Irciniastatins a and b

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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C549S289000

Reexamination Certificate

active

07439265

ABSTRACT:
The Indo-Pacific marine sponge Ircinia ramosa has been found to contain two powerful (GI50 0.001 to <0.0001 μg/ml) murine and human cancer cell growth inhibitors, denominated herein as irciniastatin A and irciniastatin B. Both were isolated (10-3 to 10-4% yields) by cancer cell line bioassay-guided techniques and named irciniastatins A (1) and B (2). Structural elucidation by a combination of spectral analyses, primarily high resolution mass and 2D-NMR (principally APT, HMQC, HMBC and ROESY) revealed unusual structures 1 and 2.

REFERENCES:
patent: 2007/0015821 (2007-01-01), Brabander et al.
De Brabander et al., “Improved Synthesis of the C17-C25 Fragment of the Anti-Tumor Natural Product Psymberin/Irciniastatin A”, 231stACS National Meeting, Atlanta, GA, Mar. 26-30, 2006 (Abstract only).
Jiang et al., “Synthesis and Complete Stereochemical Assignment of Psymberin/Irciniastatin A”,Journal of the American Chemical Society, 127(32):11254-11255 (2005).
Pettit et al., “Antineoplastic Agents. 520. Isolation and Structure of Irciniastatins A and B from the Indo-Pacific Marine SpongeIrcinia ramosa”, J. Med. Chem., 47:1149-1152 (2004).
Piel et al., “Exploring the Chemistry of Uncultivated Bacterial Symbionts: Antitumor Polyketides of the Pederin Family”,J. Nat. Prod., 68:472-479 (2005).
Shangguan et al., “A Formal Synthesis of Psymberin”,Organic Letters, 9(6):1093-1096 (2007).
Williams, Lawrence J., “Psymberin (irciniastatin A) via spirodiepoxide”, 38thMiddle Atlantic Regional Meeting of the American Chemical Society, Hershey, PA, Jun. 4-7, 2006 (Abstract only).
International Search Report for PCT/US04/38503 dated Jun. 3, 2005.
Written Opinion of the International Search Authority for PCT/US04/38503 dated Jun. 3, 2005.
Cichewicz et al, “Psymberin, A Potent Sponge-Derived Cytotoxin fromPsammociniaDistantly Related to the Pederin Family”, Organic Letters, vol. 6, No. 12, pp. 1951-1954, 2004.

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