10.3390/cells12081109. PMID: 37190018; PMCID: PMC10136503. 20: Manhas D, Bhatt S, Rai G, Kumar V, Bharti S, Dhiman S, Jain SK, Sharma DK, Ojha PK, Gandhi SG, Goswami A, Nandi U. Rottlerin renders a selective and highly potent CYP2C8 inhibition to impede EET formation for implication in cancer therapy. Chem Biol Interact. 2023 Aug 1;380:110524. doi: 10.1016/j.cbi.2023.110524. Epub 2023 May 3. PMID: 37146929.