Mca-(ala7,lys(dnp)9)-bradykinin

• CAT Number: I042533
• CAS Number: 323577-36-2
• Molecular Formula: C66H81N15O19
• Molecular Weight: 1388.44
• Purity: ≥95%
• Synonyms: (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-1-[(2S)-1-[(2S)-5-(diaminomethylideneamino)-2-[[2-(7-methoxy-2-oxochromen-4-yl)acetyl]amino]pentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]-6-(2,4-dinitroanilino)hexanoic acid
• InChI: InChI=1S/C66H81N15O19/c1-38(58(86)76-49(31-40-16-7-4-8-17-40)60(88)75-47(65(93)94)18-9-10-26-69-45-25-22-42(80(95)96)34-53(45)81(97)98)72-61(89)50(37-82)77-59(87)48(30-39-14-5-3-6-15-39)74-56(84)36-71-62(90)51-20-12-28-78(51)64(92)52-21-13-29-79(52)63(91)46(19-11-27-70-66(67)68)73-55(83)32-41-33-57(85)100-54-35-43(99-2)23-24-44(41)54/h3-8,14-17,22-25,33-35,38,46-52,69,82H,9-13,18-21,26-32,36-37H2,1-2H3,(H,71,90)(H,72,89)(H,73,83)(H,74,84)(H,75,88)(H,76,86)(H,77,87)(H,93,94)(H4,67,68,70)/t38-,46-,47-,48-,49-,50-,51-,52-/m0/s1
• InChIKey: FDQLQIBWKJMUSI-HGGPOPJMSA-N
• SMILES: CC(C(=O)NC(CC1=CC=CC=C1)C(=O)NC(CCCCNC2=C(C=C(C=C2)[N+](=O)[O-])[N+](=O)[O-])C(=O)O)NC(=O)C(CO)NC(=O)C(CC3=CC=CC=C3)NC(=O)CNC(=O)C4CCCN4C(=O)C5CCCN5C(=O)C(CCCN=C(N)N)NC(=O)CC6=CC(=O)OC7=C6C=CC(=C7)OC

Mca-(ala7,lys(dnp)9)-bradykinin is a sensitive fluorogenic substrate for ECE-1 (endothelin-converting enzyme-1). The incorporation of a (7-methoxycoumarin-4-yl)acetyl (Mca) fluorescent group and a 2,4-dinitrophenyl (Dnp) quenching group has resulted in a large fluorescence increase upon substrate cleavage[1].
Mca-(ala7,lys(dnp)9)-bradykinin is also a substrate for neprilysin, but is hydrolyzed 10-fold more efficiently by ECE-1, making this substrate selective for ECE-1[1].

Reference

[1]. Johnson GD, et al. Development of an internally quenched fluorescent substrate selective for endothelin-converting enzyme-1. Anal Biochem. 2000 Nov 1;286(1):112-8.
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