Abstract
Linear peptides derived from the membrane proximal region of the gp41 ectodomain are effective inhibitors of HIV type 1 (HIV-1)-mediated fusion events. These inhibitory peptides lack structure in solution, rendering mechanistic interpretation of their activity difficult. Using structurally constrained analogs of these molecules, we demonstrate that the peptides inhibit infectivity by adopting a helical conformation. Moreover, we show that a specific face of the helix must be exposed to block viral infectivity. Recent crystal structures show that the region of gp41 corresponding to the inhibitory peptides is helical and uses the analogous face to pack against a groove formed by an N-terminal coiled-coil trimer. Our results provide a direct link between the inhibition of HIV-1 infectivity by these peptides and the x-ray structures, and suggest that the conformation of gp41 observed by crystallography represents the fusogenic state. Other agents that block HIV-1 infectivity by binding to this groove may hold promise for the treatment of AIDS.
MeSH Terms
Amino Acid Sequence
Anti-HIV Agents/chemistry,pharmacology
Circular Dichroism
Crystallography, X-Ray
HIV Envelope Protein gp41/chemistry,genetics,pharmacology
HIV Infections/drug therapy
HIV-1/drug effects,genetics,pathogenicity
Humans
In Vitro Techniques
Leukocytes, Mononuclear/drug effects,virology
Membrane Fusion/drug effects,physiology
Models, Biological
Models, Molecular
Molecular Sequence Data
Peptide Fragments/chemistry,genetics,pharmacology
Protein Structure, Secondary
Structure-Activity Relationship
Virulence/drug effects
Chemicals
Anti-HIV Agents
HIV Envelope Protein gp41
Peptide Fragments
Authors & Affiliations
7 authors, click to expand affiliations / ORCID
Judice J K
Department of Bioorganic Chemistry, Genentech, Inc., 460 Point San Bruno Boulevard, South San Francisco, CA 94080, USA.
Tom J Y
Huang W
Wrin T
Vennari J
Petropoulos C J
McDowell R S
References (21)
21 references, click to expand
-
Structure of the haemagglutinin membrane glycoprotein of influenza virus at 3 A resolution.
Nature. 1981 Jan 29;289(5796):366-73
PMID: 7464906
-
Spectroscopic determination of tryptophan and tyrosine in proteins.
Biochemistry. 1967 Jul;6(7):1948-54
PMID: 6049437
-
A general model for the transmembrane proteins of HIV and other retroviruses.
AIDS Res Hum Retroviruses. 1989 Aug;5(4):431-40
PMID: 2788443
-
Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids.
Int J Pept Protein Res. 1990 Mar;35(3):161-214
PMID: 2191922
-
Predicting coiled coils from protein sequences.
Science. 1991 May 24;252(5009):1162-4
PMID: 2031185
-
A synthetic peptide inhibitor of human immunodeficiency virus replication: correlation between solution structure and viral inhibition.
Proc Natl Acad Sci U S A. 1992 Nov 1;89(21):10537-41
PMID: 1438243
-
A spring-loaded mechanism for the conformational change of influenza hemagglutinin.
Cell. 1993 May 21;73(4):823-32
PMID: 8500173
-
HIV-1 inhibition by a peptide.
Nature. 1993 Sep 9;365(6442):113
PMID: 8371754
-
Structure of influenza haemagglutinin at the pH of membrane fusion.
Nature. 1994 Sep 1;371(6492):37-43
PMID: 8072525
-
Peptides corresponding to a predictive alpha-helical domain of human immunodeficiency virus type 1 gp41 are potent inhibitors of virus infection.
Proc Natl Acad Sci U S A. 1994 Oct 11;91(21):9770-4
PMID: 7937889
-
Propensity for a leucine zipper-like domain of human immunodeficiency virus type 1 gp41 to form oligomers correlates with a role in virus-induced fusion rather than assembly of the glycoprotein complex.
Proc Natl Acad Sci U S A. 1994 Dec 20;91(26):12676-80
PMID: 7809100
-
The role of human immunodeficiency virus type 1 envelope glycoproteins in virus infection.
J Biol Chem. 1995 Oct 13;270(41):23883-6
PMID: 7592573
-
A trimeric structural domain of the HIV-1 transmembrane glycoprotein.
Nat Struct Biol. 1995 Dec;2(12):1075-82
PMID: 8846219
-
Molecular cloning and analysis of functional envelope genes from human immunodeficiency virus type 1 sequence subtypes A through G. The WHO and NIAID Networks for HIV Isolation and Characterization.
J Virol. 1996 Mar;70(3):1651-67
PMID: 8627686
-
HIV-1 membrane fusion mechanism: structural studies of the interactions between biologically-active peptides from gp41.
Biochemistry. 1996 Oct 22;35(42):13697-708
PMID: 8885850
-
HIV-1 subtype and second-receptor use.
Nature. 1996 Oct 31;383(6603):768
PMID: 8892998
-
HIV-1 gp41 tertiary structure studied by EPR spectroscopy.
Biochemistry. 1996 Nov 5;35(44):13922-8
PMID: 8909289
-
Chemokines and HIV-1 second receptors. Confluence of two fields generates optimism in AIDS research.
Nat Med. 1996 Dec;2(12):1293-300
PMID: 8946819
-
Core structure of gp41 from the HIV envelope glycoprotein.
Cell. 1997 Apr 18;89(2):263-73
PMID: 9108481
-
Atomic structure of the ectodomain from HIV-1 gp41.
Nature. 1997 May 22;387(6631):426-30
PMID: 9163431
-
Unusually stable helix formation in short alanine-based peptides.
Proc Natl Acad Sci U S A. 1989 Jul;86(14):5286-90
PMID: 2748584