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MedKoo Cat#: 533390 | Name: ADEP4

Description:

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

ADEP4 is a novel potent activator of the ClpP protease, causing cells to self-digest. ADEP 4 has been shown to activate the ClpP protease resulting in death of growing cells7. ADEP4 is a semi-synthetic derivative of the natural product acyldepsipeptide, factor A, with increased potency against gram-positive organisms. ADEP4 binds to ClpP and keeps the catalytic chamber open, allowing access to peptides and proteins, normally too large to access the chamber. ADEP4 shows efficacy in a lethal systemic murine infection of Enterococcus faecalis and S. aureus and lethal sepsis caused by Streptococcus pneumoniae in the rat. ADEP4 forces the cell to self-digest, and may be effective in killing dormant cells.

Chemical Structure

ADEP4
CAS#502965-06-2

Theoretical Analysis

MedKoo Cat#: 533390

Name: ADEP4

CAS#: 502965-06-2

Chemical Formula: C39H52F2N6O8

Exact Mass: 770.3815

Molecular Weight: 770.88

Elemental Analysis: C, 60.77; H, 6.80; F, 4.93; N, 10.90; O, 16.60

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.
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Related CAS #
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Synonym
ADEP4; ADEP-4; ADEP 4; ADEP 11; ADEP-11; ADEP11; acyldepsipeptide-4;
IUPAC/Chemical Name
(E)-N-((S)-3-(3,5-Difluorophenyl)-1-(((2R,6S,8aS,14aS,20S,23aS)-2,6-dimethyl-5,8,14,19,23-pentaoxooctadecahydro-1H,5H,14H,19H-pyrido[2,1-i]dipyrrolo[2,1-c:2',1'-l][1]oxa[4,7,10,13]tetraazacyclohexadecin-20-yl)amino)-1-oxopropan-2-yl)hept-2-enamide
InChi Key
BAEUBYUDIYWBPI-HQKUAFLWSA-N
InChi Code
InChI=1S/C39H52F2N6O8/c1-4-5-6-7-13-33(48)43-28(19-25-17-26(40)20-27(41)18-25)34(49)44-29-22-55-39(54)32-16-23(2)21-47(32)36(51)24(3)42-35(50)30-11-8-9-14-45(30)38(53)31-12-10-15-46(31)37(29)52/h7,13,17-18,20,23-24,28-32H,4-6,8-12,14-16,19,21-22H2,1-3H3,(H,42,50)(H,43,48)(H,44,49)/b13-7+/t23-,24+,28+,29+,30+,31+,32+/m1/s1
SMILES Code
CCCC/C=C/C(N[C@@H](CC1=CC(F)=CC(F)=C1)C(N[C@@H]2C(N3[C@](CCC3)([H])C(N4[C@](CCCC4)([H])C(N[C@@H](C)C(N5[C@](C[C@@H](C)C5)([H])C(OC2)=O)=O)=O)=O)=O)=O)=O
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
>3 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
Acyldepsipeptide or cyclic acyldepsipeptide (ADEP) is a class of potential antibiotics first isolated from bacteria and act by deregulating the ClpP protease. Natural ADEPs were originally found as products of aerobic fermentation in Streptomyces hawaiiensis, A54556A and B, and in the culture broth of Streptomyces species, enopeptin A and B. ADEPs are of great interest in drug development due to their antibiotic properties and thus are being modified in attempt to achieve greater antimicrobial activity.

Preparing Stock Solutions

The following data is based on the product molecular weight 770.88 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.

Recalculate based on batch purity %
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
1: Yee R, Yuan Y, Tarff A, Brayton C, Gour N, Feng J, Zhang Y. Eradication of Staphylococcus aureus Biofilm Infection by Persister Drug Combination. Antibiotics (Basel). 2022 Sep 20;11(10):1278. doi: 10.3390/antibiotics11101278. PMID: 36289936; PMCID: PMC9598165. 2: Yang T, Zhang T, Zhou X, Wang P, Gan J, Song B, Yang S, Yang CG. Dysregulation of ClpP by Small-Molecule Activators Used Against Xanthomonas oryzae pv. oryzae Infections. J Agric Food Chem. 2021 Jul 14;69(27):7545-7553. doi: 10.1021/acs.jafc.1c01470. Epub 2021 Jul 3. PMID: 34218658. 3: Scheper H, Wubbolts JM, Verhagen JAM, de Visser AW, van der Wal RJP, Visser LG, de Boer MGJ, Nibbering PH. SAAP-148 Eradicates MRSA Persisters Within Mature Biofilm Models Simulating Prosthetic Joint Infection. Front Microbiol. 2021 Jan 29;12:625952. doi: 10.3389/fmicb.2021.625952. PMID: 33584628; PMCID: PMC7879538. 4: Malik IT, Pereira R, Vielberg MT, Mayer C, Straetener J, Thomy D, Famulla K, Castro H, Sass P, Groll M, Brötz-Oesterhelt H. Functional Characterisation of ClpP Mutations Conferring Resistance to Acyldepsipeptide Antibiotics in Firmicutes. Chembiochem. 2020 Jul 16;21(14):1997-2012. doi: 10.1002/cbic.201900787. Epub 2020 Apr 9. PMID: 32181548; PMCID: PMC7496096. 5: Jacques S, van der Sloot AM, C Huard C, Coulombe-Huntington J, Tsao S, Tollis S, Bertomeu T, Culp EJ, Pallant D, Cook MA, Bonneil E, Thibault P, Wright GD, Tyers M. Imipridone Anticancer Compounds Ectopically Activate the ClpP Protease and Represent a New Scaffold for Antibiotic Development. Genetics. 2020 Apr;214(4):1103-1120. doi: 10.1534/genetics.119.302851. Epub 2020 Feb 24. PMID: 32094149; PMCID: PMC7153937. 6: Mroue N, Arya A, Brown Gandt A, Russell C, Han A, Gavrish E, LaFleur M. Pharmacodynamics of ClpP-Activating Antibiotic Combinations against Gram- Positive Pathogens. Antimicrob Agents Chemother. 2019 Dec 20;64(1):e01554-19. doi: 10.1128/AAC.01554-19. PMID: 31611348; PMCID: PMC7187625. 7: Blanco MJ. Building upon Nature's Framework: Overview of Key Strategies Toward Increasing Drug-Like Properties of Natural Product Cyclopeptides and Macrocycles. Methods Mol Biol. 2019;2001:203-233. doi: 10.1007/978-1-4939-9504-2_10. PMID: 31134573. 8: Brown Gandt A, Griffith EC, Lister IM, Billings LL, Han A, Tangallapally R, Zhao Y, Singh AP, Lee RE, LaFleur MD. In Vivo and In Vitro Effects of a ClpP-Activating Antibiotic against Vancomycin-Resistant Enterococci. Antimicrob Agents Chemother. 2018 Jul 27;62(8):e00424-18. doi: 10.1128/AAC.00424-18. PMID: 29784838; PMCID: PMC6105829. 9: Pstrągowski MT, Bujalska-Zadrożny M. Acyldepsipeptide antibiotics--current state of knowledge. Pol J Microbiol. 2015;64(2):85-92. PMID: 26373166. 10: Mechler L, Herbig A, Paprotka K, Fraunholz M, Nieselt K, Bertram R. A novel point mutation promotes growth phase-dependent daptomycin tolerance in Staphylococcus aureus. Antimicrob Agents Chemother. 2015 Sep;59(9):5366-76. doi: 10.1128/AAC.00643-15. Epub 2015 Jun 22. PMID: 26100694; PMCID: PMC4538524. 11: Yang GX, Xu YY, Fan YP, Wang J, Chen XL, Zhang YD, Wu JH. A maladaptive role for EP4 receptors in mouse mesangial cells. PLoS One. 2014 Aug 14;9(8):e104091. doi: 10.1371/journal.pone.0104091. PMID: 25122504; PMCID: PMC4133176. 12: Conlon BP, Nakayasu ES, Fleck LE, LaFleur MD, Isabella VM, Coleman K, Leonard SN, Smith RD, Adkins JN, Lewis K. Activated ClpP kills persisters and eradicates a chronic biofilm infection. Nature. 2013 Nov 21;503(7476):365-70. doi: 10.1038/nature12790. Epub 2013 Nov 13. PMID: 24226776; PMCID: PMC4031760. 13: Hinzen B, Raddatz S, Paulsen H, Lampe T, Schumacher A, Häbich D, Hellwig V, Benet-Buchholz J, Endermann R, Labischinski H, Brötz-Oesterhelt H. Medicinal chemistry optimization of acyldepsipeptides of the enopeptin class antibiotics. ChemMedChem. 2006 Jul;1(7):689-93. doi: 10.1002/cmdc.200600055. PMID: 16902918. 14: Young JJ, Jung LJ, Liu WT, Ho SN, Chang LR, Tsai YC, Bhaskaran R, Yu C. Solution conformation of enopeptin A, a depsipeptide antibiotic, using 2D NMR and restrained molecular dynamics studies. J Antibiot (Tokyo). 1994 Aug;47(8):922-31. doi: 10.7164/antibiotics.47.922. PMID: 7928680. 15: Osada H, Yano T, Koshino H, Isono K. Enopeptin A, a novel depsipeptide antibiotic with anti-bacteriophage activity. J Antibiot (Tokyo). 1991 Dec;44(12):1463-6. doi: 10.7164/antibiotics.44.1463. PMID: 1778798.