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. Author manuscript; available in PMC: 2011 May 30.

Published in final edited form as: J Med Chem. 2009 Apr 9;52(7):2060–2066. doi: 10.1021/jm900007a

Fig. 1 — A) Chemical structures and nomenclature for the inhibitors discussed in the paper. 1. L-N^ω-nitroarginine-2,4-L-diaminobutyramide; 2. (4S)-N-(4-amino-5-[aminoethyl]aminopentyl)-N'-nitroguanidine; 3. L-N^ω-nitroarginine-(4R)-amino-L-proline amide; 4. (±)-3-{cis-4'-[(6“-aminopyridin-2”-yl)methyl]pyrrolidin-3'-ylamino}propan-1-ol; 5. (±)-N¹-{cis-4'-[(6“-aminopyridin-2”-yl)methyl]pyrrolidin-3'-yl}ethane-1,2-diamine; 6. (±)-N¹-{cis-4'-[(6“-amino-4”-methylpyridin-2“-yl)methyl]pyrrolidin-3'-yl}-N²-(4'-chlorobenzyl)ethane-1,2-diamine; 7. (±)-N¹-{trans-4'-[(6“-amino-4”-methylpyridin-2”-yl)methyl]pyrrolidin-3'-yl}-N²-(3'-chlorobenzyl)ethane-1,2-diamine. B) Structure of 1 complexed to nNOS and eNOS¹². In nNOS the inhibitor adopts a curled conformation in order to enable the inhibitor α-amino group to optimally interact with both Glu592 and Asp597. In eNOS the residue corresponding to Asp597 is Asn368 and as a result, the inhibitor adopts an extended conformation.

Fig. 1 — A) Chemical structures and nomenclature for the inhibitors discussed in the paper. 1. L-N^ω-nitroarginine-2,4-L-diaminobutyramide; 2. (4S)-N-(4-amino-5-[aminoethyl]aminopentyl)-N'-nitroguanidine; 3. L-N^ω-nitroarginine-(4R)-amino-L-proline amide; 4. (±)-3-{cis-4'-[(6“-aminopyridin-2”-yl)methyl]pyrrolidin-3'-ylamino}propan-1-ol; 5. (±)-N¹-{cis-4'-[(6“-aminopyridin-2”-yl)methyl]pyrrolidin-3'-yl}ethane-1,2-diamine; 6. (±)-N¹-{cis-4'-[(6“-amino-4”-methylpyridin-2“-yl)methyl]pyrrolidin-3'-yl}-N²-(4'-chlorobenzyl)ethane-1,2-diamine; 7. (±)-N¹-{trans-4'-[(6“-amino-4”-methylpyridin-2”-yl)methyl]pyrrolidin-3'-yl}-N²-(3'-chlorobenzyl)ethane-1,2-diamine. B) Structure of 1 complexed to nNOS and eNOS¹². In nNOS the inhibitor adopts a curled conformation in order to enable the inhibitor α-amino group to optimally interact with both Glu592 and Asp597. In eNOS the residue corresponding to Asp597 is Asn368 and as a result, the inhibitor adopts an extended conformation.