1-甲基色氨酸

1-甲基色氨酸
	IUPAC名; 2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid; 2-氨基-3-(1-甲基-1H-吲哚-3-基)丙酸
别名	1-甲基-DL-色氨酸; DL-1-加急色氨酸; ARBRIN
识别
CAS号	26988-72-7（D/L） ; 21339-55-9（L）
PubChem	98112
ChemSpider	88584
SMILES	O=C(O)C(N)Cc2c1ccccc1n(c2)C;
InChI	InChI=1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16);
InChIKey	ZADWXFSZEAPBJS-UHFFFAOYSA-N
IUPHAR配体	4694
性质
化学式	C12H14N2O2
摩尔质量	218.25 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

1-甲基色氨酸（英語：1-Methyltryptophan）是色氨酸的分解酶吲哚胺2,3-双加氧酶1（简称IDO1，EC 1.13.11.52）的抑制剂。^[1]它是一种手性化合物，可作为右旋和左旋对映体存在。

其左旋异构体（左旋1-甲基色氨酸）微弱地抑制IDO1，但也可作为酶底物。

其右旋异构体（右旋1-甲基色氨酸）完全不抑制IDO1，但它可以抑制IDO1的相关酶IDO2^[2]，并在因IDO1活性而缺乏色氨酸的细胞中恢复mTOR信号。^[3]右旋1-甲基色氨酸也称为吲哚莫德（indoximod，或译作因多莫得），目前正在进行癌症治疗的临床试验，例如晚期黑色素瘤。^[4]

在2017年8月15日，NewLink Genetics获得了一项涵盖吲哚莫德盐和前药制剂的美国专利，至少在2036年之前享有独占权。^[5]^[6]

参考资料

^ Cady, SG; Sono, M. 1-Methyl-DL-tryptophan, beta-(3-benzofuranyl)-DL-alanine (the oxygen analog of tryptophan), and beta-3-benzo[b]thienyl-DL-alanine (the sulfur analog of tryptophan) are competitive inhibitors for indoleamine 2,3-dioxygenase. Archives of Biochemistry and Biophysics. 1991, 291 (2): 326–33. PMID 1952947. doi:10.1016/0003-9861(91)90142-6.
^ Metz, R; Duhadaway, J. B.; Kamasani, U; Laury-Kleintop, L; Muller, A. J.; Prendergast, G. C. Novel tryptophan catabolic enzyme IDO2 is the preferred biochemical target of the antitumor indoleamine 2,3-dioxygenase inhibitory compound D-1-methyl-tryptophan. Cancer Research. 2007, 67 (15): 7082–7. PMID 17671174. doi:10.1158/0008-5472.CAN-07-1872 .
^ Metz, R; Rust, S; Duhadaway, J. B.; Mautino, M. R.; Munn, D. H.; Vahanian, N. N.; Link, C. J.; Prendergast, G. C. IDO inhibits a tryptophan sufficiency signal that stimulates mTOR: A novel IDO effector pathway targeted by D-1-methyl-tryptophan. OncoImmunology. 2012, 1 (9): 1460–1468. PMC 3525601 . PMID 23264892. doi:10.4161/onci.21716.
^ IDO Inhibitors Emerging as New Players on Checkpoint Blockade Scene. Aug 2017. [2023-03-17]. （原始内容存档于2018-03-20）.
^ NewLink Genetics. finpedia.co. [2019-05-09].
^ NewLink Genetics Annual Report (Form 10-K). fintel.io. April 9, 2018 [2023-03-17]. （原始内容存档于2023-03-17）.

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[1] Cady, SG; Sono, M. 1-Methyl-DL-tryptophan, beta-(3-benzofuranyl)-DL-alanine (the oxygen analog of tryptophan), and beta-3-benzo[b]thienyl-DL-alanine (the sulfur analog of tryptophan) are competitive inhibitors for indoleamine 2,3-dioxygenase. Archives of Biochemistry and Biophysics. 1991, 291 (2): 326–33. PMID 1952947. doi:10.1016/0003-9861(91)90142-6.

[2] Metz, R; Duhadaway, J. B.; Kamasani, U; Laury-Kleintop, L; Muller, A. J.; Prendergast, G. C. Novel tryptophan catabolic enzyme IDO2 is the preferred biochemical target of the antitumor indoleamine 2,3-dioxygenase inhibitory compound D-1-methyl-tryptophan. Cancer Research. 2007, 67 (15): 7082–7. PMID 17671174. doi:10.1158/0008-5472.CAN-07-1872 .

[3] Metz, R; Rust, S; Duhadaway, J. B.; Mautino, M. R.; Munn, D. H.; Vahanian, N. N.; Link, C. J.; Prendergast, G. C. IDO inhibits a tryptophan sufficiency signal that stimulates mTOR: A novel IDO effector pathway targeted by D-1-methyl-tryptophan. OncoImmunology. 2012, 1 (9): 1460–1468. PMC 3525601 . PMID 23264892. doi:10.4161/onci.21716.

[OL-AACR-2017-4] IDO Inhibitors Emerging as New Players on Checkpoint Blockade Scene. Aug 2017. [2023-03-17]. （原始内容存档于2018-03-20）.

[5] NewLink Genetics. finpedia.co. [2019-05-09].

[6] NewLink Genetics Annual Report (Form 10-K). fintel.io. April 9, 2018 [2023-03-17]. （原始内容存档于2023-03-17）.

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