CAS: 110117-83-4; Indoximod

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21339-55-9 26988-72-7 143824-78-6

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L-Tryptophan methyl iodide 1-methylindole L-serin α-(tert-butoxycarbonyl)-1-methyl-L-tryptophanNα-(tert-butoxycarbonyl)-1-methyl-L-tryptophan Fm°C-1-Me-Trp-OH (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1-methyl-1H-indol-3-yl)propanoic acid H-indol-3-yl)-propionic acid methyl ester2-[2-(6-methyl-3,5-dioxo-8,8-diphenyl-7-oxa-2,4-diaza-bicyclo[4.2.0]°Ct-2-yl)-acetylamino]-3-(1-methyl-1H-indol-3-yl)-propionic acid methyl ester

📜Boc-D-色氨酸置于potassium Tert-Butylate,水,三氟乙酸,Lithium Hydroxide体系中,用 四氢呋喃,二氯甲烷,N,N-二甲基甲酰胺 用作溶剂,化学反应 9.33H,反应生成1-甲基-D-色氨酸
参考文献:Pentapeptides For The Treatment Of Small Cell Lung Cancer: Optimisation By N Ind-Alkyl Modification Of The Tryptophan Side Chain
标题:Pentapeptides For The Treatment Of Small Cell Lung Cancer: Optimisation By N Ind-Alkyl Modification Of The Tryptophan Side Chain
摘要:The Pentapeptide,Tert-Prenyl4Th-Nh2 (Dmephe-Dtrp-Phe-Dtrp(N-Tert-Prenyl)-Leu-Nh2),Has Recently Been Reported By Our Group To Exhibit Properties Of Substance P (Sp) Antagonist G Against Small Cell Lung Cancer (Sclc). In This Study,We Undertook A Systematic Structure Activity Investigation To Optimise This Lead Compound To Improve Its In Vitro Anti-Tumour Activity And Biocompatibility. A Series Of D-Tryptophan (D-Trp) Derivatives Were Synthesised,With A Range Of Aliphatic N-Alkyl Chains (Methyl To Pentyl) On The Indole Nitrogen (N-Ind). These Were Incorporated Into The Pentapeptide Sequence By Substitution Of The N-Ind-Tert-Prenylated D-Trp 4Th Residue With The N-Ind-Alkylated D-Trp Derivatives. These Pentapeptides Were Significantly More Potent Than Tert-Prenyl4Th-Nh2,With The N-Ind-Butyl Modification Generating The Most Cytotoxic Peptides. Compared To Tert-Prenyl4Th-Nh2,A Single Butyl Modification On The 4Th D-Trp Residue (Butyl4Th-Nh2) Showed A Similar To 3 Fold Enhancement In Cytotoxicity In Either The Chemo-Naive H69 Or The Dms79 (Originating From A Patient Treated With Chemotherapeutics And Radiation Therapy) Sclc Cell Lines. In Addition,The Di-Butylated Sequence On The 2Nd And 4Th D-Trp Residues (Butyl2Nd.4Th-Nh2) Gave Similar To 4.5 Times Higher Cytotoxicity Against The H69 Cell Line And A Similar To 2 Fold Increase Against The Dms79 Cell Line,Compared To Tert-Prenyl4Th-Nh2. The Favoured Position For Butyl Modification Was The 4Th D-Trp Residue,As The Butyl2Nd-Nh2 Peptide Gave Lower Cytotoxicity On Both Cell Lines. Butylated Peptide Sequences,When Exposed To Neat Mouse Plasma For 24 H At 37 Degrees C,Were Found To Resist Degradation With >80% Remaining Intact Compared To Similar To 58% For Tert-Prenyl4Th-Nh2. The Degradation Pathway In Plasma occurs Via De-Amidation Of The C-Terminus,Confirmed By Mass Spectrometry And Rp-HPLC Analysis. The Butyl Modification Also Conferred Resistance To Metabolism When Tested Using S9 Liver Fraction From Mouse. The Optimum Analogue Responsive Against The Dms79 Cell Line Was The Butyl4Th-Nh2 Pentapeptide,Which Revealed A Concentration Dependent Increase In Apoptosis: The Level Of Late Apoptotic Cells Rose From Similar To 36% At 2 Mu M To Similar To 96% At 6 Mu M,As Determined By Flow Cytometry,Compared To The Unmodified Peptide That Showed No Such Effect. Concluding,The Butyl Substitutions Offered The Best Perspective For High Cytotoxicity,Induction Of Apoptosis And Metabolic Compatibility Thereby Comprising An Improved Broad Spectrum Sp Antagonist Candidate For Treatment Of Sclc. (C) 2017 The Authors. Published By Elsevier Masson Sas.
Doi:10.1016/j.Ejmech.2017.05.053

专利信息

专利号:US-2022233673-A1
优先权日:2019-06-04
标 题:METHODS OF PRODUCING SHIGA TOXIN B-SUBUNIT (STxB) MONOMERS AND OLIGOMERS, AND USES THEREOF
发明人：BILLET ANNE; SCHMIDT FRÉDÉRIC; JOHANNES LUDGER; SERVENT DENIS; MOURIER GILLES; TARTOUR ÉRIC; KAY MICHAEL; FULCHER JAMES M
权利人:INST CURIE; CENTRE NAT RECH SCIENT; INST NAT SANTE RECH MED; COMMISSARIAT A LENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES CEA; APHP ASSIST PUBLIQUE HOPITAUX DE PARIS; UNIV PARIS; UNIV OF UTAH RESEARCH FOUDATION; UNIV UTAH RES FOUND
摘要:A method of producing a monomer of a Shiga toxin B-subunit (STxB) protein or of a variant thereof by peptide chemical synthesis, as well as to a method of producing a pentamer of the STxB protein or of the variant thereof. The methods are particularly advantageous as they overcome major issues typically observed in peptide chemical synthesis, including solubility and purity issues.

专利号:US-2022259212-A1
优先权日:2019-07-11
标题:Inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan 2,3-dioxygenase
发明人：BOSS CHRISTOPH; CREN SYLVAINE; KIMMERLIN THIERRY; LOTZ-JENNE CARINA; POTHIER JULIEN; TIDTEN-LUKSCH NAOMI
权利人:IDORSIA PHARMACEUTICALS LTD
摘要:The present invention relates to compounds of Formula (I) inhibiting indoleamine 2,3-dioxygenase (IDO) and/or tryptophan 2,3-dioxygenase (TDO) enzymes. Further, their synthesis and their use as medicaments in the treatment of inter alia cancer is disclosed.

专利号:TW-202309014-A
优先权日:2013-11-08
标题 :Process for the synthesis of an indoleamine 2,3-dioxygenase inhibitor

专利号:US-2018244663-A1
优先权日:2013-11-08
标 题:Process for the synthesis of an indoleamine 2,3-dioxygenase inhibitor

专利号:TW-202100523-A
优先权日:2013-11-08
标题:Process for the synthesis of an indoleamine 2,3-dioxygenase inhibitor

专利号:US-2024350669-A1
优先权日:2022-01-07
标题 :Inhibition of kynurenine synthesis and/or signaling to treat leukemia and myelodysplasia
发明人：KOUSTENI STAVROULA; GALÃ?N-DÃ?EZ MARTA
权利人:UNIV COLUMBIA
摘要:Methods and compositions for treating leukemia involving administering a therapeutically effective amount of an inhibitor of indoleamine 2,3 dioxygenase (IDO1). The leukemia may be is acute myeloid leukemia or acute lymphoid leukemia. The inhibitor can be a small molecule such as indiximod, epacadostat, BMS-986205, navoximod, PF-0684003, KHK2455 or LY3381916 or epacadostat. The inhibitor can be used alone or in conjunctions with other chemotherapeutic agents. IDO1 can also be inhibited using a CRISP-CAS system. The inhibitor can be administered orally, intravenously, intramuscularly, topically, arterially, or subcutaneously.