AdipoGen Life Sciences

Agelasine D

Name: Agelasine D
Brand: AdipoGen Life Sciences
SKU: AG-CN2-0492
Price: 240.00 CHF
Availability: InStock

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AG-CN2-0492-M0011 mgCHF 240.00

Specifications / Handling

More Information
Product Details
Synonyms	(+)-Agelasine D
Product Type	Chemical
Properties
Formula	C₂₆H₄₀N₅
MW	422.6
CAS	92664-80-7
Source/Host Chemicals	Isolated from sponge Agelas sp.
Purity Chemicals	≥97% (HPLC)
Appearance	Off-white to colorless crystals.
Solubility	Soluble in DMSO, ethanol or methanol.
Identity	Determined by ¹H-NMR and MS.
InChi Key	SHVHRNDHUVXXIF-XGBZQHFCSA-O
Smiles	C/C(CC[C@H]1C(CC[C@]2([H])[C@]1(C)CCCC2(C)C)=C)=C\C[NH]3CN(C)C4=C3C(N)=NC=N4
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry. Protect from light.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
Safety Data Sheet	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Scientific Background Information

Product Description

Antifouling compound.
Antimycobacterial and antibacterial agent. Exerts its antibacterial effect by inhibiting enzyme BCG 3185c, a suspected dioxygenase thereby disrupting bacterial homeostasis.
Associated with contractive responses of smooth muscles and inhibition of Na⁺/K⁺ ATPase.
Cytotoxic/Antineoplastic agent. Found to exhibit inhibitory activity against several cancer cell lines, including the drug resistant renal cancer cell line (ACHN).
Suppressor of RANKL-induced osteoclastogenesis via down-regulation of c-Fos, NFATc1, NF-κB and ERK.
Antiprotozoal compound.

Product-specific References

Agelasine-A -B, -C and -D, novel bicyclic diterpenoids with a 9-methyladeninium unit possessing inhibitory effects on Na,K-ATPase isolated from the Okinawian sea sponge Agelas sp: H. Nakamura, et al.; Tetrahedron Lett. 25, 2989 (1984)
(+)-agelasine D: improved synthesis and evaluation of antibacterial and cytotoxic activities: A. Vik, et al.; J. Nat. Prod. 69, 381 (2006)
Synthesis, antimicrobial and antineoplastic activities for agelasine and agelasimine analogs with a beta-cyclocitral derived substituent: A. Proszenyak, et al.; Arch. Pharm. 340, 625 (2007)
Antifouling activity of the sponge metabolite agelasine D and synthesised analogs on Balanus improvisus: M. Sjoegren, et al.; Biofouling 24, 251 (2008)
Screening of Agelasine D and Analogs for Inhibitory Activity against Pathogenic Protozoa; Identification of Hits for Visceral Leishmaniasis and Chagas Disease: A. Vik, et al.; Molecules 14, 279 (2009)
From anti-fouling to biofilm inhibition: New cytotoxic secondary metabolites from two Indonesian Agelas sponges: T. Hertiani, et al.; Bioorg. Med. Chem. 18, 1297 (2010)
Synthesis and biological activities of marine terpene-adenine hybrids and synthetic analogs: L.-L. Gundersen; Phytochem. Rev. 12, 467 (2013) (Review)
Identification of the target protein of agelasine D, a marine sponge diterpene alkaloid, as an anti-dormant mycobacterial substance: M. Arai, et al.; Chembiochem. 15, 117 (2014)
Agelasine D suppresses RANKL-induced osteoclastogenesis via down-regulation of c-Fos, NFATc1 and NF-κB: M.R. Kang, et al.; Mar. Drugs 12, 5643 (2014)

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