870677-05-7

Basic information

• Product Name: DMAPT
• Synonyms: DMAPT;UJNSFDHVIBGEJZ-KVUCBBCISA-N;Dimethylamino Parthenolide
• CAS NO: 870677-05-7
• Molecular Formula: C17H27NO3
• Molecular Weight: 293.40118
• Mol File: 870677-05-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO, Ethyl acetate, or Ethanol.
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO, ethanol, or ethyl acetate may be stored at -20° for up to 1 month.
• CAS DataBase Reference: DMAPT(CAS DataBase Reference)
• NIST Chemistry Reference: DMAPT(870677-05-7)
• EPA Substance Registry System: DMAPT(870677-05-7)

Safety Data

• Hazardous Substances Data: 870677-05-7(Hazardous Substances Data)

Usage

Description

DMAPT (870677-05-7) is a water-soluble analog of the natural plant product parthenolide, which has been found to suppress in vivo tumor growth of tobacco-associated neoplasms, such as lung and bladder cancer. It possesses the ability to inhibit NFκB and stimulate the formation of reactive oxygen species, leading to the activation of JNK. In non-small cell lung cancers, DMAPT inhibits NFκB and DNA double-strand break repair.

Uses

Used in Oncology:
DMAPT is used as an antileukemic and cytotoxic agent for its potential in suppressing tumor growth and inhibiting cancer-related processes. Its ability to inhibit NFκB and DNA double-strand break repair makes it a promising candidate for cancer treatment.
Used in Pharmaceutical Industry:
As a parthenolide derivative, DMAPT is utilized in the development of pharmaceutical agents targeting various types of cancer. Its unique properties in inhibiting NFκB and inducing reactive oxygen species contribute to its potential as a therapeutic agent in oncology.

References

1) Shanmugam?et al. (2011),?A water soluble parthenolide analog suppresses in vivo tumor growth of two tobacco-associated cancers, lung and bladder cancer, by targeting NFκB and generating reactive oxygen species; Int. J. Cancer,?128?2481 2) Estrabrook?et al. (2011),?Inhibition of NF-κB and DNA double-strand break repair by DMAPT sensitizes non-small-cell lung cancers to X-rays; Free Radic. Biol. Med.,?51?2249

Upstream product

• 124-40-3 dimethyl amine 
• 503551-53-9 parthenolide 

Relevant articles and documents

Synthesis and antileukemic activities of C1-C10-modified parthenolide analogues

Parthenolide (PTL) is a sesquiterpene lactone natural product with anti-proliferative activity to cancer cells. Selective eradication of leukemic stem cells (LSCs) over healthy hematopoietic stem cells (HSCs) by PTL has been demonstrated in previous studies, which suggests PTL and related molecules may be useful for targeting LSCs. Eradication of LSCs is required for curative therapy. Chemical optimizations of PTL to improve potency and pharmacokinetic parameters have focused largely on the α-methylene-γ-butyrolactone, which is essential for activity. Conversely, we evaluated modifications to the C1-C10 olefin and benchmarked new inhibitors to PTL with respect to inhibitory potency across a panel of cancer cell lines, ability to target drug-resistant acute myeloid leukemia (AML) cells, efficacy for inhibiting clonal growth of AML cells, toxicity to healthy bone marrow cells, and efficiency for promoting intracellular reactive oxygen species (ROS) levels. Cyclopropane 4 was found to possess less toxicity to healthy bone marrow cells, enhanced potency for the induction of cellular ROS, and similar broad-spectrum anti-proliferative activity to cancer cells in comparison to PTL.

Chamomile lactone derivative as well as preparation method and application thereof (by machine translation)

The invention relates to the technical field of organic synthesis, in particular to a small white chrysanthemum lactone derivative and a preparation method and application thereof. To the invention, small white chrysanthemum is used as the original main raw material, 11 small white chrysanthemum lactone derivatives are synthesized through a series of chemical reactions, and the derivatives have certain anti-proliferative activity on glioblastoma cells. The invention also proves that the deuterated derivative DMAPAPAPAPAPT-D6 can significantly induce accumulation of active oxygen of glioblastoma cells, thereby leading DNA damage in glioblastoma cells. Furthermore, DMAPAPAPAPAPT-D6 promotes exogenous apoptosis mediated by the death receptor of caspase, indicating DNA damage induced by DMAPAPAPAPAPT-D6 inducible glioblastoma apoptosis. , ROS accumulation caused by DMAPAPAPAPAPT-D6 treatment leads DNA damage and death receptor-mediated apoptosis, which indicates that DMAPAPAPAPAPT-D6 with novel ingredients has therapeutic potential for treating glioblastoma and can be applied to preparation of drugs for treating glioblastoma. (by machine translation)

Crystal form of small white chrysanthemum lactone dimethyl amine fumarate and preparation method thereof (by machine translation)

The invention relates to a crystal form and a preparation method, wherein the crystal form is simple to operate, is easy to industrialize, and is high in safety. (by machine translation)

USE OF PARTHENOLIDE DERIVATIVES AS ANTILEUKEMIC AND CYTOTOXIC AGENTS

The present invention provides compounds of the formula (I) wherein: X1, X2 and X3 are heteroatoms; R4, R5, R6, R7, R8, R9 and R10 are independently selected from H, halo, —OH, —NO2, —CN and optionally substituted aliphatic, cycloalkyl, heterocycloalkyl, aryl or heteroaryl; and Z is optionally substituted C1-8 straight-chained or branched aliphatic, optionally containing 1 or more double or triple bonds, wherein one or more carbons are optionally replaced by R* wherein R* is optionally substituted cycloalkyl, heterocycloalkyl, aryl or heteroaryl; an amino acid residue, H, —CN, —C(O)—, —C(O)C(O)—, —C(O)NR1—, —C(O)NR1NR2—, —C(O)O—, —OC(O)—, —NR1CO2—, —O—, —NR1C(O)NR2—, —OC(O)NR1—, —NR1NR2—, —NR1C(O)—, —S—, —SO—, —SO2—, —NR1—, —SO2NR1—, —NR1R2, or —NR1SO2—, wherein R1 and R2 are independently selected from H and optionally substituted aliphatic, cycloalkyl, heterocycloalkyl, aryl or heteroaryl; or where R* is NR1R2, R1 and R2 optionally together with the nitrogen atom form an optionally substituted 5-12 membered ring, said ring optionally comprising 1 or more heteroatoms or a group selected from —CO—, —SO—, —SO2— and —PO—; or a pharmaceutically acceptable salt, ester or prodrug thereof.